Cure Your Insecurity, Part Two: Understanding Expectations

Now that you identified a few possible sources of your insecurity after reading last week's post, it is time to think about toward what your insecurity is a response.

I will stop there for a second to repeat: Insecurity is a response. 

A reaction to something. An effect. 

Sure, your insecurity becomes the cause of many other effects in your life, but it is born as an effect. 


To understand insecurity in its simplest form, we work backwards. 

Insecurity is about competence. Competence is related to ability. Insecurity is then a reaction to a perception of ability. 

Specifically, perceived inability or incompetence.

Judgment of one's ability is based on criteria to complete certain tasks. Those tasks can include everything in life: work responsibilities, doctor's appointments, vacuuming the house, being on time for dinner, buying groceries, planning your budget, the list goes on forever.

The criteria of each task is proportional to the importance of its completion. For example, going to the doctor is more important for some people than for others, so the pressure to make and attend an appointment is greater for others, so their ability or inability to complete that task may cause more stress.  

Judging that a task is important to you creates demand for its completion. 

And this demand creates an EXPECTATION to complete the task.

Whether you put the expectation on yourself, a boss puts it on you, a doctor, a family member, a significant other, whoever, the expectation creates pressure to make sure something is completed. 

And that pressure puts pressure on your ability to complete the task. 


Depending on who you are and how you have conditioned your self-talk, there is a predictable sequence of three ways that insecurity blossoms when an expectation is presented:

  1. Knowledge:  You do not know how to complete the task.

  2. Resourcefulness: You do not know how to learn how to complete the task or who to ask for help.

  3. Self-worth: You do not think you are able to find the solution at all and you do not think you are worth anyone's time to ask.


The task is not completed and your self-talk that you are incompetent is reinforced. 


When I was younger, I thought there was a right or wrong way to call the dentist's office and make an appointment. My mom had made them for me earlier in life so I got it in my head that I did not know how to conduct the phone call. 

The expectation came from my mom over time to make the calls myself (like a big kid) but I was terrified - not because I was uncomfortable with talking to strangers on the phone but because I was stressed that I was going to somehow "fail" the task of making an appointment.

In this example, the task's expectation came from my mom and then I added the expectation that there was a right or wrong way to do it. 

The two expectations combined in a paralytic fear of picking up the phone and I preemptively perceived myself as incompetent.


We respond to and deal with expectations all day long, on every section of the pressure spectrum. The pressure of them is likely higher in some areas of your life more than others, but all of the expectations boil down to this one single question:

  • Why does it matter to you to complete that specific task?

What is your intention behind it? How does its completion serve you? In addition to considering those questions, your assignment is to stop and think about the last 24 hours. 

In the last 24 hours:

  1. What tasks did you complete?

  2. Why did you care about completing those tasks?

  3. Which ones were stressful? 

  4. Which ones were not?

  5. What expectation was placed on each task? What are the consequences of incompletion?

  6. Who placed that expectation on each task?

Write all of these answers down. At the end, you will have a lot of data - FROM JUST ONE SINGLE DAY OF YOUR LIFE - that can map out

  • what you deem important in life

  • what daily tasks cause you stress

  • what kinds of expectations make you feel insecure

Start there. You got this.

Cure Your Insecurity, Part One: Get To Know It


How many times in your life have you known the answer but did not raise your hand or your voice to share it?

How often has someone asked for your opinion and you sheepishly say "Oh, no, it doesn't matter" or "Oh, well, I dunno, I just think...."?

The sad truth is that human development is saturated with insecurity. 

It does not matter what kind of family someone had growing up, EVERYONE IS INSECURE ABOUT SOMETHING. 

The Sparknoted reason is that your parents offer the kind of love and support that they learned how to give from their parents and their relationships, and the same for their parents and the parents before that. 

This means that there is not one right way of parenting because every single approach will lead a child to be insecure about something. There is no common denominator available to prevent it. That is the way it is.


But what is insecurity?

Life is full of challenges that cause stress in people, but insecurity is tied to confidence. 

Insecurity occurs because you believe that you cannot successfully respond to that stress or challenge. 

This belief is reinforced with self-talk that prevents you from trying to face that stress or challenge again in the future.

Once it is a belief, it is even more strongly confirmed by avoidant behavior and then the all-powerful self-talk of "Oh no, I'm not the kind of person who can do ________", which protects you from the pressure of facing that stress ever.

Insecurity decreases self-confidence. Lowered self-confidence demotivates us to speak up for ourselves. 

Avoiding self-advocacy leads to self-talk that you do not need to speak up because what you say holds no value.

Self-expression gets more and more challenging the more you avoid it, so you protect yourself from the challenge by saying "Oh, I'm just a quiet person."

Great, good for you. You protected yourself from stress. 

But what will you do when something you should say could determine the fate of your career or your relationship?

What if something you know could save someone's life? Would you still stay quiet?

The problem is that people get so used to thinking that they do not have anything valuable to say that the fear of speaking out becomes paralyzing. What if someone was dying and you happened to have taken a CPR course in the past but you are stuck in the belief that you are not valuable?

Will you let the person die or will you speak out about how to save the person?

Does this sound familiar at all to your life?


Here is the deal: Everyone possesses the same amount of value. 

What you know / believe / want to say does not hold any less value than the person next to you.

Whether in your journal, at a work meeting, or on a first date, your evolution depends on your ability to face your fear and share what you want to say.


It is a process, though. Let us do it together. The first question to ask yourself is:

  • What am I insecure about saying / doing?  What do I shy away from in conversations or interactive settings?

This is not referring to things like skydiving or white water rafting, activities that are not required for your survival. 

Instead, I refer to the fear of your own confidence. 

  • About what kind of self-expression are you insecure to share with the world?  

  • And why is that the case? Where did that come from?

  • Who or what "taught" you at some point that what you think does not matter?

This is the first step to understanding what is holding you back in your career, your relationship, and everything else in your life. There is no right or wrong answer, because your answer is just as valid as that of everyone else in the world. 

Learning How To Reflect Will Save Your Life, Part 5: When To Stop Journaling For Maximum Benefit

Once I teach people how to start journaling comfortably (see last week), the next limiting thought I hear a lot is:

How do I know when it is helpful?

It is a good question but it is not the point. The act of journaling is beneficial no matter what; it takes the writer's openness and attitude toward the idea of reflection that cracks open its true value. 

Just Start Writing

I used to work on a crisis inpatient unit at a psychiatric hospital and I had taught a sixty-five year old woman how to journal for the first time in her life. 

At the beginning of a shift, I found her crying in the hallway. She said she had received bad news and had a horrible afternoon and was very angry and wanted to know how to journal about it. 

I told her "The most important thing is that you want to journal about it. That you are already open to processing it. All you have to do is sit down and start writing about your anger. What you are mad at, who you are mad at, and why."

"But then what?" she said.

"Nothing beyond that. You will know when to stop. You will notice what happens once you get into writing your thoughts down."

And she did. She wrote free hand like I do about what had triggered her, why it triggered her anger, and why she felt helpless about it. She cried throughout the process but then noticed when she was losing steam and stopped writing. 

Unfortunately, for many of you overthinkers out there, journaling is that simple. You simply write until you should not anymore. 

Criteria For Stopping

"Easier said than done, Taylor. What are the criteria for that?"

Happy you asked.

Some signs for you to stop a journaling session include:

  1. feelings of physical fatigue from mentally focusing and thinking so hard

  2. trying to force the thoughts to come 

  3. you forget why you are journaling in the first place 

Number 2 refers to the point when the thoughts are not flowing naturally anymore and you are adding extra mental effort to think of the next connection or note to write. 

Regarding number 3, sure, this means you were properly immersed in the process, and it is the point of journaling to see where the mind flows, but be mindful of the overall intention. 

I once thought that I needed to journal and dive deep into it every day, which takes a lot of time and mental force since it is not natural. It was not sustainable because my intention was no longer about the immersion but about the habit of unnecessarily journaling every day of the week. 

The Power Of Immersion

Let me give you a good example of the power of journaling:

Close to four years ago now, I hurt a close friend's feelings. I did not intend to, but I own that I did anyway. I was so distraught by what I had done and how they had reacted and the whole situation of emotions and miscommunications that I had a hard time sleeping and spun my head into a migraine. 

I went to a local cafe I loved with only my journal, ordered a milkshake, and began to write. I wrote for four hours straight before I began to feel the fatigue (#1) between my head and my body that told me the immersion was ending. 

Furthermore, I noticed that the thoughts were not flowing as naturally and the connections I was making slowed down. Writing any more would have been more effortful than beneficial. 

I felt clearer. I felt so much more connected and integrated with my emotions. 

I was still sad, of course, but I had a deep understanding of why I was sad and what my triggers were in the situation. 

For the journaling process to have lasted four hours, the content flowed way beyond the incident with my friend. And that is the point of the immersion. 

You go wherever the thoughts take you. 

The journaling had also ameliorated my migraine. 

I will say that again: JOURNALING CURED A MIGRAINE.

Journaling did not fix my friendship, but it allowed me to speak with the friend with more understanding and clarity on my role in the situation. 

Even more, the journaling taught me how to be aware of situations like that in the future.

It had been made real and I had been made accountable. 

You Are More Ready Than You Think

Do not worry, I am not telling you that you must spend four hours journaling in order to get "immersed". The immersion happens almost immediately if you are open to the process. I just happened to need four hours on that particular day to work through what was in my mind.

To recap, here is what you do need:

  1. a journal that is best suited for your personality and productivity (see two posts back to determine this)

  2. a pen

  3. a simplified starting point - what you are feeling right then, a subject that is on your mind, etc.

  4. openness to the immersion

  5. awareness to stop when you hit the energetic markers I mentioned above. 

Within that, though, go for it. See where your mind takes you. It is a fascinating and wondrous journey to go on. Enjoy the ride.

Learning How To Reflect Will Save Your Life, Part 4: How To Start Journaling So That It Actually Helps


So many people I know say that they are terrible writers. 

"I'm not a writer."

"Oh no, I can't write."

This limiting belief gets in the way of so many people learning how to access the enormous power of journaling. Much of the perceived limitation that people hide behind is due to the belief that there is a right or wrong way to journal. If people are not accustomed to the vulnerability of reflection or the practice of handwritten freewriting, then a giant mental block is formed in their brain, creating a balloon of pressure that leads to panic and........they never try to start. 

The concept of right and wrong is horrendously taboo. If you missed my post about why that is, check it out here before we continue, to give you better context.

The Problem

In this world of oversaturated markets peppering us with advertisements about what the internet thinks you need to buy, there are so many options for notebooks and planners and journals that are supposedly the miracle for your productivity and success, but how can someone know what journal is best for them if they believe that they will not be able to journal "correctly" from the get-go?

What To Do About It

The solution is to start with the end in mind. 

What makes you productive at home or at work? What practices do you have in place to be productive? What must be in place around you for you to feel productive?

For example, music needs to be playing in order to clean the house. A picture of your family must be lined up on your desk in order to start work. 

Everyone's unique productivity criterium is different and represents the way that their mind works.

In this way, the efficacy of reflective journaling depends on your awareness of what makes you productive. 

The Practice 

I started journaling in the winter of my freshman year of college. I remember it was a time where my self-awareness was blooming and I needed a way to filter the thoughts that were flooding in to my mind as college slapped me with the concept of "adult independence".

I was not so aware yet to necessarily do anything with the thoughts but I needed a place to put them. To save them.

My first journal entry ever was one simple phrase: "I am like Leonardo Da Vinci". Not because I was an artist and inventor at the time but because I recognized that I thought differently than a lot of people around me and I analyzed the world and my life in deep ways. 

This is a great example of journaling because the realization had been in my head for a while and I needed to get it out, even though there was nothing to do about it other than remain aware that that is the way that I am. 

I have a huge imagination. I spend probably 35% of every day consciously imagining life as though it were in a movie, with background music and all. Because of this, my productivity is correlated with my ability to hold on to the broader vision of something I am doing so that I can focus on the tasks that contribute to it. 

As a result, my mind does not respond well to confinement. 

This is why I am most successful at journaling freehand in a lined journal that has no prompts or schedulers or anything. Nothing that tries to constrain my mind into certain kinds of reflective structure. 

Your Turn

So again, what makes you productive?

Many people need much more mental structure than I do when reflecting, and that is okay. If you are one of those people, you would benefit from a journal that has writing prompts or specifically organized spaces for certain kinds of reflection in it so that the structure is provided for you and all you have to do is answer the questions.

Bullet Journals have become super popular because of the way they help people structure and organize their thoughts and notes with visual cues in the notebook itself.

Modern technology has advanced so far as to offer Rocketbooks, which are environmentally conscious notebooks that allow you to download pictures of your notes into a Rocketbook app and then microwave the notebook to erase the notes. 

This works well for the person who would not mind keeping the reflections somewhere but also feels compelled to burn all evidence of the reflection because of how vulnerable the process was. I know a few people like that...

How To Get Started

Clean and simple lined journals work the best for me not only because of the lack of visual constraints in the journal itself, but because it gives me total freedom to write in it however I damn want to.

I can say whatever I want in it. No one is telling me what to do.

"Okay cool, Taylor. But how do I start?"

(I get that a lot)

Start like I did with one simple phrase. It does not matter what it is. Anger is pretty accessible for people so say something you are pissed off about. For instance "I am pissed at ______________." 

It is as easy as that. 

Your next steps

Journaling has been one of the most powerful things I have ever done. It has saved my life on a couple of occasions, and continues to allow me to store information about myself beyond the confines of my head.

I want this for you as well. So start here:

  1. Determine what mental state makes you productive.

  2. Find a notebook or journal that coincides with that.

  3. Think of one simple phrase that is relevant to your life right now for your first entry. 

  4. Enjoy the boundless expanse of your thoughts.

Learning How To Reflect Will Save Your Life, Part 3: Don't Go It Alone


Our brains evolve in order to help us survive. 

This is why our brains are really good at looking around for threats or attaching its cognitive features to negative things. 

Why do you think it is easier to complain about something than be vulnerable and share something positive?

The common education system makes us think that we must store a whole lot of information in our heads in order to survive. That learning about every culture's ancient history will equip us with necessary skills to prolong our species. 

The problem is our brains cannot hold all of the information about the world, the universe, how everything works, how to use everything, how to construct everything, etc. 

Power of Deliberation

The book The Knowledge Illusion, by Steven Sloman and Phillip Fernbach, examines the limits of human knowledge and learning as well as why our brains have evolved the way that they have. They discuss the difference between intuition and deliberation. Intuition is used to deduce knowledge of something instinctively from within yourself based on information from your surroundings or the way that you have become accustomed to making decisions and solving problems. 

Intuition is a quick judgment. Deliberation, however, takes more time, employs more analytical thought, and often requires some form of collaboration, even if that collaboration is in the form of talking to yourself. 

Those who respond with more deliberation to problems or questions, as the authors note, tend to be more reflective, detail oriented, and cognizant of the limitations of their knowledge. They are much more aware of what they do not know than those people who rely on intuition and snap judgment for an answer. 

Collaboration and Survival

While I mentioned how reflection helped our ancestors to more efficiently defend themselves against sabertooth tigers, Sloman and Fernbach mention how reflection and deliberation about hunting Wooly Mammoths contributes to survival. From their discussion, deliberating and collaborating with others is beneficial in three important events related to hunting a Mammoth:

  1. brainstorming different ways to effectively hunt one

  2. creating a system through which the Mammoth meat is stored and shared fairly amongst the group

  3. creating respectful expectations for living as a cohesive community 

Each of these phases present a new opportunity for huge neurological growth as well as social cognition about who knows what and how the group can work together to survive as a community. 

Collaboration and YOUR Survival

If you are experiencing any kind of emotional event or, say, anxiety, in which your brain is getting concerned for your wellbeing, reflection can help you learn about the emotional event and why you react the way that you do. 

A lot of people panic, though, and stop there because the vulnerability is too unfamiliar and they do not know how to proceed on their own. Cue the Mammoth concept. 

Get help. Collaborate. This does not mean that you have to go find a therapist, but instead it can be as simple as walking around your house talking through your reflections out loud to yourself. Hearing it out loud will externalize the thoughts in a different way than writing it down or just thinking it, and it will be almost as effective as hearing someone else speak to you.

Start with that if you are nervous about reaching out to someone. 

If you are comfortable with going beyond yourself and bolstering your odds for survival, find someone to talk to.  A friend, a family member, stranger in a coffee shop, whomever.

PRO TIP, start the conversation like this:

"Hey, I have been reflecting on something I have been going through and I wonder if I could talk it out with you."

If you want their advice, replace the second part of that with "...I wonder if I could get your take on it." 

Hint: people are always stoked to share advice, so be careful who you choose to talk to you about your vulnerable emotional material or take their advice with a grain of salt.

You will find that the dynamic of verbalizing it to someone else makes you hear your thoughts differently than when kept in your head, the person may provide relief by simply validating what you are going through and reminding you you are not alone, or they may have perspective or advice that turns around how you have been thinking about yourself. 

Cheers to your evolution. 

Learning How To Reflect Will Save Your Life, Part 2: What Are You Scared Of?


Last week we began to discuss how self-reflection is important for your survival. It is a process of self-exploration that demonstrates how you learn new things and integrate them into your life. 

Learning new things and integrating them into daily life is what humans have It is a natural process. 

That is why we think school is a required rite of passage into human-hood. Because we have to learn stuff.

Studies have shown that happiness is correlated to one's sense of making progress in any way, big or small, which means that the urge to grow is imprinted in our DNA as a means of achieving fulfillment.

Learning = Growth = Evolution = Survival

Sounds simplistic, yeah? But here is the thing:

People are absolutely terrified of reflection.

It is mind-boggling. 

The Evolution Problem

When you are a teeny tiny baby, you are learning stuff for survival just as often as you are as an adult, but the mental framework is different. Not only are your mental skills more evolved, you have a couple things called independence and responsibility. Other than the fact that you do not have a whole lot of consciousness when you are a tiny child, you are not yet fully responsible for your survival. As a result, you do not recognize or see the value in the many things you are constantly learning. 

As you get older and learn that you are, in fact, a person and that you are different than other persons around you, you learn that there are some things you might have to do keep yourself alive. 

The problem is that you do not face that realization with "Boom, I got this. I have been learning how to survive my whole life already" because you were not aware of what you were learning when you still relied on a caregiver for survival. 

When faced with the existential "holy crap, I am human" moment, people freeze.

They feel like they do not know what to do. They get stressed. They get down on themselves. They get sad. 

Even people who recognize the benefit of self-reflection and who begin to self-reflect often hit a point where they get scared and stop. 

The Survival Problem

Why the heck do they stop? Because they are insecure. They acknowledge the consequences of not reflecting but they believe that they do not know HOW to effectively reflect. 

They think there is a right or wrong way to do it. 

What is worse, they think that the vulnerability of self-reflection is a sign of weakness. Society promotes this. And this is true for people who see the benefit of reflection. What about those who never even allow themselves to start reflecting because it is a waste of time? Darwin sits up in his grave...

The Solution

Before I teach you any more about HOW to reflect in a safe and effective way, the most important thing is to first identify what is getting in the way of your vulnerability. 

For those of you who have never wanted to fully attend to self-reflection:

  • what are you afraid of?

  • what is scary about that vulnerability for you?

  • what do you believe this level of vulnerability means about you?  

For those of you who have given attention to self-reflection but then stopped when it got too deep or too vulnerable:

  • what did you become afraid of?

  • what was scary about that threshold for you?

  • what were you learning about yourself that you became afraid to continue exploring?

  • did you feel alone and unguided?

For both categories: from whom were you taught that vulnerability is not a good thing?

Everybody reflects to different extents and everyone stops for different reasons. For this reason, I cannot and will not ever judge someone for becoming scared in the course of their own unique evolutionary journey. 

You must understand your fear of vulnerability before you can learn your unique power and increase your chances of survival. 

Learning How To Reflect Will Save Your Life. Here Is How


When you read the word REFLECTION, what comes to mind?

For some, it strikes fear.

For many, it means tedious effort and a lot of attention. 

Others never think about it.

Have you noticed that I ask reflection questions at the end of nearly every post?

Similar to dreaming while we sleep, we are always reflecting. All day every day. Our brains are constantly trying to understand what we do, see, and hear in a way of assessing if it serves our survival.

Reflection as a tool

Learning the look, sound, and movement of a sabertooth tiger was imperative for our ancestors to not only defend themselves but also learn how to more efficiently hunt. Learning only occurred because the ancestors reflected on their first interaction with a sabertooth tiger and applied what they remembered toward preparing for / against future interactions. If they had not, every interaction with a sabertooth tiger would be the first time and chances of survival would be 50/50 every time. Sounds terrible...

Think about school. Teachers drop a ton of information on us. In order to fully learn the material, we had to think about what they said to us (reflecting it in our heads) and try to make sense of it. If we were able to make sense of it, then we let our memory absorb it and then we could apply it to other areas of our lives, as needed. 

Gaining that knowledge and enabling its application to life significantly increases our chances of survival. 

Every piece of new knowledge is a tool for us to use. ("Knowledge is power", anyone?)

Reflection as medicine

Reflection is not one of the most trendy buzz words these days, but it has always maintained a solid popularity due to the fact that it is most often correlated with therapy and mental health.

This is where the bias toward difficulty arrives. 

Reflecting for the sake of your mental health can be challenging because it has a very specific outcome toward which the reflection is directed. Our above examples noted survival as the outcome, which of course is important, but we are always accumulating tools and knowledge for survival. 

In mental health, the need is not always apparent or the need is extremely urgent. Someone in denial of their emotional obstacles vs. someone who wants to commit suicide, for instance. 

The outcome is the same, however, despite the urgency: healthy survival. 

The urgency from crisis or the visible disruption in your daily functioning creates panic, fear, and anxiety because one fears that they do not have the tools necessary to kill their sabertooth, so to speak, in the immediate time frame that the challenge presents. 

This is why people give up, break down, or worse. Simply due to the fact that they think they cannot effectively reflect. 

But they are wrong. 

Let me remind you: YOU ARE ALWAYS REFLECTING. Whether consciously or not, your brain is constantly looking back at the information it is constantly receiving. 

The difference now is about you taking responsibility to do something with that knowledge. 

Reflection as a team effort

But we are going to start slow. We will do this together. 

I am really good at reflecting but I learned how to a long long time ago and it certainly did not occur overnight. Proper reflection takes time and attention. If your attention is pure, it takes a lot less time. Attention comes from acceptance, however. 

You must accept the mission before you can put effort toward it. 

In the past week, I have experienced seven things of immense power and meaning to me, each of which occurred over different frames of time but which occurred one after the other and continued to relate to and reinforce the power of the others. 

I have been quite emotional this week as a result.

I have also been reflecting on them for the past few days, but I am nowhere near "finished" thinking about how they apply to my life. Every time I try to, I get emotional again (in the grateful existential way), which is my barometer for how to schedule the reflection. 

I will keep you updated. 

In the meantime, I want you to think back to last week's post about what we hold on to and take with us in life. What did you come up with in response to the questions I asked?

This week, I want to start simple:

  1. What do you think a lot about in a given week? What thoughts or desires distract your mind. 

  2. Are they good things or bad things? Or a mix?

  3. What are the things: work? money? relationship? food? housing? travel? love? alcohol? exercise?

  4. Once you have the category, what about that category do you specifically think?

Whatever that prevalent thought is for you is the starting point for determining how you reflect, how you learn, and how to reflect more effectively and healthily in the future. 

You know, for your survival...

What Are You Holding On To? Your Stuff Says A Lot About You


I have moved quite a bit. Six times since college, to be exact. Each time, I significantly improved my ability to pack up my entire life and transport it somewhere else. 


Moving is one of the top five most stressful activities in the human experience because of the many elements of change that must be organized, coordinated, and to which one must become adjusted. People do not handle change well, so moving is like the huge monster that no one particularly enjoys coming across.

Those who enjoy living in different places still probably do not enjoy moving, but they know how to live more simply. 

As I have moved around the country, I noticed that the amount of items that I call "my life" has decreased and the type of items I make sure to bring has changed.

When I first moved to Boston after college, I accumulated so much furniture that I did not need and I probably brought every piece of clothing I had ever owned because I had no basis other than college to judge what to take with me into the big bad world post-college. 


I still have way too many clothes - even though I wear all of them - but the other stuff is what is different. For instance, I gave away a ton of furniture before this last move to Utah and prioritized a few pieces and my mattress that I enjoy using every da (humorously, a mattress is not so important in your early twenties. Adulting is weird like that). 

It is the other stuff that I want to draw attention to. Not the kitchenware or the slow cooker or the surplus silverware, or even the little boxes of trinkets that mean a lot to my life journey that I make sure to keep. I mean instead the extraneous odds and ends that you do not want to throw away but for which you simultaneously do not have a proper use, and which take up space. 

Because I am an expert mover now, I have narrowed that amount of extraneous stuff down to one single shelf on an IKEA shelving unit. 

I find myself staring at it a lot, though. It sticks out to me. It is stuff that I am not interacting with. So why do I have it? 


One box is full of blank extra notebooks. Duh. I write a lot. But now I could start my own "Journal Resale" Etsy shop. At least forty notebooks are in there. Next to it is a box of totally random objects that are unrelated to each other. They are the objects I do not want to give away for some stupid reason (luckily it is not a very big box). 

A DVD of my college soccer game footage? Sure, cool for history's sake but I am not watching it every night. 

A pack of awesome thin markers I have used with clients and for my own artistic outlet, but which I have not used in at least three years. 

Everything on this shelf is there because of potential energy. It a shelf full of things that I MIGHT use at some point, but for which I do not currently have a need. 

Whenever I get stressed and search my rolodex of coping skills, my brain immediately directs me to those two boxes and says "BURN THEM". 

I hold on to them, however, because their usefulness in the future is more significant than, say, the six trash bags worth of stuff that I reverently threw away the morning I left Boston. 

Those are the things I hold on to. I have contained it to a single shelf because of the objects' potential usefulness. This is so healthy because it is the only aspect of my life that is distractingly unnecessary at the moment, and that means that everything else I packed and moved is stuff that I use on a daily basis. 

Do not confuse my pragmatism with my belongings for materialism, though. I could of course be more minimalistic, but I think I am doing pretty well. 


In summary: meaningful trinkets from my past take up one square foot of my apartment, and objects for the future take up about three square feet. 

Now I ask you:  What do you hold on to? 

What is in your space right now that just takes up space?

How does it affect you?

Why are you still holding on to it?

Who You Idealize Says A Lot About Your Self Worth


Have you ever worshipped the ground someone walks on?

A lot of people idolize athletes and rock stars and movie stars, but they also often idealize them without knowing it. Let us explore the difference.


Idolizing someone is at it sounds: making an idol of that person. The dictionary definition of Idolize is: "admire, revere, or love greatly". An idol is defined as "a representation of God". 

We idolize celebrities and athletes because what they are able to do is so incredible that it captivates us and grabs hold of our emotions. There are many who watch the olympics and feel motivated to become the best in the world at one of the sports themselves. Even for those who do not strive to achieve what they see, there is still a healthy acknowledgement of and detachment from those celebrities. A powerful admiration that fills us with inspiration and respect. 

In these ways, idolizing others is healthy.


But then there is idealization. People often confuse the two or use them interchangeably, but unfortunately idealization is not as healthy as idolatry.

Idealize is defined as: "to regard as perfect or better than in reality". That is very different than genuine admiration or reverence. To idealize is to view a person as the perfect version of what it means to be a person. It sets a standard for what someone "is supposed to be like".

If you watch the olympics and idealize an athlete, you think that the way that that athlete seems to be must be the way that you should be in life. 

The problem is, instead of a healthy respect and admiration that leads to a proud sense of inspiration, idealizing an athlete causes the idealizer to feel inadequate, incompetent, and generally incapable of achieving what it appears is the thing the ideal human is supposed to be able to achieve. 

The idealizer gets down on themselves because they do not believe that they can attain that greatness. That thought becomes a belief, and that belief trickles into that person's self worth in their work, their relationships, and their dreams. 

The Distinction

Like in religion and professional sports, many people can idolize a single figure for a lot of the same reasons. Idealization, however, occurs very differently for everybody. 

This is due to the fact that the characteristics for which we idealize others are characteristics that we find lacking in ourselves.

And those characteristics are unique to every person.

The Consequence

What if, all of a sudden, the person or athlete or celebrity did something terrible that broke in the news (I know - these days that happens all the time)?  Even if it does not ruin their careers, it can ruin your perfect image of them as the entity that represents everything that you want to be. 

That further pummels your self-worth because the idealized person was supposed to be the thing that sustained your motivation to be greater - even if you went on feeling incompetent anyway - and now they behave in a way that shows that they are not, in fact, a perfect entity (based on your unique definition of perfection). 

It is not fair to them to be put on such a grand pedestal, but you do not care because you are distracted by how poorly you feel about yourself.

The Activity

Quite simply:

Who do you idolize in the world? Then, who do you idealize in the world or your life? 

What characteristics of them do you idealize? Do you wish you possessed those characteristics in an area of your life?

I mostly idolize actors or even the characters they play (because I am such a huge movie nerd) and feel a deep admiration for their prowess and what they represent. On the flip side I have idealized my soccer coaches growing up, some teachers, and a lot of supervisors in job settings. 

When I watched a soccer coach play in a scrimmage and heard him swear or yell at the referee, I was so disappointed. My image of their flawlessness was torn.

When I realized that a supervisor at work actually was not good at their job even though they trained me, it confused me about my time with them and my own skills in the work. 

The Outcome

Reflecting on who you idealize and what characteristics you idealize in them shows you what characteristics you long for.

When I idealized my coaches, I envied their skills and strength with the soccer ball.

When I idealized my supervisors, I wanted the confidence that they exuded all the time (even though their skills in the work were not enviable) because I was just starting the new job and did not feel confident at all myself.

Do not let this be a bummer for you because you are already bumming yourself out just by idealizing the person.

Instead, let this be a tool to identify how you would like to grow and what traits you would like to define and attain for yourself. 

Do You Want To Cure Your Insecurity? Start here



We humans do not know how awesome we are.

We are so critical of ourselves. We are the worst. We are all our own total worst enemies. Back in the day of the original humans, "work" was pretty simple. Hunt and cook food, and maintain the integrity of the living situation, all in order to serve the outcome of surviving. A very straightforward outcome and several straightforward ways to achieve it.

These days, the outcome obviously has not changed, but the ways we achieve that outcome are so much more complicated. Think about jobs in the modern centuries. Someone gets up in the morning to answer phone calls for eight hours to survive. Someone deals with fecal fluids and trash in the sewers for ten hours a day to survive. Someone even runs into burning buildings to survive, as ironic as that sounds. 

Because of the fact that money is now the means by which we survive because it buys us food and resources that promote our health and safety, we no longer have to worry about mastering the singular trade of hunting a sabertooth tiger in order to ensure survival to the next day. 

As a result, we focus on the money. There is a similar desperation to earning money as there would be to hunt food in the past, but money is ubiquitous now. Money is rarely even tangible anymore because no one carries cash, so it is this thing that we seek that we now do not even see. And it is what motivates us.


When we see our job as a means to that end of receiving money, we become robots that lose sight of why we chose that job in the first place. Worse yet, we lose sight of how our personal skills got us that job and why we are good at it. 

This is where the problem arises. 

Even people who love their job and possess their dream job do not often stop to think about what makes them so good at that job because they are focused on doing the job. 

This is a pandemic problem because the lack of awareness of our unique awesomeness is what leads us into insecurity and self-deprecation. When we become insecure about our skills, we start comparing ourselves to others. When we compare ourselves to others, we become even more insecure about our skills. See what is happening?

Pretty quickly you feel so badly about yourself that you begrudgingly come into work with the belief "I don't know why I even show up to this job" which turns into the self-story that "I hate this job so much" - as if it is the job's fault - but you never leave it or make a change. 

You do not make any kind of change because - SURPRISE - you are unconfident about making a change due to the fact that you are so insecure about capabilities. 



The individuals I have worked with in my mental health career have been wrought with insecurity. Insecurity prolongs a lot of mental illness because of what I just mentioned - that the individuals believe that they are incapable of change and that they have to remain in their distress. 

Sound like anyone you know with their work? 

My clients come to me now because they feel that distress and want so badly to change but they do not know how. They have spent a long time feeling insecure - either in a job they do not like, in a relationship that is not healthy, or about ideas they do not think they can make real - and that has become their norm. 

But they are in pain. They have lost sight of their ambition, their skills, and their values (the triad about which I have written before) and they feel trapped in a vortex of confusion about their purpose in life. It is my job to help them remember - or learn for the first time - just how uniquely awesome and powerful they are. 


I want this for you as well. Start here. 


  1. When you were a kid, what were you good at? What did you enjoy doing?
  2. Consider the work you are in right now: why did you choose that job?
  3. Better yet, why haven't you been fired? -- what skills do you bring to the work that accomplish the daily tasks?
  4. When you leave work for the day, how do you feel? 
  5. What do you say to yourself about your work that day?


  1. What is the motivator for you to be in the relationship:  love, security, convenience, companionship?
  2. Why hasn't your significant other dumped you? -- what do you offer in the relationship that keeps it alive?
  3. What does your significant other say about you that makes you swell with pride and warm fuzzies?


  1. Whether you have started a business or not, how did you come up with your business idea?
  2. More importantly, why did that idea excite you in the first place?
  3. What skill(s) do you bring to that idea or business? 

Why Wanting To Be An Expert Is Hurting Your Self-Worth


At the end of my tenure at a residential treatment program for young kids in Colorado, my boss told me that I was an expert in residential treatment because of how many years I had worked in that type of setting and the extent of training I had received throughout those years. Cool, I was an expert. But am I still an expert in it having not worked in that setting for four years?

Anyone who has first hand knowledge or experience in an area about which we would like to learn more information is often called the expert.

But is my friend who went to Iceland last year really the supreme source of knowledge for how to travel in Iceland? Nope. But I trust their recommendations. For all intents and purposes, we can call the internet an expert because of how many questions we ask it and how blindly we assume its authority. 


Expert is defined in the dictionary as "a person who has a comprehensive and authoritative knowledge of or skill in a particular area". Notable characteristics of this definition include:

  1. "Person"
  2. "Comprehensive"
  3. "Authoritative"

It is important to note that "authoritative knowledge" does not mean "absolute knowledge", but rather enough knowledge to be considered a leader in that subject area. This is important to note because, by definition, an Expert is not actually as idealized as the ultimate authority figure we often presume them to be. 


Because of the fact that we humans so often deify those we believe are experts for the sake of our own control, certainty, and survival, we place peers on a high pedestal on top of which we all would not mind spending time in our own industries. As a result, the idea of expertise becomes an idealized goal that is located so high above us.

For some, yes, this can be used as healthy motivation in their career or education, but more often than not people succumb to the pressure of becoming an expert to the point where it is instead detrimental to their career or education. 


The concept of expertise that most people seek is idealized because of the fact that it is not clearly defined for each person. Saying "My goal is to become an expert" is just as ambiguous as saying "My goal is to achieve success." 

Actionable definitions of expertise and success are unique to every person. Idealizing expertise glorifies it. Not only that, it transforms its pursuit from one of genuine fulfillment into something completely ego-driven for the sake of the title of Expert. 

Many clients of mine have come to me feeling stuck on the idealized form of Expertise because its idealization teased their perfectionism, and their perfectionism diminished their self-confidence and self-worth. 

Therefore, idealizing something like Expertise without defining it for yourself is ultimately harmful to your self-worth. 


Refer back to the dictionary definition above. Take a breath and remind yourself that an expert does not and cannot know every single piece of information in their respective industry and having an authoritative knowledge is not the same thing as an absolute knowledge. Then come up with your own definition of Expertise that is unique to your industry. 

  1. What knowledge would you possess in your image of yourself as an expert?
  2. What would you be able to do / say / teach as that unique version of an expert?
  3. What would you feel? 

Remember the triad of values, skills, and goals?  If that is drawn out as an equilateral triangle, your unique definitions of Expertise and Success will reside right in the middle.

It is YOUR expertise and YOUR success. 

Artist, Leader, Or Entrepreneur? Who You Are At Work Can Dramatically Help - Or Hinder - Your Success


What are you? 

It is a question we sometimes lump in with "Who are you?" in the deeper, semi-existential sense and, depending on who you speak to, answers are extremely variable. Luckily Tony Robbins, the master Life/Performance/Business/Development coach on the planet (he invented the field of coaching, by the way) provided some clarity last week as to how to answer that question at his five day Business Mastery seminar in Las Vegas.

He distinguished three categories of business people that he calls "Gifts of Service" in accordance with which we all somehow live our lives. 


The artist is someone who loves creating a product and takes immense pride in the process of serving a customer's needs. Artists love the product and design so much that they are scared of risk and want to protect the business and identity that they created. That way, artists are very mission-driven and focus on continually improving the product and its effect on the customer.


The manager / leader is someone who is proficient at optimizing business systems and making sure everything runs efficiently. Very detail-oriented, this is someone who is fueled by managing and organizing the needs of both the processes within a business as well as the people in charge of those processes. A manager / leader is one who does not pay as much attention to the product design and creation but still wants to mitigate risk as much as possible to ensure the business' sustainability. 


The entrepreneur is the risk taker. They spend the least time thinking about the product design and creation and instead spend the most time on the product's market fit and overall business value with the ultimate goal of selling it and moving on to another venture. The entrepreneur is fueled by the scary rush of building a startup, managing investments, and looking for any opportunity to innovate and grow. 

What it means

Keep in mind that it is common to simultaneously possess characteristics of more than one persona. It is rare to be one and only that one. The persona we inhabit can also change over time, especially once one learns more about themselves in college and then again and again in the real world after college while adopting new skills and experiencing many new things. 

I have always predominantly been an Artist because of how much I love creating things, designing new aspects of service, creative writing, and so on. Not to mention how everything I do is goal-oriented and funneled toward specific outcomes. 

A twist in the plot, however, is the fact that I am largely a Manager / Leader as well. I think it is a 60/40 kind of thing leaning towards Artist but still M/L is right up there. 

This presents itself in my brain by way of my right hemisphere exploding with creativity and then moving the energy to the left hemisphere of my brain as soon as the ideas are formed. Once the ideas move over there, the left side immediately sets to work organizing them for efficiency and sustainability. I can feel when this process happens. It is a cool mutualistic relationship between the hemispheres, and the transfer occurs so quickly once my right has created something new. The left side of the brain is like the idea protector and packages them up nicely into something usable. 

I was definitely an Artist first, playing so much with toys and Legos growing up, but I know that I developed Manager / Leader qualities via family dynamics and subsequently taking on leadership positions in jobs and volunteer experiences. Now the trick is to continue employing both together.

What it also means

This activity not only draws awareness to your dominant personality traits but it also delineates what kind of personality traits you might want to seek and have join you. For instance, the interplay between Artist and Manager / Leader in me is powerful new clarity, but it also shows me that I lack the Entrepreneur's risk-taking, turnover-focused traits.

Even though I am technically an Entrepreneur by general definition, I am very much more the Artist in the sense that I focus hard on protecting what I have created and avoiding financial risk. What this means for the future of my business is that I ought to look for and hire someone who is predominantly an Entrepreneur so that our traits balance and that other person can focus on aspects of business development that my Artist's mind does not feel naturally compelled to. 

This will make it easier for me to describe what kind of person I am looking for when I post a job description in the future. 

What you can do about it

  1. Which one are you?

  2. Are you mainly just one of the personas, or do you show signs of multiple?

  3. What does this mean for you in your job or at your office?

  4. Amongst your coworkers or teammates? 

  5. How do you think you can use this assessment to boost your team's performance and productivity?

Is Grad School In Your Future? Answer These Questions First


I have not gone to graduate school.

Sure, I have taken a class here and there and workshops galore, but I do not have an advanced degree. A lot of people to whom I talk about my business and my career ask what kind of advanced degree I have. In fact, quite a few people presume that I must have one. But I do not. 

The rules have changed over the last ten years about the significance of graduate school degrees. I started hearing more buzz about it all the way back in the 2012-ish era. I grant that many careers required graduate school, rightfully so, such as those in medicine, law, and mental health care. My opinion as the individual I am with my own set of circumstances and goals is that I do not need graduate school. That is my situation, though. I work with a lot of people who are changing careers or entering careers and graduate school is often on the menu as a side option in conjunction with or even in place of the main job.

I also know a lot of people who have unfortunately attended graduate school because they did not get a certain job they wanted or with the sole purpose of avoiding the workforce altogether.

That is so much money and time put to something that may or may not have any return on the investment or career relevance.

My standpoint is not an emotional one. I will not emphatically proclaim that graduate school is pointless and nobody needs it. Instead, my standpoint has always been practical. As a case of need. As a logical means to an end. I have not needed graduate school thus far as a factor of what my career interests dictated. I have applied a couple of times to two different kinds of programs and thought about applying a couple of other times, but no matter what it was not about to make or break my career direction.

Several years ago, I was talking with my parents about the job I had at the time and one of them made a comment about "not waiting too long because you'll have to apply to grad school sometime soon". I had expressed interest in graduate school before, but I was alarmed by the urgency. Like it had to happen. That was before I started my business.

I am currently in Las Vegas for a Business Mastery program in which I will spend twelve hours a day for five days immersed in trainings for the sake of my personal evolution and entrepreneurship. Call it a doctorate in business administration.

A business coach friend of mine casually trained me in his company's model of supporting clients' career exploration one afternoon. Call it a masters degree in career coaching. 

He said it best when he stated "BOOM, you are certified."

Professional experience and specific trainings have been my graduate school thus far but, again, I am not opposed to the idea. There is a full masters program in which I am interested that would bolster my current skillset, but I do not feel the urgency of need quite yet.

Let us think practically. In addition to his own experience and personal opinions about graduate degrees, the author of a 2016 article bluntly titled "Millennials, Don't Waste Your Money On Graduate School" poses four questions to anyone considering graduate school in their professional timeline:

  1. Why do you want to go to grad school? --- plain and simple. Necessary for a job? Because you are bored? Because you are hungry to learn? Because you want to avoid a job?
  2. Will grad school actually help you achieve that goal? ---  the goal is not enough. How perfect is the program for that goal? What criteria need to be met for your goal to be fully satisfied?
  3. Are there alternative ways to achieve that goal? --- certifications? Seminars? E-books? Online courses?
  4. Can you afford it? --- seems obvious, but a lot of people do not stop and answer this by writing down their finances and budget and forecast them over the next two, three, or six years. What would you need to do to pay for it?

Many people only need to focus on one of those questions to determine whether graduate school is a proper and practical choice. Often it is the financial question, but I encourage people to always start with the Why (shocking, since that is what my whole blog is about). I know my Why is to augment my skillsets and add value to my clients, so my practical evaluation is about when and how to pay for it.

Either you or someone you know is considering graduate school. Encourage them to answer these questions for themselves. Make a game out of it and quiz each other. Just make sure it satisfies your true genuine outcome.

How To Direct Your Own Fulfillment, Part Two: PREPARATION


Last week we spoke about the purpose behind starting a business, a certain job, or even a hobby. This week is about Preparation. The article to which I referred last week spoke to the fact that a lot of entrepreneurs who are lured in by the title of entrepreneur start their businesses without really comprehending what goes into running the business day to day and, as a result, the majority of small businesses fail. Their founders are blinded by the shiny diamond of business ownership and do not stop to wonder what kind of pressure that diamond has to endure to become shiny in real life.

This is why, as the article states, passion and a big idea is not everything. A lot of background knowledge and preparation are needed as well. 

Preparation comes in a lot of forms, though. I will not say that there is one absolute requirement, but there must be something. The article mentions how the allure of the Entrepreneur title also comes with the mindset of diving in, taking risks, and failing in order to succeed. Even though all three of those things occur in the life span of a business, starting off like that with no training wheels is a bigger risk than should be taken. And a rather arrogant one.

Think of it like going into a job interview without doing any research about the company or the position. The candidate is either arrogant or oblivious, neither of which bodes well for sustainable success. 

Preparation for starting a biz can be many things:

  • graduate school
  • undergraduate classes
  • a relevant workshop
  • relevant work experience
  • interviewing business owners you know
  • reading Entrepreneurship For Dummies
  • listening to a podcast
  • keeping your day job
  • waiting a few years
  • praying to God
  • moving back in with your parents
  • all of the above

The cool thing about this modern age is that graduate school is not required for so many jobs. The positive of this is that more opportunities are available and people can take more risks on their own, but the negative is that people think that they are qualified for the pursuit. Even worse, they think they are qualified and dive in to something like entrepreneurship equipped with nothing more than their self-righteous determination. 

I thankfully had numerous levels of preparation when I started my company:

  1. I kept my day job
  2. I had four years of relevant work experience
  3. I knew multiple people who had started businesses and had interviewed them
  4. I had wanted my own business for so many years that the idea could marinate 
  5. I had a support system for the business inception
  6. I had an exceptional level of common sense and adaptability

I did not need to go to graduate school, I did not need to move back home, and I did not read a single book on entrepreneurship or business.

That six part prep I had gave me enough of a foundation to comfortably start a business, but by far the most important tool in my toolbelt was years of relevant work experience. 

I knew it was time to start my business when I realized how my skills could be offered in a valuable way on their own. I was able to assign a monetary value to them at the outset and I was working with clients before I even had a website, company name, or email address. Having not gone to graduate school for a MBA or having not started the business with anyone but me, myself, and I, I have had to adapt A LOT over time and change so many things: my business model, my services, my prices, etc.

But I was able to adapt with confidence because I had a strong foundation of my own unique preparation.

As my business continues to evolve, so does the kind of preparation that I need. 

Now let us extrapolate for those of you who are starting a new job or new hobby:

  • What kind of background knowledge or preparation do you need for that new job?
    • What kind of research should you do for it?
    • What questions do you need to ask?
    • Who do you need to ask?
    • What are you personally interested in knowing?
  • For a hobby, what kind of supplies are needed?
    • What background knowledge do you need to know about the activity?
    • Who could you ask about it?
    • What does the activity entail?

Even though diving into something is thrilling and makes for a great, risk-taking story, it is still a risk. In a later post we will talk more explicitly about the challenges of entrepreneurship, but for now continue to consider these two questions:

What kind of preparation do you have for your current ambition?

What kind of preparation do you still need?

How To Direct Your Own Fulfillment, Part One: PURPOSE


I read an article yesterday on Business Insider about the traps that people fall into when they choose to start a business, aptly named "Entrepreneur Porn". It comes down to the question of Why they are starting the business. I will discuss a few aspects here, but the full article can be found at:

Side note: I love how the shortened link title above says STARTING-BUSINESS-ENTREPRENEURSHIP-HARD. No beating around the bush. ENTREPRENEURSHIP HARD. That is the gist before you even click the link and read the article.

As I said above and so many times before, it is all about the why. The article talks about several aspects of specifically entrepreneurship, but I would like to expand that a little bit for my readers. I do not only work with entrepreneurs and so I want to connect the points to 9-5 jobs or even hobbies and leisure activities in which people participate. The two main points that I am going to cover in two separate posts are:



The article discusses the sexy allure of calling oneself an entrepreneur or adopting the liberating mindsets of "not having a boss anymore" or "freedom to make the schedule I want". Those are all attractive, for sure, but then what? Once you LLC your company and technically are granted those freedoms, what are you going to do with the business? What next?

This is where the WHY comes in. This is all about what truly drives you. Whether you are starting a business, you work 9-5, or you started a new hobby (or habit re: last week's post), why you are pursuing that thing is the most important predictor of your future and satisfaction. Hoping to call yourself an entrepreneur or hoping to have a steady job are good goals, but they can be achieved in little time. Once achieved, you are left then with a lot of subsequent responsibilities you had not considered because your only goal was achieved at the start. After starting a business, there is a lot that goes into maintaining a business. Once you get a job, you have to show up every day and perform. 

If you only thought about obtaining one or the other, you will be in for a shock about what comes next.

It is like the phenomenon of weight loss. If you set a goal to lose fifty pounds and you do it, what then? People often cop out and say "I'll just maintain it" when really they did not set a new next goal to proactively start pursuing such that a new success is defined. 

The "allure of entrepreneurship" is something I have thought a lot about. I wanted my own company all the way back in high school, but why did I want it?  Why do I want it now?  Upon reflection, I have realized that, even though I agree with the article about how sexy the Entrepreneur title can be, that was never why I went into entrepreneurship. The title feels good, yes, for sure, but I learned that it is secondary to what really fuels me: creative independence. 

There are a lot of things about business management that I am so aware that I am not interested in and the delegation of which I am slowly learning how to orchestrate. I am proud of the fact that I own something unique and authentic, but being the "owner" is not my reason to do it. It is not my why. When my business grows and there is more of a team involved, I am interested in being its leader but not its owner, i.e. not an authoritarian dictator at the top of some hierarchy that I imposed because I own the company. That does not excite me. That is only ego. Being part of a team that is serving a brand does excite me. 

My why for entrepreneurship is the independence of it.


  1. If you started a business or want to, why do you want to be an entrepreneur?
  2. If you are currently working a "9-5" job, what does that job do for you?
  3. If you are currently searching for a job, why do you care about having a job? What is the specific motivator?
  4. If you have just begun a new hobby or are continuing an old one, how does that hobby serve you?

The reasons are different for everyone, and your unique reasons dictate your satisfaction with that pursuit. Take a minute to answer a question for yourself.

Your future depends on it.

How To Understand Your Habits - Yes, All Of Them


This is officially my 53rd blog post, which means that I have successfully posted each week for an entire year. Bloggers out there will be like "that is adorable" and pat me on the head, but it is pretty enormous considering I have been consistently working three jobs over the last few years and, prior to the last year, I had only written two unrelated posts in the first year of my business' inception. 

I am not asking for celebration. Instead, a year-long habit of anything is a powerful opportunity for reflection. A lot has changed in the last year. I separated myself from one business partnership, initiated another, combined my two businesses, and moved across the country. But I want to focus on the blog posts. 

We are habit forming creatures. Our brains crave certainty and familiarity for the sake of surviving as efficiently as possible. To an extent, that often means in the easiest way possible as well. How many people do you know who coast through existence, apparently lazy and uninterested in putting any extra effort into their daily lives than is minimally necessary? I bet you know a few. 

They are the people whom we identify as having "bad habits" or "unhealthy habits" and whom we might generalize by the food that they eat and the activities they pursue. But I am not here to bash others for the way they spend their time. This is a judgment free zone.

Habits are habits for a reason.

Instead, I want to focus on positive habits. By that I mean any habits that you enjoy or think are evolutionarily beneficial.

What habits have you maintained or started in the last year that felt good to you? 

I do not care if it is something that society at large deems unhealthy or negative, or even illegal. I want to know what habit you have enjoyed. Making consistent income? Awesome. Running three times a week? Cool. Using hard drugs and alcohol? Do you. I want you to identify at least one habit from the last year about which you are either proud, you enjoyed, or which made you feel good in some way. 

Once you have chosen it, I want you to think about and answer this question: 

What does that habit do for you?

I mean, really. Think hard. What does it give you? What do you feel other than the enjoyment or pride? What is the primary reason for that habit in your life?

Let us consider my example of this blog. Yes, a blog is a helpful piece of a brand and it is an outlet for me, both creatively and intellectually, but what does it actually do for me, deep down? 

The discipline part of the habit is cool, but for me it is about the commitment.

As a solopreneur, commitment to maintaining habits can be difficult. Discipline can be difficult to maintain (Let me hear an AMEN from my entrepreneurs out there). But what is empowering about my year of writing blog posts is the fact that I can now be confident in my ability to stay committed to something. As I reflect on the past year of writing content, I think about how I was able to unflinchingly write two posts one week because I was on vacation the next or write my post earlier in the week because I knew that Wednesday and Thursday were booked up. I think that is so cool. All commitment and no compromise. 52 straight weeks. 

Identifying that commitment empowers me. 

What does your habit do for you? What makes it so empowering? 

Maybe watching movies lets your brain feel creative. Maybe lifting weights liberates you from anxiety. Maybe listening to music helps you sleep. Whatever it is for you, it empowers you in a unique way. And whatever empowers you is likely something you crave on a primitive level. Let us label it together. 

On Transition: How To Take The Stress Out Of Change And Uncertainty


I just moved across the country from Massachusetts to Utah.

Do not worry, it was planned. For a very good reason. But despite how planned it was, moving is still ranked as one of the top stress-inducing activities for human beings. I have moved numerous times in my young adult life and, even though I am really really ridiculously good at it, it is still a daunting and difficult process. 

The part that I am best at is getting in to my fully packed car, starting the engine, and driving to wherever my new home will be. I do not feel any stress during that piece of the process. Once I arrive in the new location, a little stress comes in the form of the to-do list at the new living situation (i.e. utilities, internet, unpacking, organizing my belongings, etc.), all of which is dependent on the extent of preparation prior to the journey.

Speaking of preparation, that is where all of my stress lives. I am quite good at planning the preparation and checking off all of the things that lead up to leaving my apartment spotless and concealing the keys in the freezer for my landlord, but still the process of doing all of those things is so burdensome.

I felt a constant simmer of cortisol flow inside me for about a month and a half, my sleep was affected because my brain exploded with "WHAT ARE WE GOING TO ACCOMPLISH TOMORROW???" brainstorms the second I turned out the light, and my body felt like it was riding around on the Tilt-A-Whirl ride at the carnival (google it) swirling from work to packing stuff up to "sleep" and back to work. 

Before you determine that this is just my diary entry about how successful my trip along the Oregon Trail went and a discussion of my personal stress triggers, let me clarify that this post is about transition. 

People hate change. People fear change. It is uncertain, unpredictable, uber terrifying. Change is literally the total opposite of familiarity, and human beings are wired to seek out and settle into any sense of familiarity available. Our brains crave it so that it can log the most efficient ways to survive. 

Of course we also need novelty and uncertainty for our brains to grow at all, but human beings enjoy trying to control that uncertainty by planning way ahead for something or overanalyzing every single possible scenario even though they have zero knowledge about it. 

As a result, transitions can be challenging for people in so many different ways. 

I, for example, get stressed in the daunting preparation of moving. Others may not pack much so the preparation is super easy but they get stressed by the drive itself. 

As I mentioned above, the overall process of moving is split up into:

  1. Preparation and planning
  2. The action of the change
  3. Settling in to the new state

Moving is an easy example to use for a stressful change, but I want to think beyond that now and ask you how you react to change. 

Let us think of some examples of change, large or small, that you may experience throughout a given day:

  • a rainstorm
  • a surprise meeting
  • a car accident
  • a surprise party
  • someone buys you a drink
  • your computer crashes
  • you sleep through your alarm
  • you wake up before your alarm

See, change can be all kinds of things but those things do not have to always be a surprise. Like moving across the country or knowing you have to lead a meeting today that you usually do not have to, change causes some level of stress. 

Reflection Homework:

  1. What changes or transitions have you experienced recently that you expected / could plan for?
  2. How did you react to them?
  3. What changes or transitions have you experienced recently that you did NOT expect / could NOT plan for?
  4. How did you react to them?
  5. Did you react differently depending on whether or not the change was known ahead of time? Why or why not?
  6. Go back to the three categories above and zoom in on your reaction. Which of the three steps of the change process caused the highest reaction?

A lot of people are so distracted by the stress of their change that they are unable to perceive what specifically about that change is causing the stress. If you are able to answer the above questions, you will be able to focus in on what stresses you out the most. 

If you always stress about the same segment of a change, how might you prepare differently for that segment in the future?

If you make a list of recent changes and notice that your stress is divided up through the different segments of each change, what do those changes have in common?

This awareness will lead you to preemptively quell the stress before it even begins in the future. 

What Is Missing In Your Life? Your Skills, Values, And Ambition Assessment


What do you care about? 

I should just end this post there with that question. A real punch to the stomach that would hopefully confuse you and then stress you out as you think about how to answer it. 

I work with a lot of people starting businesses but I also work with even more people who dislike where there career is and desperately want to make some kind of change. The wall they run into on their own is an incomplete awareness of what is needed to make that change. 

A common framework that helps put structure to this mental roadblock is the definition of a person's unique skills, values, and ambition. In my class, I teach the importance of not only defining them but aligning them so that one's self-concept is rock solid. I visualize it for students like an equilateral triangle and talk about it like Tony Stark's triangular arc reactor chest-piece that he makes in Iron Man 2. When the energy is flowing through it, the whole triangle lights up with epic power. That epic power is available to anyone who puts the time and energy in to aligning their skills, values, and ambition.

Now back to you. Answer me this:

- have you ever gotten so inspired about something you care about but then you do not even start it because you do not know how to do it?

- have you ever gotten so good at something in your job and you have goals for yourself within the company but you never make progress because you do not care about the company's mission?

Let us break it down into common sense: 

1. If you care about something and you have related skills but you do not have goals or ambition, you will not be satisfied.

2. If you have a goal and skills that can help you achieve it, but you do not care about anything specific, you will not fulfill that goal.

3. If you care a ton about something and you have all the ambition in the world to go after whatever that thing is but you do not have relevant skills, you will not make progress. 

Unfortunately you cannot just have 2 out of 3.

No ambition = progress will be like molasses.

No relevant skills = you will feel incompetent and frustrated.

No core value set = you will become apathetic and aloof.

Now what is there to do about it? Assess yourself. Of the three categories with clients, I often start with values because people often have a more accessible sense of what they care about in life than the other two categories. 


Let us start with values. Here are some guiding questions.

  • what are some things in life that matter to you, in general?
  • what is important to you in your work or at your workplace?
  • what kinds of causes or societal issues pull at your heart strings or fire you up?
  • what do you care about having in a relationship or your friendships?


Skills are sometimes harder for people to reflect on, so be gentle with yourself when you are answering these questions.

  • what are some things that you consider yourself good at?
  • what is something you love doing?
  • what are your responsibilities at work? 
  • what do you do in your free time?
  • if you know specifics, what abilities are you confident in?


Ambition can be big or small, future or present. Think about any goals at all that come to mind.

  • what is your goal for your career right now, overall?
  • what is your goal for your work right now, specifically?
  • what is a goal you have for your relationships or friendships?
  • what is your personal development goal for the future - aka what are things that you want to learn about yourself, where do you want to live, what do you hope to personally achieve, separate from work?

The important thing to keep in mind is that you do not have to be able to answer every single question. I often customize these questions into only one or two that are specific to my client's situation. For you the readers, I wrote longer lists in hopes that at least one of the questions is helpful to spark your reflection. Do not put pressure on yourself to answer every one and to make sure your answers are perfect. 

If an answer comes to mind, no matter how disorganized or basic, WRITE IT DOWN. It will be your perfect starting point. 

Now, step two is to look back at your responses and feel which category either garnered the least awareness or was more difficult to answer. If only one stands out, great. If two stand out, choose one that feels most relevant to focus on first.

If it is your values, think about it again. Everybody cares about something, even if that something is video games or not going to work. 

If it is your skills, are you able to identify what skills would be helpful? If not, ask someone what they think. If so, what is a first step you can take to acquiring those skills - who can you talk to, what can you read/research, what class can you take?

If it is your ambition, ask yourself why you are having trouble identifying a kind of goal - is it because you do not like where you are at in life? If so, what don't you like?  Do you wish you could identify a goal? If so, who could you talk to for help around thinking about and defining goals?

Whichever one is most relevant for you is that on which your career satisfaction or your personal fulfillment depends. 

Jefferson Dinner, Part Three: How To End An Event Without Ending The Fun


Last week's post spoke to how the Jefferson Dinner created the opportunity for respect in the conversation so that every participant felt equally heard. This week, it is about when the conversation should end. Sometime soon I will talk about the conversation needing to end after it has been an unenjoyable interaction, but this week I am going to stick with the positive and focus on how an enjoyable situation can end without depressing those involved. 

At the Jefferson Dinner, after three DEEP questions were asked and discussed in their own turn, the Dinner host said

"I wanted to ask a last question but the conversation feels pretty full and I don't want to push it any further." 

I thought that was quite interesting because it was a strategic stop to a conversation and a powerful example of how a positive conversation can be cut off and still is appreciated. I felt equal parts agreement and disappointment when he said that because even though the mental effort needed for the conversation was rather tiring, it was still so interesting, engaging, and new thought-provoking for me. As minutes went on, I realized how profound stopping the conversation at that point had been. It allowed us to casually chat about whatever we wanted as we were cleaning up because we still had enough energy to do so, and it left us with the buzz of how enjoyable the overall conversation was, which promoted our continued thinking about the subjects long after the event. 

It often happens that we humans do not want an enjoyable experience to end. Duh, that is obvious. We want to promote enjoyment, in fact. However, there are times when a fun party becomes un-fun because it goes on too long, or a first date loses its luster because the couple got dessert after drinks and did not leave the positive energy for a second date (Okay, bad example: dessert doesn't harm anything...but you get the point).

Too much of a good thing is exactly that: Too much.

Just like pushing the limits of an amount of recreational drugs, you will not continue to get the same high. It will wane. It is also pretty human, though, to avoid ending the experience because of our natural sensitivity to loss. It feels absolute. Finite. As though it could never be experienced again. Emotional hangovers are real too after a super fun party. 

Do not fret. Here is what you do:

  • When an enjoyable interaction or situation is concluding, whether you or an external entity is concluding it, take the step in that moment to plant the seed to continue the enjoyable parts of that situation in the future. 

You cannot replicate the exact same situation because life and people move on, but following the following steps will help you feel like the enjoyment has not died forever:

  1. Identify what is so enjoyable about the situation. Is it:
    1. the subject of your conversation
    2. something about the individual with whom you are speaking
    3. something about the setting where you are
    4. something else?
  2. If your enjoyment is related to the individual before you or the conversation topic, plant the seed in whatever way is comfortable about continuing the conversation with them again, either over coffee or planning to meet up at an event again sometime in the future. If it is not comfortable to do so in that moment, reach out to them the next day and tell them how much you enjoyed the conversation and go from there. 
  3. If it is something about the setting or event, use that characteristic to focus your search for similar events or parties going forward. Doing so will help you weed out so many parties and events that may not invigorate you. 

Energy does not die, but gets transferred to a new system or setting. What was enjoyable about the Jefferson Dinner for me has lingered because of how and when the host ended the dinner. The exciting mental energy I felt during the dinner transferred from being passed around the table to inside my brain alone and I have continued to think about the subject in my head. Not only has it motivated me to write blog posts about it, but it is something that I am excited and comfortable to bring up with others and initiate discussions of my own. 

Because the party has to end does not mean that your enjoyment does.

Just transfer the energy.

Jefferson Dinner, Part Two: How To Earn Respect In Any Conversation


A while back, I wrote a post about finding your true voice and how I finally heard mine for the first time a few years ago at the Book Swarm event in Oakland, California. As I have moved around the country since then and worked on my business in different places, my true voice has come and gone, hidden from me here and there, gone on vacation a few times without telling me. It is only natural because it is connected to my self-confidence and my meta-awareness about my skills and acquired knowledge. 

Sometimes it hits me hard in conversation and I say to myself "Oh damn, I know stuff..." and drop knowledge bombs on whoever with whom I am interacting. It is so cool when you realize that you know things. You suddenly feel so powerful and even unstoppable. But it is hard to ground it and hold on to it in your awareness because there are so many moments of the day that distract you and that do not give you the chance to exclusively have the floor and fully live in that knowledge power.

The Jefferson Dinner last week, however, was just that opportunity. For those of you who did not read my post last week, shame on you. Also, to recap, a Jefferson Dinner is when a small group of people get together, eat dinner, and discuss their thoughts on a certain pre-determined topic one at a time such that everyone is heard and everyone gets to speak. 

My true voice came back from vacation just in time for my turn to speak in each of the discussions we had. 

No, I'm not telling you that Jefferson Dinners are the only times when you can feel heard and powerful. They help and they are a lot of fun, but let us dissect what about the Dinner specifically created the opportunity: 

1. Structure

The overall subject of the discussions was determined and advertised ahead of time, which told participants what to expect and also what was not going to be addressed (makes sense, right?). Furthermore, the location was predetermined and private, which provided the comfort of containment for the participants to express their opinions about the topic in a safe space. No matter the topic, the fact that the setting is preset and someone else is in charge of deciding the conversation topic, its direction, and its movement relieves the participants of a lot of pressure and energy to maintain a conversation on their own.

2. Forming an opinion

The structure of the setting and the structure of the discussion itself provides a comfortable scenario in which you may formulate and express your opinion. When the question is asked, participants naturally dive into their own brains and feverishly thrash around searching for a comprehensible personal response like a kid in Jaws swimming away from the shark. The cool thing, though, is as soon as the first person volunteers to speak, the mental ferocity subsides and you attend to the speaker. Every so often, a new little phrase will connect itself onto your response in your mind, but it does not take any extra energy or distract you from listening. 

The structure of the setting also provides the space in which you do not have to stressfully choose when to interrupt someone, raise your voice to share your opinion, or get angry when your opinion is not heard and the conversation moves on. This one is HUGE because it means that you do not have to expend any extra energy AND everyone remains civilized and amenable by the end of it. The Book Swarm discussions? Not so much... But that is for another time.

3. Respect

Here is the whopper. The crown jewel. What it is all about. You got external structure, you add personal comfort, and now all that is left is how the crowd welcomes your offering and respects your input. In the Jefferson Dinner, if the rules are followed, everyone shows you the respect your opinion deserves because you showed them the respect that they deserved. 

This is what is missing in so many conversations these days. Work, relationships, phone calls with family, you name it. Think about yourself at work interacting with a manager or colleagues. The structure of the setting is all set, you know what you would like to talk about, but BAM, you are met with disregard, inattention, and discourtesy. Maybe the listener is distracted, maybe for some reason they do not care, or maybe they are so arrogant that they cannot wait to hear themselves talk again. 

Often, this dynamic leads you, the speaker, to unsheath a nice defense mechanism and try to meet the listener where they are at on a higher level of snobby-ness than is natural and comfortable for you. Then it is a battle of defense mechanisms and you never actually express anything that you wanted to express nor advocate for yourself in an authentic and respectful way. 

Unfortunately the presence or absence of respect in an interaction determines the outcome of that interaction. 

What do we do about it? Kind of like last week, let us use these three themes as a sort of scorecard. Next time you are in the position to have a convo with someone in which you have something important to express, first ask:

  • Is there external structure around you? Is the setting familiar? What are the wild cards?  (i.e. will someone interrupt? will it be noisy? Have I been in that office before?)
  • Have you thought about what you are going to say IN A RESPECTFUL AND APPROPRIATE WAY? (i.e. what is the purest form of what you want to say, and how do you say that with etiquette?)  I capitalized those for a reason because some people take my advice to plan what they want to say but do not think about how to say it respectfully. It does not end well...
  • How can you set up the conversation such that you garner respect from the second it begins?  What can you say or how can you approach the conversation in such a way that makes it clear to the listener why you are in the conversation and what you want to accomplish in it? 

This can look like a lot of things, but often what I help clients to do in this situation is to be vulnerable and honest up front about their own reason for being in the conversation and then send the ball over the net to the listener who can now speak to their own experience. Because the word "vulnerable" is a terror trigger for many people, let me show you an example. Imagine you are the speaker:

"Hi ____________, I reacted quite strongly to some of the things that were shared in the meeting earlier. I would like to tell you about the reactions and ask you what it was like for you so I know how to go about starting my tasks." 

Though oversimplified and unspecific, this example still includes several important features to practice:

  1. you are being open and honest about your emotional reaction to something
  2. you are not downplaying or discrediting your experience
  3. you are not accusing the listener of anything, thus eliminating their need for defensiveness
  4. you are asking their opinion on a situation as well, thus opening up a respectful dialogue between you two
  5. if the listener does not respond respectfully, then that shows much more about him/her and is evidence feedback for how to interact with that person in the future 

What can you do either in preparation of a conversation or right at the beginning of that conversation that will quell power trips, offer respect, earn respect, avoid defense mechanisms, and help you feel empowered by expressing your opinion in an authentic and comfortable way?

Think of some interactions in the past and brainstorm how they might have been started differently.