Not For Everyone: An Honest Evaluation Of Self-Employment

“It is better to fail at your own life than to succeed at someone else’s.”  — Andre Gide

“Your calling is found where your deep gladness and the world’s deep hunger meet.”  —Frederick Beuchner

Have you ever wondered what it would be like to “take that leap of faith”? To go out on your own and pave the path for your own career and destiny?

In the day and age we live in, this thought occurs more than ever before, partly because the opportunities are virtually endless (specifically in the Western world, and especially for much of the U.S.).

But is it as glamorous as it sounds? Does it produce the life you always wanted to have? Will it meet all your hopes and dreams?

It’s not as easy as a yes or a no…

The Migration

With the introduction of more and more ways to monetize different aspects of your life, many people are feeling the tug toward self-employment and venturing into “entrepreneurship”. At least that’s what it feels like…

When it comes to the actual data, there seems to be a steady rise in self-employment (seen here, here, and here), but many of the studies could be in fact false positives. When the conductors of the studies are companies such as LinkedIn and FreshBooks - both of whom rely upon an increase in self-employment to drive business - it’s easy to see probable biases at play.

Yet, in recent years, there has been an obvious rise in one segment of self-employment: the “gig economy”, which includes up to 36% of all Americans according to Gallup. The advent of new technologies and platforms have enabled more people to capitalize on different aspects of daily life (such as Uber and AirBnB just to name a few). This shift has created an atmosphere that leads us to feel as if everyone is taking the leap into self-employment.

Society and culture play an oversized role in how we think and make decisions, even on a daily level. When what we hear about are more and more people working for themselves or starting side-hustles, we feel an increasing pressure to join the masses and be a part of the movement. While I am speaking from a self-employed point of view, my purpose in writing this post is to help bring more balance to the thought-process around moving in either direction.

Pushing into freedom and independence can be a great thing. When it comes to your occupation and earning a living on your own merits and effort, self-employment can be an empowering and fulfilling pursuit. But it is far from a fairy-tale life, and the reality looks much less glamorous than often assumed.

Simply put, becoming your own boss isn’t for everyone.

The Motivation

As you entertain the idea of migrating to self-employment (or vice versa), the first question should always be: why?

What is your motivation for wanting to be your own boss?

What attracts you about that lifestyle?

Why do you feel capable, competent, and called to take the leap?

Why are you discontent with your current work?

Motivations and desires are good things, but we must first understand the true source from which they flow. Too often we follow impulsive desires that stem from things on the surface that are much different than the root beneath. There must be an excavation of our heart to examine what our core desire is, and then we must bring that motivation to the light to fully examine it’s worth especially when it comes to as big of a decision as a career-shift or pivot.

It always starts with why, and usually it takes some time to truly figure that out.

The Wiring

Not only do you need to discover and recognize your “why”, you also need to properly examine and understand your personal wiring.

Every single human being is different. There are no two people who share identical representations of each other. We are all a collection of: 1) inherited tendencies and 2) life experiences, and both components begin to differ the second you enter the world outside the womb (and even within the womb).

This highlights the importance of self-awareness: knowing thyself. You must be able to clearly see who you are and how you operate. As Timothy D. Wilson pointed out in his book “Strangers To Ourselves”, our actions are primarily instinctive, stemming from the subconscious - or the “adaptive unconscious”, as he refers to it. This means, in order to make conscious decisions that are aligned with how we typically (and naturally) operate, we must understand our internal wiring and our inherited tendencies in order to choose the path we are best suited for.

This is an important part of the process. It takes time to sit with yourself and really uncover the motivations, beliefs, and desires that influence the decisions you make and the actions you take.

Ultimately, this will help you answer the question: Am I suited for self-employment? Am I able to take on the risk of putting food on the table and paying bills on my own? Am I disciplined enough to be my own boss and tell myself what to do even when I don’t feel like it? Am I conditioned enough to have the endurance to outlast the inevitable hardships and setbacks that await?

The Tradeoffs

Now that you have discovered your motivation and recognized your wiring, the next step is to examine the tradeoffs.

Everything in life comes with a cost, whether it is perceived or not. By doing x, it means you cannot also do y. And if you do choose to try and do x and y, then your ability to do either x or y will both be diminished in some capacity.

As humans, we tend to focus on the negative aspects of where we currently are and the positive aspects of the places we aren’t. This applies to friendships, occupations, locations, and beyond. The grass looks greener when it’s not the grass right in front of us, the shade of green we look at every single day.

And that highlights the importance of understanding novelty. Novelty always looks attractive. The new, shiny object that promises joy and satisfaction. The answer to all of our problems. The experience that will change our lives. But all of these ideas turn a blind eye to the downside of novelty — the reality that novelty is more subject to decreasing satisfaction and increasing demand than any other part of life. It’s the same type of addictive cycle that drugs often produce. We need greater and greater novelties for that novelty to still be novel, and the pleasure / fulfillment of that novelty increasingly diminishes.

Pursuing novelty is never sustainable.

By clearly seeing and recognizing the tradeoffs that come with either traditional employment or self-employment, we can more objectively determine what we value most and which route facilitates those values.

Gains and Losses

Here is a shortlist of the things you gain and lose with whichever path you choose to take, based on my experience thus far:



  • Fully Control Time

  • Fully Control Decisions

  • Maximum Flexibility / Adaptability

  • Able to work from home / anywhere

  • Empowering


  • Isolating / Frustrating 

  • Decision-Fatigue

  • Work never stops

  • All responsibility falls on your shoulders

  • Takes patience to build and scale

  • Can’t do it alone - always comes from the support of others

  • Work from home (yes it can be a downside as well)



  • Less concerned about producing (less pressure)

  • Benefits

  • Safety Net

  • Have tasks decided for you

  • Have structure created for you

  • Have teammates and others to collaborate with

  • Have bosses for accountability

  • Have consistency 


  • Less control / ownership

  • Slower moving bureaucracy

  • More consistency and mundane

  • Dealing with co-workers / social dynamics

  • Less of a culture of personal excellence

Most of what I’ve mentioned are the experiential aspects of the decision. There are many other components involved including: earning potential, the type/line of work you are pursuing, retirement, healthcare needs, and other factors that drastically affect the quality and substance of our lives.

The point being: self-employment is not for everyone. In fact, I would side with the statistics and say it probably isn’t for you.

You Always Want What You Can’t Have

The ironic part about either side of the coin is that they often both want what the other has. During the past few years many from the self-employed side have flocked to co-working spaces and local cafes when they find that working from home isn’t as glamorous as it’s talked up to be. On the flip-side, those who have a traditional 9-5 would often pay big bucks to be able to work from home (or so they think).

And speaking of 9-5, when you have that structure imposed on you, many will want the flexibility and freedom of working / deciding your own hours instead (like the self-employed side). Whereas, many on the self-employed side (myself included) are often fighting to impose that very 9-5 structure into their day so that they don’t end up working into the wee hours of the night, turning every day of the week into a workday (more common that not for self-employed in today’s culture).

I point out these contrasting perspectives to show that whichever side of the coin you fall on, the goal is to marry the two opposites and meet in the middle. If you are an employee, it’s helpful to try to implement practices that will best support your most efficient and effective work, which may include spending some time working from home if your employer can be convinced. Likewise, if you are self-employed, it’s important to clearly define your work hours and your work space so that you don’t waste precious time with typical “house” tasks and duties instead of attending to your business.

The End

Whether it be traditional employment, self-employment, or a combination of the two, the goal is to thrive. We thrive by appreciating the blessing of where we are, while never settling or remaining in our current place (personally and professionally). It is precisely this tension that, as Viktor Frankl points out, produces a healthy human.

“Mental health is based on a certain degree of tension, the tension between what one has already achieved and what one still ought to accomplish, or the gap between what one is and what one should become.”  - Viktor Frankl

And, lest you be deceived into thinking that just because is simple it means it’s also easy, I will leave you with a quote from one of the most successful businessmen of our time:

“None of this is meant to be easy. Anybody who thinks it’s easy is stupid.”  — Charlie Munger