Becoming Self Employed

Apr 25, 2025

For as long as I can remember, I’ve dreamed of working for myself. Although this goal hasn’t changed, how I envision it has. I used to imagine self-employment as creating and running a traditional “company.” I’d have employees, an office, a mission statement, and more of what people typically associate with corporations.

As the possibility of becoming self-employed has become both more enticing and more financially feasible over the last handful of years, I’ve realized that creating a “traditional” company is far from what I want. Instead, self employment boils down to something very simple to me: the freedom to pursue whatever I want, whenever I want, wherever I want.

I don’t care about founding a unicorn, ringing Wall Street’s bell the day my company goes public, or having ~preferred shares~ in a room full of C-suites in suits. My end goal is freedom. And while it’s simple enough to sum up in a single word, I won’t be surprised (or disappointed) if it takes an incredible amount of time and effort to get there.

Getting to this simple conclusion took a while for me as it slowly distilled in my mind over time. Thankfully, some of my past writing was also particularly helpful for me here, such as continually asking “why” for the things I believed I wanted:

Whenever I set my goals I like to first spend time deeply reflecting on the items I believe I want to accomplish and then whittle down why I chose those things. Doing this helps ensure that I set goals that I truly care about and am interested in accomplishing for the right reasons. It’s often useful for me to think backwards here and say “If I accomplished this goal today how would my life be different and why would it matter?”. — Goal Setting, December 20th 2024

After a lot of reflection, I realized that freedom was almost always at the foundation of my most important goals.

Another concept I’ve been thinking a lot about recently (from another one of my articles, Taking no risks is the biggest risk of all) is this graphic:

Simply put, this image depicts that if what you’re doing and want to be doing run parallel to one another (i.e. they’ll never intersect), you’ll never achieve what you’re after. Two people fall into this camp:

People who aren’t yet sure of their goals
People who are too risk-averse to veer towards their goals

Either camp isn’t a great place to be. You’re either hoping and waiting to stumble upon your goals when you should be focused on building them, or (arguably worse), you know what you want but are unable or unwilling to pursue them.

This second part of the equation, making decisions that actively move me closer to my goals, is something that I’m working hard to prioritize this year. While in some way it can be scary to do this, it’s also exhilarating.

I won’t regret attempting and failing at self-employment; I’ll regret never trying and wondering what could have been.

Where you can find me online:

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