How Working for Myself Helped Me Take Control

Control is a big deal for me. It is one of the key drivers of my life.

Before I worked for myself I felt controlled by circumstances instead of controlling them. Most of my time was controlled by how others wanted me to spend it. My money was controlled by what others thought I was worth. My work was controlled by others’ priorities and values.

Let me be clear. I’ve had amazing jobs—jobs that truly allowed me to make a difference in the lives of others. I’ve worked for amazing people—people who pushed me to grow my skills as an employee and a human. Most of these amazing people are still my close friends to this day.

The thing is, I wasn’t satisfied. I kept defining things that I thought would make me happy and eventually checking those things off.

  • More autonomy over my work
  • More flexibility in where and when I worked  
  • More money

I checked those boxes while working for other people. I still wasn’t fulfilled. I felt trapped by the structures I had to operate within as an employee.

I watched people who didn’t deserve it get promoted and paid more than people who did. I watched bureaucracy rob people of their agency to make decisions about what was right and necessary. I watched hierarchies decide what was valuable and what people and ideas were worth. I watched people who did most of the work get paid less and get less recognition than people who just thought about work in theory.

And so I leapt. I quit what, on paper, was the best job I had ever had.  

I started doing contract work as a stop-gap as I tried to figure out what my next thing was. I never wanted to work for myself. My parents have owned their own business my whole life and told myself growing up that I never wanted that. They have been very successful but I also saw how stressful it was weathering up and down markets, being responsible for other people’s livelihoods, and working all the time to make sure everything was running smoothly.

After a few attempts at careers, partnerships, and other ventures I realized that, like my parents, I actually couldn’t work for someone else. Not that I couldn’t have made it work, I had plenty of opportunities to partner with great people on what would have been lucrative and interesting work. The thing I realized was, in working for someone else, I would still be ceding control of my time, work, and life. I’d still be letting others make decisions about what I was worth.   

I learned that operating within traditional systems of work was never going to get me what I wanted. I couldn’t play the game of incremental raises, performance reviews, office politics, pointless promotions, and warranted terminations framed as resignations. I had to step outside of that system and build my own framework that allowed me to rely on my own value and competence. A framework that gave me the flexibility to control my time and income, and take on diverse work that kept me engaged.

Is that the right path for everyone? Definitely not. Working for yourself comes with responsibilities and challenges that can make the payoff less-than-worth-it for some. But I’ve realized that I have no choice.

I am reminded every day that there are limitations to what I can and should control. Letting go of control will be one of the lessons I have to learn over and over again throughout my life. Working for myself has taught me to take control of the things that really matter to me and given me a context in which I can control them.


Get the manifesto in your inbox.

Weekly content to jailbreak your hustle.

No spam. Unsubscribe at any time.