A mistake I’ve made in year one

March 21, 2016
3 min read

Being too hard on myself.

When I moved to New York City in the winter of 2006, I didn’t have a job lined up. It was the first time that I was responsible for myself, no safety net, and not much savings on hand. My parents told me if I didn’t find a job in three months, I would need to go back home in California.


I did everything to get a job and started paying for living expenses. I had to weave my own safety net and I was very risk adverse. Before I jumped into any new job opportunity or moved to a new area, I always stayed conservative. Having a steady paycheck and the stability of going to a job every day is something that I valued greatly.

Through years of working in design, I would jump from job to job. I found that I was being more and more risky with my job choices because I wanted to do work that I would be proud of.

As an independent designer and working for yourself, one of the major downsides is the lack of stability in pay. You pay your own health insurance and pay both sides of the taxes (~35–40% tax rate). You have no retirement savings account, no additional benefits, and have to wait 30–45 days on client payments.

This instability stressed me out a lot and I had to make a lot of lifestyle choices. The first six months felt like I was walking in the dark about how much rolling capital I needed to make this work. I held myself accountable for every working hour in the week. I stressed about not meeting my projected billable hours weekly. In the back of my mind, I always felt that I needed a plan B, C, D and E. Always building my mental safety net.

When I had my ducks in a row. I didn’t know how to stop. My thoughts were like a runaway train. When I had enough financial cushion for to be unemployed for a year, I pretended I didn’t. I felt the anxiety to constantly prevent “a rug being pulled from under me.” This kept me up at night, worrying about financial stability and how to make sense of everything.

One day, I looked in the mirror and I saw I had about ten strands of white hairs from my scalp. That’s when I knew I had to stop.

I spent way too much time worrying about impending risks that never really happened. You can say that I played this very safe and I am financially responsible. This time wasted could have been better spent on projects, social support from friends, or furthering a skillset.

I think this experience could not have been any different if I turned back time. It was an invaluable learning experience that allowed me to be braver and more clear headed with my target direction. I realize that being confident in your own skillset plays a great role in being successful.

Don’t waste time dwelling on bulletproof plans that you have in place. Always look back and self-evaluate, but also learn to change directions and move forward in a positive fashion. Spending time worrying about things will not improve any situation, only actionable plans do.


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