How I prepared to be self-employed

Before diving head first into the world of self-employment and entrepreneurship, I tried to minimize as much risk as I could in advance. I didn’t want to be worried about money or whether or not I would fail so without really knowing when that jump would happen, I did some things to prepare. In hindsight, it made the jump a little less stressful.

I saved up a few dollars

The biggest worry for most people who are self-employed is whether or not they can make rent next month. Money was also one of the main reasons why I didn’t jump sooner. I wasn’t ready to deal with not having the consistency of a paycheck to cover my basic personal expenses and the occasional night out or shopping spree. So here’s what I did:

  • I made a goal to save a good amount of money by the end of 2016. This helped put everything in perspective and gave me something to work towards. I perform better when I have a deadline and goal in mind.
  • I transferred about 25% of my paycheck into savings every month. I started doing this ever since my second job but once I made this 2016 goal, I upped the percentage. I was lucky to have a job that paid well and have an apartment that was relatively inexpensive but I tried to pick a number that wouldn’t hurt. It’s important to note that I never saw or touched that money, it went straight into my savings every time.
  • I worked myself to the bone on the side. I took on way too many freelance projects and even taught a class. While doing this made the biggest difference, I wouldn’t recommend this tactic unless you’re ready to not have a social life for a few months. The only thing I would do differently is instead of taking on a few small projects with small budgets, I should’ve taken on one or two big projects, with big budgets. I just took whatever came my way since I’m not used to securing freelance work without referrals anyway.
  • I never touched my savings even after I hit my goal and surpassed it. I never touched it. And if I did, I replaced it.

Do what you gotta do to save up enough to cover your personal expenses for at least a few months.

I got over my fears

The other worry I had was what would happen if I failed. Apart from being able to pay rent, this is the other fear most people can’t conquer. What happens when s**t hits the fan. Knowing this, I thought about the worst case scenario and came to terms with it.

For me, it was whether or not I could get a job or secure freelance work and make enough money to keep my head above water. I’m lucky enough to be in a field that’s always in demand so it didn’t take long for me to come to terms with that fear. While it wont be easy going back to the 9–5 or having to do the freelance grind, at least I know I have options. Having options (and saving enough money to have a solid runway) helped conquer that fear.

So think about the worst case scenario, acknowledge it, think about your options if that scenario happened and decide if you’re okay with it.

I gave myself a deadline

Initially when I thought about taking the leap, it felt scary but not only for the reasons I mentioned above. I think it felt scary because I didn’t have a plan. Once I gave myself a deadline to work towards, I had more confidence to make the jump. I decided to give myself 6 months to figure out if this life was for me. After that I would decide to either keep going, get a job or do something else entirely.

As with my work, having a goal and putting a date to that goal somehow made the dream more tangible.


If you’re thinking about going off on your own to do something amazing (because it will be ;), then make a savings goal with a timeline and reach it. Think about the worst case scenario and get over it. Give yourself a timeline to work with.

Did all that? Then rip the bandaid off and just do it. I’m rooting for you.


PS. Did you recently make the jump to do your own thing? Share what you did in the comments.

PPS. I also want to know your story! Please shoot me an email at

Do it with passion or not at all,
– Kim Goulbourne aka “Bourn”

CommentsDid you recently make the jump to do your own thing? What did you do?

arrow View Full Journal More Posts in Life arrow