Aspiring Freelancer Series: Transitioning from a side-gig to full-time


Last week I did a quick ask me anything about freelance or running a business to my fellow designers on the ‘gram and got an overwhelming amount of responses, so I’ve decided to begin answering a few of them through this new blog post series. If you have any specific questions for me, feel free to comment on the post below and I’ll be sure to consider writing about it for the next one!

On this first post, I’m going to share a little bit more in what the transition looked like for me when I quit my job. This was one of the biggest questions I had when first starting out, so it’s something that I’m passionate about sharing.

To make things clear, I worked at my full-time job about 2.5 years before leaving. I began working towards freelance about 6 months into working there, so in total I spent about 2 years working on a side-gig while also maintaining a full-time job. I think this looks completely different for everyone. I know some people who spent 3-5+ years working towards freelance, but I also know people who jumped right in only after a few months. I had a goal in mind of leaving my job after 3 years and was passionate about making sure that it happened. There’s no right or wrong answer to time, it’s just what worked best for me.

So, let’s rewind. When I started working towards leaving the corporate world, I was young. I wasn’t married or engaged and was still on my parent’s health insurance. I didn’t have anyone to provide for financially except myself. I think there’s a lot of pros and cons to this. At the time, I was a little bit envious of people who had a spouse that they could rely on financially because I thought it would make my transition so much easier. But looking back, I don’t know that there’s really any easy way to making the leap. I do know I’m glad I was able to experience it on my own because it forced me to figure it out for myself.

For about the first year and a half of working towards freelance I was making decent side cash, but it was definitely not enough to support myself full-time. The positive side to this was that I was able to pay down a lot of my student debt, while also working full-time and saving more each month. I’ll be the first to admit that I’m naturally just a spender, so I liked having the extra money to not feel like I was living pay check to pay check.

Once it got closer to the year and a half mark, I got more and more serious about leaving my job. I started thinking about when and how I could make the leap, what I should have in savings, etc. I saved up about 3 months worth of my 9-5 salary so that I could at least give myself a grace period as I made the transition.

The last 6 months of having a side-gig and doing the 9-5 life was straight up exhausting. Before, I had worked some nights during the week, usually on Sundays too, but not a ton more than that. Now, I was working every single night from about 5pm to 10-11pm. Sometimes on Saturday, a lot of the time over my lunch hour, sometimes early in the morning BEFORE work, and always on Sunday. I was emotionally exhausted and I knew that it wasn’t a lifestyle I could maintain.

It got to a point where I was going to need to turn away work in order to maintain my sanity. I was maxed out and there weren’t any more hours in the day to give to my business. I had decided to take a chance on leaving. Joe and I had JUST gotten engaged, which I have to say I don’t recommend experiencing your first year freelance and wedding planning at the same time, but it was nice to know that I had a plan for health insurance the following year.

Before I quit, I figured out what I needed to make each month in order to make what I was making at my full-time job and also factor in expenses of doing business and taxes. I had a goal of how I could achieve that number each month.

The first month freelance for me was a little slow. I think I barely hit my goal which made me really nervous, but only a month later I had exceeded it and then figured out shortly after that I was going to be just fine.

I think when you’re first looking at leaving a 9-5 it’s hard to gage how much money you’ll be making, how much work you’ll have, etc., and there isn’t really any good way of finding out until you take the leap. My biggest piece of advice I’d give is to not quit you’re 9-5 before you’re ready. Had I quit when I wanted to, I wouldn’t have been prepared for life as a full-time business owner. There’s absolutely nothing wrong with having a 9-5 and even if you feel a little silly for having multiple side gigs or people thinking you’re crazy for working a lot, just remember that it’s worth putting in the hours and the late nights.

The last thing I want to say is this. There will never be a good time to “quit your job.” I think towards the end as I was getting maxed out, I kept looking for a green light but still felt so unsure. I eventually just had to take a chance on myself, knowing that worst case scenario isn’t THAT bad. I’m so glad I took a chance.