5 Reasons I Decided to Go Freelance

Over the next few weeks I’d like to document the process I’ve gone through to switch to working for myself full-time, the applications I use to stay organized, what I’m learning as I go, and how I’m managing my schedule. I always love looking back on this stuff for myself, and I have small hopes that some people might be interested in reading this as well! I know I’m always curious about what other people do and what their workflow is.

The conditions that existed for me to choose to go freelance full-time were perfect (in my opinion).

1. I was willing to quit my job.

This was the first, and biggest condition in choosing to work for myself. I was willing to quit my job because I was unhappy and wanted a change. I had been applying for jobs throughout the spring and was lucky to get a few interviews and offers, and started realizing that I actually could go – and had options! That was an amazing feeling, especially after being down for quite awhile about my job. But also, it made me realize that I was marketable, and that the idea of leaving my job was not only not scary, but totally doable.

2. My finances were in a good place.

I have the good fortune (ha! pun) to have been paid decently at my last few jobs, share a pretty low-cost apartment with a roommate, and have a normal amount of bills that I could cover comfortably with my salary. Along with extra freelance wages for the past year or so, I’d been saving pretty aggressively, and felt like I was in a good place should I fall on hard times for a few months. That peace of mind is BIG.

On a related note, my old car (my beautiful junky 2000 Saab 9-3) blew its turbo two weeks ago so yeah – having a padded savings was VERY helpful in this situation!

3. I had contracts lined up.

When I was deciding what do next in my career, I was incredibly lucky to have a few options after searching for awhile. I was balancing 2 full-time offers at traditional agencies, one of which would require a move. I had an existing contract with a company I love working for, and they had the need for me to put in more hours than I currently was able to offer to them. I also had the offer of 2 part-time contracts as trials for full-time work, at decent hourly rates and for a long enough time period that I could see either working out.

I realized that this was not likely to happen again in such a perfect order. I’ve always wanted to work for myself but I assumed I wouldn’t be able to until many years down the line. It meant I could be work more meaningful and fulfilling hours, and get paid more for it. Because all of the contracts are part-time, I am paid a slightly higher rate than a full-time job would be able to offer, which in turns really helps offset the additional costs of working from home and working for myself (like office costs, healthcare, taxes, etc).

4. I was mentally ready for the change.

I knew that working from home would be tough for me, since I’m a very social and extroverted person. I LOVE people, and working in a basement-level apartment does not really equal “social”. So going into the change to working from home and for myself instead of working in a structured 8-5 office, I knew things would be hard and very different. I was prepared for a few tough days (which still happen!), but I knew they would be inevitable.

I stocked my fridge with delicious and healthy snacks. I made lists of all of the recipes I’ve wanted to try for lunch and dinner but haven’t had the time to make. I planned out co-working days in local coffee shops, texted friends who also work from home, and made sure to set my alarm, shower, and get dressed every single morning without fail. This helped me establish my own routine and force myself into that work mentality.

5. I was physically ready for the change (aka record-keeping).

Prior to quitting my job, I spent months reading about taxes and bookkeeping and how to track expenses for freelancers and small businesses. I set up a separate bank account and started keeping and organizing all of my receipts each month. I asked friends who freelanced what system they used to keep track of their work, money, and tasks, and consulted with an accountant on the best way to organize all of my bills and finances for tax purposes. I’m still figuring this out, but I’m happy to feel at least semi-stable in how I’m handling this. I think this will be worth its own blog post sometime soon.

These are the reasons I decided to work for myself full-time. I was so ready with all of these items that when the time came to make the move, I just did it – it felt almost like there was no change at all. Months of thinking, planning, and reading really helped with that in the end. I’m still learning lots and plan to keep documenting this as things change.