What No One Told Me About Going Freelance

When you have a full-time job, especially one you’re itching to leave, it’s easy to get lost in freelance daydreams. The unstructured schedule, lunch dates and ‘work from the park’ sessions, amazing pay, unlimited vacation… That’s the daydream I got lost in, at least.

When I decided to leave my job last June, there seemed to be a shift happening. Every other person I spoke to was dipping their toes in the freelance world — and they couldn’t get enough of it. “I work half the time and make twice as much.” “I never set my alarm, cook all of my meals, and have never been happier.” “I only work on projects I love.”

It’s no surprise that I was sold. Going freelance felt like I was taking control of my destiny and choosing happiness — and freedom, and luxury, and monetary glory. Boy was I in for a rude awakening.

Freelancing requires more work and dedication than I ever imagined. It also requires strategic prowess that I was not aware of, and admittedly still do not have.

Here’s what I wish I’d known, and looking back, how I would’ve done things differently.

Build a foundation before you set yourself free.

If possible, give yourself 2–3 months to build a network and base of potential work. I was convinced that I’d have work within a month after quitting my job. But the truth is, conversations that began nearly a year ago are still ongoing. It took me a LONG time to find work, and even so, it was very sporadic and didn’t come with the price tag I was hoping for. In retrospect, I wish I’d toughed it out at my job a few months longer and started planting the seed for future freelance work. While liberating, it’s scary to take the plunge into the unknown. Make it easier by having a small safety net of prospects.

Figure out how to market (and sell) yourself.

One of the reasons I left my full-time job was because my role became highly sales-oriented and it didn’t fit my creative persona and desires. Little did I know, knowing how to sell yourself, and WHAT to sell is pertinent to your success as a freelancer — at least in my experience. When I started having conversations with prospects, I was burnt out and confused. I knew I had desirable skills to offer, but when asked what I wanted to do next the only thing that came to mind was, “I want to do work I care about with passionate and compassionate people.” While honest, no one wanted to hire me for having a big heart and broken spirit. And the truth is: I didn’t know what I wanted to do. An existential crisis followed and I felt doomed. Fortunately, a quick and inspirational read of The Crossroads of Should and Must: Find and Follow Your Passion set me straight. It took several months and a lot of experimenting, but I now have a clear answer when asked, “How can you help?” The confidence and clarity of that response will win projects.

Doing what you love doesn’t always pay.

One of the most appealing things about my freelancing daydream was the hefty paycheck that coincided with meaningful work. I’ve never been overly motivated by money, but the prospect of making a lot of it while doing work that made me happy thrilled me. But throughout my months of self-discovery, I learned that I like working with small companies and startups. And companies at that stage often don’t have big budgets — or any budget for freelancers. I spent the first few months as a freelancer turning down every opportunity that didn’t excite me. While I don’t regret saying no, I now have a clearer sense of how to balance the work I love with the lifestyle I love. While freelancing does afford you the opportunity to say no, it’s important to have a project that pays consistently, and pays well. That is what allows you to do the work you love at a lower price. Plus, every project is an opportunity to learn more about your strengths, likes, dislikes, and things that aren’t worth even the highest paycheck.

Relax, already.

Figuring out what you want to do is hard. Working in a non-structured environment is hard. Going out and selling yourself every week is hard. Maintaining an online presence is hard. Working hard… is hard — even when you enjoy it. There will be setbacks, projects will dump you (sometimes for reasons completely out of your control), you’ll panic, you’ll doubt yourself. But you will also recover, and learn. You have to be equally as patient as your are determined and you have to learn to go with the flow. This has been the hardest part for me, but it’s also what’s made me grow the most. I wish I could say it gets easier, but as I approach my one year anniversary as a freelancer, I can confirm that isn’t the case — at least not yet. But looking back on the struggle and the amazing learnings that came from it keep me at ease.

Life as a freelancer is amazing in many ways. I currently spend half the day with my dog, I often work in my backyard (and in my pajamas), I cook a lot more than when I was full-time, I can exercise any time of day and visit my favorite studios at off-peak hours… I can’t complain. But it has been a wake-up call, too. I rarely feel like I’m doing enough, making enough, establishing myself enough, etc. I also find it harder to turn off when I’m working with multiple clients and managing several different email addresses. With all good things come difficulties, too. I’m just glad that a year later, I finally know what to expect.