What I wish I knew before going freelance

Five-ish lessons from my transition to self-employment

In April, I left my full-time role as Head of Marketing to pursue self-employment. My decision to leave was personal, but ultimately, I wanted more autonomy and some breathing room after 12 years of working in startups.

The transition from full-time to freelance can feel scary to many, and objectively, it is. Leaving a salaried role often means the loss of stability and introduction of risk. And you have to solve the annoying jigsaw puzzle of retirement funds and health insurance.

To my surprise, I felt relatively calm. That’s partially because I can mooch off my partner’s health insurance, and partially because I know most startup jobs aren’t as stable as they’d like us to believe.

It’s also because I’ve freelanced as a side hustle since 2020. When COVID hit, my salary was slashed by 40%. I took matters into my own hands, cold-emailed a handful of CPG brands, and secured my first project.

Given all of the above, my transition went smoothly. It was easy enough for me to find new clients and make the leap. I share that not to brag, but to introduce the possibility that going out on your own isn’t actually as arduous as it might seem.

Still, even a smooth transition had its surprises. The silver lining is that now I can share with you everything I wish I had known before becoming self-employed.

My ideal freelance work setup

Lesson #0: Know your numbers

It feels irresponsible to start this letter without acknowledging the importance of finances during a career transition. You need to know your numbers. Anna Mackenzie has an excellent resource for this, which I used when planning my departure from my full-time role. Bookmark it now if you’re considering self-employment.

Don't quit your day job (yet)

Lesson #1: Don’t underestimate the admin of it all

Hire an accountant you trust and decide whether you want to be an independent contractor or incorporate. After a conversation with my accountant, I chose an S-Corp for tax reasons and because I had a clear understanding of my projected income, which allowed me to put myself on payroll. That said, I didn’t realize how much admin was involved in incorporating, opening business bank accounts, and implementing new systems to track expenses.

If I could go back in time, I’d have done all of this sooner, while I was still in my full-time role. Depending on when you sign clients, it may create extra paperwork to transition contracts from your name to a separate entity, but it’s typically an easy change.

Finally, I must mention one of my favorite freelance admin tools: Harvest. I use it for time tracking and invoicing, and I highly recommend it.

Lesson #2: It’s okay to say no

I intended to give myself a break when I left my job. Instead, I took on 40 hours of freelance and fractional work in addition to writing for False Start. Old habits really do die hard.

Though I was calm through the transition, there was still a scared little troll nested in my brain, telling me I needed to take every opportunity that came my way (“because what if I never get any more work ever again?”).

In hindsight, I wish I had taken on less. Now, I’m starting to decline new projects that I would have usually accepted from a scarcity mindset. It’s hard, but I think it’ll get easier with time.

Lesson #3: You need other self-employed people

As it turns out, I’m not the only person who’s made this mistake while transitioning to self-employment for the first time.

I’ve only recently started connecting with more consultants and freelancers, and it was instant “I’m not alone” relief. I heard from one woman who took on two 30-hour-per-week gigs to start, and another who is in a full-time maternity leave role and has another client on the side. It was reassuring to learn that I wasn’t the only one who overcommitted in the beginning.

Lesson #4: Structure isn’t the enemy

I recently discovered that I’ve been working seven days a week. My schedule was entirely self-inflicted, driven by a desire for autonomy and rejection of traditional work schedules.

I’m in an office a few days a week for one of my clients, so I have some forced structure. But the other days? I was flexing my freedom by taking off weekday afternoons, only to make up for it with late nights and weekend work. I felt utterly exhausted by Monday morning, as if I were trapped in an endless cycle of daily to-do lists.

Now, I’m taking weekends off like a sane person, which means setting myself strict deadlines during the week. I feel better already.

Bonus: Showing up to an office forces me to get dressed

Lesson #5: Celebrate your freedom

Make space for intentional fun to celebrate your liberation from the 9-5. I try to do one thing each week that I wouldn’t have been able to do in a full-time role.

Suggestions for luxurious weekday activities:

• Grab lunch at a fancy restaurant with a friend

• Go for a long walk

• Book a midday workout class

• Read with a cup of coffee on the couch

• Get a facial

• Watch a comfort show

Obviously, these are not groundbreaking, life-changing activities. But doing them at 11 am on a Wednesday? Downright THRILLING.

What other questions do you have about going freelance? For those who have made the transition, what else surprised you? Drop your lessons or questions in the comments.