Five Lessons I Learned After Nearly Two Decades of Freelancing


started freelancing in 2002 after getting laid off from a web design agency that, boosted by the dot-com bubble of the late 90’s and early 00’s, grew far too quickly. When I landed my first freelance project with a company based in Australia, my hourly rate was unsustainably low. But I had done it — I’d gotten my first freelance gig.

I’ve worked with dozens of clients in the years since then and changed the focus of my business several times. I’m currently in the midst of changing it yet again. There are certain things that I know now that I wish I’d known when I was first starting out. They’re lessons that I likely couldn’t have fully grasped (or believed) without experience. Here are the top five.

Lesson #1: Freelancing is more secure than working full-time.

In 2002, the idea of freelancing felt shaky and uncertain, but the gig economy was growing thanks to a combination of technology advances and the Internet. I got my first few projects fairly quickly and found that work was plentiful, if not always consistent.

I quickly discovered that building a roster of freelance clients gave me the kind of job security that I’d never experienced as a full-time employee working for one company. As my list of clients grew, so did my security. If I lost a client, I still had money coming in. I learned not to let any one account dominate my income and that finding new clients was as much a part of my job as working on existing accounts. The reliance on myself to find new work can be exhausting and even scary, but it’s also incredibly liberating.

Lesson #2: It’s essential to ask for what you’re worth.

It took me a few years to learn this lesson, but when I finally did my bills became a lot easier to pay. When you freelance in the U.S., you have to cover all your expenses and this includes self employment tax at a rate of 15.3%. Self employment tax is the money you pay towards Social Security and Medicare (if you work for someone else, they are required to pay for half of this). This 15.3% does not include income tax which, of course, I’m also responsible for paying.

My business overhead also includes purchasing health insurance, office equipment and supplies and most travel expenses. Other things to consider: I don’t get paid time off when I’m sick. I don’t get vacation time. I don’t get severance pay when I lose a client and I don’t get paid for the administrative tasks involved with running my business and finding new clients.

I didn’t account for any of this when I first started out. Thus, my rate was far too low. I am still paying for this mistake. These days I don’t take on a project unless I’m comfortable with the rate, even if that means turning work away completely.

Lesson #3: You don’t need to apologize for everything.

I’m a perfectionist and a people pleaser, two characteristics that made self-employment particularly stressful for me when I first started out. I noticed that I was apologizing for everything. If I didn’t get back to someone immediately, I would start my email or text with an apology. If I didn’t get paid on time, I would apologize for asking about the status of my payment. If I followed a client’s instructions, even though they went against what I advised, and the outcome was poor, I apologized instead of pointing out that this is something I’d warned them about.

My constant apologizing diminished my authority as an expert in my industry. It made it difficult for me to ask for a fair hourly rate from new clients and raise my rate with existing clients.

I still struggle with the urge to apologize for every perceived failing or mistake. To be clear, I do apologize if I drop the ball or make a mistake. But I also consciously curb the desire to apologize for not being perfect. I made this shift about ten years into my freelance career — right about the time I started asking for a higher hourly rate.

Lesson #4: You will make mistakes and that’s okay.

When you first start freelancing, you will make mistakes and some of them will be expensive. I once paid a subcontractor over two thousand dollars for a task he screwed up and I had to redo. That costly mistake taught me a lot about how to work with subcontractors. I learned to be exquisitely clear about how many hours they should spend on a given task and the outcome I expected from them.

I once worked with a client who was extremely hands off. Months would go by with minimal interaction or responses from him. I’d had a bad feeling about it, but I thought he needed me to take charge because he was so busy. I should’ve gone with my gut. When his wife (and co-owner of the company) realized how much he was paying me and how little input he was giving me to do my job, she not only fired me, but demanded I refund all the money he’d paid. I should’ve gone with my instincts and pushed back when the client became unresponsive to my attempts to check in.

My point is that mistakes are inevitable. I learned that fairly early on, but the lesson I really learned is how to manage and mitigate mistakes. If a client is unhappy, I try to work with them to resolve the issue, and ensure that if we do move forward, we fix whatever caused the misunderstanding so it doesn’t happen again.

Lesson #5: Freelancing offers freedom — it’s important to recognize this.

When I first started freelancing I had a full-time employee mindset. I’d sit down to work by or before 9:00 a.m. and I stay at my desk with minimal breaks for at least 8 hours. We put my daughter, then two years old, into day care and my husband worked part-time and helped care for her so I could keep working like this (even though it was stressful for both of us).

I soon learned that there was no good reason for me to keep this schedule. My younger daughter was born in 2004 and as my kids grew, my work schedule naturally shifted to revolve around their needs. I drove them to and from school, went on field trips, and stopped working when they got home in the afternoon. I never missed a single school event — not one play, or performance, or community day. Freelancing enabled me to be there for them.

When my older daughter was diagnosed with cancer, I was able to take large chunks of time off without any impact to my client work at all (I had two subcontractors working for me by this point). My business kept running and money kept coming in, although my income was impacted, I could still pay the bills.

The flexibility of freelancing is something I’m perpetually grateful for, particularly as I grow older. I can find projects that match my skills and work at my own pace without worrying about competing with a younger workforce.

My current schedule looks much different than it did seventeen years ago. My older daughter died almost three years ago and my younger daughter is a teenager. My time is more my own and I’m realizing that another shift is in order.

I’m experimenting with what that means from a scheduling perspective, exploring a four-day work week and shortened work days. Down time is now a necessity for me. My brain doesn’t function the way it did before I lost my daughter. The freedom to take the time I need to recharge and reflect is a necessity.

Occasional poet. Writer of sad essays. Novelist. Birder and amateur photographer. I enjoy trees.

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