Lessons from 9 Years as a Freelance Writer

Today is the first day of my 9th New Year of working as a full-time freelance writer. Deciding to quit my corporate cubicle job to become a freelance writer was the best decision I’ve ever made in my life. My dreams have come true. I make a good living, I work with AWESOME people all over the world, I’ve gotten to provide my family with a comfortable life and dream-come-true trips fo London, Paris, Prague, Tokyo and more, and I’ve done it all while working from home, at my own pace, on my own terms, following my curiosities and learning a little about a lot.

I could not be more grateful for my career, and the thrill of getting to do this for a living still has not worn off – even the little things like getting to go out for lunch with my family at 2:30 p.m. on a weekday instead of being stuck in a cubicle. Even though this life as a freelance writer can sometimes feel risky and lonely, even the hard times are still pretty good. I love being a freelancer and I want to keep doing this – or something like this – forever.

Here are a few things I’ve learned over the years of building my business as a successful freelance writer:

Focus on Relationships, Not Transactions

I’m proud to have established a lot of long-lasting relationships with clients and editors. I have been working for some of the same people and the same organizations for five years or more. Some of my clients have stayed with me even as they have moved on to new jobs or started new companies of their own. It’s always worth staying in touch with good people. Instead of trying to squeeze every last dollar out of every transaction, I’d rather preserve a longer-lasting client relationship and keep lots of dollars coming in over the years.

Elance Really Work(ed)…For Me! 

I got my start as a freelance writer in January 2009 by signing up for a profile on Elance, now known as Upwork, a project bidding site for freelance work. And I met some of my best clients on Elance, some of whom I’m still working with several years later. I had a good experience with Elance but I kind of gradually stopped using Upwork after they raised their fees – the last I checked, they were charging per-project commission fees of 20% of the first $500 you earned with each client (it’s complicated; I can’t remember the exact details so I could be mistaken) – but the point is, Upwork was no longer as good of a deal as its predecessor Elance used to be. The platform deserves to make money because they’re creating value for freelancers by giving us the opportunity to connect with clients – but 20% is ridiculous. Not even Hollywood agents charge that much. I’m not sure if Upwork is still as good of a proposition for new freelancers as Elance was for me back in January 2009; I’m not sure if I still would recommend it.

Don’t Be Afraid to Do Everything Wrong

I have weird ways of working that no conventional full-time employer would ever tolerate. I do everything wrong. I don’t keep regular hours, I don’t set an alarm clock in the morning, I don’t hold myself to a fixed writing schedule everyday, I don’t keep track of lots of things that I could probably be tracking to improve my efficiency. I probably have undiagnosed, unmedicated ADHD. I waste vast amounts of time on the Internet and on Facebook and just daydreaming and brooding and thinking.

But when I’m on? I’m ON. In my own weird way, as a freelance writer, I’m one of the best in the world at what I do. Even though I work from home and I tend to be reclusive and I wear the same pair of pajamas for days at a time. I probably don’t have the healthiest lifestyle but I manage to keep cranking out the work and meeting my deadlines and paying my bills, and that’s enough for me.

Money Comes and Goes 

Being self-employed can be tough. It can feel risky and lonely. There are times where you might not have enough work, might not have enough money coming in, when you might feel desperately vulnerable and alone. That’s OK! You have to learn to accept, and even enjoy, the ups and downs. There are going to be lean times of year. Sometimes projects fall through for reasons beyond your control. Sometimes your client might be slow to pay, for reasons beyond their control. Freelance writers need to build up resilience and learn to keep calm and carry on.

One of the best bits of advice I ever got was: “The thing that separates the most successful people from the rest is: they know how to relax.” I’ve found that to be true in my own life as a freelance writer. I used to be in a state of near constant anxiety, even when things were going well: “Am I making enough money?? Do I have enough work?? Am I making the right decisions with my business and my financial plans?? Is this all going to come crashing down at any moment???” Over time, especially as built up a bigger base of business, I learned to “let go and let flow.”

Another bit of advice that I got from a fellow self-employed friend: “Most of the things you worry about never happen.” It’s true – any one of us could be struck down by catastrophe at any time. But most of the time? Just keep working.

Define Success By Your Own Terms 

I’m not one of these people who’s extremely visible on social media as being an avatar of Internet Business Success. I kind of don’t care. I don’t really need to be a public figure or have a “brand” or speak at conferences or have a big audience or be a media thought leader or celebrity or influencer to be successful at doing what I do.

My business model is simple: I write things for money. Sometimes I ghostwrite articles for tech startup CEOs, sometimes I write technical white papers, sometimes I write press releases and PR pieces, sometimes I write blog articles under my own byline. Sometimes the stuff I write is creative and fun and a labor of love; sometimes I’m in it just for the money but I still put in an earnest effort on every project and I only work with people that I like and on projects that I believe in.

I’m still grateful for every project and every paycheck. I started out doing projects for $30 an article (I charge a LOT more than that now) and I built a new full-time income for myself, $200 at a time. Just getting to be successfully full-time employed as a freelance writer, on my own terms, is enough for me – for now!

Find Joy in the Work

The ultimate success as a freelance writer is in the work itself. What really motivates me? It’s not just the money, it’s about that feeling of creative flow that comes from bringing a well-crafted piece of writing into the world. The work I do is not always glamorous, but it’s always meaningful if I can do it with sincerity and earnest effort. In my own small way, I’m trying to use my talents and my brain power to help make the world a little bit smarter and better. I care about all of my clients. I find meaning in the process of creating good content, making the words flow better, bringing compelling ideas to life, and being part of a team of creative collaborators who are having fun and learning together.

Being a freelance writer is the best job I’ve ever had. I hope to keep celebrating many Happy New Years in the years ahead.

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