14 years of freelancing

Like this post? Please share it!

In August 1999, I walked in the front door of my house with The Box: all of my personal belongings from the last corporate job I ever plan to hold. Looking back on 14 years of freelancing, I can only marvel at how quickly it’s gone—particularly compared with the preceding two-year stints in various magazine, marketing and public relations staff positions that seemed much longer than the time elapsed on a clock.

I didn’t make the decision lightly or capriciously, and I made sure not to make what my dad used to call an acrimonious departure. (I won’t get into the details here, but let’s just describe the bridge as smoldering rather than burning; a few years later, I counted my former employer as one of my best freelance clients.) The fact is, I’d been planning to pull the ripcord for nearly a year, but nobody knew other than me and my wife (and even she gasped a bit when I plunked The Box on the kitchen counter). We tightened up the budget, saved as much money as we could, and the rest needed to travel from my brain through my fingertips.

So, some random thoughts now that I’ve passed my second seven-year itch.

Smooth seas make poor sailors. As it turned out, I cruised through the first two years with plenty of business. The economic slowdown of 2001, when my phone stopped ringing, was another thing entirely. Surviving that rough patch gave me the confidence that: 1) I could persevere through the inevitable difficult financial times; and 2) no matter how bad things got, I didn’t need to retreat to corporate life. (A hat tip to Peter Bowerman and his first Well-Fed Writer book, which threw me a lifesaver when I needed it.) Living below our means, and of course, having a go-to-hell fund, were key elements to the strategy.

Client relationships are everything. I’ve quoted the Herb Brooks line from Miracle before: “You think you can win on talent alone? Gentlemen, you don’t have enough talent to win on talent alone.” So, too, with running your own business. The market is going to value your ability to persuade, sell, collaborate, manage, and create lasting partnerships more than your creativity. Bad clients are an opportunity cost; great clients not only make your work worthwhile, their referrals are essential to building a business without always having to scramble.

Learning from experience. Once you’ve been freelancing a while—and assuming you actually *like* freelancing—it’s easy to look back on your former worker-bee self with mixed emotions. Could I have made the leap sooner? Why was I slaving away for that company when I could have been making money for myself? But one of my longtime freelance designers made a great point to me this morning: A tough corporate job is a boot camp. You’re learning from experience, often the hard way, and gaining the knowledge and networks that make independence possible. Same thing goes for client relationships and freelance jobs that don’t go according to plan: Experience is what you get when you don’t get what you want. There’s value in that, even if it’s not always the most pleasant educational curriculum.

To celebrate my anniversary, I’d simply like to say thank you to all of my fellow freelancers and clients for your insights, inspiration, and friendship. It means a great deal.

In the comments: How long have you been freelancing? What’s the biggest lesson you’ve learned?

Photo courtesy of Patrizio Martorana.

Like this post? Please share it!

Like What You've Read? Subscribe to Dr. Freelance

* indicates required


  1. says

    I’ve enjoyed seven years of freelancing, and I’m still learning. I haven’t wanted to quit, but it’s definitely hard work.

    I appreciate what you’ve shared. You’ve shown us that life is indeed a journey. Keep sharing your insights. Here’s to many more anniversaries as a freelancer!

  2. says

    Happy anniversary! I’ve been a full-time freelance editor for just over five years–I left my last staff editing job in August 2008, but I did freelance work on the side for six years before that.

    I agree with your statement about the primacy of client relationships. Positive and constructive client feedback is invaluable. It makes me feel as if my work is an indispensable part of the publishing process and helps me keep going when work is slow or boring. And yes, referrals are a treasure. I’ve gotten several big, well-paying, essential-to-my-bottom-line projects as a result of referrals from terrific clients who appreciate my work and understand the value of (thoughtful) editing. I love editing, but I’m not sure I’d still be freelancing if it weren’t for certain clients who help make all the work worthwhile.

  3. says

    Jake, when they walked me out the door at my former job ten years ago, I had seen it coming and had prepared for it. It still stung, but it helped to have my ducks in a row. I was working with clients that same week.

    Love every point in this. I think the first two are especially true, and ones we freelancers need to etch into our brains permanently.

    My biggest lesson echoes your first point: I learned that if you want work, you have to be looking every day. You have to be in front of new clients and existing clients regularly.

    Another big lesson: it’s a business. Run it like one. Don’t let anyone tell you how much you’ll earn — decide that for yourself and don’t settle for less.

  4. says

    Thanks all for the well wishes and comments.

    Cassie, that’s the key, and well worth it to push through the challenges.

    Jill, I feel the same way–I write and edit because it’s the way my brain is wired, but my desire to work with someone depends on factors other than the project itself.

    Lori, I don’t know anyone who hustles better than you or is more open about how things work out!

  5. says

    Congrats, Jake, on your success! I feel like such a youngster. And trust me, there’s not too many scenarios where I can say that. 😉

    I’ve been freelancing five years. You are right – the time flies. I particularly like your last point as I often beat myself up for not making the move sooner.

    The biggest lesson? Discovering what you want from your freelancing. That can change, but if you work against (or ignore) what you want from your freelancing, it makes the journey less rewarding. In my humble opinion. 🙂

  6. Aline Lindemann says

    Nice job, Jake! My biggest lesson is simple — quality matters. There are times when I’ve succumbed to the temptation to work faster in order to get as much stuff written in one sitting as I can. Inevitably, I had to sit down with those same pieces to rewrite. And though rewrites are part of the gig, sometimes they really suck!

  7. says

    That’s a good one, Cathy. There’s a lot of freelance advice out there, much of which is diametrically opposed (niche vs. generalist, blog vs. blogless); you need to figure out how you work best. I’m a black-and-white kind of guy in my own business, but my commentary here tends toward giving both sides for exactly that reason. Batteries not included…some assembly required.

    Thanks, Aline. When the mood strikes (or deadline looms), I need to get as much on screen as possible. I find it less efficient to write perfectly the first time—it’s more like dump-and-fix! But, as above, there are plenty of people who do it the other way around.

  8. says

    A short, illustrative return to being an employee reminded me that running my own business is the better option. Congratulations on happily hitting the 14 year mark!

  9. says

    Thanks, Dava, and congratulations on rejoining the independent world. Sometimes a step back on the other side of the fence shows where the grass is *actually* greener. 🙂

  10. Shaun Hoobler says

    I love freelancing. And I don’t want to go back to the fast-paced, stressful corporate world anymore.