18 years of freelancing, 18 business lessons

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business lessons on the 18th birthday of freelancingI used to know the exact date I walked out of the corporate world with The Box and started my freelance business. Today, I only remember that it was in August 1999. Yep, as of this birthday my business is old enough to vote, buy a lottery ticket, join the army, or drink in Canada and much of Europe. Here, in no particular order, are 18 business lessons from 18 years in business:

  1. As freelancers, we pride ourselves on our independence. In some ways, that’s a pretty little lie. The truth is that the advantage of self-employment isn’t pure independence–it’s the freedom to choose the people or businesses we work for, on what, with which partners, and when. We’re free to change the terms of the deal.
  2. We’re responsible for the level of interaction we have with others, whether in real life or in virtual channels. If you don’t like or respect or enjoy the people in your network, that’s a choice you’re actively making, every day. You control the freelance ecosystem you’re creating. Along those same lines, social media has made it a lot more fun and interesting to be a freelancer.
  3. Technology blows my mind. I’ve submitted projects from a dozen different countries, from a sailboat, and from a car going 75 mph. (No, I wasn’t driving!) I’m really glad I don’t have to hand-code html anymore, send photocopied portfolio samples via snail mail, or print 500 books at a time.
  4. I always found conferences to be a psychological drain back in my corporate days. Now that I choose where to go, I find them energizing and enlightening.
  5. Handwritten thank-you notes are the best available tool for client retention and business development. Gratitude is a pure good.
  6. As I’ve written about countless times in the past, connecting with complementary creatives is absolutely essential to my business success and happiness.
  7. Whether in formal organizations or informal channels, I can’t help but learn something new every day.
  8. I’m always inspired by the diversity of the client enterprises and ideas I have the good fortune to engage with.
  9. If you don’t value your work properly, clients won’t either.
  10. Never take negative stuff personally. As the mafia movies tell us, “It’s just business.”
  11. You will inevitably lose big-dollar clients and great clients. Be prepared, mentally and financially. Having an emergency or go-to-hell fund isn’t ultimately about paying the bills when things go pear-shaped, however: They’re designed to prevent you from making decisions out of desperation.
  12. It always helps to focus on the end users of your creative output. (Only trying to please the clients themselves doesn’t benefit them in the long run, although that’s sometimes the way it works out.)
  13. Invoicing is a pain in the neck, but it’s pretty nifty to receive two or three checks in a single day.
  14. There is no best way to run a freelance business—you need to find what works for you and heed the business lessons you learn along the way. That will involve experimentation, which means failures as well as successes.
  15. Referrals make business easier and more lucrative, but they don’t happen overnight, by accident, or solely because of your creative talents.
  16. The adage of “speed/quality/cost, pick any two” is utter B.S. You have to deliver quality work; only speed and cost are negotiable.
  17. Every year, I get better at the game—and it is a game—making more good decisions and fewer bad ones. That’s cool.
  18. The best thing in the world is having long-term relationships with clients who simply “get it.”

In the comments: How many years have you been freelancing? What are some of the most important business lessons you’ve learned?

Photo by Delaney Dawson on Unsplash. (There’s no way my dogs would put up with putting birthday hats on their heads.)

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    • says

      Thanks for the confirmation, Kathy! (You’re one of the people that consistently teaches this old dawg new tricks, so thank you for that, too!)

  1. says

    The single biggest turning point to my freelance career was when someone told me that I had to set aside time to work “on” my business not just in it. Finding that 10% of time to build my skills and my client base made a world of difference. 20 years this fall.

    • says

      You make an excellent point, Adrienne: It’s easy to get focused on the dashboard instead of the road ahead. (And, like Kathy above, you’re one of the colleagues I learn from all the time–thank you!) I thought you were a year or two ahead of me–20 years is a swingin’ milestone.

  2. says

    I’ve been freelancing full-time since 1984! I did freelance writing on the side for several years before that, and sold my first freelance articles while still in high school.

    Most important business lessons include:
    You can’t remember/include everything in every contract/agreement; some new headache is always likely to crop up.
    Never assume – always ask questions, even if they seem silly or dumb, before accepting an assignment.
    Beat deadlines instead of meeting them.
    Communicate with clients – don’t surprise them with problems or delays. Most will be understanding as long as they know what’s going on.
    Strong networking skills are essential. Be the colleague who gives as much as s/he gets.
    If you aren’t enjoying a project or working with a client, do your best with the current project and don’t work with that client again.
    Never give up!

  3. says

    Congrats, Jake.

    I’ve been an independent since ’86, with a few full-time employment forays here and there. Your opening paragraph really resonates. In moving east, once again I was suckered into taking a contract publishing team gig at a ’60s-structured, one-time Fortune 100 company that is—once again—trying to reinvent itself. I lasted a month in that repressive, continually panicked environment that had no clear direction forward.

    This time I think I can definitely say, “Never again.” It’s far better to consult and not have to get all wrapped up in others’ political posturing.

    • says

      Thanks, Chris. Looking on the bright side, I bet your boomerang-corporate experience is helpful in understanding/empathizing with your clients who remain in that world! Not a bad thing, at all.

  4. says

    Wow. This was an EXCELLENT post! I just celebrated my ninth year as a freelance business owner. Even with all of the ups and downs, I will NEVER be someone else’s employee ever again.

  5. says

    I’ve been freelancing for an even 20 years now. I’ve learned a few key lessons lately that have boosted me:

    1. BE BOLD. Double your rates now and then. Turn down work you don’t want. Be open to growing.

    2. Assess now and then and make changes. Change your client roster, go in a new direction, or (gasp!) stop working weekends! Be in control of your business by making choices.

    • says

      Yes! and Yes! to those business lessons, Laura–thanks. Although I personally don’t mind working weekends if it means 1) raking in some extra dough and 2) getting to play hooky during the week.

  6. says

    Smashing post, Jake!

    I’ve been self-employed for 12 years. Some additional thoughts:

    1) Every year it gets noisier; make sure you can hear the voices that count.

    2) Echoing Adrienne’s point, there’s the work we do and the work we do to get the work we do; make time for both.

    3) Don’t be afraid to test something new even if it scares you silly; if it doesn’t work, at least you tried.

    4) Listen and learn from the young; they are courageous and vital, and can blow away the cobwebs.

    • says

      Thanks, Louise! Four more excellent suggestions. At this rate, we could easily get into triple digits…but I’m planning to retire quite a bit before I get there in years 🙂

  7. Richard Adin says

    Very interesting list, Jake. I have been a full-time independent editor for 33 years. Alas, I disagree with several “lessons” you list, but there is one you state that I think is the overriding lesson that every freelancer needs to learn and absorb: “9. If you don’t value your work properly, clients won’t either.” Actually, I would add a corollary to that lesson. I think every freelancer needs to learn and chant the mantra, “I am the greatest _____!”, which is the chant of self-confidence.

    Some of the lessons I have learned are these:

    1. If I do not believe in my own abilities, no one else will believe I am skilled either.
    2. Even though my business does not generate millions of dollars in revenue annually, I still need to approach my business as if I were a multimillion-dollar business.
    3. There is no path to success that doesn’t include the willingness to say “no.”
    4. Learning business fundamentals and applying them to my profession is a key to success.

    • says

      Thanks, Rich. Thirty-three years is impressive, and those are excellent additions to the.growing list. Thanks for taking the time to comment–and I appreciate your discreet notification about my typo, now fixed!

  8. says

    Thanks Jake, great post and lots of good comments.
    I’ve been freelancing for 8 years and still love it, particularly the fact that I can make my own decisions (whether they’re right or wrong). I’d add to the list ‘Find a positive in the negatives’. For example, I hate admin, so when I started the business I worried that I wouldn’t cope with that side of it, but in fact I love finding methods and technologies to reduce the time I need to spend on admin.
    Best wishes for the next 18 years!

    • says

      Thanks, Hilary. The risk in a numbered-list post is inevitably that you forget something or have to leave some out, so I’m glad to be surrounded with smart colleagues who can pick up the slack!

      I think admin is a tough one for a lot of people, so I dig the idea of making it an internal competition to make it less painful or time-consuming.

  9. says

    Terrific article! Next spring, I’ll be celebrating 25 years as a freelancer. I can think of 2 comments to add to you excellent list:

    1. Freelancing is introvert-friendly.

    2. Don’t be a dick.

    • says

      Ha, Carol! #2 is funny, accurate, and a pretty good rule for life in general. I skew slightly extroverted, but know that’s a smaller slice of the pie in our industry. Thanks for reading and commenting.

  10. says

    Congrats, Jake, on your 18th birthday! 🙂 I thought I’d never say this to almost anyone, but I’m 10 years younger. 🙂 I’ve been doing this gig for 8 years. I feel like such a pup in this crowd.

    As I just received an email from a potential client who refused anything but an hourly contract, I would say several of these lessons apply. One great thing of me starting my business after 30-plus years in corporate life is I’m old. And the older I get, the more things roll off my back.

    • says

      8 years? Seems like we’ve know each other for longer than that! In any case, I agree completely with the principle of letting stuff roll off your back. We only have a finite amount of time and energy every day, and best to spend it on things we can control. Thanks for taking the time to comment, Cathy.

  11. says

    Great post for all entrepreneurs as well! I’ve been in business for myself for almost 23 years and the biggest lesson I’ve learned is to show up every day. You will have highs and you will have lows, but if you keep showing up you will build a sustainable business! Never give up.

  12. Matt Hutson says

    Hey there Jake,

    I actually haven’t started freelancing yet but I’m strongly considering building up a freelancing business and I find your site very useful. I’ve visited a few other sites that didn’t quite do it for me.

    The thing I love about your writing is that it’s personalized and I know that’s important when writing a blog. So, as I said before, I haven’t started freelancing yet but what I have been doing is writing on a book blog for the past 9 months.

    I really enjoy it quite a bit, connecting with my audience and writing about what I enjoy, but there’s nothing tangible about it. So, I was thinking that if I buy my own domain and change my direction a little into proofreading and editing it’ll be a great choice for me. I’d like to make it into a platform where clients can come and connect on a personal basis starting out with just me but later hiring other freelancers.

    What do you think of my idea? Is it plausible?

    Matt Hutson

    • says

      Hi Matt, my apologies for the slow reply. You were buried in my spam folder amongst a couple hundred offers for cheap mortgage loans and prescriptions! Sure, your idea is plausible. I always recommend Peter Bowerman’s “The Well-Fed Writer” as a starting point for freelance businesses. There’s also a wealth of business-oriented information at Katharine O’Moore-Klopf’s Copyeditors’ Knowledge Base. Best of luck, and keep me posted on how it goes!