Notes from the past to my future freelance self

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freelance selfIt was August 1999 when I bolted my corporate job and launched Boomvang Creative Group as a full-time freelance writer and editor. If I could step back to day 1 of 19 years of self-employment, here are some notes I would have provided to my future freelance self:

  1. Clients work with freelancers they like and respect, and the reverse is true, too: Tepid or one-sided relationships absorb too much mental and physical energy, no matter what they pay.
  2. You can’t go wrong by making the client look good.
  3. Empathy is paramount when you’re dealing with someone else’s ideas and aspirations.
  4. As long as the client is pleased with the final product, you need to find a way to be happy, too. (Even if you’re not thrilled with the results and don’t want to include the project in your portfolio.)
  5. The biggest sign of trouble with a client is when you see a name on call waiting or in your inbox and think, “Ugh.” Extra points for an audible groan.
  6. It’s way more fun to get two checks on one random day than a regular paycheck every two weeks.
  7. Freelancing is a better education on a wider array of topics than your business degree.
  8. Feast or famine only bothers you if you let it. (And if you don’t plan for it.)
  9. No number of clients in the bush is worth as much as one in the hand.
  10. Referrals and warm leads are even more valuable than you realize. (Far better than anything that comes over the transom.)
  11. Having a diverse array of clients, industries, and media types is your best insurance policy. Because…
  12. You will lose clients through no fault of your own and without warning. (Prepare accordingly.)
  13. The smartest thing you can do is embrace the business side of freelancing. In fact, that may turn out to be even more enjoyable than the creative part.
  14. You don’t have to love every project, but you need to find something to help you push through. (It’s OK if that something is money.)
  15. Stop feeling guilty about mistakes you made, things you didn’t do, clients who didn’t work out, etc.
  16. There is no “right way” to freelance. Experiment. Incorporate and refine what works; stop doing what doesn’t get results or anything that irritates you.
  17. Running a one-person show (see Paul Jarvis re: minimalist business) is a perfectly noble enterprise. Partnering with skilled, expert freelancers has plenty of advantages over managing employees.
  18. When you wake up eager to start the day, pretty much every day, that’s a darn good sign you’ve made a smart choice.
  19. Nineteen years from now, Future Freelance Self, you will not be where you thought you’d be. (That’s not an excuse to not make plans—it’s an argument for creating systems, not just goals. h/t Scott Adams for introducing me to that concept.)

I’ve done previous anniversary posts before—business lessons at 18 and also here at 14—if you care to take a click down memory lane. That’s it for now. Thanks for reading, and have a great (long, for those in the U.S.) weekend!

Photo by Sophie Elvis on Unsplash.

In the comments: How long have you been freelancing? If you could go back in time to the day you started, what’s the one thing you would tell your future freelance self?

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  1. says

    I’ve been freelancing full time for a decade now (!), and your advice to yourself is right on. I’d probably add: Always be prepared to lose the client you make the most money with. It’s so easy to put off marketing in order to make quick, easy money with a long-standing client, but you will eventually lose that client, probably through no fault of your own. Be ready for that to happen by having a nice, diverse client list. Your numbers 11 and 12 cover that, but it can’t really be overstated.

    • says

      Hey Dava, long time no talk–and that’s awesome that you’ve notched 10 years! (I feel like you were pretty new to it when we first connected way back when…) You make an excellent point about the specific danger of losing anchor clients. Thanks for commenting 🙂

  2. says

    I’ve been freelancing since 1989. Thinking back, I’d tell my future self that freelance writing will lead you down some unexpected paths. Surprises (mostly pleasant) and the occasional pothole lie ahead.

  3. Jenn Woolson says

    I’m just hitting the 18-month mark. I know I would go back now and say to my past self, “What on earth were you waiting for?” Every day isn’t easy, but it’s interesting and it’s mine to succeed or fail. Thanks for being part of a great group who gave me a collective shove in the right direction.

    • says

      Hey Jenn! Glad to hear from you, can’t believe it’s already been 1.5 years. You know, I sometimes had the same thought about “what were you waiting for,” but in hindsight, there was a reason the timing transpired as it did 🙂

  4. says

    I started freelancing in 1995, so 23 years now. I’d tell myself that starting and succeeding with my own business would be one of the best things imaginable for my self-esteem and my satisfaction with life!

  5. says

    Outstanding post, Jake, and one of your best. I started freelancing as an illustrator back in June, 1989, and it’s a mind-boggler to think I’m closing in on 20 years. I’d tell myself this: Early on you’re going to price some jobs too low. They’re going to be more complex than you think. You can’t just submit a bill for more than your original quote. You can talk to the client about it, explain the situation, and ask for more money, but you have to stick to your original quote if the client says no. Your reputation is at stake. There will be some things you have to write off to experience, and that’s OK– all part of learning how to be a freelancer. Great post, thanks again.

  6. says

    Jake I knew you in 1999. In fact I knew you better then than I know you now! That day you walked out of corporate you became a hero and role model for me and so many others. A guiding light for the independent thinkers and competent doers. It’s been awesome following you and knowing you’re fulfilled. Congrats on your 19th…keep it up old friend!


    Sent with my freelancing fingers from the shoreline of Lake Chapala, Jalisco, MX

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