Goodbye Yellow Brick Road: A Freelancer’s Retrospective

Chuck Borowicz
May 1, 2017 · 8 min read
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Photo credit: Craig Garner

Today I’m saying goodbye to the freelance life. Unless some amazing opportunity came along freelancing was a five-year plan for me. Two years in I’ve had the pleasure of solving some complicated problems with fantastic design agencies, leads and end clients. I’m not closing the door of my shop forever (no one can guarantee direction like that) but I’m no longer actively seeking freelance work in a full-time, 9–5 capacity.

When I made the leap to freelancing the intent was simple: establish repeat clients in the first 2–3 years and make a profit after taxes. If I’m not putting something into savings after year 3 it’s not going to work out. Real talk: that’s probably everybody’s plan when they start out. The day-to-day isn’t that simple. There’s a lot of reevaluating and adjusting that happens along the path.

It’s been a crazy and rewarding time and as I often do, I like to take a look back before moving to the next thing. There’s some interesting kernels of truth in my experience as the chief design officer of me [pause for polite laughter] and it’s anything but leisurely lunches and emails on the beach.

Freelancing is a Lifestyle

Enlist a Partner

Get a Rate

  • The Taxman Cometh. Obviously, everything earned is gross (not net) and it’s up to the freelancer to pay the applicable taxes. Fun fact: self-employment initiative in the States will sadly be penalized with a self-employment tax. Keep that in mind.
  • My Time Has Worth. I hit the books and ended up basing my pricing strategy on a model from Pricing Design by Dan Mall. I highly recommend this book as I reference it often. In it Dan walks through several pricing models but the one that worked for me was based on what I thought my time was worth. In essence, if I’m giving up things I want to do to work on someone else’s project, what’s that worth?

I also learned about the push-back. “Could you come down on your rate?” Clients can use project duration and their repeat business (great for freelancers) as leverage to negotiate a better rate. “I will stick around if I can pay you less.” I had to be ready to lose a project (a paycheck) to stand firm on my rate. That’s extremely hard when starting out, especially when you want to retain a great client. Remember, you’re the one paying all the taxes now and potentially working burnout hours for peanuts will be a disaster.

Get an Accountant You Can Count On

I had much better luck working with a dedicated accountant from a small, local outfit. Great since I wanted a single point-of-contact. The chain-store alternative only offered a rotating staff (no dedicated contact) and I wasn’t interested in going over my history repeatedly. Plus, going the local route meant I could ask questions all year; that’s something else the chains wouldn’t do for me.

Get It In Writing

Will work happen on-site or remotely?
Get that in writing.

If there’s travel involved will I be reimbursed?
Get that in writing.

Will I have to buy software or will it be supplied?
Get that in writing.

Time commitment; date ranges, times of day the client wants me around?
Get that in writing.

I have a rate. Does the client agree to it?
Get. That. In. Writing.

I’m sure you get the point. If a potential client won’t abide, walk away.

Commencement Fees

For me, asking for money upfront caused tension. Even saying, “commencement fee” caused confusion. Those words sound like an additional fee, not a part of the total. I learned to be very careful when I spoke about deposits (if not everything else). Afterall, words mean things. Occasionally I lost what I hoped would be a new client because I insisted on the deposit for new engagements. For that reason I never asked repeat-clients for it.

The commencement fee is up to you. It’s a matter of trust, so if you feel like you can build a client relationship without it then don’t get hung up on it. Some advice is better for agencies than lone freelancers.

If You’re Remote You’re a Ghost

  • Ask to be invited. Get involved in scrums and standups. You’re billing for the time, so be sure to ask permission before jumping in.
  • Be present. Keep IM or Slack open. Impromptu activities are often announced here. Get in the groups and keep an eye out during your working hours.
  • Remind others you are interruptible. Repeat after me: “If you need me I’m around for feedback or brainstorming. Please consider me interruptible.” Announce it daily.

Unfortunately, none of this advice will help with remote isolation. Aside from going for walks and having a hobby, it’s been a hard nut to crack. Remote work is a lengthy, tangled subject (people are writing books about it!) and I’m only scratching the surface here. I’m sure I’ll have more to say on the subject one day.

Join a Freelancer’s Organization

A Fractured State of Being

Finally, Mindfulness


Acknowledgements: Doors don’t always open by themselves. If you’re reading this and you helped me make a connection, gave me advice or simply passed my name along, I sincerely thank you. My extended thanks to past employers who allowed me to share work; those examples and narratives were pivotal as I took my first steps into freelancing. And if you’re a client reading this… thank you, thank you, thank you! Let’s not lose touch. 🙏

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