Goodbye Yellow Brick Road: A Freelancer’s Retrospective

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

“So, do you freelance or do you have a job-job?” I’ll never understand this question. Being a freelance designer meant that I lived in a constant state of hustle and flow. When I wasn’t designing I was looking for my next client engagement. The pace wasn’t 9–5 and good luck “turning off” at whatever “end of day” means (you can use rock quotes on those if you want to). When things are good and the checks are steadily coming in the freedom is amazing. Go for a walk. Ride a bike. Play the ukulele. It’s your schedule and you’ll live or die by it. The other side of that coin is that when there are no clients and your bank account is dwindling it’s scary as hell. “Ramen tonight, honey?” Ooo, chills! Freelancing is a job-job and it’s work-work.

Enlist a Partner

Speaking from experience, questions and doubts come up in the day-to-day and you’ll want someone you can trust to talk to if only to validate what you already know. This crucial role could be a close friend, your life partner, your business partner, etc. In my case it was my wife (who is awesome) which makes sense since my choice to freelance full-time had significant impact on both of us. When it came to travel versus obligations at home, having someone else who understood both sides was a gift.

Get a Rate

Unless the work was pro bono, clients vetting me wanted to know how much I charged before telling me project details. Best to have that magic number at the ready. Leading with, “it depends on the scope” was, unfortunately, a path to losing work. I wanted to charge a fair price but… ya know, I wanted to make a profit too! Also, I didn’t want to scare potential clients away with a big number. The rate I chose came down to two things:

  • 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

Whether you’re going the sole proprietor or LLC route (there are reasons to do either that I won’t get into here), I highly encourage you to enlist help with your taxes. Freelancers in the U.S. will likely be introduced to Schedule C, wherein you pay quarterly taxes based on your expected annual income. It’s tricky to figure out and it wasn’t something the chain-store accountants were ready to help me understand, although they were very interested in helping me identify business deductions.

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

The statement of work and contractor agreement form are essential documents. I wouldn’t start a project without having them countersigned. These papers are a legal agreement that protects both parties; my client is assured quality work as well as discretion and I am assured payment within a timeframe of my choosing. Simple, but vital.

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

Truth? I never had a client who wanted to pay a deposit. The word, guffaw comes to mind. I was introduced to commencement fees in Mike Monteiro’s book, Design is a Job. (It’s brilliant, go read it as well as his second book, You’re My Favorite Client.) On paper, asking for one makes sense because I’m using it to protect myself from potential loss by requiring my client to give me a percentage of the total due before work starts. If agreed to, as Mike says, “now we both have skin in the game.”

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

I was remote most of the time, working from my home office for clients that were on the east coast and the midwest. Essentially, I was an extension of the larger design team but not in-person. It wasn’t a big leap for me. Having previously worked for a remote-based UX agency I became accustomed to the culture and knew I’d need a dedicated space, an environment I could control for video calls, remote group sketching, etc. and a good ISP. Here’s the thing though; I never got used to the isolation. At end of day there’s no “goodbye” or “see you tomorrow.” I also didn’t get to attend or know about every meeting; there were times it would have been good for me to have been there virtually. Like a ghost, I had to be summoned or invoked to participate. It’s a strange dynamic that sheds light on how hard (but not impossible) remote can be, especially when you’re an outsider to the larger group. Fortunately there are ways to counteract it:

  • 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

I have a new respect for freelance designers. Their hustle is amazing. It’s criminal how often I’ve heard or read about someone not getting paid or getting sucked into speculative work without pay. I managed to avoid those pitfalls because I joined a freelancer’s union. Groups like this are fantastic at providing free literature about the rights of freelance designers and can offer avenues for legal advice too. The sense of community it brought to me as a remote designer was beneficial.

A Fractured State of Being

Freelancing meant I would need to wear multiple hats: the designer, the scheduler, the shop owner and the bill collector. These personas work in tandem, sometimes protecting each other. The designer wants to get to work and focus while the scheduler dictates how long the designer can work on a project before pivoting to another or forcing a break. Meanwhile the shop owner is making connections and bringing in more work that the scheduler will have to weave into the designer’s calendar. The Robin Williams-esque flow is only interrupted when the bill collector says I haven’t been paid on time. At that point the bill collector mediates with the client and the scheduler plans accordingly. The orchestration made me realize how protected I was in the singular but essential role of designer.

Finally, Mindfulness

Taking stock of the present moment is what kept me happy and working hard during the hustle. It’s worth asking yourself, “mind full or mindful?” From day one I wanted to do good work for good people; being able to choose what I worked on was a breath of fresh air. However, my path certainly wasn’t illuminated or paved in that ideal. The path was made in a decision to focus on the day-to-day instead of my larger third-year goal. The projects, the collaboration and (dare I say) the ties I made with other people became my focus. If those things prevailed I trusted that success would follow. The big picture as was told here is better used as a retrospective.


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. 🙏