Going Indie

Freelancing lessons learned the hard way • October 1 2023

This is a gloss of and reaction to a presentation that Rob Hayes and I gave at a DesignX meetup, shortly after we’d both left full-time jobs to venture out into the world of self-employment. We both ultimately went back to in-house positions, but the thinking is still worth sharing, IMO.

When I started my freelance practice (especially compared to the other times in my career I’ve been a freelancer), I was less concerned with trying to do a specific type of work, and more focused on building a business that attracted a particular kind of customer. I had enough confidence in my skills that I wasn’t concerned about doing the work, what I cared about was finding the clients who wanted that kind of work done.

I think there’s a spark of entrepreneurialism in most creative people. If you’re spending all day building a product, there’s probably a thought ticking over in the back of your mind saying Hey, maybe I could be spending this time building something that I have a more personal relationship with – whether that’s in terms of ownership, or direction, or area of interest, or all of those things. There might be a bit of necessary arrogance (or confidence, if you like) here too – you need to believe that the thing that you do has value, that there are people out there who will pay for you, specifically, to do something. There are lots of designers out there, you are personally bringing something special to the table.

In my case, the impetus to freelance was formulated around the idea that my employer at the time (Wealthsimple ❤️) was doing things that no other startups were really tapping into, particularly as regards their approach to product design. That doesn’t mean other companies couldn’t be doing it, just that no one was showing them how. Ah-ha! An opportunity to fill a gap in the market.

There were three big freelancing assumptions I needed to prove out:

1. Do customers actually understand what the service you’re offering is? I tested that by having three distinct productized offerings on my site. Which of those things did people specifically respond to? What made them say “Ah, this is the thing that will solve my problem”?
2. What’s the correct pricing model? Product design is generally always in demand, but what will the market bear? For me, dialling this in was generally saying a number and then offering ‘escape hatches’ if they flinched. Post-script: In retrospect, this is a dumb way to price your services. I priced per-project, rather than offering an hourly rate, which is perfectly fine. But! I should have had a well-considered costing model from day zero and turned away clients that weren’t a good fit. We live and we learn. 🙃
3. The biggest assumption of all: was I correct? Was there actually a gap out there for this business I’m trying to build? (At that point: kinda! But ultimately no, on which more further down in this post.)

Great, I’d decided to strike out on my own, how did I make that happen?

First off, extricate yourself from your current job. You probably don’t to leave a big mess for your ex-coworkers, which forces a bit of a self-assessment: what are all of the things that you were working on that now need to be successfully handed off? How can you replace yourself seamlessly on those projects, what are the essential downloads of your contextual knowledge into someone else’s brain? I consider this a professional courtesy – when you’re departing for any kind of new position, leave the place as you wished you’d found it.

And then: build the damn business. Make a big announcement on your social channels! Have lots of coffees! Keep yelling about your new gig wherever your clients hang out. This all comes down to something that has been and continues to be the largest contributor to my career: networking! Nobody’s going to make a bet on you if they don’t know you, or know what you can do. People in this industry tend to be super nice, and will absolutely signal boost you – but they need to know you exist.

More practically, how will you survive while you’re getting this thing off the ground? When I left my full time job, I was in the extremely fortunate position of having a runway for my new venture. I could run the business for ~6 months without landing any new work. Part of deciding to go independent is to be very real with yourself about your resources – how screwed are you going to be if this doesn’t work out? What’s your exit plan when and if?

But: don’t worry about the fact that your business has a built-in expiration date (or do worry constantly! up to you!). Execution is the be-all and end-all for freelancers. You need to have a demonstrable and consistent record of successes you can point to and say “I shipped that. I could do this for you too.” You’re going to be wearing a lot of hats (hype man, accountant, PM, etc.) but if the work itself isn’t up to par, you’re going to have a rough time.

So after running my own studio for a few months, what were my takeaways?

• This is the soundbyte: be patient and keep grinding. You aren’t going to go from zero to full-blast successful company in a month, but you control the factors that will allow that to happen. Keep having those coffee chats, keep pitching people on the parts of the work that you think are valuable and the problems you want to help them solve. Build your brand and shout  about it.
• Be choosy about the work you take on. There were definitely some types of projects and some industries that I just wasn’t interested in. That lack of enthusiasm will show up in your work. Be clear (to yourself) about what you want to be doing. Picking a few niches where you can make the most difference – working with a specific tool, working in a specific vertical – will allow you to be focused with your time and bandwidth.
• Don’t underestimate how much this will change the rhythm of your life as well as your career. I went from working in a busy office with my best buds to sitting alone at my kitchen table. It was lonely and isolating. I scheduled a weekly hangout with another freelancer, just so we could talk shop and feel like someone cared.

Looking back at this overview with the benefit of several years, I think my biggest takeaway was to be more honest with myself about where my strengths were. I love doing the work, I love working with a team, and while I find some aspects of running a business to be stimulating, it was an adminstrative slog that I wasn’t prepared for.

I ultimately did use my exit plan (get a job again) and I think that was the right choice for me. I might run another type of business in the future but I don’t think I’ll try to run a product design studio again – or not with the same approach, at least.

Going independent really teaches you where the rubber meets the road. There’s a lot of invisible work happening under the hood of most businesses that’s now on your shoulders, and it might turn out to be a terrible decision or the most exciting work you’ve ever done. Only one way to find out.