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How I Grew My Freelance Business from $0 to Six Figures

Lessons learned from the ups and downs of building a design business for 18 years.

The slow learn (getting my feet wet)

As a teenager, back in 1990’s small-town Iowa, I did the usual childhood jobs like neighborhood lawnmowing. But I was never interested in the minimum wage employment path. No fast food or retail jobs for me. Somehow I knew I’d be more entrepreneurial. (Thanks parents!)

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What I learned

Freelancing works best when you can start small and prioritize learning over earning. Unless you have a great mentor, you need heaps of experience to discover your path by trial and error. Just because you think you’re pretty good at your craft, that doesn’t mean you’ve got a clue how to run a business.

The build-up (time to organize for growth)

I graduated from university and then “what next?”. Still not interested in hunting for a job when I could create my own business instead. The freelance thing worked small-scale as a student. Why not grow it into a full-time gig? It was worth a shot.

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What I learned

Most business success requires some risk and bravery. Freelancing is no different. My privilege of living a low-cost lifestyle allowed me to take the risk of going hard for my goal of full-time freelancing without the pressing demand for a big salary right away. If it failed, I could still eat. If it failed, I could always find a regular job.

The big move (and local rebuild)

After getting really settled in my freelance life and committing to it full-time, I had a drastic life change. I decided to move the other side of the world, from Iowa to New Zealand, with my kiwi girlfriend (now wife).

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What I learned

Change happens. It can be scary but almost anything can be overcome. Moving set my business back a year or two, but that’s life, and it was well worth it.

The comfort zone (got dangerously comfy)

After slowly building new local New Zealand connections I landed a regular role as a contract designer for a nearby web development shop. I did ALL of their design work, acting almost like their sole design employee, yet I remained a remote contractor with a lot of autonomy.

I fell off a freelance cliff, but built a parachute before I hit the ground.
Or, the danger of having too many eggs in one basket, and how to bounce back when that basket disappears.

What I learned

Getting too comfortable makes you stagnant. In retrospect, aligning myself so closely with one client for too long stifled my growth, freedom, and earning potential. Having too many eggs in one basket proved a risk that could (and did!) easily backfire.

The extreme networking (a foundation for growth)

The eight previous comfy years made me neglect business development. My networking, marketing, and personal branding all slumped because new projects came too easily. When things are going good it’s easy to forget that nothing lasts, and I made the mistake of not using the good time to prepare for what would come next.

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What I learned

You never know when one casual connection can turn into gold. Many of the people I met during that year were wildly enthusiastic about working with me, but then nothing came of it. Others sat quite for one, two, or more years and then contacted me out of the blue with exciting new projects.

The liftoff (finally freedom & success)

My freelance business recovery was slower than I’d have liked, but not sluggish enough that I couldn’t stay afloat. Eventually, all the new connections I made during my time of extreme networking started paying dividends, and in a few quick years my business took off.

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What I learned

The top echelon of freelance success is defined by a few simple things: expertise, learning, reputation, professionalism, and efficiency. If you consistently do great work (while continuing to learn so it gets better and better) and build a strong reputation for it, your name will get out there. If you act like a reliable professional and flawless communicator, clients will love working with you and come back for more. And if you hone your processes and learn to work quickly and efficiently, you’ll deliver great value to your clients, allowing you to maximize your rates and profitability.

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The future (growth)?

What’s next? That’s a difficult question.

The freelance business growth dilemma
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What I’m still learning

Maybe growth for the sake of growth isn’t necessary? Maybe it’s OK that I stay a successful one-person company forever. Despite what business gurus tell you, not everyone has to be an entrepreneur.


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