Lessons learned from the ups and downs of building a design business for 18 years.
I’ve run a one-man freelance design business since 2001. Over the past 18 years, it’s grown into a respected, reliable six-figure career.
I’m 36 and I’ve never held a full-time job. Freelancing is all I’ve known.
It wasn’t easy and nothing happened overnight. But with self-discipline and consistent hard work, freelancing has given me a higher income, greater fulfillment, and far more flexibility than traditional employment.
Here’s how I built up my indie design business from day one.
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!)
I studied art and design at university, graduating with a BFA in digital media. It was as a student that I first got a taste of freelancing.
I advertised web design services through local flyers in popular shop windows around town. I asked professors and family members if they knew anyone who needed design help. I slowly gained local connections and small web design jobs I could work on the side. As a full-time student, this meant just a handful of hours a week on one freelance project at a time. I made $20/hour on that first job. For the next one, I increased it to $25.
I was happy for the experience and a trickle of income, and they were happy to get a cheap, local contractor they could rely on. It wasn’t much yet, but it was a taste. And I was hooked.
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.
Set yourself up in a position where you can facilitate that learning before your life depends entirely on your freelance income. Start as a student, or start in the evenings and weekends while you cling to your day job until you can make the leap.
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.
I was lucky to live in a small town with a low cost of living. The first place I rented after graduating cost a few hundred dollars a month. I had no dependents yet, and the privilege of growing slowly.
I continued building local connections but I started supplementing that with global outreach. I scoured job boards for any web design work across the country that could be done remotely. Lots of emails sent with no replies. But enough replies that I could build up my workload over the next 6 months. Suddenly I’d created a full-time job for myself.
I had to take nearly everything that came my way, and not all of it was fun or rewarding, but on each job, I learned something new. I got better at design — but more importantly — I got better at business. I was charging around $50/hr and making enough to easily support my modest lifestyle with little stress. Not bad for an early 20’s guy with little real-world work experience.
I figured out how to invoice and budget. I improved my communication processes. I learned how to organize my files.
This is also the time when I got my first long-term repeat client — a relationship that brought us steady work for many consecutive months. I learned quickly that if I wanted to make a career of this, I had to treat it like a business, not just a dude doing casual gigs.
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.
If you want to create a freelance life, plan some breathing room to grow slowly and deliberately. Build yourself a safety net so you’re brave enough to go all-in. Half-ass freelancing doesn’t work. It takes consistency and bold commitment.
Whether you’re just starting out or have already been freelancing for years, search out long-term client partnerships. It’s infinitely easier to get work from someone you already know than to build brand new connections.
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).
I had to abandon what I’d built over the past few years. But I knew I could build it again, and do it even better next time.
Some of my clients stuck with me, but most fell away. It was like starting all over again. I had zero local connections in my new home country. But I planned to change that quickly.
My one advantage was that I moved from a town of 10,000 people to a city with a population of 2 million. My opportunity for local work was bigger than ever before, and I grasped that with both hands. In fact, I decided to to go ultra-local and focus mostly on potential clients in my home city of Auckland.
Meanwhile, I upped my game on the biz-dev side too. I registered my own company and got a business bank account. I hired a local accountant and learned to better track my income and expenses. I got more serious about contracts, processes, and setting clients expectations. I knew if I could be more professional and reliable than my competition, work would find me. And it did.
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.
When you work in an online global market it’s enticing to try for international work right away. But as counter-intuitive as it is, my experience is the opposite. Focusing on local connections builds a far more trust, which leads to profitable and sustainable business in the long run.
I also learned that the more serious you get about your own business, the more quality clients you attract. The small amount of time and money necessary to register a company and get your business finances in order is 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.
Work was easy. They provided a steady stream of projects to fill at least half my time. I rarely had to worry where my next project was coming from.
The relationship grew over 8 fruitful years together and we got super comfortable working with each other. I was charging between $75-$100/hr (NZD), gradually bumping up my rates every year or so. I didn’t want to price myself out of this comfortable relationship, but I had to adjust my prices as I learned new skills and got more efficient.
Everyone was happy until suddenly they weren’t.
The company was sold and new management came in. Then out of the blue, I was told they didn’t need my services anymore. Half of my work has gone without a hint of a warning. It was a kick in the guts. An extreme business wake-up call.
Read the full story here:
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.
I learned the lesson of diversification, as I was thrust into a deep hole that only extreme networking could pull me out of.
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.
I found myself suddenly with only half the clients I needed, very few active connections, and a deep feeling of panic. How was I going to build back up to a full-time freelance design workload quickly?
The answer was to network my ass off. I approached anyone and everyone I could find locally who shared my values of quality and professionalism — people I’d be proud to partner with. I defined my dream clients, and actively pursued them. I organized countless “meet and greets” to learn what design help local businesses needed, and grow new connections.
When work was slow I spent my time building relationships, rebranding my business, and getting my client communications polished. I was also redefining my services and honing in on what made me most valuable to my clients.
I was prepping everything so when my new connections finally delivered work, I could take off like a rocket.
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.
Networking is a game of patience. Plant seeds and give them time to grow. Water them every now and again to remind them you’re still looking after them, but don’t shove anything down their throats. When the time is right, they’ll come back to you, and the relationship will grow into something great for you both.
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.
I had more variety in project sources than I’d ever had before: Multiple larger design and development agencies sub-contracting me for UX/UI design work; Medium-sized corporations, tech startups, and small businesses all contacting me directly as a result of my carefully crafted online reputation and word-of-mouth referrals.
The setback of losing my biggest clients turned into the kick in the butt I needed to get my business in a healthier, sustainable long-term position. For that, I’m very glad it happened, despite the discomfort it caused at the time. Had I stayed in that relationship for many more years it would have stifled my growth and my business would be less reliable than it is today. The forced diversification it caused me became the foundation for rapid growth and success.
Over the past few years since that recovery, I’ve landed four unique and fun projects in an industry I love (and pro-actively pursued), architecture. I’ve led massive website and web-app design projects spanning 6–12 months — high-stakes work with millions in revenue on the line — the scope of jobs that are rarely entrusted to a solo freelancer. I’ve worked in industries like travel and tourism, technology and app, design and architecture, fashion and eCommerce.
But more importantly, the quality of my clients has increased dramatically. I’m working for clients who understand communication. Who value design enough to budget adequately for it. Client’s who stress the details nearly as much as I do. Value clients, not cost clients.
When you work with great people, it almost doesn’t matter what the job is. The work becomes a joy, and the better money is just icing on the cake.
I’ve steadily raised my freelance design rates up to NZ$100/hr, then $120, $130, and now $150. Every year when I realize I’m too busy and I have to turn down a lot of work, it’s a signal that I need to be charging more. And every time I raise my rates I’m surprised that it has little impact on the number of new jobs I land. If anything, it leads to better jobs, as a high rate pre-screens out lowball clients.
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.
All of these qualities take time to build. It wasn’t until 15 years of freelancing that I felt I had started to master it. It’s only now that I’ve learned enough to feel qualified to share my knowledge and experience. Years and years of committed hard work is the path. There is no shortcut.
The future (growth)?
What’s next? That’s a difficult question.
Am I approaching a plateau in freelance business growth where the market simply won’t tolerate significant future rate increases? Probably.
Do I wish I had more diverse or passive income streams so I could move away from always trading time for money? Yes of course. But it’s not that simple.
You see, what I’ve done to date is created an awesome job for myself. I love it, but if you remove my personal time and effort, there’s no value left. If I want to grow significantly from here, I need to be more entrepreneurial and start building processes that are larger than myself.
That usually means adding more people — outsourcing or hiring.
But how do I do that when my business is based on my personal reputation? I am my business. Clients hire *me* because they want the quality of work my reputation demands. I can’t decide to outsource work and increase volume in an attempt to earn higher profits. It would take a crazy amount of training to get a contractor or employee to deliver the kind of thinking and execution my clients expect.
And I want to stay hands-on. I want to keep doing creative work, not become a people manager and salesperson. If I stay a one-person business, my extreme efficiency allows me to minimize all the other stuff so I can focus as much as possible on the creative work I’m passionate about.
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.
The freelance life has the potential to be really simple. No managers or coworkers to disagree with. Nobody telling you what work you have to do or exactly when to do it. It’s just you and your craft, in an intimate relationship you can’t find anywhere else but when working for yourself.
It can bring great clients, satisfying projects, a flexible schedule, and good work/life integration. Why mess that up adding other people to the mix?
Maybe solo freelancing is perfect just the way it is.