Freelancing has created an amazing job for me, but it’s just a job. The income stops if I stop working. I’m still trading my time and attention for money. There’s no legacy, no systems, no intrinsic business value larger than myself to sell or pass on. I am my business.

Don’t get me wrong, I love it. I run an efficient operation that allows me to spend most of my time hands-on with my design craft, intimately helping wonderful clients solve their most important UX and visual challenges. I work from home, never commute, and enjoy a good life balance with my family. I can’t complain about my privileged middle-class lifestyle, but that doesn’t stop me from wondering if I can create something even greater.

Is Paul Jarvis right when he says staying small is the next big thing? Or am I missing an opportunity to be more entrepreneurial by leveraging efficient systems to scale up and build something larger than myself? It’s a dilemma that haunts me. I’ve failed to find a path to growth that works for me.

Why grow?

• I’d like to move away from always trading my time and attention for money. Diversified and more passive income streams are good.
• I’d like to create something larger than myself. A system that could keep going even when I stop working. Something with value beyond my own experience that could be sold or passed on.
• I’d like opportunities for more intimate collaboration, and to attract larger clients with more meaningful projects and higher budgets. There’s a plateau to what kind of work clients will trust to a solo freelancer, and I’m already bumping into that ceiling.

Why is it so difficult to grow beyond a business of one?

In “How to Grow Your Business Beyond Solo Freelancing,”

Marilyn Wo

succinctly outlines the same concerns I face when contemplating the prospect of growth. Here’s a quick summary of the “self-restrictions” we have to overcome:

1. I risk losing quality and reputation

I think I have to do everything myself, because who could do it to the same level of quality as I do? My clients choose me because of my unique skills and experience. If I were to hire someone else to take over my job, the quality may drop and I may risk my reputation.

2. I’m not a manager

I don’t want to spend more time training and managing other people, because that leaves less time for hands-on creative work. Any path to growth that turns me into a manager instead of a creator isn’t a path for me.

3. I’m not a salesperson

I’m an introvert and I hate doing sales. I build systems that bring clients to me so I don’t have to seek them out. I love making things, not trying to persuade potential clients to buy something. To make matters worse, if I hire people, a fatter pipeline of work is needed to keep them busy, which means even more marketing and sales.

4. I love doing creative work

I can’t see any way to grow without outsourcing some of my work. But I built this business because I love strategizing, conceiving, refining, designing, and delivering my creative solutions. I couldn’t imagine someone else doing this part of the work in my place and delivering client work that isn’t by my hand.

5. I want to stay lean and pass that value on to my clients

I’m by no means the cheapest freelance option (quite the opposite), but I’m still cheaper than a design agency. I take pride in running an efficient business and providing excellent value for my time. The complexity of hiring employees would require me to raise my rates and risk alienating a portion of my clientele.

Is there a way past these fears and self-imposed restrictions to grow a solo creative business without losing connection to my craft?

Is outsourcing or productizing repeatable tasks the answer?

Marilyn says yes. She explains how she grew from a business of one by auditing her time, recognizing repeatable, technical tasks, and delegating that less creative work to others so she could focus on the higher-value jobs and business growth. It’s allowed her to increase quantity and earn more while doing less.

But to my great disappointment, that formula doesn’t apply to my freelance business.

I spend a fraction of an hour per month creating invoices. A few hours per year updating my website. As little time as possible responding to requests for proposals and quotes. In comparison, Marilyn spent tens of hours per week on stuff like this before she created processes to handle it for her.

Farming those tasks out to a contractor or employee would earn me a few hours a month. It’s not even worth the time to find and train someone.

I spend most of my time communicating with clients to understand their needs and then crafting design solutions to satisfy them. That work is too intimately connected to break any task off and hand it over to someone else. Part of my value is my holistic approach based on a combination of breadth and design specialization. Fragmenting my process would destroy one of my unique value propositions.

Growth for me, then, must come in the form of giving up control of my creative work, and bringing someone else into the fold who can either replicate or complement my skills and quality of service.

The obvious choice would be to hire a junior designer and start my own small agency. But that means a ton of training and quality control to ensure no drop in quality. It also means more sales and marketing to drum up more work to keep this person busy.

Hiring employees and growing an agency is an all-or-nothing proposition. It’s hard to backtrack from that decision. As

Karen Banes

says in ‘Why I’ll Always Be a Solopreneur”:

“There’s amazing freedom in NOT being responsible for employees.”

I don’t think I’m ready to give up that control. Maybe I’m not an entrepreneur after all.

The artist vs. entrepreneur

Everyone wants to be an entrepreneur. Stories of instant online success and billion-dollar companies founded in a garage make for glamorous inspiration. I’ve always considered myself entrepreneurial — you have to be to start your own business of any kind, even if it’s a solo freelance operation. But I’m just now coming to terms with the fact that entrepreneurship may be incompatible with my ambitions to create.

Leela Cosgrove

’s piece, “Face It: You’re Not An Entrepreneur,” hit me like a brick. I never understood why I found growth so difficult until I read her crystal clear definitions of the difference in mindset between creators and entrepreneurs.

I couldn’t possibly explain this better myself, so here’s a direct quote from Leela’s fabulous profile of artist vs. entrepreneur.

(She uses “artist” in its broadest sense, meaning creator, craftsman, or designer. Not “fine artist.”)

Entrepreneurs are good quitters. They know when to walk away.

Artists suck at letting go. They hold on to things long past the point of them making sense, because they care so much.

Entrepreneurs primary motivation is The Win — this doesn’t have to be financial. It’s the attainment of the goal, whatever that goal is.

Artists primary motivation is The Work.

Entrepreneurs normally have several ventures running at any given time and don’t care which one takes off.

Artists may have more than one thing going on, but all of those things will typically be focused on the same outcome.

Entrepreneurs are good leaders. They find great staff and delegate.

Artists tend to get by on passion, they find it difficult to let go of the reigns.

Entrepreneurs endgame is to sell.

Artists typically haven’t thought about their endgame — because they don’t consider that the game has an end.

Entrepreneurs look for funding.

Artists are horrified by the idea of giving even a small percentage of their business to someone else.

Entrepreneurs can tell you exactly what business they’d go into next.

Artists can’t imagine being in any business other than the one they’re in.

Entrepreneurs will be involved in many businesses throughout their lives, often in completely unrelated industries.

Artists may be involved in different businesses — but always in the same space with the same end. Often, if given the choice, they’ll stay in the one company forever.

If your passion is building processes, growing teams, and selling businesses, you’re an entrepreneur.

If your passion is the subject of your work — you exist to create a particular kind of product or service — you’re an artist.

If you’re like me, you associate mostly with the artist.

You care too much about your craft to let go and delegate any of your passion to someone else. Your endgame is the process of creating great work, not building a big business payoff. Following the popular advice that everyone can and should be an entrepreneur is actually harming what matters to you most.

Entrepreneurial ambitions make logical sense for business growth, but my creative mind shoots them down.

I find myself to be 80% artist and 20% entrepreneur. And perhaps that’s the problem. If I were 100% artist, I could accept that a business of one is perfection. My dominant viewpoint says it is, but the other 20% tinkers in the background, thinking of ways to bust out some entrepreneurialism without upsetting the artist’s control. That 20% may never shut up.

I think I’m business schizophrenic. I can’t settle on a single personality and that’s why no path to growth sits well with me. Entrepreneurial ambitions make logical sense for business growth, but my creative mind shoots them down because they inevitably lead to a shift in priorities away from The Work.

How does an entrepreneurial artist grow?

I still haven’t found the perfect answer. It’s frustrating not being able to conceive a clear plan for growth when growth seems at odds with what I love most about my job. I believe there is a way to move beyond a business of one, but it will take a new perspective or unexpected opportunity I haven’t yet seen.

How can I grow without risking a drop in quality and reputation, or losing connection with my craft?

I want to remain a creator — that’s why I started this business in the first place. And business is good, so I don’t want to rock the boat. How can I grow without risking a drop in quality and reputation, or losing connection with my craft?

As a colleague suggested, “Maybe that 20% entrepreneurial itch can be scratched outside your current creative design work.” I think he’s spot on. Rather than trying to change my design business to accommodate growth, I could start a side hustle to explore other income streams and modes of self-expression, without disrupting what I’ve already built.

Or could I remain content that a business of one is as good as it gets, and growth for growth’s sake isn’t necessary?

I’ve never found advice that directly addresses this conflict. If you’ve solved this dilemma, I’m very curious to hear from you!

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