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Writer's pictureJoel Mattern

Lessons Learned From Jumping Off a Cliff: My First 3 Months as a Business Owner and Solo Designer


Greek statue holding laptop computer and walking off a cliff

On November 1, 2023, I did something most people would consider to be quite risky: I left my stable office job as a soon-to-be senior designer at a growing insurance company celebrating its ninetieth year in business to work for myself. As I sat down at my workspace in my home office that day—the way I had done for years during the pandemic—my mind was percolating with a variety of emotions and thoughts. I wasn’t unprepared, I wasn’t scared, I wasn’t regretful; my mind that day contained unequal parts ambition, appreciation for life, humility, faith, hope, and, yes, uncertainty.


For the past nine years, I’ve operated a freelance design business while working full-time as a marketing manager and designer in the staffing and insurance industries. It was never an attempt on my part to build my own company; rather, I got tired of everyone I knew asking me to design things for them. My first client was my grandmother (check out her antiques here), and a slow-but-steady stream of print jobs soon followed. I started doing what most designers start out with: business cards, one-pagers/flyers, postcard mailers, and invitations, but soon found work from a well-known custom-exhibit supplier designing large-scale graphics for trade show display systems. This was when the little side business became real to me.


Nine years later, and I’m sitting here preparing to write a blog about the lessons I’ve learned in my first quarter-year in business for myself. Luckily, I’ve landed a diverse and colorful array of clientele and jobs and have learned how to do/be/sell things I didn’t know beans about prior to the time of this writing. Most importantly, I’ve realized what most only consider as one adage among a buffet-line of adages: when you let go and let God provide, you become stronger, better, but more humble, more grateful, more aware. And that’s what life should be all about anyway. I think I’ve finally learned how to live, at 42. Life finally makes a bit of sense.


So, what have I learned in the first 3 months as a business owner? Probably too much to include in a blog post of <3,000 words. Probably things that a lot of non-business owners already knew. Nevertheless, here are a few things that I discovered over the past few months.


  1. Loneliness is real—even for introverts and loners. Growing up, I definitely fit the mold of the aloof-loner-artist type. I had a few close friends but didn’t require their constant company to feel content. I was happy practicing my guitar and collaging cassette and cd covers out of magazines and old books. I loved drawing my toys more than actually playing with them. In short, I’ve been a designer and artist since I could hold a pencil, and it was something that always made me extremely happy to participate in. Despite my somewhat uncanny ability to exist comfortably at long intervals in solitude, I’ve found that even I come to my inevitable crossroads with loneliness. Being your own boss (arguably head servant to the client) means that you don’t report to anyone for anything, you don’t have to deal with office gossip, and you can decide whether you get the day off on a whim (conversely, weekends often cease to exist); it also means you don’t physically interact much with actual people. This is a problem no matter how much you tell yourself it isn’t. So, build in some sort of safeguard against loneliness from the start. Coworking spaces are expensive, libraries are too quiet, and Zoom meetings only dangle the forbidden fruit of connectedness tantalizingly close to our emotional core. Meet your clients in person as much as possible, take walks in busy public places, or spend your non-designing workdays at the local coffee shop where you are likely to be surrounded by flesh-and-blood human beings.

  2. It’s your job to tell the client what they need (despite what the client tells you they want). I have awesome clients (yeah, I’d still say so even if I had terrible ones, but I’m being honest), and they are all extremely competent at what they do and in the services they offer. But they don’t know design. If they did, they wouldn’t be paying me my expert fee. Time and again in this short 3-month window as a solopreneur/agency owner, I’ve gone into meetings or consultations with prospects that already have it all figured out (even though they tell me they are open to suggestions). It’s my job to take their initial vision and flesh it out using the principles of design in such a way that flaws, errors, and bad ideas are exposed and ultimately eliminated. And it always plays out this way. If I don’t always know (being the designer) what a brand should look and feel like to effortlessly convey its message and appeal to its target audience, how in the world does the client or anyone else know? It’s a best practice in my mind to collaborate with the prospect or client on what they consider to be their vision, but ultimately sell the product of sound design. Any lesser an offering is a disservice to the client and to the industry of design altogether.

  3. Creatives should read less Brené Brown and more Father Brown. I’ve been meaning to read more Chesterton, but my point still stands: what we read as creatives affects how we think as creatives. This is why I have been reading a lot more fiction and surrealist poetry as of late; thinking in pictures, imagining surreal landscapes, and listening in on two fascinating characters in scintillating dialogue with one another primes our brains to think in new, abstract, and unconventional ways. These are fundamental tools of the creative trade, so we ought to be sharpening them as often as possible. In short, read more fiction and less motivational fluff.

  4. Work as much as you see fit. Since the beginning of the new millennium, we’ve shifted our focus from rewarding workaholism to mandating time off, and I feel both are unhealthy extremes. People work, think, and interact uniquely. Some people enjoy working longer hours to feel the sense of accomplishment in a hard day’s work, which then allows them to better enjoy the personal time they feel they have earned. Others may be quicker thinkers, quicker workers, and need or desire less interaction with colleagues, and therefore can complete their work hours ahead of those around them and should feel free to take an appropriate amount of time for themselves. I no longer gauge my productivity solely on billable hours, but also on planning, managing value-added services for my clients, keeping up the books, writing and reading, and a whole slew of other activities that aren’t necessarily being billed back. These garner emotional and psychological rewards in lieu of monetary gain, which pay huge dividends in the long run.

  5. The epidemic of the double space after a period is far more widespread than I realized. And it really is.


I’ve had so many incredible experiences thus far in my short career as a business owner, and if I could sum it all up in one seed of advice for the curious, I’d have to say attitude and faith are the key drivers of success for me. Staying positive is usually only possible for me with enough faith that God is in control. This basic formula is the bedrock upon which my interactions, hopes, dreams, and business in total is built upon. In a corporate world that still feeds off the self-glorification of the professional, choosing to operate in faith, reading and writing to stimulate individuality, and embracing your values over the revenue grab aren’t easy or common practices (even among the gurus who tout these totems to the gods of industry). Staying genuine, passionate, positive, and on the cutting edge of excellence is the daily goal. Everything else is beyond our control.

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