Illustrators, designers, photographers, writers, editors, artists and other skilled, creative solo-practitioners, this letter is for you. We’re living in tumultuous times. Like me, you’re probably feeling the negative impacts recent tech-industry developments have had on us. Add running a successful business to the mix and it all feels impossible. Will we be okay? How will we survive?

One thing I know for sure is that we need each other right now. Community is everything in times like these. It’s been an absolute game changer for me over the past 17+ years of running my design business.

Hop into my time machine with me… 

I started my business in 2008. Doing so during what is now known as The Great Recession, was an impossible idea. Or so I was told. The reactions I got when I told people I was going solo were discouraging to say the least.

Despite that, I was tired of my livelihood being at the whim of employers actively laying everyone off. Their constant attempts to convince workers that they’re “family,” only to turn around and discard them without care weren’t lost on me. Job security, in the modern era, is a mirage. Once that became clear, I realized the one person I could trust to sustain the life I wanted to live was me. So, I bet on myself and officially opened my doors for business that March. I haven’t looked back.

Image: Notes written about 3 months prior to officially opening my doors for business in 2008.

It’s a lot of work to be an artist in these times.

I’d be lying if I said it’s been easy. It hasn’t.  Running a small, one-person business requires constant adaptation. And while new technologies can be exciting, the transition into the internet age has presented many challenges to artists. 

From the outsourcing and exploitation of overseas labor to create marketplace bidding sites, to early concerns around copyright and IP protections in the 90s  which were justified with the rise of GenAI today. The latter of which has big-pocketed bullies living by sayings such as “move fast, break things” and “ask for forgiveness, not permission” building off the backs of our work without our consent.

The muck comes at us from all directions and it’s exhausting work, but we always find a way, stand up for what’s right, and fight back.

We need to remember that it’s our skills, talent, methods, quality of work, and care in everything we do to help our clients that is central to what we offer. It’s our knowledge, ingenuity, and creativity in solving problems that keeps us afloat. All things that require a great investment of time and practice to accumulate. Machines, marketplaces, or software can’t do that. No matter how you twist it. Our creativity is our power. It isn’t going anywhere. It’s ingrained in our humanity. Period. 

Community matters.

As solo-practitioners, we often run our businesses and navigate our struggles alone. The feelings that come from having to constantly defend ourselves and our work are magnified when isolated. 

I was lonely. Everyone I shared my struggles with replied with the same fix, “it’s silly to do it on your own when you can just work for someone else.” They didn’t get it. No matter how I tried. It wasn’t only about work, but my autonomy and designing a life I wanted to live.

In my search for connection, I attended a Dr. Sketchy’s Philly event, a self-labeled “debaucherous” time where artists come together to draw alt models while enjoying music and a drink or two. Needless to say, I had a great time! It was only a few hours, but everyone was so chill and easy to talk to – some were even self-employed, like me! Suddenly, everything changed when I found other people going through similar struggles. I realized this is what I was missing when I started my business back in ‘08: My people.

Image: Me co-hosting (w/The Midwives Collective) Dr. Sketchy’s Philly in 2009 • Photo by Jimmy McMillan

So, over the years, I formed my own groups. Whether via my own creations like SELF Philly or South Jersey Creatives, or through established channels as the Director of Dr. Sketchy’s Philadelphia – that’s right! The session I attended was the last. So, I reached out to Molly Crabapple, creator of Dr. Sketchy’s, and put my hat into the ring to keep it alive. It was that impactful for me! – or as the Philadelphia Freelancer’s Union Spark Leader, I made sure I found my people. And it helped. It helped tremendously.

Image: The SELF Philly crew at Indy Hall, Philadelphia, PA • July 2019

Having access to like-minded people, making a living with their creative skills, is incredibly helpful in unlocking new perspectives I hadn’t considered before. Doing it alone is possible, but why struggle when I can lean on others who get it? It’s such a relief when I’m feeling stuck to get the support or push I need. 

Community built for and by the self-employed.

Seeking out and building community around my work and art has been a life saver. And like you, I need it now more than ever. Which is why Maki and I have given Work in Progress, a community built in 2020* to address the needs of small business owners at the start of the pandemic, a makeover to speak more to the arts community.

The foundational design is strong and unchanged. It’s always been about a community of solo-business owners supporting one another. A place to tap in for support, share your work, and get insight or feedback. This iteration is a natural progression into Maki and I’s personal community of creative solo-practitioner, small business owners.  

That’s why I’m inviting you to join us at Work in Progress!

At WIP we host coworking sessions (multiple per week – scheduled and spontaneous), monthly Roundtable discussions, and member-led office-hours to help you in your journey as a creative owned small business. Your voice matters here. As a community, we’re a work in progress and always open to your ideas and input as we grow.

Interested? Learn more about our community here. Then, apply here!

Spots are limited, and we take applicants on a first come, first served basis. Our aim is to keep things comfortable, intimate, and to make space for developing real friendships. So, fill out an application and we’ll review it ASAP.

Have questions? Email us!

*Big shout-out to my good friend, Alex Hillman of Indy Hall, who was my partner in building the first iteration of Work in Progress back in 2020. Forever grateful for your collaboration, support, and friendship.