Two Months Self-Employed

And Seven Lessons Learned


After completing several design jobs for my first client, I can definitively say that miscommunication was my most consequential mistake. I worked for weeks building a product without regular sign-offs along the way. At the end, my price was staunchly contested as the scope and complexity of my work was not communicated well enough to justify it. You absolutely must take the client through the entire journey with you.

It’s also imperative that you have structured process. I’ve been doing a bit of research into PM and Agile methodologies, and studying other designers’ ways of guiding a client. It doesn’t matter how creative or talented you are if you can’t get your client on the same page as you.


As the rest of the world has long been aware, but I have managed to neglect until now — clients have some very predictable patterns. I’ll often complain to colleagues about these issues, and they’ll just end up laughing and finishing my sentence. As I’m now aware, there are entire subreddits and memes dedicated to client problems. Ignorance aside, I’m relieved to discover that I can predict some issues ahead of time, and that others in the industry have already come up with some clever ways around them.


Drawing Restraint

This synopsis of Matthew Barney’s Drawing Restraint series always stuck with me:

The central theme of the series is the relationship between self-imposed resistance and creativity. Barney’s theory is that encumbrance can be used to strengthen an artists output, much as resistance is used by athletes to build muscle.

As much as it may seem that idle time would maximize creativity, I’ve actually found myself less creative. Something about having a rigid work schedule at a 9–5 job makes those few idle moments that you have seem all the more special. At least when you’re not overly exhausted. I believe it’s about balance. Your mind needs some kind of outside pressure to fight against. Some kind of conflict to make you want to problem-solve your way out of. But then you need those moments of decompression to let all of that pent up escapism flow. So if you are self-employed and are able to mimic the schedule of a full-time job, you may end up maximizing your creativity as a result. Just a theory. Still working on it.

Idle Hands

If you aren’t the type of person who can find work for yourself when there nothing is set in front of you, you can’t survive self-employment. I’ve spent some time pacing around, obsessing over conflicts of a previous project when I could have put it aside and focused on the next thing. And on days when I don’t have anything to do, I could have been networking, learning, building my site, or any number of things. You have to find work for yourself at all times, because that stretch of work-less-ness can go on for weeks or months before you build a strong client base. That’s a lot of wasted time. Seize every moment.

Having Foresight

Before making the move to self-employment, I was working with another independent contractor for a client who I asked for self-employment advice. She said,

Live 3 months ahead at all times. You may getting a a lot of work one month, and suddenly slow down the next. You have to be financially prepared for that at all times.

Luckily I was somewhat prepared for that, because now I know exactly what she was talking about. The chasm between one client and many clients is a difficult one to traverse. Make sure you have the strength and resources to cross it.


Ego-Less Design

Getting over your ego in design-work is huge. You’re not actually solving problems until you can step outside of your own head and feel empathy for the needs your clients and their users. The non-egotistical approach is the only approach.

Making Connections

Networking is essential to survival. And if you’re going to network, you have to be able to get past surface qualities of people you meet. As someone who has historically been pretty judgmental, this has been an uphill battle. Sometimes you have to just get over yourself and give people a chance, because everyone has something to offer — apparently.


Don’t reply to annoying or maddening emails first thing in the morning. Wait until you have woken up, exercised, meditated and thought about, written and revised it. Come to negotiations and sign-offs prepared, calm, and confident. Leave emotion at the door at all times. Stay classy.


Getting from a place of relative non-existence to a reputable status, at some point, requires comparing the success of others’ to your own lack thereof. I’m still somewhere in this awkward limbo, but when you’ve literally quite your day-job, you don’t exactly have time for that shit.


It’s a way of life.