One year in, and it feels damn good.

May 1, 2024

The wild unknown.

May marks one year since I made the jump to life as a full-time independent contractor. It was a big step to leave the familiar bustle of life in an agency, but it was time for a change. After years of preparation and convincing myself I wasn’t about to make a huge mistake, I finally committed to solo life. Fast-forward a year, and here I am with a smile on my face.

If I could sum up my experience this past year in two words, they would be thankful and proud. I am thankful for all the clients, brands, collaborators, and advocates who believed in this type-obsessed hippie from some small town in Idaho. I also feel incredibly proud of all the kick-ass work we created together. These relationships and the work we crafted during this time will always be special to me.

The independent path isn’t for everyone—probably most people, if I’m being honest. That said, It wasn’t quite the post-apocalyptic wasteland that some say it is. One of the biggest things I was worried about before making the switch was staying engaged while working remotely. I love working with other creatives. I especially love digging in during concepting sessions. This is my happy place, and I had a fear that the concept and direction chops I pride myself on would somehow vaporize in a silo of loneliness from my home office. Though I knew that fear was irrational and total bullshit, I still tried to follow three simple tenets to prevent it from happening. I wanted to share these below, along with some insight on what I learned over the first year, for anyone considering the transition to solo life.

Prepare your landing.
Though there is no amount of preparation that will remove all the anxiety you feel when making the switch, there are things you can do to make the transition a little easier on yourself. Last year, I wrote a short post about the steps I took HERE. It might seem obvious, but anything you can do to get things up and running beforehand will be time well spent when you decide to flip the switch. These might include portfolio updates, contracts and legal, planning for retirement, insurance, billing systems, possible clients, and getting projects in the pipeline. The idea is that when it’s time to step on the gas, things are already running smoothly. In my case, I was working outside the standard full-time hours of my day job until I built enough business to sustain a full-time workload of my own projects as well. It was a bit of a sufferfest for the few months that I essentially worked two full-time jobs. But this workload gave me the confidence to step out with peace of mind.

Meet with other creatives every week.
Meeting with creatives, preferably creatives you don’t already know, even from disciplines other than your own, will keep you from getting in your own head and add a fresh perspective. It also radically expands your network as a bonus—for many introverted creatives, this is huge. Thank you to everyone who took the time to meet with me this past year—we had some great conversations along the way. On this same note, I also recommend going to creative conferences alone. I did this for the first time last spring at Lincoln Design’s Into the Woods Creative Conference. At first, I was worried about not having the usual pack of coworkers to mob around with for three days, but without this safety net, it encouraged me to break out and make many more connections.

Find trusted advisors and listen.
Find a couple of confidants/peers with whom you can talk through the tough stuff—things like bids, negotiations, and tricky client situations. Be very selective. This resource will keep you from getting in your own way and confirm you aren’t taking crazy pills when heading into uncharted waters. Make sure these people know their shit. Like really know their shit. For example, don’t take advice on high-end editorial design from someone who doesn’t have a proven track record in high-end editorial design.

In closing, I’m feeling proud of myself for making the leap and extremely thankful for those who had my back. I especially want to thank my badass wife for her unflinching support throughout the process. And though there are still challenges in solo land, they are my challenges. And that ownership feels damn good. I’m also happy to report that the skills I was worried about slipping during the switch not only survived but flourished after going solo. If you are a creative reading this and have questions about the unfiltered truth of going solo, please reach out.