Baseline #24 – The Scariest Part of Going Independent

Joey Banks

Joey Banks

— 6 min read
Baseline #24 – The Scariest Part of Going Independent

Hello again! 👋 When I was deciding if going independent was the right move, I found myself wrestling with what felt like a thousand questions, each carrying both excitement and a steady dose of panic and anxiety. Could I find enough work? Was I really ready to leave the structure of a team and full-time position? What if I’m just not good enough, and this whole thing is one big mistake? Oh, and don’t get me started on the daunting but necessary task of finding healthcare.

Each question only led to more questions, which is the theme of this post: learning to manage the unknowns. I’d love to share the experience and some of the practices that have helped me over the past year of running Baseline full-time. Let’s dive in!

(Also, a very special thanks to my wife for her support and encouragement. I know for certain that I couldn’t have done this without her! ❤️)

Fear of the Unknown

I’ll forever remember that first day of this new career path. For months, it had felt as if I had been standing on the backend of a diving board, with the ladder down close by and rails to hold onto. I hadn’t decided yet, and there was still time to climb down. But on that first day, I was suddenly at the edge of the board, no longer having anything to grab and no way down if I needed it, only the option to jump.

If you’re from an area where it often snows, you may remember that special but odd feeling of a snow day. You were supposed to be somewhere, and yet you were at home. Honestly, the first few days felt exactly like this, and it was odd to imagine what meeting I might have been with my old coworkers or what task I’d be working away at as I occasionally glanced at the clock.

Going out on your own can feel incredibly isolating, as it often does feel like a perpetual snow day. And when you’re first beginning, with all those questions and unknowns circling about you, it can all feel a little overwhelming.

What’s important to remember, and something I’ve often had to tell myself, was that I’m far from the first person to try this path of independence out! Nothing that I’m doing or trying here is unique or unknown. Although it has felt, and still feels, as if I’m going against the grain in so many ways, without realizing it, this move has actually allowed me to join a huge new community of designers, developers, and creators who are all on a similar path.

You’re Not Alone

Within my first few weeks, I made it a goal to reach out to others who were or had once been independent. I had been networking and meeting with peers at adjacent companies for years, but I didn’t know many who were out on their own. Those I reached out to were incredibly generous with their time, and with every conversation, I felt less alone and less isolated because there were people who had done it all before.

Around the time I was deciding whether or not to go full-time with Baseline, my good friend Joe Fabisevich was also transitioning from a full-time role to going independent to run with his new and very wonderful app, 🔗 Plinky. On FaceTime one morning, we decided that making this a regular call at the start of each week could be helpful. The goal was to openly discuss what was top-of-mind for us—whether it related to our businesses, the challenges we were facing, or sharing unknowns, like how the heck to go about opening a Solo 401(k).

This recurring call has been so helpful for me, as it’s provided me with a structured way to keep in touch with someone else who’s also facing similar challenges and experiencing all of the highs and lows that come with going out on your own. I know that I’m incredibly fortunate to have a friend in my life like this, and if you can, meeting with someone you’re close with can make all the difference in helping you through the scariest parts and unknowns of a new career adventure.

A very big thank you to Katie Cooper, Dan Mall, Tom Genoni, Buzz Usborne, Jon Delman, and Joe Fabisevich for all of their time and guidance. 🙏

Don’t Be Afraid to Ask for Help

When considering a career transition like this, many might think that going independent means doing it all alone, since you’re, well, out on your own. But I’m here to demystify that this doesn’t have to be the case—nor should it!

As I’ve continued forward, I’ve discovered that there are so many tasks that I’m good at and, more importantly, enjoy doing. I love working in Figma and helping teams create their component libraries. I love writing documentation and teaching designers how to use the things we’re building. But do you know what I don’t love? Taxes, filing for trademarks, reading over lengthy contracts, and trying to distinguish between words like irrevocable or nonexclusive. For all of the tasks I’m unable to do or don’t feel confident enough to make the best decision, I try to turn to experts to help.

A surprising learning I’ve had is that for nearly every problem I’ve faced—or will likely face one day—there’s usually someone or an entire business dedicated to solving that issue. From CPAs and subscription-based legal firms to project management consultants and tooling or workflow resources, there’s almost always a service or resource out there that’s ready to help.

One of my biggest fears is realizing, too late, that there’s something I should have been doing all along. Now, I know that I should be paying taxes, and I promise you that I very much do, but what if there’s something else I haven’t thought of or just aren’t aware of? This fear of not knowing what I don’t know can sometimes create a massive layer of panic that’s hard for me to shake.

Getting into the habit of documenting everything as I go has been one of the most effective ways to take all those open questions and ‘what ifs’ circling in my head and place them where I can take action. Whenever I have an open question or a "huh, I wonder if I should be doing..." moment, it goes straight into a note to return to when the time is right.

Whether it means reaching out to an expert—a contract lawyer, a CPA, or even another independent friend—learning when and how to turn to others has saved me time and an immense amount of anxiety. It’s also working as another reminder that I don’t have to do it all alone and that there are people whose job it is to help should something ever come up.

A Few Final Thoughts

If there’s just one thing I’ve learned from this whole experience so far, it’s that going out on your own rarely means doing it alone. From my wife, friends, and family to previous managers, coworkers, and those I’ve been able to connect with online, I’m realizing just how much support I’ve had throughout the past year. I couldn't have made this decision and career transition without them, and I’m constantly discovering that everything that once felt unknown and daunting now feels like a natural part of the workday.

If you’re considering going independent or up against huge uncertainties, remember that all the support, resources, and answers are out there. I promise it will all become less intimidating, especially after the first big hurdle—which you will clear. It won't be long before it feels like it's just another Tuesday.

In case you missed it...

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Thank you to everyone who supports the course—I’m excited to wrap up this year with this community! 💛

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