A couple of days ago, I had the privilege of hanging out with the delightful Femke van Schoonhoven - digital designer, freelancer, and lover of side projects - during her short layover in Denver. We spent the day wandering around the city, talking about everything from her own repositioning to the cost of transporting pets back to New Zealand (turns out, it's a lot).

Eventually, though, the conversation turned to my recent struggles with burnout, and quitting my job to work independently.

"I've been wanting to start doing some design and UX freelancing," I told her, "but I'm just not sure if I'm going down the right path. It just feels like I'm stuck at only about 70 or 80 percent confidence in what I want to do."

"Wow," Fem replied - "that's pretty good."

"If you're feeling 70 or 80 percent confident in anything you're doing," she said, "then you're doing pretty well."

The conversation moved on, but her point stuck with me. Dealing with unknowns has always been a struggle for me. Whether it's small things, like dinner plans changing at the last minute, or bigger decisions around finding a clear path forward with my work, I've always been the kind of person that carefully considers all the options before making a move.

Facing decisions like this - where the outcome can’t be predicted, and the consequences of making a bad decision seem much more dire - throws me for a loop. I get so caught up trying to understand what might happen, that it's way too easy to stall out and end up not making a decision at all.

That's exactly why Fem's point hit so close to home. Now that the feelings of burnout are wearing off, the emotional decisions - to quit my job, to start blogging, to work independently - are giving way to rational ones, about what kind of business I want to create, and the concrete things I need to do to get there. Those emotions that were driving me to make decisions under unknown circumstances are wearing thin, and it's becoming easy to slip into the relative comfort of not making decisions at all.

Comfort is the enemy of progress.

My conversation with Fem helped remind me that to keep moving forward, I need to break out of my comfort zone, and start making some decisions - even if I can’t predict how they’ll turn out.

Get comfortable with being uncomfortable

A huge part of being a successful freelancer, entrepreneur, or independent is being able to confidently make decisions, even in conditions of extreme uncertainty. This isn't something that comes easily, and I think it's also something that takes practice. It’s also something that never really goes away, even for an experienced freelancer like Femke.

The truth is, decisions and their outcomes are never as black and white as they seem. There's no right or wrong - only better or worse. I can't think of a single entrepreneur that made perfect decisions the first time, every time, on their way to becoming successful. In fact, even if you make the best possible decision given the circumstances, things tend to change so quickly that the outcome will almost never be what you expect.

Unfortunately, most people’s idea of entrepreneurship is that you’ll have some sort of “lightning bolt moment” and suddenly the clouds will part and the right path will open up before you. In reality, though, it takes a lot of testing, experimentation, and iteration to find the right path.

Your first steps will always be uncertain. The sooner you make a move, the sooner you start learning what works and what doesn’t.

Get busy, and maintain the momentum

I've written about maintaining momentum before, and overcoming self-doubt by making a habit of action. Then, in a fine display of imperfection, I stopped blogging for two months. I know, I know.

Turns out Isaac Newton was right, though - when you're moving, it's much easier to keep moving, and when you stop, it's much harder to get going again. If you're like me - trying to move from a career where you're never really responsible for maintaining your own momentum, to working for yourself - staying motivated without external deadlines and accountability is hard. I've found that keeping myself busy with writing, designing, and creating stops me from overthinking decisions and all the possible outcomes, and makes it much easier to keep moving.

Fem's advice here was simple. "Don't try and figure everything out up front," she recommended. "Just get started. You’ll learn so much more by iterating in public than by shooting in the dark. Plus, if you screw up, no-one's going to remember your failures anyway."

Find a way to be held accountable

This is the big one for me. As an introvert, it's a huge struggle to reach out to people I respect, like Fem, to talk to them about what I'm dealing with, and to ask for help.

One thing I have discovered, though, is that writing is a bigger help than I expected. It's a great way to collect my thoughts in a structured format, and often just the process of putting them down on paper helps me see how to move forward.

It's kind of a catch-22, though - if I'm not writing and creating, I overthink, and when I'm overthinking, I'm not able to create. That's why it's so important to find people who can help break the cycle, and push you to keep moving and creating, even if you don't feel 100% confident.

Trying to keep moving on your own is hard - it's just too easy to stop pushing yourself. Like Fem says, surrounding yourself with people who truly want to help you succeed is the best path to success.

So today I'm making some commitments to you guys to start putting some of this into action.

  • I'm going to start writing a newsletter for my audience every week. Even if my writing isn't as good as I want it to be, even if I can't give advice on freelancing or being a great entrepreneur, I'm going to keep writing and keep moving forward. I need you all to help me stay accountable, though - let me know what you want me to write about, or what you're struggling with, and I'll do my best to help however I can.
  • I'm launching my freelance business, Letterbox Lane, tomorrow. No more trying to make all the right decisions the first time - I'd rather start small and learn as I go. I want to help small businesses and startups build profitable digital products and websites by designing elegant, intuitive, and enjoyable user experiences. Even with the end-of-year slowdown, my goal is to find my first client by the end of this year. Is this what I'll end up doing forever? Probably not. But getting started is more important than getting it right the first time.
  • I'm going to make an effort to break out of my comfort zone and meet people. Hanging out with Femke was a great reminder that I really can't solve any of these problems on my own. Most of my friends are engineers and 9-5ers, so I'm making a conscious effort to meet people that push me to be better.

The one thing I know for certain is that uncertainty is here to stay. Not knowing whether you're making the right call is simply not a good reason to hold off on making decisions. Femke's right - 70 or 80 percent confidence is more than enough to move forward, even though it may not feel like it. The sooner I can find ways of dealing with it and continuing to move forward, the better.

Luckily for you, you've joined the ride - hopefully I can help you out along the way.