Over the past 18 months, I’ve been trying on a new role and persona as the founder of Build First, an AI learning lab I officially launched last summer.

While you might think that learning new technology or figuring out how to make money would have been the harder part, for me, the struggle has actually been something much more foundational: Rewiring my programming from “order muppet” to “chaos muppet.”

I imagine many of us who have worked in highly structured operational roles may relate to this feeling, so I decided to write this post to share more about it. For the vast majority of my career, I was the “responsible” one – the structured and organized person who helped visionary leaders structure their thoughts, organize their project plans, and get shit down. This took me very far for a very long time. I could have kept doing it forever. Except, there was just one problem: I wanted to start shit myself, too.

As it turns out, when you start something brand new, the world doesn’t care about perfectly groomed spreadsheets and details. They want to see ideas and movement. So for the past year, I’ve been teaching myself how to resist the urge to spend my free time “cleaning up” after myself, and instead edge myself toward a more uncertain path of what new thing might come next.

Every now and then I look over my shoulder and shudder at the metaphorical mess I feel like I’m leaving behind in my own kitchen. But then I remind myself: Innovating requires us all to find our inner chaos muppet.

The muppet theory of business goes a little like this:

• Order Muppets keep things organized and the wheels turning (think: Kermit the Frog, or Bert)

• Chaos Muppets break the rules, make things up as they go, and create pure energy (ie: Miss Piggy or Ernie)

The best businesses, teams, partnerships, and stories need a little bit of both. This is what makes shows like The Book of Mormon so brilliant and relatable. Elder Price (played by Andrew Rannells) is the classic order muppet, whereas Elder Cunningham (aka Josh Gad) breaks all the rules and makes things up as he goes.

You might have a “default muppet state” in life, but “founder mode” requires a little of both. Which means, if you’re setting off on your own (as more of us seem to be doing these days), you need to not only recognize your inner muppet, but actively find ways to counter-balance it.

As it turns out, this is easier said than done. There are some weeks that are far too orderly and I over-correct into the operational details of my work, and there are other weeks where I float above it all like a balloon, completely untethered to reality, with no one to hold the string.

I’ve stayed at hacker houses at crypto conferences, I’ve hosted AI hackathons in castles in foreign countries, and I’ve even gone mini-viral by live-blogging a near-death experience from a hospital. I’m still not pure chaos, but I’m learning how to live with structured messes. Here are three things I recommend:

One of the things that really helped me edge out of my “order muppet” ways was spending more time with more chaotic people (in the best way possible!). As it turns out, chaos muppets have a ton of fun, think outside the box, and aren’t afraid to try new things. Over several years of spending time among a lot of other founders, I learned a few things: Failure does not equal death, pivoting is totally natural, and creative collaborations are key to success. Seeing how natural-born “chaos muppets” adapted easily to changes in market dynamics made it safer for me to recognize the pattern in myself. I can now identify my own creative cycles in a much more nuanced way.

Ninety-nine percent of the things I’m not doing aren’t due to lack of interest but due to fear of failure. Ask yourself, “What am I avoiding because I’m scared?” Then take the smallest step toward that thing. Unfortunately for me, I am very good at avoiding things that feel scary (often, by keeping myself too busy). If you find that you are spending more time rationalizing something vs. just doing it, you might be stuck in a loop, too. To reach escape velocity, you have to get comfortable being uncomfortable. I’ve been pushing myself toward uncomfortable things on a near-daily basis for the past couple of years. It’s a habit, which means it takes practice.

I’ve always been envious of people who have tons of free time to “riff” on ideas just for fun. When I’m in an overly “order muppet” state of mind, I tell myself I don’t have time for fun or to play. But this is a massive problem, because playing invites creativity. By lowering the bar for “bad ideas only” this helps me not take myself too seriously, even if the idea is truly far-fetched, like my latest: Running a hackathon on an airplane.

Over the past year, I’ve pivoted three times. I’ve started and shelved projects that I loved. I made friends, I lost them. I lost money, I made some of it back. And then I started to find clients who wanted to buy the same thing – or packages of that thing. I made some software to help me manage it all, but I burned myself out trying to run all of the operations, delivery, and sales on my own. In other words, I’ve successfully flipped the script. But it’s no fun to live in constant free fall. Here are three ways to add a bit more order among the chaos.

Late last year, I had a really stressful moment in my business where I needed advice from a lot of people in my network. While people were more than happy to help, I also heard one thing loud and clear: “If you want help during times of crisis, you need to keep us posted during the normal times too.” So in December, I started sending out monthly Build First updates to about 40 people in my close network. Most of these are fellow founder friends who have “been there, done that” or investors who have better pattern recognition than I do about state changes in founder mode.

This has been an incredibly helpful exercise for me. For the first time in years, I set monthly revenue targets for myself, and I report out on them. I share my wins and my losses, and the forcing function of sitting down monthly to organize my thoughts is often more helpful than any individual response. I also feel much better knowing that there are at least a few other people out there who have some awareness about the state of my play in my chaotic world.

At the beginning of this year, I was feeling incredibly underwater because while I had finally started to close regular business across a healthy client list, I was getting completely stuck in operations, logistics, invoicing, and contract management. It was really hard for me to get excited about Build First “out there” while I was drowning in my own paperwork and bookkeeping (alone) “in here.”

Luckily for me, I found that while doing the day-to-day logistics was starting to feel tedious, building AI agents to help me do that work kept it interesting. I leaned into my own advice to others and created an end-to-end business operating system for myself, linked up to my email, calendar, call transcripts, and Google Drive. Today, I am at about a 3-click proposal, 2-click contract writer, and 1-click invoice generator. Now I get to teach other people how to do that, too. A win-win. If you can’t find ways to get yourself excited for the tedious work, it’ll be really hard to stay on top of it long term. At least until I can afford more human help to get me to the next level.

Build in structured windows for “cleanup mode.”
Now that I have an actual business to run, I realized I needed to start acting like Build First was my job, and not just my chaotic side project. So this year I started to bring back order into my week. Mondays are for invoicing and contracts, Fridays are for creative fresh builds, Tuesdays - Thursdays are for client work, business development, and pipeline management. While this isn’t a perfect fit every week, it helps me to have a relative schedule in mind that includes some of the routine “maintenance” work.

One of the most powerful things I’ve learned from enmeshing myself among such a wide variety of order muppets and chaos muppets in my career is also one of the simplest: “Have fun.”

I was initially pretty shocked to hear Gary Vaynerchuk (founder of Vayner Media, among others) say this on an Instagram reel with Tara Keeney. He’s the guy who built a business empire around his own brand of being Gary V. How could he not consider that real life?

But the way he concludes is this: It’s all a game. If you can’t distance yourself enough to recognize that the game of business is just like any other game, you’ll never be able to objectively look at your own situation and make the right calls. When you play games, you need to have fun. When you’re having fun, you think more creatively, and you’re more open to new possibilities and ideas.

As it turns out, it’s really hard to have fun when you’re worried about whether you can pay your bills. It’s really hard to make clear decisions when you can’t cover your own rent (or when it’s raining in your kitchen). I truly empathize with anyone who is in this camp right now. I’ve had some seriously low moments in the last year as I’ve begun to figure this out for myself, and I’ve also seen many friends get stuck along the way, opting to go back to full-time work (at least for the short term).

While it’s tempting to call it, wait for a rescue, or blame it on external factors, I think the real wins come from acknowledging that each of us has our own inner “order muppet” and “chaos muppet” waiting to come out. We just need to know which one to call up at the right moments to make sure the show keeps playing.