Jason Sherman

In this episode of Strap On Your Boots, I answer one of the questions I get asked most often How do you decide what to work on next Looking back on a career that spans startups, AI, filmmaking, music, writing, and entrepreneurship, I share the framework that naturally emerged over the years. I discuss why I rotate between creative and technical projects, how curiosity shapes my decisions, why timing matters just as much as the idea itself, and how AI has become an invaluable tool for challenging assumptions before I commit to building something new.

Listen to the Podcast episode here:

Get ready to strap on your boots. I’m your host, Jason Sherman, and there’s one question I get asked more than almost any other. It usually comes after someone learns a little bit about what I’ve worked on over the years. They’ll look at my background and say, “How do you decide what to work on next?”

It’s a fair question because, on paper, my career doesn’t seem to follow a straight line. I’ve built software companies, developed AI platforms, directed documentaries, written screenplays, hosted podcasts, recorded music, taught entrepreneurship, and every once in a while I’ll disappear for a few months because I’m deep into learning something completely new. From the outside, it can look like I’m bouncing from one random idea to another.

The funny thing is, it doesn’t feel random to me at all.

In fact, I don’t think I’ve ever really sat down and explained how I make those decisions because, for a long time, I wasn’t even sure there was a process. I just knew that certain projects pulled me in at certain times, and over the years I started recognizing patterns. Looking back now, I realize there actually is a framework behind it. It just isn’t one that I intentionally created. It developed naturally after spending decades moving between technology, filmmaking, writing, business, and creative work.

One thing I’ve learned about myself is that I rarely choose my next project by asking which idea has the biggest market or the highest chance of making money. Those things matter, of course. I’m not pretending they don’t. If I’m going to dedicate months or years of my life to something, I want to believe there’s an audience for it and that it has the potential to become financially successful. But that’s almost never the first question I ask.

The first question is usually much simpler.

What have I been doing for the last year?

That question probably sounds strange at first, but it’s become one of the most reliable ways for me to understand what I actually need next.

If I’ve spent a year immersed in filmmaking, my brain is usually ready for something completely different by the time the project is finished. Producing a documentary requires an enormous amount of patience. You’re researching, scheduling interviews, traveling, reviewing footage, editing, solving production problems, working with composers, narrators, graphic artists, colorists, sound designers, and dozens of other moving pieces. It’s incredibly rewarding work, but it’s also emotionally and creatively demanding in a very specific way.

When I finally finish a project like that, I don’t immediately start thinking about another movie.

I usually find myself wanting to solve problems instead of telling stories.

That’s often when software starts pulling me back in.

Programming exercises a completely different part of my brain. Instead of thinking about emotion, pacing, dialogue, and visual storytelling, I’m thinking about systems, workflows, user experience, architecture, and how hundreds of individual decisions fit together into something people can actually use. It’s still creative work, but the creativity feels different. Rather than asking how an audience will experience a scene, I’m asking how a customer will experience a product.

Then something interesting happens.

After spending months designing software, thinking through technical problems, and making logical decisions all day, I eventually start missing storytelling again.

I’ll have an idea for a screenplay.

Or a documentary.

Or maybe I’ll sit down with my violin and start recording music because I haven’t done it in a while.

That’s when I realized I wasn’t changing projects because I had become bored. I was changing projects because each discipline was giving my brain something the others couldn’t.

I think that’s an important distinction.

Boredom usually comes from losing interest.

What I’m describing is more like creative balance.

I’ve found that if I spend too long inside any one discipline, even one that I genuinely enjoy, I eventually start craving a different kind of challenge. It’s almost like different parts of my brain need their own form of exercise. Storytelling stretches one set of muscles. Programming stretches another. Music forces me to think differently than either of those. Even learning a new language changes the way I process ideas because it requires paying attention to entirely different patterns.

For years I thought these interests were competing with one another.

Now I think they’re helping one another.

When I write software, I become better at organizing complex systems, and that skill unexpectedly helps me structure films and documentaries. When I spend months writing dialogue, I become more aware of how people naturally communicate, and that carries over into product design because good software is ultimately another form of communication. Even podcasting has influenced the way I think because speaking through ideas out loud forces me to organize my thoughts differently than writing does.

None of those connections were obvious while I was living through them.

I only started noticing them after enough years had passed that I could look back and see how each project quietly prepared me for the next one.

I think that’s one reason I never worry too much when someone tells me my career seems scattered.

From the outside, I understand why it looks that way.

From the inside, it feels remarkably connected.

Every project leaves something behind that I end up using later, even if I don’t realize it at the time. Sometimes it’s a technical skill. Sometimes it’s a creative technique. Sometimes it’s simply a better understanding of how people think or communicate. Those lessons have a way of resurfacing years later in places I never would’ve expected.

That’s probably why I’ve stopped thinking about careers as a straight line.

Most people imagine a career as climbing a ladder, where every step takes you higher than the last one. My experience has been much closer to exploring a landscape. I’ll spend time in one area until I feel like I’ve learned what I can, then I’ll head in another direction that looks completely unrelated. Eventually I discover that the two places are connected in ways I couldn’t see when I first started walking.

Looking back, I don’t think I’ve ever truly abandoned one interest for another.

I’ve simply been adding tools to the same toolbox.

And that realization changed the way I think about choosing my next project because I no longer feel pressure to pick the one thing I’ll do forever. I’m simply trying to choose the challenge that makes the most sense for where I am today, knowing that whatever I learn from it will almost certainly find its way into something I build tomorrow.

Another factor that plays a huge role in deciding what I work on is something much less exciting than inspiration.

It’s time.

I think a lot of people imagine that every new idea deserves to become a project immediately. I used to think that way too, at least to some extent. I’d get excited about something, and there was this urge to start building it right away before the excitement disappeared.

Over the years I’ve learned that’s usually a mistake.

Not because the idea isn’t good, but because timing matters just as much as the idea itself.

Every project asks for a different level of commitment. Writing a screenplay is very different from producing a feature documentary. Building a software platform is a completely different commitment than recording a piece of music. Some projects can realistically be completed in a month or two. Others can quietly consume the next several years of your life if you’re not careful.

That means I can’t evaluate an idea in isolation.

I have to evaluate it against the reality of my calendar.

If I know I’m waiting for funding, or I’m between major software releases, or I’m waiting to hear back from film festivals, that window of time naturally influences what makes sense to pursue next. Sometimes I know I have six or eight weeks where I can dedicate myself almost entirely to something new. During that period I might decide to write a screenplay, compose music, redesign a website, or finally learn a skill I’ve been putting off.

At other times, I know a much larger commitment is right around the corner. Maybe we’re about to begin building a new platform. Maybe a documentary is entering production. Maybe an AI product is about to consume every available hour of my day. When I know that’s coming, I’m much less likely to start another project that deserves the same level of attention.

I’ve become comfortable admitting that some ideas simply belong to another season of my life.

That was surprisingly difficult for me to learn.

When you’re naturally curious, every interesting idea feels urgent. You start worrying that if you don’t build it immediately, someone else will. Or maybe you’ll lose enthusiasm. Or maybe you’ll forget about it entirely.

The reality has been almost the opposite.

Some of my best ideas became stronger because I didn’t touch them for months.

Instead of rushing into development, I started having conversations with them.

That probably sounds strange, but it’s honestly the best way I can describe it.

When I have an idea today, my first instinct usually isn’t to start building. My first instinct is to start asking questions.

I’ll sit down with ChatGPT, Claude, Gemini, or another AI model and spend an hour simply exploring the concept. I’ll ask it to challenge my assumptions. I’ll ask it why the idea might fail. I’ll ask whether similar products already exist, what weaknesses it sees, what features are missing, and whether I’m solving a real problem or just creating something because I personally find it interesting.

Sometimes those conversations completely change my opinion.

I’ve gone into them convinced I had an incredible idea, only to realize thirty minutes later that I was solving a problem almost nobody actually has.

Other times the exact opposite happens.

I’ll begin with a rough concept that feels half-developed, and by the end of the conversation I’ve uncovered opportunities I hadn’t considered at all. The idea becomes clearer because someone, or in this case something, kept asking questions I hadn’t thought to ask myself.

I don’t see AI as replacing my creativity.

I see it as accelerating my thinking.

It’s like having a room full of people who are willing to play devil’s advocate without taking it personally.

That alone has probably saved me months of building products that weren’t ready yet.

Once I feel like an idea survives those early conversations, I still don’t immediately start developing it.

Instead, I begin documenting it.

This is another habit that has evolved naturally over time.

Years ago, I might have written a few notes in a notebook and hoped I’d remember them later. Now I’ll often create an entire folder for an idea that may never become a real project.

Inside that folder I’ll start collecting everything I can think of. Maybe it’s a product specification. Maybe it’s a rough business model. Maybe it’s sketches of the interface or notes about potential customers. Sometimes I’ll write marketing copy before the product even exists because I’m trying to understand who I’d be talking to. Other times I’ll map out the technical architecture just to see whether the idea actually makes sense.

The interesting thing is that none of this feels like wasted effort.

Even if I never build the product, I’ve clarified my thinking.

I’ve learned something.

I’ve tested assumptions without spending months writing code.

And if I eventually decide the timing is right, I’m not beginning with a blank page anymore.

I’m picking up a project that’s already had weeks or months of quiet thought invested in it.

I’ve accumulated a surprising number of folders like that over the years.

I have folders full of startup ideas, screenplays, music concepts, documentary or film concepts, game ideas, even physical products. Some are products that may never exist.

Every once in a while I’ll open one after six months or even a year, and I’ll have a completely different perspective than I did when I first created it. Sometimes I’ll realize the idea wasn’t nearly as good as I thought. Other times I’ll immediately recognize that it’s much better than I gave it credit for because I’ve learned enough in the meantime to finally understand how to make it work.

I’ve stopped thinking of those folders as unfinished projects.

They’re more like conversations that I’m free to continue whenever the timing makes sense.

That shift has removed a tremendous amount of pressure from my creative life because I no longer feel like every good idea demands immediate action. Some ideas are meant to be explored. Some are meant to wait. And occasionally, the ones that wait the longest become the ones that are ultimately worth building.

As I’ve gotten older, I’ve also realized that I don’t measure the value of a project the same way I used to. Earlier in my career, I probably spent too much time wondering whether something could become the next big thing. I think that’s a pretty common mindset among entrepreneurs because we’re constantly exposed to stories about companies that grew into billion-dollar businesses. Those stories are inspiring, but they can also quietly influence the way you evaluate your own ideas.

These days, I’m much more interested in whether a project is going to teach me something I don’t already know.

That’s become one of the most important filters I have.

Whenever I start thinking seriously about a new idea, I ask myself whether I’m simply repeating something I’ve already done or whether this project is going to force me to grow in some meaningful way. It doesn’t have to involve learning an entirely new profession. Sometimes it’s just a chance to improve a skill I’ve already developed. Other times it’s an opportunity to step into unfamiliar territory where I know I’m going to make mistakes, and honestly, that’s usually where the biggest growth happens.

When I decided to make documentaries, I had no idea how much I’d have to learn. It wasn’t just about operating cameras or conducting interviews. I had to become better at storytelling, understand pacing, learn how to organize hundreds of hours of footage, work with composers, narrators, and editors, and figure out how to keep a project moving over several years. There were countless moments where I felt completely out of my depth, but looking back, those experiences made me a better communicator in every part of my career.

The same thing happened with software.

Every platform I’ve built has introduced challenges that the previous one didn’t. Technology changes so quickly that you never really reach a point where you know everything. There’s always a new framework, a different way of thinking about user experience, advances in artificial intelligence, or improvements in development tools. At first that felt overwhelming. Now I’ve come to appreciate it because it means I always have something new to learn.

That curiosity has become one of the few constants throughout my career.

When people look at my résumé, they sometimes assume I’ve changed directions over and over again. I understand why it looks that way, but from my perspective I’ve simply been following my curiosity. The projects changed because the questions I wanted to answer changed. One period of my life was about understanding startups. Another was about learning filmmaking. More recently I’ve become fascinated by artificial intelligence because I genuinely believe it’s one of the most important technological shifts we’ll experience in our lifetime.

If I lose that curiosity, I think I’d lose a big part of what motivates me.

I also think curiosity is what keeps burnout from becoming permanent.

Everyone gets tired.

Everyone reaches a point where they need a break.

The mistake is assuming that a break always means doing nothing.

For me, a break often means working on something completely different.

Writing a screenplay after months of software development doesn’t feel like more work. It feels refreshing because I’m solving a different kind of problem. The same thing happens when I spend time recording music after a long filmmaking project or when I dive into a new technology after months of writing. The work itself is still demanding, but the mental shift makes it feel energizing instead of exhausting.

That’s another reason I don’t worry too much about having multiple interests.

For years I thought I needed to narrow my focus because that’s the advice you hear so often. People tell you to specialize, pick one thing, and become known for it. There’s certainly value in becoming exceptionally good at a particular skill, and I have a lot of respect for people who’ve devoted their lives to mastering a single discipline.

I just eventually realized that’s not how I’m wired.

I’ve accepted that I’m probably always going to be interested in technology, filmmaking, writing, entrepreneurship, music, and whatever new field captures my attention five years from now. Instead of seeing those interests as distractions, I’ve started viewing them as different expressions of the same personality. They’re all driven by the same desire to create something meaningful, solve interesting problems, and keep learning.

Maybe that’s the answer I’ve been looking for all along.

When people ask me how I decide what to work on next, they’re usually expecting me to describe some complicated prioritization system or productivity framework.

The truth is much simpler.

I pay attention to what excites me, but I also pay attention to what challenges me. I look at the amount of time I realistically have available, think about the skills I’ve been using recently, and ask myself whether another project might exercise a different part of my brain. If an idea survives all of those questions, I’ll spend time developing it on paper before I ever commit to building it. Sometimes that process confirms it’s worth pursuing. Other times it tells me to leave it in a folder for another day.

I’ve become comfortable with both outcomes.

Looking back, I don’t think any of the projects I’ve worked on have been wasted, even the ones that never became successful businesses or finished products. Every experience has contributed something to the next chapter. A startup taught me lessons that helped me manage a film production. Filmmaking made me better at telling stories about technology. Podcasting improved the way I communicate ideas. Artificial intelligence has changed the way I brainstorm, research, and solve problems. Each project has quietly influenced the next one in ways I couldn’t have predicted when I started.

That’s probably why I don’t spend much time worrying about whether I’m making the perfect decision.

There probably isn’t one.

There are simply opportunities that make sense for where I am today, and others that might make more sense a year from now. The challenge isn’t finding the one project that’s guaranteed to be successful. The challenge is choosing something that keeps me engaged enough to keep showing up, teaches me something I’ll carry into the future, and feels meaningful enough that I’d still enjoy the work even if nobody else ever knew I was doing it.

When I look back over the last twenty-five years, that’s really been the thread connecting everything I’ve built. The technologies have changed. The industries have changed. The projects have certainly changed. What hasn’t changed is the excitement of learning something new, creating something that didn’t exist before, and wondering where that experience might lead me next. That’s what keeps me moving forward, and I have a feeling it’s the same question I’ll still be asking myself many years from now when someone inevitably says, “So… what are you working on next?”