Can Meaning Really Pay the Bills?

The last time my wife and I argued about money, I don’t even remember what started it.

“Argued” isn’t really the right word. We almost never speak to each other in anger. But there are tense moments, and they usually creep in over something trivial — like how much I spent at Del Taco last month — or something very much not trivial, like the cost of insurance.

Those moments settle in like a pressure-laden fog. Eventually, the conversation stops being about money at all. It becomes about fear. About the weight of building a life that matters while trying to make enough to keep the whole thing from falling apart.

I’ve always worked jobs where the bills got paid — almost always on time. The bank account has often hovered around zero. I have a habit of landing in roles where there’s a mountain of problems to solve, and my hero complex kicks in. I solve them, usually. But the work has often drained me. Some days were fine. Some, even fascinating. But many days, I felt like I was spending the best hours of my life proving my worth in rooms where the compensation didn’t match the sacrifices.

Now I’m trying something different — a little crazy. I’m building two companies. The work is mine. It’s challenging, often enjoyable. Sometimes I feel like a fraud. But I still find meaning in it.

Meaning, unfortunately, doesn’t generate revenue.

There’s no paycheck attached to “fulfilling.” And it doesn’t do much to soothe the tension that rises when another bill hits and another proposal doesn’t close.

We’re not in crisis, thankfully. But we’re not coasting either.

There’s a question I keep coming back to — because I like to ruminate and pre-ruminate: Can I really build something that feeds my soul and pays the bills? Or is that just a story I tell myself because I’m tired of trading time for money in jobs that don’t reflect who I want to be?

I know it’s a privilege to even ask. Most people work because they have to — because housing, food, and clothes don’t appear from vision boards or personal branding.

And I’m not trying to opt out. Not even close. I want to be someone who carries what’s mine to carry. As long as I’m capable, I couldn’t live with myself if I asked society to step in and provide for my family. I pay my taxes. I try to give to others when I can. I don’t expect a free pass. I just want to find a way through that doesn’t bury the best parts of me under obligation, overwork, and the ever-present pull to prove something.

Most days, I believe the tradeoff is worth it. Some days, I wonder if I’ve just traded one kind of stress for another.

When my wife and I talk about money, we both bring our stories to the table. We don’t fight often — almost never — but finances have a way of poking at the parts of ourselves we’d rather ignore. For her, it’s about safety. For me, it’s about control — or maybe the fear of losing it. We want the same thing: a life that’s honest and stable and sustainable. But the path is paved with late nights, early mornings, and spreadsheets that never seem to balance quite the way I want them to.

“Think and grow rich” might be one of the dumbest things anyone has ever said.

Not to get too nerdy, but there’s a scene in Interstellar I keep thinking about. They land on a water planet orbiting Gargantua and realize — too late — that what they thought were mountains are actually waves. Massive, sudden, and impossible to outrun. That’s what the financial side of self-employment feels like sometimes. You think you’re walking into something manageable, and then a few unexpected expenses crash through it all.

But I chose this.

And I’d choose it again.

Even though I’m not sleeping better or worrying less, I care more about what I’m building. I care about doing work that challenges me and draws on the skills I’ve spent two and a half decades building. This is about making something that feels like it matters. That kind of work doesn’t guarantee success, but it offers something I never found in my last few jobs: the feeling that I’m not running the wrong race. That I’m not waiting for a weekend to feel like myself again.

Years ago, I met a young family living on a coffee plantation in Guatemala. Their home was built with tarps and corrugated tin. They had almost nothing — but they radiated something I couldn’t name at the time. It wasn’t peace. Not really. It wasn’t job satisfaction. Maybe it was alignment. They knew who they were. They weren’t proving their value through performance or motion. They weren’t chasing the version of success I’ve been chasing for 25 years.

But back here, I live in a world full of expectations. I live in an American suburb. With car payments, wedding plans, health insurance, and birthday parties. I live in a house full of growing kids who are learning what matters by watching what I prioritize.

So I show up. That part hasn’t changed.

I pitch. I write. I build. I try.

And I wonder: can I do this in a way that gives us what we need — and maybe a little of what we want — without sacrificing the version of me I like the most?

I’m still figuring it out. There are weeks where it all feels like it’s clicking. Projects move forward. Clients say yes. A little money rolls in. And then I fly across the country to pitch a product I believe in to people who love it but don’t fund it. Suddenly, the calendar is thin, and the bank account isn’t what I hoped.

I don’t think there’s a big answer. At least not yet. Maybe ever.

What I’m learning is that the real goal might not be balance. It might be resilience. It might be choosing to get up every morning and remind myself that the work I’m doing matters, even when it’s hard to prove. That my value isn’t my revenue. That I can build something whole without having to chase success the way I used to.

I used to dream about early retirement. About building an empire. These days, I think I just want to stop feeling like my only worth is how much I produce or how many hours I log.

Meaning might not pay the bills.

But it’s the reason I keep finding a way to.