Purpose-Driven Entrepreneurship Is Hard

You know the shape of the story, you’ve seen it a thousand times: someone has an idea, raises money, scales fast, exits big. There’s a TechCrunch piece, podcast episodes, maybe keynotes, congratulatory postso n social with up and to the right growth. That’s the typical story the tech industry tells about success… and, well, it is a real story. It works for some people. It also chews out, burns up, and destroys way way way more people.

But… there’s another story that almost nobody tells, because it’s not loud and sexy and exciting or dramatic. It doesn’t have an ending, which is part of why it’s hard to tell. It’s the story of people who’ve been building for a long time, who could have taken the big-money path a dozen times and chose not to—not because they couldn’t, but because they saw something else.

These are my trail notes from that path, a collection of thoughts and notes that I’ve tried to organize so it’s useful to others who feel like there must be a better way.

The hunger

When you’re starting out, you’re so hungry!! the hunger is everything. You want to build, learn, grow, do all the things. You want to prove you can do it. You admire the people who’ve done it, the icons (yup, you’ll get a pair of circular rimmed glasses 🤓) and founders (put on that hoody yo 🤘) who made something from nothing. You study their playbooks. You measure yourself against their metrics: revenue, users, valuation, title, reputation, resume, experience, etc etc. The hunger teaches you real things—how to ship, how to endure, how to show up when you don’t want to—and building is a skill you’ll carry forever.

But underneath the hunger, there’s a different signal. You’ll feel it before you know what it is… it sounds something like: Do I actually want to play this game? Is this it? or is this just what everyone’s doing because everyone’s doing it?

🌱 Think of this as a seed in the soil. It might sit dormant for years. It doesn’t need your attention yet. But it’s there.

First: your relationship with struggle

Before any of the rest of this matters, there’s something nobody puts in the “how to be a founder” guides.

You have to learn to love the struggle itself.

You’ve all seen the clip of Alysa Liu talking about how she loves struggling. You can’t just white-knuckle through it: you have to find something you love in it, your mind craving the feeling that says this is where growth happens, and growth is the point. For me it was games and athletics—hours of dying on the same level, failing the same trick, going back in because you just wanna figure it out 🎮. Frustration is the practice.

Everything that follows (the small daily choices, the paradoxes, the long invisible road) is hard. Not “16-hour hack” hard. Hard in the way that questioning your own assumptions while everyone around you seems certain is hard. If struggle feels like failure, you’ll bail at the first identity-level challenge and run back to the default playbook. If struggle feels like signal… I’m in it, I’m learning, I’m making progress… then the whole path opens up.

🌱 This is the quality of the soil. Before anything can grow here, this relationship with difficulty has to be in place. Everything else is downstream of it.

The accumulation

The idea that you “find your purpose” is one of the most misleading narratives out there. It implies a moment, a flash of clarity, a bolt from the blue. In my experience, that’s not how it works at all.

Purpose builds the way soil builds. Slowly, through countless small choices, most of which don’t feel significant when you’re making them.

You share something valuable with someone who’s technically a competitor (a real insight, not a polished nothing) because it feels right. And afterward you notice: they’re not your enemy. They’re the only people in the world who truly understand what you’re building. You’re working on the same problem, driven by similar passions, and you’re going to make different things anyway because you are different people. There’s space. There’s always space. A rising tide.

You say no to something that looks impressive on paper (the rocket ship startup, the big raise, the prestigious title) because something in you knows it doesn’t fit. You can’t fully articulate why. You just know. And that “knowing” costs you something, because everyone around you would have said yes.

You help one person solve a real problem, actually solve it, in a their-life-is-a-little-better-now way… and the feeling is complete. You helped someone. And now you want to do it again. And you do, slowly at first. Building.

You choose autonomy over prestige. Coherence over optimization. Learning over winning.

None of these feel like “finding your purpose” in the moment. They feel like small bets. Tiny defections from the default playbook. But they accumulate. At some point (you’re not entirely sure when, and it’s impossible to pinpoint), you look up and realize you’re standing on ground you built through practice.

That’s how it actually works. A long accumulation of choices that pointed the same direction, even when you didn’t have a name for that direction yet.

🌱 Season after season. You can’t rush soil. You can only keep adding organic matter, one handful at a time, and trust the process.

The narrowing

My friend Patrick and I have a name for this: playing on hard mode. Not all at once—it accumulates, one decision at a time.

Every year you build, you see more of the map. You watch a certain kind of partnership blow up three times, and now you can spot the structure before the first meeting ends. You see a pricing model that looks clever and know exactly where it leads in eighteen months. You recognize the raise that doesn’t match the product—too much capital chasing a growth curve before the thing works (or, not enough capital when the product demands it because you stubbornly try to bend reality to get a different model to work). You hear “tons of interest, customers love it” and ask how many have paid, and the room gets quiet 😅. You see brilliant technology and no clear answer for who, specifically, will write the check. You take the meeting with the bigger company that’s suddenly eager to acquire, and you can feel the competitive intelligence fishing underneath the flattery 👀. You’ve been down enough paths to recognize the dead ends from the trailhead.

Experience is pattern recognition, mostly.¹ Researchers found that experts see more structure than novices—by recognizing patterns faster, not by considering more options.² A chess master looks at a board and perceives clusters of meaning where a beginner sees individual pieces. The experienced founder looks at a business model and sees where the pressure lands in year three. Same information, completely different resolution.

So the map fills in. That’s one force at work. Now layer on the principles.

Every “no” from the previous section—every time you chose coherence over optimization, autonomy over prestige—those are active constraints. Saras Sarasvathy studied expert entrepreneurs and found they don’t start from goals and work backward.³ They start from who they are, what they know, who they know—and treat constraints as creative inputs. She calls it effectuation. The constraints are the game.

And the math backs this up:⁴ each constraint you hold shrinks the space of moves you’re willing to make. Every additional objective you refuse to sacrifice reduces the feasible region. Sustainable, purpose-aligned, family-compatible, non-extractive, long-horizon—each one is a filter, and the viable set gets smaller with every filter you add.

Two forces, pressing from different directions. Experience reveals the dead ends. Principles rule out the paths you’re not willing to take. What’s left is narrow—genuinely narrow—but it’s yours. You can see most of the walls, and the ones you built yourself define you, your product, your business, your way of life.

The hard part is the communication gap. You’re standing in a corridor you can see perfectly, making decisions that feel obvious from where you are—and the people around you think you’re being stubborn. Or overthinking. Or leaving money on the table. Research on expert-novice gaps shows this is structural, not personal.⁵ The curse of knowledge is that you can’t un-know what you’ve seen, and you can’t easily show someone else what’s visible from where you’re standing.

The decisions are often clearer than they’ve ever been—it’s hard because almost nobody else can see the corridor you’re in. Welcome to “playing on hard mode” 😎

🌱 The path gets narrower, and it gets more yours. Everything that grows here, you planted on purpose.

The paradox

Somewhere in the accumulation, you hit a different kind of challenge. It’s not tactical (“how do I get customers?”). It’s existential:

How do you build within a system you’ve started to see through?

You care about helping people. You also need to reach them, which means marketing. And marketing, at its worst, tells people “you’re incomplete, this completes you.” That kind of messaging is hard to stomach once you’ve seen the machinery behind it. But you still need to reach the people you can genuinely help. So you sit in the tension: how do you invite without manipulating? How do you grow without extracting?

You watch peers raise big rounds, hit milestones, get celebrated. Something flickers… not quite envy, more like a question: am I doing this wrong? And then it passes, because you know what that path costs and you’ve chosen differently.

You hold metrics as useful signals and you use them, because they carry real information. They’re instruments, not identity. The scoreboard isn’t the game.

This is the part that’s genuinely hard. Not resolving the tension, but being in it. You can build and question at the same time. Serve and sustain. Grow and let go. You notice your own ego when it shows up (“oh, hello again, I’m anxious about growth metrics 😅”) and you greet it with something closer to humor than panic. The paradox doesn’t resolve—it nests. And the muscles it builds are the ones that make everything that follows possible.

🌱 This is the season of pruning. The hardest, most counterintuitive work: cutting back to create space for the right things to grow. It looks like loss. It’s not.

The long game

After enough accumulation, after enough time holding paradox… something settles. You just look up one day and realize the inside matches the outside. What you believe, how you spend your days, what you build, how you treat people… they’re coherent. Not perfectly, but recognizably.

You designed your life. Not theoretically, not “someday when I exit”—right now. The autonomy isn’t a reward you earned at the end. It’s a choice you kept making along the way.

Each person you help genuinely matters to you. You solved a real problem for a real person, and the feeling of that is gratitude. Actual gratitude 🙏. That’s enough. That’s the whole point.

Every challenge is growth, in the you sense. The business isn’t separate from your development… it is your development. You’re always learning, not because you’re behind but because you’re awake.

The metrics that matter don’t fit on a dashboard. Nobody writes the TechCrunch piece about coherence. But you’re playing a different game entirely.

🌱 The harvest. Sustaining, not extractive. The garden feeds the gardener as much as the gardener feeds the garden.

Reminder: these are notes from my path, yours will differ

A few honest caveats, because the honesty matters more than the narrative.

This is one path. Different ways of building work for different people, and the person who raises venture capital, scales fast, and builds something enormous isn’t doing it wrong. They’re on different terrain with different rewards and different costs. I have no interest in judging their game from mine.

There’s survivorship bias here, and I want to name it plainly. I chose this path, I’m standing on it, I love the view. Would I say the same things if I’d chosen differently? I genuinely don’t know. Nobody gets to run the counterfactual.

What I can say… maybe the only thing I can say with real honesty… is that this path is coherent. The inside matches the outside. The work reflects who I actually am. And the life I’m living is one I designed, not one I defaulted into.

It’s hard. It’s very meaningful. And I wouldn’t trade it, not because it’s the best path, but because it’s mine.

If any of that resonates… if you feel a different signal underneath the hunger, even faintly… you’re not imagining it. That feeling is real, and you’re not the only one who has it. Send me a note, I always love connecting with outher purpose-driven founders taking the road less traveled. ✌️