When the main business asset has feelings

On resilience, success, and entrepreneur wellbeing. AKA why mainstream business advice often fails to help us succeed as human entrepreneurs.

There is one asset involved in almost every consequential part of a business that is unusually inconvenient.

It needs approximately eight hours of unconsciousness every night. Its perception changes under stress. It makes mistakes. It gets frightened by imaginary futures. It sometimes loses motivation despite excellent incentives. It can get everything it thought it wanted and still be unhappy…

Unfortunately, that my friends, is you. And me.

The human entrepreneur making the decisions. Moving the needle. The person who may be the single biggest reason their dream business works out, or crumbles.

And yet, funnily enough, in our pursuit of building businesses, there is remarkably little advice about how to deal with these inconveniences of being human.

Which I find strange.

Humans aren’t machines, right?

The fact that humans aren’t machines is often treated as a reason to take wellbeing more seriously, to see ourselves as tender creatures who need more time staring wistfully at trees.

Fair enough.

But stopping there misses the more practically important point: it may also help us rethink how we understand performance, resilience, and success.

When I was in business school, I got the satisfying impression that businesses were machines: identify the inputs, optimize the processes, improve the outputs. (I probably should’ve been more suspicious. It all sounded too neat, considering there are humans absolutely everywhere but I was young and dumb…)

Interestingly, there’s a historical reason for this. Economics and business studies grew up admiring fields like physics, borrowing their language of measurement, predictability, efficiency, and control [1]. It sounded much more “hardcore scienc-y” than being a social science studying, well, human systems.

Admittedly, I felt really cool using that technical-sounding lingo myself. And I bought into the idea that once you knew what factors make a business work, the rest was just execution.

But somewhere along the way, I ran into a big problem: it wasn’t actually true.

I could know what I needed to account for in my business. I could have the plan, the perfect process, the tools, the technology, the information, and a reasonably clear idea of what would happen if I consistently put in the input. It would all work out.

So the story goes.

If that were all it took, though, we’d all hit our business milestones happily ever after and swim in riches.

But it’s not that simple, is it?

Because the bottleneck is not the knowledge, the plan, the task, or the tech.

It is the doing the building.

Building while feeling helpful feelings, thinking helpful thoughts, recovering from failures, creating a supportive environment for yourself, your family, and your business, finding meaning in my day-to-day, and generally keeping the human doing all this in good condition…

And none of that sits neatly outside the work. It directly affects whether you can do the work at all, and how well you can do it.

Which made the missing variable in my beautifully neat business model rather obvious:

Me.

The human doing the building.

A human entrepreneur has complex, sometimes contradictory feelings. We speed up, slow down, lose confidence, regain it, change our minds, do it all over again.

And the mainstream business advice is: just do it anyway. Execute. Follow the plan. In other words: behave more like a programmable machine.

Except that the human me keeps stubbornly behaving like a human. And we label it as irrationality, inconsistency, weakness, or “human error” when it’s simply evidence that this asset is, well, simply human.

I’d argue that accounting for real human aspects isn’t making business advice softer.

It’s making it more accurate. More real. And frankly, more useful.

Things we probably need to rethink

But everyone loves a neat founder story

So if we want a more accurate picture of the human entrepreneur, it’s worth looking at where our current one came from…

Once upon a time, there was little Jonny.

He grew up poor, with neglectful parents. But through grit, smarts, and perseverance, he won a scholarship to a prestigious university, dropped out, founded several businesses, burned out, recovered, and eventually built one into a multibillion-dollar company.

You know the story.

When it comes to building businesses, this is about as raw as many of the stories get. The light shines firmly on the the grit, the extraordinary capacity of the entrepreneur to keep going. And, of course, the billions at the end.

The story may be technically true while still being profoundly incomplete.

We rarely hear what actually enabled Jonny to keep going. Who helped him. How he dealt with fear, doubt, exhaustion, rejection. Whether he processed any of it or simply learned to function despite it.

We hear even less about who else absorbed the cost. What happened to his health or relationships. Whether persistence was always the wise decision. How much luck and timing mattered. Whether he is actually happy now, or ever was.

What we’re left with is a strangely narrow picture of what a strong and successful entrepreneurship journey looks like.

It’s not news that entrepreneurship has historically been a predominantly male world, so it’s perhaps no surprise that some of its ideas about strength resemble traditionally masculine, and sometimes precarious, ideas of manhood: be tough rather than affected, consistent rather than responsive, tireless rather than embodied, victorious rather than reflective.

Research on precarious manhood suggests that manhood is often treated as a status requiring continual social proof. [2] In an entrepreneurial setting already saturated with stories of independence, risk-taking, and heroic persistence, that can make it harder to admit uncertainty, dependence, or limits.

This isn’t an argument that masculinity, or men, are the problem. It’s about a particular, incomplete idea of what strength and success look like, available to people of any gender in our culture.

Put that together with our fondness for a good success story, and you get a very recognizable entrepreneurial hero:

They come from somewhere unlikely. They take the risk. Things get very bad. They keep going when lesser mortals would have stopped. Eventually the bet pays off big, and looking backwards, every hardship becomes proof of their extraordinary toughness.

That’s a bedtime story.

It’s not advice.

Whatever happened on the inside gets edited out.

And perhaps that’s the very part that would help the rest of us most.

The upside of being a terrible machine

If business success is the goal, and if the entrepreneur really is a crucial business asset, perhaps we should be a little more interested in what happens inside it.

And when we look, we find much more than the grit and perseverance our founder stories tend to celebrate.

Many of the inconvenient human features we’ve been trying to manage away can start looking remarkably useful too.

We get scared, but fear can tell us something matters. We doubt ourselves, but doubt can make us reconsider a terrible idea. We get tired, and eventually discover that tired humans don't always make great decisions.

But we also love. We care about people, understand what matters to them, build relationships, earn trust, and create communities.

We can hold contradictory feelings at once. We learn, adapt, change our minds, and change ourselves. We imagine things that don't exist yet and find ways to make them real. We make meaning from what happens to us, and turn painful experiences into better judgment, new ideas, art, wisdom, or something useful for someone else.

And we can devote years of our finite lives to building something simply because we believe it matters.

What if Jonny’s story were more like:

Jonny’s health had become obstacles to building the business and life he wanted. Even way before the burnout, he hadn't felt good: constantly on edge, exhausted, dreading getting up each morning. He had learned to cover it and kept going anyway. When that stopped working, he finally sought help and changed how he built. He learned to question old beliefs that had held him hostage, work with his mind and body instead of against them, he led himself with more honesty, and for the first time, he felt this deep sense of steadiness and agency. His wife was crucial in this journey. He learned to let someone else carry him sometimes, too. Together, they went on to build a company worth billions. But by the time the billions came, they were already living the life they loved. The money was almost a nice little side effect.

None of this is machine-like. Or heroic.

But look at what actually helped him build:

Self-awareness, honesty, trust, perspective, agency, openness, courage, steadiness, flexibility… all these human strengths (and more) may be less celebrated than grit, but they’re no less important to building something difficult, meaningful, and successful.

And like any other capacity we rely on, these are things we can understand, nourish, practice, and strengthen.

Human entrepreneurs need a human definition of success

If success simply means building a profitable business and keeping it going, then “just keep going” is okay advice.

Many entrepreneurs like to say you’ll eventually succeed if you do something for long enough. But neither endurance nor business profitability alone equals success.

I think we’re missing one word here: well.

You succeed if you do something long enough and well enough.

Well enough to keep making good decisions. Well enough to recover when things go badly. Well enough to remain caring about people and the world beyond yourself. Well enough to protect the health that makes all of it possible. Well enough to enjoy some portion of the finite life you are spending building the thing…

A business can succeed while the human (or humanity) building it fails rather spectacularly at living well.

I don’t think the answer is to care less about business success. It’s to expect more from what we call success in the first place.

Hytti and colleagues’ study of 22 Finnish male technology founders shows that “entrepreneurial masculinity” is not one fixed thing: as men negotiate business and fatherhood, they may reproduce, adapt, or resist prevailing ideals of entrepreneurial success and masculine responsibility. [3]

Which is rather hopeful.

The entrepreneurial ideal isn’t set in stone. We get to question what we inherited, keep what serves us, and build new versions of what entrepreneurial strength and success can look like.

I’d like us to take the human asset seriously enough to ask more of how we do entrepreneurship, and more of what we call success.

Because the main asset in your business does, inconveniently, have feelings.

And perhaps that isn't such bad news for business.

Or for the life you're building alongside it.

References

• [1]
  • Mirowski, P. (1991). The when, the how and the why of mathematical expression in the history of economic analysis. Journal of Economic Perspectives, 5(1), 145–157. https://doi.org/10.1257/jep.5.1.145
  • Örtenblad, A., Putnam, L. L., & Trehan, K. (2016). Beyond Morgan’s eight metaphors: Adding to and developing organization theory. Human Relations, 69(4), 875–889. https://doi.org/10.1177/0018726715623999
• [2] Vandello, J. A., Bosson, J. K., Cohen, D., Burnaford, R. M., & Weaver, J. R. (2008). Precarious manhood. Journal of Personality and Social Psychology, 95(6), 1325–1339. https://doi.org/10.1037/a0012453
• [3] Hytti, U., Karhunen, P., & Radu-Lefebvre, M. (2024). Entrepreneurial masculinity: A fatherhood perspective. Entrepreneurship Theory and Practice, 48(1), 246–273. https://doi.org/10.1177/10422587231155863