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Why Some People Build Their Own Rules.

Stewart Moss
Stewart Moss |

Every founder starts with a question: Why me?

Why do some people take the leap, while others stay put?

Why do certain personalities thrive in uncertainty, while others find comfort in structure?

It’s not luck. It’s psychology.

Entrepreneurship isn’t a single personality trait - it’s a stack: a combination of beliefs, motivation, risk logic, and habits that make action more natural, uncertainty more tolerable, and failure less fatal.

This article unpacks what decades of research — including from Harvard Business Review and Harvard Business School — tell us about what makes an entrepreneur tick, and how you can build those same foundations deliberately.

The Entrepreneurship Stack: Traits, Beliefs, Logic, Habits

Harvard research suggests entrepreneurs tend to show higher levels of:

  • Openness to experience – curiosity and idea exploration.
  • Conscientiousness – the ability to execute consistently.
  • Internal locus of control – belief that outcomes come from one’s actions, not luck.
  • Self-efficacy – confidence in one’s ability to learn and adapt.
  • Need for achievement – intrinsic motivation to push boundaries.

These traits show up again and again across large-scale reviews linking personality to entrepreneurial entry, persistence, and success (HBS, Personality Traits of Entrepreneurs).

But traits only set the foundation. The real difference lies in beliefs and logic — how founders interpret uncertainty and act within it.

Entrepreneurs use what Harvard calls effectual logic — starting with who they are, what they know, and whom they know, and then co-creating opportunities through commitment and iteration, rather than prediction.

It’s not “I have an idea, I need funding.”
It’s “Here’s what I can do today with what I have — and here’s who might join me.”

When Misfits Become Builders

Not every founder fits neatly into corporate systems. Some underperform in traditional roles - not because they lack ability, but because the environment stifles the autonomy and experimentation they need to excel.

Harvard’s research on Self-Determination Theory (Deci & Ryan) shows that peak motivation occurs when three needs are met: autonomy, competence, and relatedness.

Corporate environments often restrict the first - autonomy - with hierarchy and process.
Entrepreneurs, by contrast, design autonomy into their lives by default.

According to Harvard Business Review, people with high autonomy orientation are 2.7 times more likely to found companies within five years.

They don’t reject structure — they redefine it.  That’s why many founders describe themselves as “restless” or “misfits” in traditional jobs. Constraint doesn’t crush them; it catalyses them.

When structure limits growth, they build their own structure instead.

Are Entrepreneurs Really More Comfortable with Risk?

Not exactly — they’re better at reframing it.

A landmark study from Harvard and PNAS found that while entrepreneurs show higher risk tolerance than corporate managers, they’re not thrill-seekers — they’re risk architects.
They actively design systems to make uncertainty survivable.

Behavioural economics (Kahneman & Tversky’s Prospect Theory) helps explain why: most people are risk-averse for gains and risk-seeking for losses. Entrepreneurs differ in that they frame losses as learning — and learning as inevitable.

They don’t ignore fear; they manage it by shrinking the downside.

Founder practice:

  • Test before you commit.
  • Pre-sell before you build.
  • Partner before you scale.

That’s not recklessness — it’s risk engineering.

Why Some People Act — and Others Wait

Howard Stevenson’s classic Harvard Business Review definition of entrepreneurship still holds:

“Entrepreneurship is the pursuit of opportunity beyond resources currently controlled.”

What separates actors from waiters is belief. People who believe they can influence outcomes (high locus of control) and learn what they need as they go (self-efficacy) are more likely to start. They don’t need certainty to act — just enough clarity to take the next step. The difference is mindset, not IQ.

The Founder Mindset: Patterns of People Who Build

Founders who thrive in early-stage environments share several psychological signatures:

  • Bias to action – progress through iteration, not perfection.
  • Comfort with ambiguity – clarity built through motion.
  • Pragmatic excellence – excellence where it matters most.
  • Purpose-driven energy – meaning fuels endurance.

These patterns echo across HBR’s research on entrepreneurial success: curiosity, resilience, and optimism predict startup survival far more than raw intelligence.

People who shine later in scale-ups, by contrast, often prefer process, predictability, and depth — invaluable qualities, just in a different season of business.

A Self-Assessment: The Entrepreneurial Stack

Score yourself 1–5 for each statement (1 = rarely true; 5 = very true).

  1. I act before all the data is in, then adjust quickly.
  2. I believe my choices influence outcomes.
  3. I’m energised by messy problems.
  4. I can wear multiple hats without losing focus.
  5. I seek feedback early, even when uncomfortable.
  6. I convert big unknowns into small tests.
  7. I enjoy building partnerships from scratch.
  8. I keep promises to myself — habits stick.
  9. I pivot without panic.
  10. I recover fast from setbacks.

Scores of 38 or higher indicate strong entrepreneurial tendencies. Mid-range scores highlight trainable traits - particularly locus of control and action bias.

The Entrepreneur’s Playbook: Train the Stack

1. Upgrade Beliefs (Control & Confidence)

  • Keep a “cause and effect” log — weekly actions → outcomes.
  • Practise “20 reps” of a stretch skill (e.g., cold outreach) to build mastery.
  • Map who you know, what they know, and how you might co-create value.

2. Redesign Risk

  • Cap downside: time-box experiments and budget small.
  • Reframe “losses” as data — learning reduces fear.

3. Switch Decision Logic

  • Start with what’s in your control: skills, network, insights.
  • Build outward through stakeholder commitments — pilot customers, partners, mentors.

4. Hire for the Game You’re In

  • Early hires: autonomy, curiosity, breadth.
  • Growth hires: focus, structure, reliability.

The Founder’s Takeaway

Entrepreneurship isn’t genetic.
It’s learned behaviour repeated under pressure.

The best founders don’t wait for courage — they design it.
They shrink the unknown, act fast, and build systems where failure teaches more than it costs.

Whether you’re a lifelong “misfit” or a leader learning to leap, you can build the same entrepreneurial stack: autonomy, action, and adaptability.

Because the truth is, entrepreneurship isn’t about escaping structure.

It’s about creating a better one.

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