Stormy Simon | Why We Don't Bet On Ourselves (And Why We Should)

Mental Models, Performance, Business & Entrepreneurship |

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Here is my weekly email with some insights and ideas pulled from conversations I had on my podcast.


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Why We Don’t Bet On Ourselves (And Why We Should)

There’s something about being an entrepreneur that seems to attract the risk-takers. Well, it makes sense, doesn’t it? If you’re going to forge a new path in the business world, there are no footsteps to follow. There’s no one to say, “Yeah, that’ll work!” because there’s no certainty in a new endeavor.

It’s a bit of a gamble, and that means we have to bet on our only horse in the race — ourselves. But it doesn’t come naturally to everyone; in fact, some of us feel held back by invisible barriers, and pushed down by intangible ceilings. Life has taught us to be careful and to play it safe.

If you look at the most successful entrepreneurs, though — Jeff Bezos, Oprah Winfrey, Richard Branson, and even Thomas Edison — you’ll find that they all have one thing in common: they had to bet on themselves to find success. At points in all of their careers, they were their own sole supporters.

So why don’t we bet on ourselves? Why do we choose to play it safe instead of taking a chance and going for broke? Let’s explore some of the reasons and then look at how to overcome them.

Betting On Yourself: It’s Not So Simple

At surface value, backing yourself seems like the obvious requirement for a successful career. Believe in yourself! Go for gold! But it isn’t that simple, is it?

Maybe in the beginning, it is — but what about those first few months, when every cold call you make goes unanswered and every email you send is met with radio silence? What about when the naysayers start to pile up or when your own doubts take hold?

It’s easy to say that we need to back ourselves, but there’s a definite survival instinct within all of us that says playing it safe is the way to go. Even cheetahs will stop pursuing prey if they’re uncertain of a kill.

I find it interesting, then, that some entrepreneurs seem to breeze through the trepidation. They go into business with an idea doomed to fail and simply assume they’ll be successful in the end. Why do they do it? And why can’t we all?

The Intricacies of Boundless Confidence

I’m fascinated by the personalities of entrepreneurs. When thinking about this newsletter, I knew there was something more to this idea of backing yourself — something rooted in our genetics, perhaps, or something that is instilled in us from a young age.

Here’s what I found.

Risk-Takers Are Nurtured, Not Bred

This is one of the most interesting studies I’ve ever come across. With the intention of finding out whether business-minded families breed entrepreneurial children, the research team found something more intriguing:

“Our findings are that a difficult childhood with challenging experiences, which could include such factors as loss of a parent, parental divorce or economic hardship, influence [entrepreneurial] attitudes.”

In other words, this research found a basis for the idea that rough childhoods can foster a certain boldness in the face of adversity. Findings from the Creating Useful People podcast seem to back this up:

“…change and disruption tend to be seen as unsettling for kids. However, what I see is that the need to overcome change and adapt to new circumstances has given people an advantage in their career or businesses. They learn not to see change as a big deal. They learn that they can overcome it. They learn to not fear the unknown.”

This makes a lot of sense to me. When you grow up with only yourself to rely on, of course it would become your natural inclination. Bet on yourself? Why bet on anyone else?

And we don’t have to look far to find a handful of entrepreneurs who grew up in the rough:

  • Jan Koum, founder of WhatsApp, immigrated from Ukraine with his mother and lived in poverty from childhood into adulthood.

  • Tony Robbins was terribly abused by his mother as a child — but he now speaks about this experience as a driving force behind his determination.

  • Bethenny Frankel, founder of Skinny Girl, grew up with a very absent father and an alcohol-addicted mother.

  • Stormy Simon — a highly successful businesswoman who I recently interviewed — became a single mother at the young age of 17.

  • And of course, Oprah Winfrey speaks openly and often about the way her childhood abuse has shaped her life.

The list goes on and on.

Adversity Isn’t a Prerequisite

At this point, I paused my research to take a breather. Does a person have to struggle through such adversity for a bit of self-confidence? What’s really going on here?

If we look at the issue of childhood adversity, it begins to make sense. There’s no rule that says you need to face X amount of abuse, or that your parents need to be dirt-poor, for you to develop the capacity for greatness. It just so happens that adversity forces people to develop certain skills: resilience and adaptability.

(This is all leading somewhere — stay with me.)


According to the American Psychological Association, “Resilience is the process and outcome of successfully adapting to difficult or challenging life experiences.” It’s easy to see, then, how resilience rises up in sufferers of adverse childhood experiences. If they can adapt, they survive — and that resilience follows them into entrepreneurship.

I found this fascinating study on the Chinese Famine of 1959–1961. Of the immigrants who lived through the famine, those who experienced the most hardship — and at a younger age — were more likely to become entrepreneurs. They would have required an unthinkable amount of resilience and self-reliance to make it through the famine.


When I think of adaptability, I immediately think of Walt Disney; who could forget the way he built a thriving company in the middle of the Great Depression? He adapted and pivoted his way through the most difficult of times to create a lasting legacy.

Growing up, as it turns out, Disney’s parents were dirt-poor — and they weren’t overflowing with affection, either. His childhood was spent bouncing from one place to the next as his parents looked for work.

That adaptability, that resilience, and self-reliance he developed as a child followed him into successful entrepreneurship. And it’s partly why we remember his name today.

So… What If Your Childhood Was Peachy?

The reason I shine the spotlight on resilience and adaptability is that they’re not exclusive to a life of hardship. Really, these are skills anyone can learn. It’s just about understanding their importance and then doing the work to develop them.

You see, we don’t have to wait for adversity to hit us in the face before developing these skills — we can create our own adversity. We can purposely put ourselves into situations where we’re forced to be resilient and adaptable. Together, these two skills combine and produce self-reliance. We can bet on ourselves no matter the odds.

How To Develop Resilience and Adaptability

To round out today’s newsletter, I dug around for some tried-and-true methods of boosting your self-reliance. Here are some practical tips for developing resilience and adaptability:

1. Use expressive writing.

Backed by science, expressive writing is about allowing yourself to regurgitate past events onto paper. For example, you might think back to a difficult situation and write out every emotion and thought you associate with it.

Next, you reflect by writing the positives that came out of the experience. Hindsight is 20/20 — and by forcing yourself to acknowledge the good, you find solid proof of your ability to bounce back from hardship.

2. Do something you’d never try unprompted.

No, I don’t mean try a new dessert or read a book that intimidates you a little. I mean find an activity so far out of your comfort zone that it’s hardly even on your radar. Not athletic? Join a team sport. Never had to speak in public in your life? Try toastmasters.

If you fail, it builds character and resilience. If you find out that it’s your new calling, you build self-confidence in knowing that you adapted to something new.

3. Dig into your childhood.

Whether you faced adversity as a child or not, it’s always valuable to know your roots. Where do your deepest fears stem from? What’s your attachment style? How did your parents and upbringing influence your level of self-confidence?

There’s nothing so freeing as understanding yourself properly. It’s intimidating if you’ve never looked inward before; you may even struggle to keep attending sessions after you hit the first few sore subjects. But you will understand your motives, and in doing so, find a path to greater self-confidence.

4. Separate your identity from success.

A huge barrier to taking risks is the fear of failure. I’ve talked about it in my newsletter before, and I’ll keep talking about it. Our relationship with success and failure determines our ability to take risks and bet on ourselves.

Whether you do this through therapy, meditation, or research, detach your identity from your success. Understand that even the most capable people fail. Successful entrepreneurs aren’t ‘better’ than the ones who fail; most of the time, they are the people who kept trying after failure.

The Outcome of Betting On Yourself

If you go without self-confidence for long enough, you don’t feel the need to change or embolden yourself. Life is safe — your risks are calculated. There’s no need to change because you haven’t been hit with failure.

But you also haven’t been hit with true success, or as much success as you could have achieved.

We’ve all got invisible ceilings over our heads that stop us from reaching our highest potential. Here are some limits you might not have even realized were there:

  • You don’t embark on a business venture if no one agrees to partner it with you

  • You only brainstorm ideas within your area of expertise — even if other areas intrigue you

  • Your ideas are variations on other people’s concepts because your original ideas ‘will never work’

  • You only cold call prospects if you know they’re in the market for your product

  • There are certain VC firms or investors you won’t approach because they ‘only fund the unicorns’

  • You stay in unsatisfying jobs for a long time rather than trying new things

Any of those hitting home? I feel them, too. It’s so easy to overlook these little ceilings, but they prevent us from believing in our own potential and taking critical chances.

Betting on yourself means there’s no limit to the things you can try.


Regardless of how you grew up, remember that the skills of a confident entrepreneur can always be learned. Trust in your own judgment and make those bold decisions that move you in the direction you want to go. Don’t settle for less than what you deserve and never doubt your abilities — because at the end of the day, if you don’t bet on yourself, who will?

As always, thanks for reading! Let me know in the comments how you’ve bet on yourself and the outcome.



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