3 things I learned about risk taking and entrepreneurship


My wife Paige has been a medical assistant for two years.

He has a great salary, great benefits, the opportunity to help people – everything you would ever want at work.

But even though everything looked great on paper, behind the scenes things started to unravel.

In the last year, she has been facing extreme burnout (is not the only one). It turned out that working in medicine in a team with a shortage of staff during an endless pandemic was difficult. And not the kind of grinding where you might think things would be better if I worked somewhere else. Paige has had that burnout when you wonder why you even came into this career.

This is not a great place to be. I’ve felt that before, and maybe you are too.

At the height of her job misery earlier this year, she longed for it find a way out. We spent many nights with her after she got home from work, tossing around ideas about what to do next.

There were many options on the table:

  • Find a new work clinic, but stay on the same specialty
  • Try a completely different specialty than emergency care
  • Become a personal trainer (large salary reduction, but better work-life balance)
  • Become a dietitian (lower salary, but better work-life balance)
  • Start your own online health training company
  • Become an agent for the sale of medical devices

During our many late night conversations, I began to notice a pattern. And the things I’ve noticed in Paige are the same as I’ve noticed in many others who feel trapped in their work with no way out – especially people thinking about entrepreneurship.

We almost always overestimate the risk

Not to spoil the story, but Paige eventually decides to start her own online health training company (you can follow her Instagram here). If she had been asked two years ago if she could be seen starting a business today, she would have literally answered. But it’s here.

For her, the decision to give up a well-respected medical career and pursue an online business was no small feat. This is probably true for anyone in her position who is considering a similar move. There have been many other guesses and there will certainly be more.

In my opinion, most of the second guess that happened came from three errors of thinking. And I think most people, of course, have the same misconceptions about risk, especially when it comes to a major career change or immersion in entrepreneurship.

Observation no. 1: People tend to associate new ventures with risk, but risk exists everywhere

A graph showing how our perception of risk differs from reality.

Of the six most feasible options Paige had for a fresh start, it was easy to make holes in each. It took almost no effort to justify how each of them could end up being a bad idea.

  • Risk of clinic replacement
    • What if this burnout is not typical of my clinic?
  • Danger of changing specialty
    • What if this burnout is not typical of my area?
  • Risks of becoming a personal trainer or dietitian
    • What if the work is not as fulfilling or intellectually stimulating?
    • What if I can’t earn as much as I do now?
  • Risks in setting up an online health coaching company
    • What if I can’t create an audience?
    • What if I can’t get customers?
    • What if everything fails and I have to go back to get the right job?
  • The danger of becoming an agent for the sale of medical devices
    • What if I’m not good at selling?
    • What if commission work is too unpredictable?

Obviously, there can be many things wrong with any of these options. You can’t blame her for being afraid of change when it’s so framed.

But here we need to look at the bigger picture.

We assume that her current job is risk-free. But is that true?

  • What if she’s fired?
  • What if she’s fired?
  • What if stress helps to make a medical error and endanger someone’s health?
  • What if stress is slowly shaving her years of life? That’s the thing.

A stable ratio of 9 to 5 is stable… until.

Any of the above can happen every day. And if you’re reading this, the same goes for you (just mistake “medical error” for a cardinal sin in your career). Everything can be taken away like that.

Risk is everywhere, no matter what. But once you realize it’s always there, it’s easier to stop living in fear of what might or could happen. It allows you to follow what you want despite the risk.

Risk is inextricably linked to our lives – no baseline value is nothing.

Observation no. 2: It’s easy to forget the near certainty of staying unhappy at a job you hate

For all the perceived risks associated with a daring move and trying something new – no matter which option she chose – there were many things that were 100% guaranteed to happen if she stayed in her current job.

  • It would always have a heavy burden on patients
  • She should always rush through scheduled appointments to stay on schedule
  • You should always work more than 40 hours a week
  • She should always get permission to take time off
  • I would have another 30+ years of that until retirement

This is absolute certainty if it stays. He’s been there for two years; she knows what can be improved and what cannot.

In fact, we cannot even consider them as “risks”. They are inevitable.

I think when we’re faced with a big career decision, we focus on the risks of what might go wrong with the new thing. Let’s take a look what could go wrong if I leave, against what will continue to suck if I stay.

We intertwine the situation in our heads and don’t even realize we’re doing it. It is natural to avoid change, even if you want change to happen.

Observation no. 3: The worst case scenario, if it happens, is almost never as bad as we think

Paige eventually decided to start her own business, which may have some of the worst: “What’s the worst that can happen?” Scenarios.

So really, what’s the worst that can happen? Here is a possible doomsday scenario:

  • He doesn’t get a single customer and earns $ 0
  • Burn most / all of your savings
  • She loses 6-12 months of time she could receive for work
  • He has to go back and get the right job because the bills still have to be paid
  • She suffers minor embarrassment from family and friends cheering her on

Now this is the worst of the worst. There are many ways a start-up can turn out to be negative, but this exact scenario takes the cake in terms of danger.

Because of the arguments, let’s say he has a 10 percent chance of that happening. Unlikely, but there is still a lot of risk that is nothing.

But it is exactly what happened to me when Ben and I started DollarSprout. After about 9 months of trying to get things off the ground, I was completely out of money and my credit cards were almost depleted. I had to go back and get a job, but the only thing I could find at the time was a 50 percent pay cut. It was at a psychiatric clinic.

That was the worst possible outcome for me at the time. The unimaginable scenario became very real.

And yet life went on.

We did not allow slow progress to prevent us from giving up on this, even when I earned $ 11.36 an hour as a regular medical assistant at a psychiatric hospital.

In o ten months later, DollarSprout made enough money to allow me to leave that job and give entrepreneurship another chance. Four years later (knock on wood) I’m still alone.

The worst of the worst happened and yes, it was severe. It was more than stressful. I hated it.

But even that didn’t last forever and in the end I was able to come back anyway.

I think a lot of people would do better in such situations than they take credit for.

Don’t be afraid of a 10 percent chance of disaster, as disaster is almost never as severe as we think it will be. It probably won’t happen at all, and if it does, life really goes on. You will be fine.

TL; DR: If you want to do something, do it. Don’t let the fear of risk hold you back, as in most cases, risk is the greatest of all.



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