What's the Hardest Thing About Being an Entrepreneur?


What do you think?

Is it balancing your work load with your family and friends? Is it trying to learn all of these new things all at once? Is it the pure stress of having to work too much?

And, do any of you have any tips for how you deal with these difficult things?



I think one of the hardest things about being an entrepreneur is understanding fear, and not letting it paralyze you.

I had this insight on the ski slopes (oddly enough)… I was just back from a knee surgery, worried about getting hurt again, and staring down from the top of a really challenging run (note: I’ve been skiing for 50 years and I’ve skied lots of pretty tough runs). I realized that if I let the fear control, I would be “all wrong” - leaning back on my skis, seeking safety - and in fact, what I need to do to succeed was lean into the slope, get my weight forward, reach into the gravity.

It’s not about ignoring the fear, or “conquering” it - not in my mind anyway. It’s about seeing it, recognizing it, recognizing that it can distort your perspective, and also recognizing that it’s there for the simple reason of trying to keep you safe.

So embrace it: see it, listen to it to a point, have it be your constant companion on the journey - because it will be no matter what. But don’t let it stop you from moving forward, from trying things. Build skills that give you the tools to move through it - much as you might practice skills on an easier slope before skiing the really hard stuff.

I hope this is helpful!


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Hey Martin!

Great answer - do you think there’s a point at which leaning forward isn’t the right answer? How do you know when the risk is too high? Do you turn to your investors or mentors to figure this out?

  • Claire


Hmmmm - interesting question. What I’m hearing in the question is: when is the right time to stop?

While it’s a personal decision on everyone’s part, and friends, family, funding, work/life choices all come into play, the most “outside” signal to keep going or to stop has to come from customers: what are you hearing from them? Are you hearing that you’re meeting a big need (see 4U’s framework)? Are you hearing that people want your solution? One of the most common mistakes that I see people make is believing so much in their product/solution/technology that they forget to listen to the customer. If the market isn’t telling you to keep going, you should probably ask yourself if you’re really attacking a real problem or have the right solution.

Make sense?



That definitely makes sense. However, I’m thinking about companies like Starbucks and Google that no one wanted to invest in, and no one seemed to think there was a market need for - but look at them today! Is this just a personal decision to keep investing your time in your product?



Hey @Martin - is there a quantitative way to see what the market’s telling you? how do you decide when the market’s telling you to stop?



So - interesting question - I just had this conversation last week with several professors who teach Entrepreneurial Management. And our conclusion is that there are three criteria for stopping - any one of these should cause you to stop:

  1. When you’re trying to prove that you have a business, what you’re doing early-on is running lots and lots of tests, using various MVPs (minimum viable products) to test one variable at a time. The idea is to reduce risk in the startup as you get more knowledge, and by reducing risk, to increase value (and thus make fundraising a whole lot easier). So one of the ways you know when to stop is when you’ve run all the tests you can think of, and they’ve all “failed” - in the sense that they’re not giving you positive signals that there’s demand for your product and/or that you can’t deliver it with positive unit economics. When those two things are missing (no market demand and/or no positive unit economics), then you don’t have Product-Market Fit and it’s time to stop.

  2. When you’re out of money, and

  3. Just before you can no longer “fail well” - that is, if continuing means that you’d be breaking the law, committing fraud, negatively affecting your employees (e.g., not paying them), or ruining your relationships with family, colleagues, customers, partners or investors.

Above all, it’s important to “fail well” - because life is long, opportunities will arise again, and, in my opinion, nothing is worth jeopardizing relationship or your own moral code.

I hope this is helpful!

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