What's the Hardest Part of Being an Entrepreneur?

What’s the Hardest Part of Being an Entrepreneur?

Let’s start with what isn’t…

I’ve been wondering what the hardest part of being an entrepreneur is a lot lately. I’ve struggled for much of my life with this question. Like a lot of people, I erroneously thought idea generation was the hardest part. Then, after coming up with an idea, learning it wouldn’t work, and doing so again and again, I realized that’s probably the easiest part.

Product validation was how I found out most of my ideas weren’t great. I also found out a few ideas may have potential. So, that part didn’t seem too hard. Not for me anyway, though I’m sure, like everything else, different people have different experiences. That’s what makes answering a question so broad in scope very difficult. Still, I think it’s worthwhile to try.

What I’ve Learned

I’ve spoken to people I know and others online in places like Reddit. One of the most common responses I see to this question is profound self doubt and uncertainty. The latter is very relatable, whether you’re an entrepreneur or not.

Everyone faces uncertainty, and while I’m no biologist, I believe we may be evolutionarily hard wired to fear uncertainty. With uncertainty comes the potential for danger. Entrepreneurs, of course, face more uncertainty than most people. Entrepreneurship is one of the most uncertain endeavors anyone can engage in.

Self doubt seems to go hand in hand with uncertainty, and is a natural byproduct of entrepreneurial ambition. Creating and leading a business is such a daunting task. There are so many moving parts and unforeseen challenges arising constantly. It’s pretty easy for any self aware person to feel smothered by questions about their ability to handle the litany of obstacles standing in the way of their startup succeeding.

And self awareness is a very important trait for entrepreneurial success. So if you’re not feeling any self doubt, THAT’S what you should be worried about.

These, and other, more specific problems I’ve learned entrepreneurs struggle with, like a technical founder not knowing sales and marketing, arise from an axiomatic problem everyone has to varying extents.

That problem is not knowing what you don’t know.

Technical founders sometimes think creating a successful company is like Field of Dreams. They think “if you build it, they will come.”

But anyone who’s so much as launched a company, and plenty who haven’t, know that’s rarely, if ever, true. So, really, these technical founders didn’t know they didn’t know how difficult it would be to sell their solution.

Similarly, entrepreneurs don’t know of all the willing voices of experience that can answer the questions they have. They don’t realize who can provide the guidance they need to increase their chances of success. Many don’t often realize they need to reach out to someone who can guide them. So, of course, it doesn’t occur to them to do so.

What’s to be Done?

So, how do we combat self doubt and uncertainty?

Well, if you’re here or anywhere else hearing something similar, you’ve by now learned you’re not alone, and can conclude that since your struggle with self doubt and uncertainty is common, it’s not something unique to you, just like it wasn’t unique to everyone else who has experienced these feelings. For those who overcame the feeling of being crushed by perceived inadequacy, their overcoming was not unique to them, so anyone else dealing with these feelings should take solace in the notion they too can overcome.

How do we learn what we don’t know that we don’t know?

Well, the good news is that if you second guess yourself because of self doubt, that can actually be helpful for this issue. Learning is, of course, the key to knowing anything you don’t already know, and doubting you know the answer to something naturally causes you seek out the answer.

I would take it a step further. Question everything, never hesitate to reach out, be it to people who you can count on to help you, or to random folks on Reddit in pertinent subs. Do like Rene Descartes and practice Cartesian Doubt, and break everything down to first principles, then question your way to the answers you seek.

It may sound cliched and hackneyed to say this, but the only way to fight ignorance, which we all possess, since that’s what not knowing something is, is by learning.

In Conclusion, the Hardest Part of Being an Entrepreneur…

Is almost everything, as far as I can tell.

As for a few other, more specific problems I’ve seen people mention but didn’t cover, like balancing family, social life etc with being an entrepreneur and how we should deal with them? I don’t have that answer yet, since I am just beginning my entrepreneurial journey.

If anyone would like to add some perspective on that, dealing with self doubt and uncertainty, learning about what you don’t know you don’t know, and any other issues you’re aware that entrepreneurs struggle with, please leave a comment! I would certainly love to learn more.

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