Know When To Say F-It
9 years ago

I think you need to take more risks.

A client of mine (first-time CEO) was asking me what she should do. Raising her “B round” of funding was harder than she expected, and she was getting tons of feedback from potential investors that a strategic pivot to a more familiar business model might make it easier for them to write the big check.

“I know I could make it work, sell the company in a few years for a decent valuation, and walk away with a win for my investors and for me.” She said with that tone of voice…that she was trying to convince herself of something.

The advice I gave her is advice I think we all need sometimes — especially when you have pressure from investors, customers, friends, and family…


“You’ve heard the phrase a million times: People invest in people. In fact, I’m certain that the early investors said something to that effect when they gave you your first money-in. ‘We believe in you, and we’re really investing in you.’

That means that literally the only way you can fail is if you fail to be you. In this case, failing to be you means failing to make important decisions based on what you know to be right.

Failing to be you means settling for product quality you know is poor.

Failing to be you means taking the safer path because other people told you it has a lower chance of failure.

Failing to be you means hiring someone because someone else thinks they are a good fit.

Failing to be you means pivoting because it would be easier to raise money if your vision looked more like what other people might expect.”


I understand why you/we/I do these things. We don’t want to fail. And we’re smart enough to know that we don’t know everything. So when the really hard decisions need to be made, that’s when we look around for validation the most. That’s when we most want someone else to tell us what’s right, wrong, good, bad, smart, and not-so-smart.

But there’s something worse than failure, in the domain of regrets. And that’s knowing that you didn’t actually follow your own instincts. To end up wondering if — when you had your idea in the first place — you actually saw something incredible just on the other side of the horizon, or whether your vision was just a mirage.

I don’t think we become CEOs or entrepreneurs because we want to succeed. I think we do this because we want to know if the future we get so excited about can actually be brought about. By comparison “succeeding” is easy. Just follow the many formulas for past successes.


What’s hard is succeeding at creating the future we imagine is possible. Success by itself is not worth the risk of failure. But the possibility of realizing your unique vision is worth that risk.

And the only way that can possibly happen is if you make sure that you and you alone make the really, really hard choices.

The kinds of choices where no one can know how they will turn out. Where the pros and cons are hopelessly speculative.

All the people (including me) that have said, “I believe in you”, were really saying, “I believe in your subjective perspective to make those hard choices as well as they can be made.”

So when you have a hard choice to make (or when you are pretending that you don’t have a hard choice to make)…

Get advice. Seek mentorship. Get clear on your values.

And then say F-it.

You’ll never actually know what’s right. You can only do what feels best to you. You can only do what gives the future vision you see the best possible chance of becoming reality.

And make your judgement call.

And that judgment is exactly the reason you’ve been given the honor and the privilege to make those hard choices in the first place.

So I think you need to take more risks. Don’t you?

Where will you start?



Artwork: Envision Boy by Android Jones. Please support the work of Android Jones by visiting

Facebook comments: