The Fear of Failure

07 Jan, 2026

I received a note this morning from a founder in the frontier hardware space.

After a grueling process over many months, he was able to consummate the sale of his business to the leading company in his industry.

The grit required to persevere in a challenging sector is admirable. Or a sign of insanity. Or maybe both.

The note got me thinking about the fear of failure.

As someone who has spent most of his working life as a founder—often working with other founders—I think there are three layers to this fear:

The fear of failing — The obvious fear is that you could take a risk and lose. It entails financial and opportunity costs, but it’s part and parcel of entrepreneurship.
The fear of being seen to fail — This is less of an issue in the United States, which—by and large—has a culture that venerates risk-taking and the self-made person. However, this is definitely not the case in other countries, and it has acted as a handbrake on innovation and entrepreneurial activity.
The fear of feeling like a failure — This is the layer I don’t see many people talk about, but it’s the one that should actually be feared. It is pernicious, and it can lead to a doom loop of self-criticism and negativity that is detrimental to one’s health. What’s worse is that it can be insatiable: ‘success’—define it how you will—doesn’t cure it.