The Case For Boldness and Grit

Photo: Patrick Tomasso

This is something I’ve been thinking for a while and I’ve been meaning to write down. In the paragraphs that follow I’ll try to make the case for embracing boldness and grit as a working philosophy.


The main pushback we’ve seen in the last few years against the concept and spirit of boldness is mostly due to the word being coopted and misused. It has a negative connotation of stubbornness, bullying, ignoring advice, ignoring opinions and several other toxic behaviors — especially in business contexts. Another issue that can be observed is executing reckless and careless decisions and then hiding behind “being bold” to justify them. But what I’m here to tell you is that boldness is nothing of the above. Boldness is really about making tough decisions as a team, or organization. Boldness requires leaders to be cogent and trustworthy, not pulling rank and implicit enforcement of hierarchy. Boldness is about embarking, as a group, on a path which has no guarantees of success — or a path that has yet not been forged — after considering other alternatives and having a deep (and shared) understanding of the risks involved.


Like boldness, grit has a bit of a bad reputation due to its misuse and abuse. Grit isn’t about putting up with toxic behavior or an excuse for being dismissive and indolent. Or is about being misused as the premise for being outwardly brash and gruff. Grit is about perseverance and managing adversity with aplomb. Grit is able to express, as an individual or group, honest and unrefined thoughts or concepts, yet never losing your sense of empathy. Grit is about pragmatism with a modicum of stoicism. It’s not an abandonment of perfectionism, but rather it’s a raw iteration to make progress.

The Case

I fully admit this is fully anecdotal and a personal take. I claim no statistical or scientific rigor about this. I posit that, in the whole, startups have become complacent, conforming and risk averse. There are very few companies out there willing to forge their own path (as it was fairly common up to 4–5 years ago) and make bold statements in any industry and have the grit to see it through. There has been a pendulum shift from the “fail fast” extreme to the “everything must be impeccable” extreme and in that swing a lot of the good parts — like boldness and grit — were lost. My hypothesis and missive here is that companies that embrace a healthy amount of boldness and grit to their operational stance will find more success than those who don’t. Comfort and safety are more expensive for a startup than most founders and investors are willing to admit.



Software, hi-fi audio, data, financial markets observer.

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