π€ career risk
The final alphabetical bit, for now. Thanks for reading.
As we noted, it's hard to be different and many otherwise smart, insightful, clever people choose not to because of the career risk associated with failing unconventionally.
The best way to reduce career risk is to embrace the right stakeholders. If the people involved in a venture expect unconventionality they're less likely to react negatively towards it. Howard Marks put it this way:
"There's a book out called The Warren Buffett Way and I was asked to write the forward for the latest edition and I wrote something called βwhat makes Warren Buffett Warren Buffett and I listed the things that characterize him; extremely high IQ, unemotional, great analysis, understands what's important, looks at the important things, ignores the unimportant things, and on and on. The last one was one of the most important; he's not afraid of getting fired. He doesn't have to worry about the interim consequences of error. Most people do."
Independent operators, like Buffett, keep their career risk low with aligned stakeholders as well as operations with low overhead.
Buffett would never have invested in a company like Instagram during its venture capital rounds but he'd have applauded their approach because founders Kevin Systrom and Mike Krieger limited their career risk. After a fundraising round, one admitted that they could last a long time on that much money because all they needed was peanut butter sandwiches.
Put another way, with more time (due to more money thanks to lower expenses), they could try things out to find their product-market fit. They could take more chances and not worry so much about career risk.
In addition to aligned stakeholders and a low overhead the one other thing that seems to reduce someone's career risk is career capital. Coaches with many years of success can try things that others can't. For example, when Bill Belichick goes for it on fourth down and fails he'll get more slack and keep his job whereas someone more junior but in the same circumstances, will not.