Keeping stamps

“We are prone to overestimate how much we understand about the world and to underestimate the role of chance in events. Overconfidence is fed by the illusory certainty of hindsight.” - Daniel Kahneman?

When I started writing to share my thoughts on LinkedIn and launch my newsletter, I aimed to record the challenges of a startup, share the bad news as it happened, and the daily highs and lows. Without having the shinny result of success or a reputation as an entrepreneur or writer.

Many business and how-to books are written after success, sharing insights on how people navigated their way in the business world and what tools and principles helped them, and with good reason. I don’t think how to authors would get much attention without some proof of legitimacy.

I believe we still read and write about entrepreneurship because it is an unsolvable equation. Once the results are in, it’s relatively easy to deduce why we are so successful with the clarity of hindsight. “I knew that would happen,” the words often spoken after something already happened. Ah yes.?

Hindsight bias is the term used to explain how we “knew” it was going to happen after an event unfolds. After observing the result, we deduce an explanation, molding the “how-to” part to fit a known outcome.?

My wife and I recently spent a few nights at Victoria Falls and on the Chobe River. The morning we left SA, I got the usual instruction of taking the passports out of the safe, replying, already done. I only felt my legs weaken when I realised the passport control officer was flipping through the old full passport that I was warned about back in 2019. Hot out of the gates, my vacation brownie points were in the red. Honestly, I also didn’t know how many border posts we would cross and how many stamps I would need space for in the days to come. Twelve. Out of South Africa, in Zimbabwe, out Zimbabwe, in Botswana, out Botswana, in Namibia, out Namibia, in Botswana, out Botswana, in Zimbabwe, out Zimbabwe, and in South Africa.

Every border crossing was a teary-eyed negotiation followed by a sense of achievement. Africa has a talent for producing this feeling of accomplishment. Apart from the full passport, past examples include disappearing into the traffic after ignoring a traffic officer and walking through customs with a suitcase full of biltong.?

I can go into the how part here, explaining how not to argue with any government official or put your bag on the scanner behind a large group of people to give yourself a good chance of slipping through unnoticed—choosing the accomplishment narrative.?

Or perhaps the official was a family man, and he didn’t want to hold up the rest of the group, or the person behind the scanner was having a no admin day.?

Hindsight is not always the best sight in success or failure because it is a story we tell ourselves.?

And in hindsight, I should have moved my old passport to a different location because I knew this would happen.