The Wrong Lesson.

A friend texted me last week: How come you haven’t written anything about The Odyssey? -given my love for Nolan and history!

Well, I was late to the movie, and then work took over. Writing is still the sidekick; I have an entrepreneurial life to run- maintaining what we have build, toying on my nextBiGThings, and also talking with other builders and operators.

However, I did finally watch The Odyssey a few weeks ago. But more than Odysseus, I went into rabbit hole for the another word Homer gave us: mentor.

An “odyssey” is a long journey. “Mentor” also comes from the same story, from the man Odysseus leaves behind with Telemachu. Today the word is synonymous with guidance.

Athena also takes Mentor’s form while guiding Odysseus. Today, we use the word as: someone older who gives advice, makes introductions, warns you about mistakes.

A comment from Sumant on my last post, Have Fewer Opinions, pushed me here. His point was simple: we routinely fail to distinguish an observation from an assumption, a working hypothesis from a fact, even an emotional reaction from an argument.

We keep hearing some version of “twenty years of domain experience” in founder and investor conversations. Sometimes it means exactly that. But sometimes it means one year of experience repeated twenty times because the original assumptions were never reopened.

Experience is not compounded thing, esp if you are NOT making mistakes AND learning from that. We discussed something adjacent in Freedom of Failure: failure is useful only if it damages the original explanation. Otherwise, we simply absorb the event and preserve the story.

So, if the first classification was wrong and nobody goes back to inspect it, tenure merely gives the mistake a longer history.

Let’s assume a founder makes a chaotic early decision but the company succeeds; so now this has becomes “visionary instinct”. Another founder behaves almost identically and fails; so we will call it as reckless execution.

A favourable market/perfect timing can turn improvisation into a playbook. Scale can make luck look like wisdom.

When the number works, the strategy was right. When it misses, execution failed.

Convenient.

Founders are often at their best when they still know they are inexperienced.

As we are forced to learn quickly, test assumptions, change course and build conviction from contact with the problem rather than from reputation.

The danger often comes later, when repeated success hardens that learning process into a set of answers.

That may be the harder test of experience: not how many situations you have seen, but whether each new one still has the power to change your explanation.

Seniority introduces another problem.

As careers progress, many people gain experience while losing direct contact with the work that originally produced it.

A banker can discuss digital customer behaviour through dashboards without sitting through an actual onboarding journey, which in India is often still painful.

At some point, experience can stop being a discovery mechanism and become an archive of views formed under earlier conditions.

The experienced operators I trust most tend to stay close to the raw work. They still open the document, test the product, speak to the customer, try the tool. Their experience helps them ask better questions; it does not exempt them from checking.

That is also where I now place the mentor.

A mentor may be a your customer, colleague, someone much younger who happens to be closer to the raw work or just a reader. Sumant did this with one comment.

The qualification is not age. It is a combination of proximity and independence.

Every odyssey does need a mentor. Not because the journey is difficult, but because experience can teach the wrong lesson just as easily as the right one.

Which of the lessons I carry from experience were actually earned, and which were simply never challenged?

And who around me still has permission to say:

“I think, you learnt the wrong thing from that.”