The Amateurs who Solve What the Experts Can't

Hey Friends,

This month I’ve been thinking about amateurs.

The word gets used as an insult — someone not quite serious, not quite qualified. But it comes from the Latin amator: lover. An amateur isn’t someone who does a thing badly; it’s someone who does it for love, not for a credential or a paycheck.

This month’s Field Guide is about what that means for the work only you can do — and about the fear, usually money, that keeps us from it.

This episode is its perfect companion. I recorded it before Everyday Ambassador moved to Substack, so most of you have never heard it — and I think you’ll enjoy it.

It opens with Natalia Antonova, an open-source investigator who works with amateur online detectives — “some guy named Bob in Florida,” as she puts it — who crack cases that stump Interpol.

Then I sit down with Christian Madsbjerg, the business consultant and philosopher who advises some of the world’s largest companies not with spreadsheets but with what he calls epistemological humility: the willingness to show up knowing nothing, observe, and truly listen. Christian tells the story of how years of simply watching people helped move Ford toward electric vehicles.

We close with Northwestern students on what an outsider’s perspective makes possible — and how often it’s the source of the most kindness.

• Show up knowing nothing, on purpose. Madsbjerg’s “epistemological humility” isn’t a weakness to hide; it’s the stance that earns trust and surfaces real insight. Try leading a hard conversation with “I’m here because I don’t know.”

• Observe before you opine. Madsbjerg compares an amateur perspective to going to the gym: spend a little time each day simply describing what’s happening around you before you judge it. It’s a muscle, and most experts have let it atrophy.

• Recruit the amateurs. Some problems require a crowd of people who care. Ask who, outside your field, might see what you can’t — and invite them in.

• Trust that insight travels on its own. You don’t need the credential for a true observation to carry. Say the useful thing even when you’re the amateur in the room.

• Follow the “juicy” question. Madsbjerg left a professorship because the work wasn’t fun enough. Curiosity — the question that pulls at you — is not a distraction from the work. It often is the work.

If this resonates with you, share your thoughts and experiences in the comments:

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Here are three more ways to take it further this month:

• Read the framework. This month’s Field Guide goes deeper into the amateur move and the money question underneath it — the fear that keeps us from the work we’d do for love.

  The year I stepped off the straight and narrow

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  Jul 9

  

  Last month I asked you what single thing most stands in the way of doing the work only you can do to change the world — was it not knowing what to do? Fear of what people would think? A lack of a supporting community? Eighty percent of you gave the same answer: money, and how you would support yourself.

• Bring your questions to our live AMA. On Wednessday, July 22 7pm Eastern, I’m going live to talk all of this through and answer your questions — open to everyone, with the replay for paid subscribers. Post your questions in the comments here and I’ll take some live.

• Come talk it through at the Everyday Ambassador Salon. At our next Salon on August 7 at 7 pm Eastern — the small monthly gathering I host — we’ll explore amateurism together. One of our members, a former Silicon Valley executive, will share his experience of leaving the straight and narrow path. If you’ve been curious about the Salon, you can join just this one session with a day pass and see whether it’s for you.

Credits: This episode was produced by FP Studios with support from the Humboldt Foundation. Our on-campus producer was Mia Perkins.