• The Soloist
  • Posts
  • Tinkering Is Better Than Knowledge | #21

Tinkering Is Better Than Knowledge | #21

How to succeed online through trial and error

Tinkering Is Better Than Knowledge

No. 21 — read time 5 minutes
Welcome to The Soloist, a weekly newsletter where I provide actionable ideas to help you become a healthy, wealthy, sovereign entrepreneur.

On a cold and windy December day in 1903, two brothers from Dayton, Ohio flew the first powered aircraft in history.

Orville, the younger brother, piloted the first flight covering 120 feet in 12 seconds. His older brother, Wilbur, piloted the fourth and final flight of the day covering 852 feet in 59 seconds.

This historic event was a monumental shift in how humans would traverse the planet. If you ask anybody off the street who the Wright Brothers are, most people would know.

What most people don't know is that neither brother had any formal education or training in aeronautics or engineering.

Neither had any schooling beyond a high school education.

Instead, what they had was a lifelong passion for tinkering, and an obsession with flight. Sparked by a toy helicopter they received from their father as children, they would spend their adulthood taking profits they made from their bicycle shop and re-investing it into flight experiments.

Tinkering, not knowledge, led to the discovery of human flight.

We see this repeated throughout human history. The list of inventors with no formal education include Thomas Edison, Benjamin Franklin, and Steve Jobs. Great cathedrals of Europe such as Notre Dame, Santa Maria del Fiore, and the Basilica of San Francesco, were all built by architects in medieval times several hundred years before the introduction of formal geometry.

Why Tinkering Isn't More Popular

Tinkering is inherently low status.

You spend years making no money. It can seem like wasted time. It's driven not by a desire to achieve prestige or money, but by a genuine interest in a specific field.

But tinkering, unlike knowledge, is one of the most asymmetrical bets you can make. It is better than knowledge.

When students arrive on campus as freshmen, they have to choose a major. Most of the students have their minds made up, all but certain they want to go into Computer Science or Accounting. They march on their path towards their goal, accumulating knowledge.

After four years and a considerable sum spent on their education, they enter the workforce only to realize that they may not actually enjoy the work. Or that line of work is now threatened by the rise of AI.

They've "wasted" both time and money on a path that no longer looks as interesting as it once did in their minds.

This top-down approach has tremendous downside risk.

Tinkering limits the downside while keeping all of the upside.

Instead of a guess at the outset with further investments to see if the guess was right, it would be a series of low-risk experiments. For instance, it might mean taking on apprenticeships or learning online while engaging in the actual work. For aspiring developers, that could mean building a project on the side.

Learning by doing.

To put it in mathematical terms, tinkering is convex (upwards sloping curve). Knowledge is concave (downward sloping curve).

Nassim Taleb's book, Antifragile, explains how things that benefit from uncertainty are convex. Things that are hurt by uncertainty are concave.

Don't get too hung up on the math. In simple terms, convex is capped downside unlimited upside, concave the opposite.

Taleb renamed concave 'antifragile' — things that gain from chaos.

Self-Employment As Convex

One of the biggest hurdles for people looking to leave 9-5 corporate jobs and explore entrepreneurship is the terror of direct exposure to the uncertainty of the market.

W2 jobs shield employees from uncertainty and volatility. The uncertainty of markets still exist, but the "steady paycheck" smoothes the volatility allowing you to be lulled by a false sense of security.

But as the 250,000 tech workers laid off the last 6 months learned, the uncertainty was always there, even if hidden.

Where entrepreneurship has a leg up on W2 is the ability to tinker across many experiments, in parallel, in order to limit downside risk while still benefitting from high upside.

This idea is counter to the fiction that is sold on media outlets like TechCrunch and Shark Tank. The notion that you need to be "all-in" on a single idea is not only dangerous, it misses the whole fun of self-employment — tinkering.

Tinkering, running experiments, failing, are all core parts of the diversified approach to entrepreneurship that marries a love of the process with positive asymmetry.

Tinkering can also be done part-time. Many online entrepreneurs start out part-time. Both Ben Meer of System Sunday and Eve Arnold of Part-Time Creators Club started out part-time. They benefited from tinkering on the side.

Almost every overnight success you see was a 10 year experiment in the making.

6 Steps To Convex Tinkering

As I made the switch from working on VC-funded businesses to working on my own, I noticed a pattern emerge in my approach.

It's a pattern I've adopted over my career dating back to my first entrepreneurial ventures.

Here's a predictable 6-step process to stack the odds in your favor:

  1. Understand how asymmetry works

  2. Write out all of your strengths (things you know cold)

  3. Rank them by Upside and Effort (filter by low effort, high upside)

  4. Begin experimenting (commit to 30-60 min per day)

  5. Show your work (talk about what you’re learning)

  6. Manage the ego (the ego will be afraid of looking stupid)

Experimenting in areas where you have a Venn diagram of natural strength, low effort, and high upside, you put yourself in a position to gain from uncertainty.

The hardest part of this process is managing the ego.

As I mentioned earlier, tinkering is low status.

Unless you show your work. This is where the idea of using your sawdust comes into play.

Because of the internet, you can build an audience simply by talking about the experiments you're running, how they're going, and what you're learning.

So the only area left for the ego to fight over is the resistance to killing any projects that are underperforming.

There can be no sacred cows.

Remember, you're tinkering.



P.S. Whenever you're ready, there are 3 ways I can help you:
  1. If you save a lot of bookmarks on Twitter (like me), try dewey.
    the easiest way to organize Twitter bookmarks (I'm one of the makers).

  2. If you're looking for coaching on business or audience growth book a slot here.

  3. I’m putting together a course on how to network online to grow faster. If you’re interested sign up here.

This week’s newsletter is brought to you by Beehiiv.

Beehiiv is the only email service provider with a built-in referral program. Explode the growth of your newsletter by using the most powerful persuasion tool out there, word of mouth.

Start growing your newsletter faster here.

If you enjoyed today's newsletter, please share it with your friends and family!

If this email was forwarded to you, consider subscribing to receive them in future2