The Illegibility Tax

In the spring of 1833, a 24 year old in New Salem, Illinois was watching his general store fail. His business partner drank too much to work and saddled them both with debt they couldn't service^[1]. Creditors seized his only assets (his horse and surveying tools) and sold them at auction. A friend bought them back for $120.

He had no formal education, failed as a store owner, failed to win a seat in the state legislature the year before, and was now broke in a failing river town. He took odd jobs splitting rails. He taught himself law by borrowing books. He was muddling through.

There are two kinds of career stories: legible and illegible. A good rule of thumb is if what you're doing is hard to explain to your grandparents, that is an illegible story. If you can compress your story into a neat box ("I am a doctor", "I work at Google", etc), congratulations, that's legible. The challenge with the illegible path is it makes you pay extra to be believed, while legible paths get the benefit of the doubt. When something doesn't work out on a legible path, you still gain the credibility of the institution (a flopped Google product launch is still a Google product launch). Without the credentialing, you pay the illegibility tax.

If you'd asked anybody in Illinois, let alone Washington, who our man in 1830s Illinois was, they would have said he was nobody. He was paying the tax.

He started a law practice 70 miles east in Springfield, riding between small-town courthouses. He was developing judgment. In 1846, he was elected to the US House of Representatives, opposed the Mexican-American War against President Polk, lost popularity, and returned to Springfield after a two year term. He lost a US Senate race in 1855, and another in 1858.^[2] He was illegible right up until the moment he wasn't. His name was, of course, Abraham Lincoln, and the path from bankrupt shopkeeper to the presidency was so improbable that even the political class of 1860 couldn't explain it.^[3]

Lincoln muddled through – and the odd jobs, failed campaigns, the long education through rural court houses in Illinois – shaped him into the person he needed to be when the moment arrived. A credentialed lawyer from a good family, rising through the legible channels, would not have been Lincoln.^[4]

That same spring, another 24 year old (in fact, they share the same birthdate) was 7,000 miles away off the coast of South America. He had been at sea over a year and still got seasick every time the ship left port. He was still over two years away from observing the finches that would one day be known by his name.^[5]

His father, a wealthy physician, pushed him towards a legible path for British elites. Our man dropped out of medical school^[6] and enrolled in a theology program as a fallback to appease his father^[7], who called the Beagle journey a waste of time^[8]. The voyage was supposed to last two years. It would last five. The reason he was on the ship at all was as a gentleman companion for the captain, whose predecessor had shot himself at sea during the first Beagle voyage. Near Maldonado that May, he wrote a comment that could have as easily been made at home: "the people all look at me rather kindly but with much pity & wonder". Charles Darwin returned to England in 1836. He would not publish On the Origin of Species until 1859, the year before Lincoln was elected president of the United States. Each had a quarter century of muddling before becoming great men of history. The muddling was the process.^[9]

In 1849, while Lincoln was practicing law in Springfield and Darwin was sitting on his theory in Kent, Danish philosopher Søren Kierkegaard published The Lily of the Field and the Bird of the Air, offering the lily and the bird as models of being what they were meant to be. The lily doesn't aim to be the most beautiful, it just grows. The bird doesn't explain its song, it just sings. Something is gained through silence – stop talking long enough and you hear what is being said.^[10]

Lincoln in Illinois and Darwin on the Beagle were in silence. Not fitting into a neat box (which would have been much nicer!), forced them to pay attention to what was in front of them. Because of this silence, they recognized their moment when it arrived. Lincoln saw the popular sovereignty crisis of the Kansas-Nebraska Act^[11] for what it was because he'd spent years listening to how ordinary people thought about slavery and union. Darwin noticed beaks of finches on different islands adapted to local food sources because he spent years in curious observation.

Muddling through is the silence you need to make recognizing the moment possible.

At least, I hope so. I learned this the hard way.

I spent a few years building startups in partnership with corporations. They helped test ideas, invested, and became early customers. We launched thirty companies, but feedback cycles are long and the model bets on the power law^[12]. No company had become a home run, and the model was still unproven when I had to move on. "It's still early" is a hard sentence to build career credibility on.^[13]

Last fall, it was ten minutes after the call started, and it was clear it had ended. The former energy secretary said he had to prep for another meeting. I was wasting his time, and he was right.^[14]

He had taken the call as a favor, and had enough context on my interest in nuclear power – a sector in the middle of a renaissance – to take the call. He was not unkind about any of this. I received what I believe to be a sincere invitation to get back in touch when I had more progress. I left feeling like a college kid at a career fair.

That afternoon at the park with Teddy, joyful chaos of kids and parents everywhere, all I could do was offer a thousand yard stare into the distance sick to my stomach. I had been working for over ten years, with daily stresses and ups and downs, and it was still a round trip back to the career fair. Had I wasted a decade?^[15]

That call was the most painful moment, but it elucidated a pattern. Earn a warm introduction. Prepare notes, an agenda, ideas. Have a (usually!) energizing conversation. Follow up. And watch the momentum, very politely, drift into the sunset.

The language I used to describe what I'd done didn't match the language of their world. I was illegible^[16], which feels like a liability for now, but maybe an asset soon.^[17]

I find solace that Lincoln and Darwin muddled through. I'm running into opportunities I never expected.^[18] The connections that feel most natural are outside venture capital and startups, with people more interested in how the world works than in the specific mythology of the startup world.

One introduction led me to a local brewery CEO. We met at the brewery and neither of us was quite sure why we'd been connected. We talked about faith, Norway, and how to make it easier for distributors to sell your beer. He focused on making a profit as a means to putting his employees and community ahead of himself. Eventually a business problem came up I could help with. And for the first time in months I got a burst of energy, from a totally unexpected place. To this day I don't think he has asked me to explain a venture studio. It helps that I was paid in beer.

Progress came from being curious and useful.^[19] Fernando Pessoa in The Book of Disquiet called a lack of recognition "The nocturnal glory of being great without being anything!".

There is a quiet dignity in illegibility.^[20] And I'd be lying if I said it was enough. It's hard to do anything meaningful if nobody will collaborate with you or share in what you're creating. A favorite poem builds on the ideal of humility (emphasis mine)^[21]:

I want to be famous
so I can be humble about being famous.
What good is my humility
when I am stuck in this
Obscurity?

If you're working on the illegible path, you can't will yourself into recognition, and you can't will yourself into being satisfied without it. You can keep showing up, working to understand and help the people and situations in front of you. The illegible story asks you to muddle on.

Hebrews 11 holds up Abraham, Moses, and the prophets not as men who reached the promised land but as men "commended for their faith, yet none of them received what had been promised." The payoff came in ways they didn't expect.

I don't have this figured out. I'm lucky to have some good people join me on the path.

Charley Berno
February 2026, Washington DC

Addendum

Wendell Berry reminds us "It may be that when we no longer know what to do, we have come to our real work, and when we no longer know which way to go, we have begun our real journey… The impeded stream is the one that sings".