Mental Mentors

how to find a mentor

“We should hunt out the helpful pieces of teaching, and the spirited and noble-minded sayings which are capable of immediate practical application—not far-fetched or archaic expressions or extravagant metaphors and figures of speech—and learn them so well that words become works.”


I’ve always struggled to retain certain information. Unfortunately, it often applied to topics we covered in school: derivatives, the meaning of The Scarlet Letter, and the state capital of Washington (I had to look it up, it’s Olympia) remain beyond me.

But for some things – information about my favorite artists and authors, for example – I have a steel-trap memory.

I don’t bring this up to show off or look like a dick on the internet (though it seems likely I’ll accomplish the latter before we’re done here). I bring it up because I believe the ability to seek and retain information from a small number of sources can pay off exponentially.

Let me explain.

Totally by accident, I’ve become an expert on many of my influences. I don’t mean “expert” in the traditional sense. I’m no literary scholar, and I don’t have an advanced degree.

I do have intuition. I’ve spent hundreds of hours engaging with the ideas of people who have most influenced me; that effort has given me a feel for their views. I’ve absorbed their key beliefs and learned their strengths and weaknesses.

Today, I have 15-20 of these mental mentors rattling around my brain. Their advice allows me to avoid learning from experience, which is slow and painful. Rather, as Bismarck advised, I can learn from the experiences of others.

Have you ever been in a tough spot and heard your parents’ advice echoing in your head, telling you what to do? It’s kind of like that.

As someone who just admitted to hearing voices, I worry that my credibility is on thin ice here. But this cultivation has had life-changing results, both tangible and intangible: my mental mentors have helped me develop my values, make critical decisions, and avoid damaging missteps. Any success I’ve had in life is creditable to them.

As Seneca wrote, we must sit with work that resonates with us and attempt to absorb the author’s teachings. We must ingest their wisdom, letting it give us energy and direction.

In other words, we should eat our mentors – with salt. Everything tastes better with salt.

Today, I’ll share my recipe for intellectual cannibalism, carefully calibrated over years of trial and error. It takes a while to make, but it’s the most nourishing meal there is.

Source one (1) piece that resonates with you

The quality of ingredients matters a great deal, so I suggest searching widely for that source. Locally-sourced foodstuffs are great, but locally-sourced ideas are often less so.

We all have a starting point, influence-wise, and it’s probably close to home. It’s likely our parents, friends, work colleagues, or something we saw in a movie.

But we can’t limit ourselves to one discipline, type of person, or medium. We must scour the earth for only the finest ingredients. This has two parts:

1) Developing an openness to ideas and experience

2) Intentionally pushing beyond our comfort zone to new genres, mediums, and dissenting opinions

The first point is surprisingly difficult to implement. Openness begins with humility. You must be willing to take onboard information that challenges you. It doesn’t matter what you’re reading or listening to if you think anyone who doesn’t share your worldview is full of shit.

For most of us, there’s ego tied up in our unwillingness to listen. We believe our views are best – after all, if they weren’t the best, we wouldn’t have them in the first place.

But how closely have you examined this particular belief? When you zoom in on it, most of our views are unconsciously adopted from the world around us.

We know you get sick from going outside with wet hair in the winter, everyone on the other side of the political aisle is a kook, and the T. Rex was the coolest dinosaur.

It turns out none of this is capital-T True, but it’s easy to believe if we never seriously examine ourselves.

The key is to infuse yourself with a dash of humility. You’re a chef searching for the best ingredients, not a county fair contestant explaining why your recipe makes a blue ribbon-worthy pie. Your position on nearly everything must be held as temporary – a belief, for now, but always subject to change.

“Never let your ego get so close to your position that when your position goes, your ego goes with it.”

Colin Powell

When you seek out different opinions than your own, pushing beyond your comfort zone becomes much easier. There are three tips I’ve found helpful in my ingredient search:

Find gateway thinkers. I enjoy authors who provide gateways to other great minds, like Robert Greene, Ryan Holiday, and Austin Kleon. Their books are amalgamations of many potential influences I haven’t yet encountered, and they wear them on their sleeve (and in their bibliographies). These are excellent starting points.

Look for specifics. When searching for my ingredients, I’m not looking to evaluate an author’s ideas or arguments on the whole; almost everyone with something interesting to say has at least one Olympic-level bad take that I must ignore to get the good stuff. Instead, I focus on specific things that I can steal from each person.

Feel free to medium-hop. I wouldn’t limit myself to books. YouTube explainers, TED Talks, podcast interviews, blog posts, and whatever else a search might turn up is interesting. Most productivity cultists overrate podcasts and books but underrate YouTube videos. Do what you will with that information.

Seeking interesting ideas is a bit like fishing. Most days, you won’t catch much. But if you’re out there long enough, you’ll inevitably come away with something to show for it.

If you keep putting your line in the water, you’ll occasionally have a bonanza of a day: a book that shakes your worldview, a podcast that introduces you to a fascinating new field, or a mental model that clicks. These are the kinds of ingredients you can build a dish around.

Gather secondary ingredients

Most people, when they find a book they love, they’ll put it down and…move on with their day.

No! Fuck no!

People who truly speak to you – the kind of people who can make something that changes how you see the world – are few and far between. If you find one of those people, don’t let them go, and don’t drop the subject. When you find something that resonates with you, pounce on it.

You’re looking for excellent adjacent things – role players in your recipe to add flavor. A mild obsessive tendency can go a long way here. A few of my favorite tricks:

  • Find out who made it and how they did
  • Figure out what else they’ve made that might be of interest
  • Listen to their interviews on YouTube or listen to podcasts they’ve been on
  • Read from the bibliography or the podcast’s show notes
  • Read their website
  • Re-read or re-watch their work
  • Write down notes about their ideas
  • Learn about the themes of the work or the sources of the ideas it contains

Once you’ve swarmed someone’s work, interviews, and other assorted media, you get to take their brain out and play with it. Write about it. Talk to your friends about it. Quote their work in emails. Relate whatever’s going on in your world to things they’ve said, written, or made art about.

This is the process of building your dish. You’re playing with the ingredients, tweaking an idea here or a source there.

The discovery process and adjacent roads can occupy you for a few weeks to a few months. This is the point. A deep understanding of a few people’s ideas is far more potent than surface connections with dozens of others. Time spent with one person’s brain isn’t linear – it’s exponential. Twice as much time is four times as good.

Savor this process; it’s the best part. Discovery is thrilling. Finding something that makes you sit back in your chair with a mile-wide grin or immediately pick up your phone to text your friends is infinitely better than rushing a half-cooked dish to the table so you can start the next one.

Mix and blend ingredients. Salt to taste.

Now that you’ve brought all of your new ingredients together, it’s time to mix them with some of your familiar ones.

You’re building a house blend, customized to your unique palate and ideal flavor profile, comprised of all the advisors you’ve accumulated in-person and otherwise.

In so doing, you can build on the ideas of one mentor using another.

If I was trying to figure out what to prioritize in a career search, Ryan Holiday’s advice to seek “not what will pay me the most, but what will teach me the most” might pop into my brain. I might think about being driven by purpose rather than passion, which I also learned in one of Holiday’s books.

I might also think about where the next job should fit in my “career portfolio,” a concept popularized by Marc Andreessen. How much risk have I taken in my previous positions? Given my stage of life and financial situation, how much can I afford to take right now?

In other words, the “latticework of models” famously referenced by Charlie Munger can become a latticework of mentors, stitched together by intersecting, complementary ideas.

Conflicting advice is no less valuable. One of my guiding principles is optionality – the right, but not the obligation, to do something. However, I’ve also learned from anti-optionality voices like Peter Thiel, Nat Eliason, and Elon Musk. Disagreements between mentors help me test my beliefs and learn which ideas to apply where.

Creating, assembling, and maintaining this latticework of mentors is what I think people mean when they talk about being lifelong learners.

You can learn one-off facts, understand historical context, or memorize dates, but absorbing your mental mentors and building the latticework that connects them into a philosophy of living is where real knowledge is born.

Eat slowly, with chopsticks

Earlier in this article, I mentioned that many of us can hear our parents’ voices in critical moments. They offer us advice, reassurance, or criticism, depending on the situation.

It’s a useful feature of our brains – when we’ve digested the way someone thinks, we carry a mental version of them around with us. They might pop up at random intervals, or we might consciously pull them into our psyche as we grapple with a problem and debate our next move.

Few would deny these mental mentors’ power, but most use only the factory settings: our parents, friends, and colleagues.

I find this stunning and sad. When we get a new apartment, we spend hours agonizing over which pieces of furniture will express our unique perspective on the world. We obsess over our physical surroundings, painstakingly choosing the things we’ll look at and interact with each day.

We apply no such standard to our brains. It’s no wonder that we stumble around in the dark, unclear what to try or where to go.

We could leave the most important things in life to chance. Or, we could cultivate a set of mentors to light the path. Which process would you trust to deliver a positive result in a high-stakes game?

Rather than conducting a scattershot search for knowledge, canvas the work of someone who feeds your soul. Ingest their thinking repeatedly, interact with it, play with it, obsess over it – and you’ll end up building a model of their way of thinking.

Then find someone else who changes your worldview and repeat the process.

Building your latticework of mentors takes time; it’s not One Simple Trick or a lifehack or even a way to Get Cash Now.

But by spending dozens or hundreds of hours ingesting their ideas, you’ll create the perfect meal to nourish your brain for a lifetime.

Further reading:

Steal Like an Artist – Austin Kleon (Amazon)

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