6 min read

What I Learned from Tynan: Lessons from the Quintessential Man

I love the internet. It’s full of fascinating people, sharing what they do and what they love.

Imagine reading blogs from:

  • a startup founder
  • a digital nomad
  • a full time poker player
  • a book author
  • an avid teetotaler
  • a tea fanatic
  • a person who bought a private island
  • a person who lives in an RV

The lessons you could learn! So many perspectives and situations and ideas!

But wait.

What if I told you...

...these are all the same person?

His name is Tynan. Stan Lee (of Marvel comics fame) dubbed him “The Quintessential Man”.

Tynan is the founder of Sett and Cruise Sheet. He spends the majority of his time traveling with just one backpack.

This unusual life journey arose not from willy-nilly excitement seeking, but from a set of principles that you can learn too.

If you want to live a life that’s off the beaten path, you have got to read Tynan’s work.

Photo of Tynan

*Tynan of Tynan.com*

I’ve never met Tynan, but because of his writing I’ve made big decisions I never would have before:

  • Traveled Asia for 3 months
  • Decided to work for a startup
  • Bought my own private island (just kidding...for now)

Tynan.com has 1240 blog posts. That’s more than two posts a week for 15 years straight. If that weren’t enough, he’s written 7 books.

In case you don’t have time to read 1240 blog posts, I’ve distilled two lessons I’ve picked up from Tynan, and given you a starting point to learn more.

Lesson One: Live at the Extremes

Tynan dropped out of college to play poker full time. Before moving into a '96 Rialta Winnebago, he lived in Hollywood with 5 pick-up artists. In his thirties, Tynan worked 12 hour days to build Sett, a blogging platform, all while travelling most of the year. Now, he owns property in Vegas, Budapest, Hilo, and Halifax, just to have homebases around the world.

Tynan’s life choices are extreme.

Most of us think, “wow that’s crazy,” and go back to our desk jobs. But Tynan thinks you’re the crazy one.

Living at the extremes is safer than sticking with the herd.

Whatever the masses do becomes a commodity. Each person doing the exact same thing as you reduces the potential rewards. Imagine getting laid off during an industry downturn. Now you have to compete with a crowd for your next job.

By definition there are less people at the edge. At the extremes, you have more opportunity to find a good fit for your particular set of skills.

Tynan's idea of contribution: push the boundaries of what's possible.

“I feel like this is how you contribute to society, even if it’s in a very small way.”

This all comes with a caveat: don’t do random things just because they're weird. Every extreme thing that Tynan did was chosen deliberately. He thought it was a good idea, even if no one else did. The aim is to do things that seem crazy in the moment but in retrospect look like good decisions.

Ask yourself, what’s interesting that no one else is doing? What combination of skills do I have that no one else does?

Being extreme makes it easier to get what we want.

It seems like Tynan lives a crazy life of luxury, wearing Rolexes and traveling all the time on cruises. In reality, he's cutting what he doesn't care about to a bare minimum, so he can spend freely on the things he does care about.

Tynan knows what he desperately wants, and is okay letting go of everything else. This allows him to spend extra time and money to get exactly what he's looking for.

Most of us buy things that reflect our class, not what we want.

"devoid of any serious thought on the subject, people slide into convenient socioeconomic molds."

What do you own that's just "nice-to-have"? What are your actual desperate-wants?

The limits of possibility are further than you think.

Speaking of unusual purchases: at 19 years old, Tynan and his friends decided to buy a school bus. What a crazy out there idea! Who thinks of buying a school bus!

Tynan writes: "It seemed as though some authority figure would appear out of nowhere and say, 'Come on guys, this is ridiculous. Go back to school.'"

But no one stopped them. They were able to buy the bus: "the normalcy of the transaction, handing over cash for a title and some keys, was striking. What seemed like a big deal really wasn't."

We all want to do crazy things, but immediately shut them down because no one else is doing them. How many times have you said no to an idea that was “too out there?” How many school buses are you ignoring, even when you really want it?

More from Tynan on living at the Extremes:

Lesson Two: You Can Train Yourself

You're not Tynan. How can anyone operate at the extremes when there's so much peer pressure against it? What is Tynan's secret sauce? How does he do it?

Train Yourself to Enjoy Discomfort

Here's how: “We love to complicate the process of training a human, but really it's just as simple as training any animal:"

  • Start now.
  • Reward good behavior.
  • Repeat the action.
  • Reward yourself for the process, not the outcome.
  • Set challenge level appropriately

This is the key to every seemingly impossible behavior Tynan takes. Once you figure out that humans can reward themselves mentally, you can train yourself in all kinds of situations. Want to eat more vegetables? Scarf 'em down, then  stand up! Throw a fist pump! Celebrate with a shout!

Train yourself to want the right thing, rather than forcing yourself to do the right thing.

"You might say that [eating vegetables and working hard] sounds boring to you. I believe you, but all of the things I say not to do sound extremely dull to me. Who's right? Both of us are, it's just perspective."

Practice taking action just outside of your comfort zone. You’ll quickly find that it wasn't as difficult as you thought. Keep rewarding yourself mentally, and you'll get better at that too: “self-praise reinforces your ability to generate your mood from within.”

Building Trust In Yourself

This kind of training not only makes it easier to live at the extremes, it builds an internal sense of trust. Think about that coworker who always gets the job done. Why do you trust them? Because if you ask them to do the job, it happens.

Want to be a more timely person? Make it to your appointments, even if you have to drop other important work to do it: "it's better to stick to your commitments in the short term, the painful consequences train you to not make that commitment in the future"

Train yourself to trust yourself. Just like you trust your coworker to do what they say they will, you build trust in yourself every time you stick to your own word.

How to love the mundane

All of this training isn't to become some boring robot, churning out tasks because it's good for you. If anything, it leads to more enjoyment:

"I sometimes see people encouraging me to have more fun, not work so hard, etc. I get where these ideas come from, but they couldn't be farther from the truth. I don't get stressed at all with doing this stuff. I love it. Enjoyment and happiness comes from attitude and process, not from setting or result. It took me a really long time to actually believe this and to internalize it."

If you have to it anyway, you can love doing the dishes, love working, love healthy food. Build more positive experiences into your daily life.

"I try to be fully present whenever I do anything, whether it's washing dishes or drinking tea with friends. It's that whole commitment to the present that allows me to see all of the positive details of each experience."

More from Tynan on training yourself:

What Else?

There are so many more lessons to unpack from Tynan. His work covers a multitude of topics: minimalism, relationships, introspection, how to allocate time; I can’t possibly do them all justice.

I'll leave you with one more quote, on happiness:

Happiness is essentially the process of becoming honest with yourself and the world. You see yourself for who you are: good, but imperfect, and capable but not beyond error. You see that the world is a good place, but not a perfect place. You accept that billions of things will happen in your presence during your lifetime, and that not all of them will be exactly what you wanted them to be. You understand that your mood is the product of your reactions to external forces, not the forces themselves. With practice and will, you can ply those reactions to match your logical and honest view of the world.

You can find more from Tynan here:



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