Issue #63
#63 - Wisdom from Jeff Bezos, a Poker Champ -- and Ants 🐜 -- on risk-taking, exploration, and knowing when to go all-in
April 21, 2023

What's up, everybody?

Last week we ended the newsletter with 3 questions:

  1. What am I working on and thinking deeply about right now?
  2. Is that something I truly care about? Something I want to lead on, if even in some, small way?
  3. If so, am I making the time and space to be able to think and work deeply on it?

Today, there's a related question we want to ask: how do I know when to go deep on something? How do I know when to commit -- to an idea; a place; a risk; a job, a career?

This week, we suggest that the key to that question often lies in effective exploration. In our 3 Stories, we look at the upside of being an eternal explorer, as well as the dangers of dabbling without committing or focusing on anything. And in the end we conclude that there are massive gains to be had by learning to go both broad, and deep:

Story #1 - A world-champion poker player shares what we can learn from ants -- yes, 🐜 's -- about the benefits we accrue by perpetually exploring.

Story #2 -
But where do we draw the line between healthy exploration -- and a lack of risk-taking and commitment? What are the downsides of only ever exploring and diversifying our bets? From Story # 2 we learn that the risk of doing that -- not least, to our individuality -- is real.

- What "one, last thing" would you say to the company you had built from scratch over the course of 25 years? Story #3 is what Jeff Bezos felt compelled to share with his employees in his final letter to them. Hint: it's also got to do with maintaining our originality. 🙌🏻

Thanks, always, for reading and exploring with us -- and have a great week!

Aki + Usman

P.S. Our podcast on issue #62 -- "On Leadership: Finding the Conviction Needed to 'Shape the Wave', and 'Take People to Where They Don’t Want to Go' " -- is here.


#AlwaysExploring #DeepANDBroad #HedgingBets

Annie Duke is a world-champion poker player and a best-selling author. In her latest book, "Quit: The Power of Knowing When to Walk Away", she writes about what we can learn from ants, as a species that has survived for 100,000,000 years. Give or take. 🤯

She explains that when ants find food, they use pheromones to communicate with others in their colony -- and they exploit: they go after the food. But simultaneously, a minority of ants also continue to wander around -- to explore the environment for the next opportunity.

The point she makes is: always be exploring. Even when you're going "deep" on something -- and especially in a world that's changing as quickly as ours -- it behooves us to balance both exploration and exploitation; it makes sense to balance exploring new ideas, even as we concentrate on something worth exploiting.

The idea is akin to diversification; to not having all your eggs in one basket. For example, in work terms that are especially relevant to 2023: there is real benefit to keeping an ear to the ground for new opportunities, even when we're in a job that we enjoy and are focused on.


#OverIndexing #AvoidingAverage #BigSwings #OutsizedReturns

In this post on his blog, John Luttig explores "the index mindset", a term he borrows from the index funds that are popular with investors. The idea of an index fund is that it's safe. Diversified, and easy. You can just "set it and forget it".

But Luttig explains that while:

Index funds have come to dominate public markets, the shift towards indexing is spreading across tech, careers, and culture too – in what I call the "index mindset".

No doubt, there are real benefits to investing in index funds. But there are at least two big risks to allowing this mindset to seep into too many other areas of our lives. One is the risk to our individuality: that by indexing in so many realms, we might become "an average of everyone else". Indistinct, undifferentiated, and blended into the masses. (And it's worth noting that in an age dominated by machines, algorithms, and efficiency, this risk -- and the effort required to avoid it -- are greater than ever).

The second risk is that if we only ever chase "optionality", if we only ever dabble and explore, if we only ever spread and hedge our bets, if we only ever play it safe, if we never take "big swings" -- if we never concentrate by going deep and committing to something from time-to-time -- then we risk missing out on the events, jobs, careers, people, and dreams that can lead to a truly "rich" life, broadly defined. We risk missing out on the outsized returns that can't be achieved if we always index and diversify.

So what's the upshot here?

Perhaps it's that we ought to dabble, and explore, constantly. But we do that in part so we can know when to go all-in. And then, from time to time, we take those big, hard, scary swings. Knowing that even if we strike out, there is much to be had from the pursuit of something great.

It turns out, one of the most successful entrepreneurs in history agrees: ⬇️


#ResistNormal #Survival #StayAtypical

Our last story here relates to Story #2 in that Bezos is asking -- practically begging -- us to remain distinct. To resist the forces that pull at us and make us normal, or in Story #2's terms "average". His very last line is about not letting the "universe smooth you into your surroundings."

But Bezos' wisdom also ties to Story #1, about the way ants have managed to survive for so long. Indeed, if you click on the full letter, you can see that Bezos frames his advice to remain distinct as crucial to personal and organizational survival.

But he is also clear-eyed and honest about the effort required to retain this originality:

We all know that distinctiveness – originality – is valuable. We are all taught to “be yourself.” What I’m really asking you to do is to embrace and be realistic about how much energy it takes to maintain that distinctiveness. The world wants you to be typical – in a thousand ways, it pulls at you. Don’t let it happen.
You have to pay a price for your distinctiveness, and it’s worth it. The fairy tale version of “be yourself” is that all the pain stops as soon as you allow your distinctiveness to shine. That version is misleading. Being yourself is worth it, but don’t expect it to be easy or free. You’ll have to put energy into it continuously.

And he ends (quite poetically, we note, for a titan of industry):

To all of you: be kind, be original, create more than you consume, and never, never, never let the universe smooth you into your surroundings.

Thanks for reading. 🙏🏻

Work moves pretty fast. If you don't stop and look around once in a while, you could miss it.
Join over 1,000 subscribers — sign up today for free.
© 2021 TalentStories, Inc. All rights reserved.