What's the worst that could happen?

Fear-setting and a thousand versions of you

Hello to the 745 smart, motivated, and curious readers receiving today's newsletter - and a special welcome to the 126(!) who joined us over the last two weeks. That's a record increase for this little newsletter. Whether you found us via last week's piece on crypto and the metaverse, or this kind article that the CFA Institute published on my personal story, I'm grateful you're here. Oh, and by the way, make sure you read all the way to the bottom of this article for an exciting announcement and an experiment. Okay, enough preamble. Let’s get started.

💡 The big idea


Maybe it's just me. I don't know. But I think we all secretly know that we could do better. That we're not quite achieving our potential.

Maybe I've got delusions of grandeur. Or perhaps I’m just an irrational optimist.

Both are possible.

But I feel like I could do better. Like WAY better. In almost every part of my life.

"So far, this newsletter doesn't have a very Thanksgiving-like feel to it, Greg," you might think. I know, you're right. But stay with me.

The phrase "living your best life" has always felt plastic and cliché to me, but I do honestly wonder: Is this my best life?

Of course, it's impossible to say without having other versions of one's life to compare it to, but what if we could do exactly that?

A thousand versions of you

Here's a thought exercise for you: Imagine running a series of computer simulations of your life. In each simulation, you make a different set of decisions. You study Finance in one, Law in another. You move to Boston in one, stay in Bangalore in another. You marry your high-school sweetheart in one, you go it alone in another.

We could run the simulation a million or a billion times but for the sake of argument, let's say we run it 1000 times.

The question then for you is this: If you run 1000 simulations of your life, how does the one you are currently living compare to the rest?

Statistically speaking, it's unlikely that it’s the best—or the worst.

But where is it—if you're really honest with yourself? Top 50%? Top 25%? Top 10%?

Now think about this: No matter where you put yourself on that spectrum, you've still got upside.  Room for improvement. (Unless, of course, you literally think this is the best out of 1000 lives that you could have possibly lived... in which case, maybe I'd ask you to run that simulation a million times).

So why then are you and me not living that best possible life?

The answer likely comes down to two related factors: fear and complacency.

Whether or not we consciously choose to admit it, we are all afraid.

  • We're afraid of being laughed at.

  • We're afraid of disappointing someone.

  • We're afraid of failing.

And once we've made any kind of progress in life, we're afraid of giving it all back. We become complacent. Instead of seeking "the best" we settle for “good enough…”

  • In our careers

  • In our relationships

  • In our fitness

And that, as Ms. Gonzalez eloquently states below, is lethal.

So what can we do about all this fear and complacency?

First of all, let's not get caught up in the past. We drive ourselves crazy regretting decisions that we've already made. But what is the point? What's done is done.

Instead, we need to look forward.

Enter: Fear-setting

We’re all intimately familiar with goal-setting—and as we get ready to flip the calendar to a new year, it’s a natural time for many of us to be thinking ahead.

But what if we’ve been looking at goals the wrong way all along? What if the much more effective way to actually bring about the change we so desire is not to set goals, but rather, to set fears?

Fear-setting is a concept introduced to me by Tim Ferriss, who credits the practice for taking him from near-suicide to living what most would argue is (my words, not his) a one-in-a-million type of life.

“Fear-setting has produced my biggest business and personal successes, as well as repeatedly helped me to avoid catastrophic mistakes.” —Tim Ferriss

Fear-setting is the process of investigating one’s own fears with a specific focus on those that are holding us back from doing whatever it is that we deeply desire to do.

Here’s how it works (Ferriss even has a template for this):

A three-step process for fear-setting

Step 1:

The first step involves cataloging your fears and potential responses as follows:

  1. Define — As specifically as you can, define all of the many horrible things that could go wrong if you were to pursue the path that you desire. Ferriss recommends listing 10 to 20 fears—nightmare scenarios—in as much detail as humanly possible. Once you do this, you’ll be staring at exactly what it is you fear.

  2. Prevent — Next, you list the actions that you could take for each fear that could potentially prevent the worst outcome from happening or at least lessen the impact of each nightmare scenario.

  3. Repair — And finally, again for each fear, list the actions that you could take to undo the damage if the nightmare scenario did indeed come to pass.

Step 2:

Ask yourself the following question:

What might be the potential benefits of (at least) attempting the thing?

And indeed, has anyone ever done what I am afraid to do? And by chance, did they have fewer resources than me (time/money/intelligence, etc)?

Step 3:

The final step involves calculating the downside of NOT taking the risk that you are pondering:

What will be the costs of inaction over 6 months, 12 months, and 3 years? Emotionally, physically, financially.

And that’s it. Three simple steps.

The theory here is as follows: Seeing your fears in black and white helps you to grasp how realistic they actually are (or aren’t). And listing the actions that you could take to either prevent or recover from these worst-case scenarios helps you to understand that in all likelihood the risk you’re afraid to take is unlikely to be fatal (to your career, your relationships, your finances, or your life).

Finally, seeing that the cost of inaction (complacency) may be higher than that of action can be eye-opening.

It might, in fact, be enough to nudge you into action.

We all spend too much time worrying about what could go wrong if we take a risk. And not enough time worrying about what may happen if we don’t.

Or as my friend (and Intentional Wisdom reader) Rich Howe (quoting Sam Adams’ founder, Jim Koch) recently shared:

Rich took a big career risk of his own and it’s paying off.

Of course, bravery is not always easy to come by. And make no mistake, that’s what we’re talking about here: Bravery. Courage.

It might not be feasible for you to take that big risk you dream of. But it probably is realistic for you to at least start taking small, definitive steps toward it.

Author, Caroline Paul, calls this “micro bravery.” She likens bravery to a muscle—one that needs to be exercised in order to grow stronger. She believes that many of us, especially women, have not been taught to exercise this muscle nearly enough.

I like that idea. Micro bravery. It makes taking risks seem slightly less intimidating.

In fact, if you think back on the accomplishments in your life that make you most proud, I suspect you’ll see this pattern in hindsight. You’ll see small acts of micro bravery, one building upon another until you achieved the success that an outside observer might view as destined all along.

But nothing’s destined. We need to go out and make things happen. To conquer our fear. To get past the complacency.

I’ll leave you with this, which comes from my second most-popular article of all time:

“…if 100 years from now, not a single person on Earth will remember you—much less anything you did that was embarrassing or a failure—what do we really have to fear?”

Seriously, what do we have to fear?

That’s it for this week. But don’t go yet… there’s more…


Announcement: Intentional Wisdom - the podcast

Okay, this is going to happen. My own small act of micro bravery here. I am announcing right now that I am going to make the Intentional Wisdom podcast happen. I even have my first guest booked! I’m psyched.

Here’s what I plan to make: A show covering similar topics to this newsletter: careers, habits, motivation, physical & mental health… and maybe, just a tiny little bit of cryptocurrency.

I want to make each episode practical and actionable. I want you to listen and take away one or two small things that you can implement right away to make your life just a little bit better.

That’s the plan. Stay tuned for official launch dates and all of that.

Seneca said: "We suffer more often in imagination than in reality."

I was a little nervous about announcing this podcast. But I just did it. And it wasn’t that bad. I told you this micro bravery stuff works.

Don’t go yet! Still more 👇


Photo credit: @Sigmund Unsplash.com

📚Content Diet

Maybe this is bad form, but I’m recommending two of my own articles as part of this week’s Content Diet—both Thanksgiving-themed.

Remembering the Mother of Thanksgiving — Sarah Josepha Hale has been all but forgotten by history. But you need to know how she single-handedly willed the holiday we know today as Thanksgiving into existence—through brute force and almost unbelievably dogged persistence. Inspiring on many levels.

Gratitude is More Powerful Than I Thought — Okay, okay, I got there in the end with some Thanksgiving content, but seriously 2021 was the year I actually fully and completely bought into gratitude. And its power has astounded me. Learning the many physical and mental benefits has changed my life. Maybe it will change yours, too.

One more Turkey Day consideration as you sit around this Thanksgiving watching football and probably too much cable news with the fam…

And after the festivities come to a close…

I’ve been going down a rabbit hole of Huberman Lab podcasts recently. If you haven’t listened yet, give it a whirl. He’s got some incredibly well-researched episodes on just about every health-related topic. I’m currently fascinated with this one on intermittent fasting.

And for those who want to dive a bit further into fear-setting, I highly recommend going straight to the source and watching this 13-minute TED talk from Tim Ferriss.

I just have one more thing for you… 👇👇👇


☕ Finally, finally… I’ve gotten asked a lot over the past year and a half how you can support Intentional Wisdom. Well, I feel a little awkward adding this but I’m going to try it. If you’d like, you can now “buy me a coffee” (and leave me a message) by clicking the button below. If you choose to do so, I will of course be eternally grateful. And well-caffeinated.

Buy Greg a Coffee!

Thanks as always. Happy Thanksgiving to those in the U.S.

And see you in two weeks!

— Greg