What Iffy

No matter how confident we want to be about a course of action, we can all sometimes feel a little “what iffy.” It’s natural, because before we collapse the wavefunction, there are anywhere from dozens to even thousands of plausible choices and their outcomes, yet we’re going to move forward down but a single path. You stare at the fork in the timeline and it’s only natural that your mind asks “what if?”

Let’s say someone offers you a bet: roll a single die, and choose either the group of numbers 1-5 to bet on, or the number 6. Pay a dollar to bet, win a dollar if you win. If you choose to bet on 1-5 and the die comes up 6, you were still correct to have bet on 1-5.

Why? Because you can’t change the past nor predict the future. Knowledge of present outcomes can’t be handed backwards through time, so it was correct when you made the bet to make the choice that most likely led you where you wanted to be. There will always be outliers. Don’t let that frighten you – instead, let it comfort you. Things are just as likely to randomly work out in your favor as not, so when it comes to the slings and arrows of outrageous fortune you might as well just take it as it comes.

Productively use your “what ifs.” So many people ask that question, but don’t actually try to answer it! “What if I don’t get this job,” someone says, wringing their hands and sweating profusely. But they stop there, totally paralyzed. Well… what if? What would your next step be? Go that extra few paces in your mind and the worry often vanishes.

The answer to “what if” is always the same. The universe will continue on, and you with it. You’ll make new decisions and choices and the endless pattern of your life will stretch out to the horizon, just as it always has.


I cannot remember the last time I was bored.

I’m not sure I’ve ever been bored. Given access to everything I normally have access to, I have virtually unlimited future projects. I even have several Evernote files of projects I want to do categorized by how unlikely it is that I’ll ever do them.

Even if I didn’t have access to my normal arsenal of boredom-crushing projects and activities, I have an active imagination and lots of things I want to think about – I’ve been able to comfortably think to myself without an ounce of boredom many times.

(In fact, true story – my father and I went on a long road trip, just over 8 hours, when I was ten years old. I didn’t make a peep the entire time, just stared out the window. Never slept, didn’t bug my dad, didn’t play with any toys. Even then, I was perfectly comfortable in my own head for extended periods of time.)

So when I read this story, I was really amused. Here’s the short version: psychologists left people alone in a room with no source of distraction whatsoever except for a device they could use to deliver electric shocks to themselves. They only left them in there for 15 minutes, and yet a quarter of the women and more than 70% of the men shocked themselves at least once during that time. Some lots of times!

Now, you may be thinking what the authors of the study are thinking – humans are highly affected by boredom and would rather shock themselves than be bored even for a short time.

I disagree with that conclusion.

You see, as I’ve hopefully demonstrated, I am practically immune to boredom. I’ve never encountered a circumstance where boredom would affect me negatively. At the same time, I can tell you right now that I would shock myself within 30 seconds of being in that room.

Not to alleviate the boredom! But because I, like apparently 70% of my fellow men, am curious about novel experiences.

Let me imagine myself in that room, and then tell you what I’d be thinking: “Hmmm, all alone in a room with just this shocker, huh? Well, since I’m in an environment where they’ve hooked me up to this thing, I can guarantee it won’t really hurt me. So at worst it’ll give me an interesting but harmless sensation, and at best it won’t do anything and someone is just trying to see if I’ll do it. I’ll get a better story either way, so I’m definitely pushing this button and–“ BZZZZZZZZZZZZ!!

When we don’t have anything else to do, we seek out new experiences. But we seek out new experiences even if we do have something else to do. Curiosity trumps boredom every time.

Surf’s Up

When you climb a mountain, you get all sorts of benefits. A greater view, a sense of accomplishment, the thrill of adventure. But you also get one other thing – an ever-growing gap between you and the ground.

People like to climb social ladders. I get it, I do it too. But we so often race so hard to climb that we don’t put anything underneath us. We go higher and higher, but our position also grows ever more precarious.

When someone surfs, they can only go as high as the wave beneath them. There’s no way to go any higher – nothing above you to grab. Think of that as you network and seek promotions and hob-nob with your elders. Remember that if you’re always ascending by pulling yourself up, you’re leaving nothing but empty air beneath you.

As you climb, remember that a safer ascent comes from being lifted. Don’t forget to network with people more junior than you. Mentor them, build those connections. Create systems of lasting importance for those that follow. Mark the trails you blaze and leave maps for others.

As you climb, leave something beneath you. If you climb to 200 feet and slip and fall, it’s awfully nice if there’s a structure that’s 198 feet tall beneath you, and you’ll thank your past self for building it.

Delegated Community

If you will ever have to delegate something, it’s best to do it as early as possible. Minimize your ramp-up period, train as little as possible. Use as much of the available time that you’ll be around to just be accessible for questions and feedback.

This is parenting and management advice. Tell your kids to make their own lunch – they’re hungry, they’ll figure it out. Don’t hover over your team when you assign them a task.

In both cases, they’ll make a mess here and there. Don’t kid yourself – you would have too. Your involvement might have made different messes, but not no mess at all. So let them make the mess while you’re there to see, clean it together, and push them back in.

Pulling Weeds

When I was a junior in high school, a girl from my class who I had no relationship with beyond “classmate” came up to me and asked if she could buy weed from me.

I was pretty stunned. I had never used, let alone sold, any drugs in my life. I was pretty opposed, in fact. I certainly hadn’t given anyone any signals, direct or otherwise, to the contrary. And I didn’t know this girl at all beyond a name in attendance in the morning, so I asked her what gave her the impression that I was the right person to ask.

“Nothing,” she said, “but you seem resourceful, weird, and not like a snitch. So might as well start with you.”

What absolutely incredible networking! This girl was a genius. Look at the assessment she made! Even though I wasn’t one, I certainly fit the “stoner” archetype well enough – strong dislike of authority evidenced by lots of smart-aleck remarks in class and frequent detention. Somewhat counter-culture wardrobe (though considerably less cool than I thought of myself at the time). We shared a lot of the Advanced Placement classes, so she knew I was at least not a total idiot. Based on just this knowledge, she figured she could safely ask me if I would sell her weed and not face any consequences if she was wrong. Best case scenario she gets her goal, and worst case scenario she just gets a ‘sorry, nope’ – no risk that I was going to run to the school administration and narc.

Now, this story happened more than two decades ago (ugh) and back then weed was a LOT less legal than it is now, so there was actually a decent risk to what she was doing. And yet she made savvy assessments and went after what she wanted.

Now compare that to you. You probably want something right now. Maybe a new job? A promotion? A date? And these things are legal, but you’re still more hesitant to ask someone to get you closer to your goal than that girl in my junior class.

And there’s the other huge lesson – not only is it silly not to ask when the risk is so small, but it’s also silly to wait to ask until you’re sure you’ve got the “right” person. That girl figured that even if I couldn’t sell her weed, that there was a decent chance that I had a better lead, that I could at least get her closer to her goal. That turned out to be true, by the way – I didn’t smoke, but I knew plenty of people who did, so I directed her to one of them who in turn was able to get her hooked up. Networking!

Just remember that lesson, people – when in doubt, pursue your goals like an 11th-grader looking to score some pot. You’ll probably do better.

Our Own Devices

Considering how much of our flow of information is moderated by a small collection of very specific gadgets (always, but now more than ever!), I’m surprised at how easily we avoid choice architecture when it comes to them.

“Choice architecture,” by the way, is a neat concept from the world of behavioral economics. Here it is in a nutshell: people buy items that are on the eye-height shelves more than they buy items that are on the bottom shelf, all else being equal. You can go from a 12% organ donor rate to a 99% organ donor rate, even if both systems are totally voluntary, just by changing whether the default is “opted in” or “opted out.”

So “choice architecture” is changing the defaults about our lives – not removing choices, but restructuring them. It’s putting the candy in a difficult-to-reach back corner of your cabinet, out of sight, while putting the healthy foods in the front of the eye-level shelf in your refrigerator. It’s putting your bike in the garage in such a way that you’d have to move it out of the way to access your car.

In my case last month, it was deleting the mobile app versions of certain social media sites I used from my phone. I didn’t delete my accounts or anything. I could still access those sites via browser. But that’s a lot less convenient than clicking the app button – and it worked. In the time it would take me to access the sites by browser, I’d remember why I didn’t want to in the first place. It was using inconvenience as a habit-breaker.

It can work in reverse, too. I genuinely read more when I have a convenient e-reader, so that’s very nice to have. In fact, by making sure I have a nice, new-model Kindle and a somewhat crappy phone with little customization effort put in, I’m more likely to indulge in genuine reading than mindless scrolling.

The thing about these little nudges is you can do them without much internal resistance. Pulling bad habits up by the root, going “cold turkey,” often gets met with a huge outcry from whatever negative part of you was fed by that habit. As a result, sometimes that voice wins and we don’t do anything at all. But you can trick that voice, a little – nudge by nudge.

Rear View

How long ago does something need to have happened before you can accurately examine it?

If someone asked you to picture “the 70’s,” then lots of images might come to mind. Fashion choices, musical influences, political events, and so on. Things we recognize as having a uniquely “70’s” vibe. Would those things have been recognized as such at the time?

We tend to think of our own culture in terms of “default.” No one thinks they have an accent, for instance, but everyone does – to someone else. We think of things happening right now not as uniquely “20’s,” but as just “normal.” We don’t think of our food as “regional;” it’s just normal food, and everything else is measured against that.

Even science fiction tends to reinforce this kind of view. One thing I’ve always noticed in things like Star Trek or Star Wars or whatever is that there might be tons of different sentient species out in the fictional universe of that particular franchise, but they’re always deviations from an average represented by humans. For every species that’s bigger than humans, there’s one that’s smaller. For each species more peaceful, there’s one more warlike. One more advanced, one more primitive. There’s rarely if ever a space opera where say 95% of other sentient species are larger than humans. Because we always think of our own microcosm as the default from which all other things deviate.

So when you look back at an event or time period, that’s a lot like looking at a foreign culture or alien society. It might have unique characteristics, but you’re framing them in your mind in terms of how far they deviate from your own experiences in the present. That can make it hard to get a realistic view of the significance of those events.

Keep that in mind even when looking at your own personal history. You can look at your own life 20 years ago and think “I was so much more foolish then, so much more reckless,” but that’s because you’re framing it against your current life. You certainly don’t feel foolish or reckless now, but by this method in 20 years when you look back on your current life you’ll judge yourself accordingly.

Don’t undervalue the experiences and choices you made in the past. Understand them, reflect on why you made them, and if you wouldn’t make the same choices today – don’t just chalk it up to capricious youth. Build on that, combine your forces with that younger you, and don’t just let your present be a default to be deviated from. Build a future exactly how you want it.


When we build something new in our lives, we often make the smart move of supporting that new endeavor with a little extra “outside help.” For instance, if starting a weight loss journey, it’s not uncommon to have an “accountabili-buddy” to motivate you. Or perhaps you use one of those services that lets you bet on your own weight loss. Maybe you ask a spouse or roommate to hide, lock up, or dispose of unhealthy foods.

These things are scaffolding. They’re meant to support the construction of a new thing – in this case, healthy eating habits. Habits, like cathedrals, are hard to build. It’s perfectly fine to need to support their construction with something additional while you do so.

But there is a hidden trap here, one that can snare you if you’re not careful. That trap is coming to rely so much on the scaffolding that you never remove it – and thus, never really finish building what you set out to build.

Scaffolding is short term. You can’t expect to maintain healthy eating forever on the back of spouses hiding cookies and apps where you bet on your scale. At a certain point the new thing has to be an internal thing, something that will stand under its own construction and support its own weight within you. Scaffolding eventually collapses.

I am actually hugely supportive of the “scaffolding” technique of building habits. Inertia is real, and in order to change we need to defeat many demons. If you want to quit smoking, I support everything from nicotine patches to support groups to anything else you can think of. But you cannot rely on those things forever. You must, at some point, finish the cathedral.

Lead With The Deal Breakers

So many people, in their initial interactions with others, hide their most unusual or unique characteristics. As a result, they delay heartbreak – delay it, but not prevent it.

For instance, imagine you’re excited about a first date with someone. You want it to go well, so you hide the fact that you’re an avid snake breeder and you have like a thousand snakes. The date goes well! And then the second date comes around and they find out about the snake farm and they run screaming. What was the point of hiding it? If something’s important to you, lead with it.

Here’s a fun example – the Nigerian Prince scams. You know those email scams where someone writes to you claiming to be a Nigerian prince with millions of dollars they just want to give you for some flimsy reason? They’re always super obvious, the grammar atrocious, the email address suspect, etc. Want to know something crazy? They do all that on purpose.

The people behind those scams are actually quite sophisticated. They have more than sufficient command of the English language to write a compelling and believable email. They could come up with a better initial “pitch.” But they don’t, on purpose. Their reason makes perfect sense once you know it: they want to eliminate, as early as possible, anyone smart enough not to fall for the full scam.

You see, you can trick a LOT of people into going 3-4 emails deep with you on a scam if you’re a good writer and con artist, but the number of people who actually go all the way to giving you their bank details is way lower. That’s a lot of wasted time – you don’t want to be emailing back and forth with hundreds or thousands of people, 99% of whom figure you out before you get a dime. It’s better (from the scammer’s perspective, of course) to just make what you’re doing so obvious that the only people who engage at all are the people who will fall for the whole thing. And clearly some people do: the scam wouldn’t exist if it didn’t generate enough money to be worth it.

So those scammers are horrible, but we can learn a valuable lesson from them. Put the things that are going to eliminate people up front. If you’re looking for friends, a relationship partner, a new job, anything – lead with the weirdest stuff. Because somewhere out there is someone who loves snakes as much as you do, and you don’t want to miss your chance with them because you’re busy wading through a sea of ophidiophobes, pretending to be something you’re not.


Have you ever seen the movie “The Princess Bride?” Of course you have, what a ridiculous question. (And if you haven’t, it’s one of the finest films ever made, so go watch it.) There’s a scene where the main protagonists are trying to plan their attack on the bad guys, and the lead asks for a list of assets from his compatriots. It’s sparse. He brainstorms out loud, wishing he had some random mundane item and it turns out they do – which makes him mad that it wasn’t listed among the assets in the first place.

(Go watch the scene if you don’t like my summary!)

The reason I bring this scene up is because it’s actually harder than you might imagine to conjure up a complete list of all your assets on the spot. Here’s an example: write down a list of everyone you know.

Daunting, isn’t it?

You could write for hours and still miss people. That’s one of the advantages of social media networks; they’re a sort of inventory management system for your friends, loved ones, and professional contacts.

And the reason I bring that up is because if you can’t even list your assets, you’re certainly under-utilizing them. You don’t even know what tools you have at your disposal! Want a sure-fire way to network better? Introduce people that both know you, but don’t know each other. Figure out connections that can add value.

When you introduce two people that may benefit from the connection, you improve both of their lives. That’s two people with a reason to be grateful for your existence, a reminder that you’re awesome, and at least a marginally improved situation that you helped cause. Do that enough, and the spillover effects back to you are HUGE. But how can you do that if you don’t even know who you know?

Every so often, inventory your own “assets,” especially the intangible ones. You might be one wheelbarrow away from a breakthrough – and it was there all along.