Season 5, Episode 1 | "If you form yourself to what's easy, you'll look pretty indiscernible from everyone else."

You're forming yourself every day, whether you know it or not. The question is which direction. Dane and Mitch kick off Season 5 with a reframe on what "learning the hard way" actually means: not stumbling through crashes or just punishing yourself, but choosing a way that is hard as a skill worth practicing. They dig into the false promise of optionality, why more choices leave us weaker instead of freer, and what it costs to keep every door open. If you've been drifting while calling it flexibility, start here.

Never Settle Promo

Chapters:

• 00:00 Introduction
• 01:22 The Hard Way
• 04:58 Choosing
• 06:24 False Promises Exposed
• 09:19 The Myth of Optionality
• 14:17 AI and Agency
• 17:21 Practice Shapes You
• 23:06 Narrowing

Mentions:

• Hamnet - The play based on Hamlet. Dane references a central moment of one character giving up their life for another.
• Seth Godin - Author and marketer. Referenced for his piece on "the infinite tail."
• Chris Anderson - Author of "The Long Tail." Referenced as the origin of the long tail concept in creative markets.
• CrossFit - Referenced for the phrase "getting comfortable being uncomfortable."

Anchor Actions:

1. Pick One Hard Way: This week, identify one specific area where you've been taking the easy path. Choose the harder route on purpose. Not to prove anything. To practice the skill of choosing.
2. Close a Door: Optionality is quietly making you weaker. Pick one option you've been keeping open "just in case" and close it. Commit to what's left.
3. Refuse the Rescue: When someone offers you an easy out this week (including yourself), or when you're tempted to offer one to a friend, pause. Ask if the hard thing might actually be the gift.

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Mentioned in this episode:

Sponsor: Never Settle

Never Settle is the creative tech and marketing agency that has been MWOD's creative partner— helping with branding, designing our website, and various growth marketing projects. When we started MWOD, we knew we had something that could help a lot of people, but communicating and enrolling people online to build their life around voluntary discomfort is a tough sell. We needed a partner who could understand what we were really doing and help translate that into an online presence that moved people. Never Settle is that partner. They took our vision and made it clear. No small feat for an organization promoting the one thing nobody wants to do. They’re genius. If you want to learn more about how they can help make your vision a reality, head over to neversettle.it/MWOD

Never Settle Promo

How are you forming yourself as a person?

Cause you're forming yourself as a person somehow. And it is happening by your decisions, by your indecisions.

There's no neutral state, either I'm in paralysis and drifting away where something is gonna pick for me, or I'm learning the hard skill of choosing even when I get it wrong, knowing that I probably will get it wrong a lot. But it's not about right or wrong.

It's about the skill of choosing, the skill of deciding, and increasing the strength of those decisions over time.

Are you gonna form yourself towards what's easy or are you gonna form yourself towards what's hard?

And if you form yourself to what's easy you'll look pretty indiscernible from everyone else. If you're wondering what easy looks like, just look around. Easy is everywhere. Everywhere.

As humans we prefer the path of least resistance. We crave convenience, the payoff without the price. But when our lives revolve around comfort, it doesn't deliver. Living in perpetual comfort leaves us weak and asleep. This podcast is an invitation to flip that script, to choose the unlikely path, to get the life you really want through voluntary discomfort.

This is Strong & Awake. I'm Dane Sanders.

Dane, we're back. We're alive.

Amazing. Another season.

Another season. I'm really excited for this one. We talked a little bit, if you're listening to this or watching this, you've seen the trailer that's out. But we wanted to spend just a little bit of this episode talking about what we're talking about, kind of the meta and the theme of this season, which is learning the hard way.

And I think many of you heard that and have a certain idea of what that means and what that looks like. And I'd love to hear, Dane from your perspective what it's actually gonna be like in this season.

Yeah. Yeah, on some level you don't need a whole season of a podcast to explain what learning the hard way means.

We've all been learning the hard way our whole lives. When we were kids and we overestimated our ability with our little BMX bikes going off of a ramp and you crash or whatever, you learn the hard way. When you're you think your joke is really funny in a social context in junior high school, and you say the joke and no one laughs, in fact, they lau- they're laughing, but they're not laughing with you, they're laughing at you you learn the hard way.

And we can go on and on with all these examples, and the common thread in all of those is something went h- hard. Something went in a direction you didn't want it to go, and it went there, and despite it going there, maybe you learn something. And I just wanna say up front we may talk a little bit about that dynamic near the end of the season, but I actually...

I wanna be really clear up front, that's not what this is about. It's actually not about learning despite things not going the way you would prefer, the hard way. It's actually learning a way that is hard. It's actually learning a, a skill that we're calling the hard way that is, I believe, perhaps one of the most important skills one could learn in the cultural moment we live in.

And I, and I don't know if this has been true in every, every era. In fact, I'm speaking even on... When I say cultural, I mean macro. We, and we'll get into the details about that in a second. But some people might be listening to this and they're just in the thick of hard. My dear friend I've been talking about him a lot lately, my friend Richard who's been diagnosed with brain cancer he's in the middle of a hard way that he didn't pick.

And I don't know that this season is necessarily for him. It could be. I think it, it could be great actually the more I think about it. But it's not something I would prescribe. It would be something that he would have to choose and go, "Yeah, even in the middle of this terrible season that I'm in, I'm gonna pick the hard way."

And I think that would be wise but maybe insensitive for someone to prescribe to someone like Richard in the situation he's in. And whether or not you're in a tough moment or in the spectrum of possibility you're in an easier way moment, in either case, the degree to which you can find the courage to learn how voluntary discomfort could benefit your world...

And actually, that's not quite right either. It w- I don't want you to learn about it. I actually want you to practice it. And our hope is that with each episode, as we get into topical analysis of common phenomena that people are experiencing all the time, you can see the hard way through that that you choose.

And when you choose that hard way, the skill that I'm alluding to will become not only second nature, but you'll see benefit from it, benefit that most of the people that you live life with don't know what you're experiencing. It's a weird phenomenon. And we know this because whenever anyone's going through a hard time whether they choose it or it gets chosen for them, the common response of everyone around you who care about you is, "Oh, are you okay?

Oh, that sounds terrible. Oh, how can I give you some relief?" All the rescuers show up in our lives and they're like, they wanna give us a way out. And what we're saying is if you can bear it, Would you consider choosing a way in, not a way out? Could the hard way actually, in, in very specific contextual circumstances that we're gonna talk through with every episode, could you build your life around choosing the hard way, to volunteer for the hard way as a means to get something that, that nobody else has, to get a kind of gold that is so rare?

And th- this metaphor of gold is really important here. It's a rare mineral. It's a rare thing, and we're in a world where we're desperate for people to have this rare thing, this, this capacity to navigate terrible and hard and difficult. And that's what I wanna emphasize here. Learning the hard way is good news.

It's not just how to get something out of a bad situation

I love that. The, it's like it's turning it from simply just the means, but also the very thing that that we get.

That's right.

And I think you'll find, listener, as you're listening to each of these episodes, we're gonna do our best to stay on, on track here and focus and point each of these episodes to really zero in on a false promise or something that, stands in the way or prevents many of us from actually realizing that skill or that capacity or that ability.

Whether that's, in the Christian tradition it would be, like, you've got the, the big three. You've got the world, the flesh, and the devil, telling you all these false promises. And, similarly, we've got the world and these marketing messages and these false promises out there.

Yes. We have our own innate desires to rescue ourselves or avoid pain. ... And then maybe the devil's in there too. I don't know.

I'd add a fourth, and that's just- ... again, that, just the person trying to bail you out, whether that's you or a friend.

A well-intentioned friend. And this is where I I would, I'd do almost anything to have, to take away what my friend Richard's going through right now. It's just awful. My wife and I saw the movie Hamnet the play on Hamlet. It's gonna win a bunch of things in, in, in the award season.

It's unbelievable. But without spoiling anything, there's just this central moment where one character kind of gives up their life for another. And, there's something in that I get. I get why there's like I wanna save my friends from suffering." That's good. I understand that. But if the suffering's ac- what in what other context do humans actually get benefit? If we can somehow the, the line that we hear all the time in, in communities that understand this, like the CrossFit communities, getting comfortable being uncomfortable.

Th-this is the premise. This is h- these are the means by which you've, you get access to this special capacity. And we wanna talk about that. And I'll also just give one other qualifier on the front end, and this is always the danger of, you and I helping to lead a community of people.

We were both lamenting before we hit record today how this weekend was a, a total my... Terrible. I did this all wrong. And, so there's not some high horse here where somehow you learn a skill and get such a great capacity that you no longer succumb to the easy way. At least not in, in anyone I know.

There's something kinda built into our probably our biology that it's a lot to overcome. And it's still, it's worth it. It's worth endeavoring to, to move in that direction 'cause we de- we just desperately... I need it as an individual. We need it as a collective.

And if we don't find it I think we're in far more trouble than what we think is hard right now. If we think this is hard, wait. Just you wait. You're gonna want to have done the work in advance of what really hard looks like.

Yeah. And I think- we're certainly on this path ourselves and, we're not gonna have some guarantee.

You, You will have arrived by the end of this season. You'll have all the answers.

We're getting into the topic for today, which is like the idea of optionality. And we've talked about this, if you're familiar with past seasons, we've talked about this kind of idea from different angles multiple times.

And part of that is because this is one of the very pervasive kind of myths or false promises in our culture that we tell ourselves, is like the more options, the better. And the other reason we've talked about this so much is because, like Dane was saying, like we haven't arrived. This is still something that I struggle with as recently as, this morning or this weekend that we're navigating and like you were saying, lamenting.

So without further ado, I'd love to get into this, this whole idea of optionality and the tension that we have pulling us to either have our days and our options and everything blown wide open the world is our oyster, there's so much opportunity, the allure of that, the false promise of that.

And then also on the other side of things where you're over-planning, habit stacking is everything, you need to have perfection, Yeah, I'd love to, I'd love to dig into, to that in whatever order you would like, Dane, as we knock off- Yeah ... the rust on this new season.

Yeah. Let's talk s- first about options.

There's no question that we live in a season historically as human beings where there's never been more options available to more humans in the world than now. But none of these options are intrinsic options. Just notice they're all outside of us. They're all extrinsic options. So a number of years ago, there was a really interesting piece that Seth Godin did c- not long ago around he called it the infinite tail, and before that, it used to be called the long tail. So Chris Anderson came out with this idea of the long tail, which I won't go into in depth here, but the, the, the, the notion is it used to be that you used to try to sell a book or a movie or some creative thing that you made up and you needed to sell it really quick because once it, once the moment, the news cycle has passed, y- you're done.

And the long tail recognition was when you have a digital world, you had infinite... uh, well, at that time, a whole lot of inventory. You could leave it on the shelf digitally for as long as you'd like without cost, and as a result, it, the library would always be there. Now we're in a new era, says Seth Godin, and I don't disagree with him, of the infinite tail where the level of options isn't just a lot.

It's infinite, like never ending. And this is a bit of a, It almost feels like a Greek mythology kind of thing. Like a never ending possibility puts per- people in a state of never picking, of never actually choosing a thing, 'cause if I choose this, I'm not choosing all these. And it used to be all these felt like a lot.

Now, all these feel like everything. So we're kinda suspended, and internally we aren't learning. The, the... We're not developing a capacity to make strong decisions, even strong decisions that don't turn out the way you would prefer, because there's just this false promise that if I just wait longer, the perfect solution that will give me no pain, all pleasure and is just right will choose me somehow.

So that's kind of one n- angle on this false promise of options is I actually don't need to decide. Why decide when the, the next... like the, the newest option's gonna come? Could be the newest version of a, a device. It could be why pick a movie to watch on a Friday night when I could watch 45 more trailers?

It could be... It j- it doesn't matter. It's just a series of never ending and increasing options coming my way- incentivizes me to not pick. And if I don't learn the skill of choosing I'm at a massive deficit. I actually don't have a capacity. And the call in those kinds of moments, when you're aflod with things, is just pick.

Pick the wrong thing even intentionally if it helps you. Knowing it's not gonna be as good as it could be, 'cause it probably isn't, but you're picking. You're n- you're... I think there's actually, this is a, a big leap, but when I think about this generation globally around younger generation and there's, and like the, the rising age of commitments to things like marriage and like it's amazing how it's spreading out.

People are ... They're just not picking. Like, why bother?

I don't think that's too much of a reach or a leap to connect those two.

Yeah. '

Cause that's so true. Yeah. I,

you can research forever- Ever ... or, wait, don't buy the upgrade yet to the new phone or whatever you're saying because the next one's right around the corner, and then-

Yeah

next thing you don't ever pull the trigger on anything,

yeah.

Yeah.

And the and this kind of s- kind of illusion of abundance abundance of options and abundance of time, th- 'cause they, they relate, right? I have all these options. I could, I c- I can wait and pick, but the truth is if I never pick, I will run out of time.

That again, you're gonna be in a victim posture. Something's gonna pick for you, and this is deeply problematic. Deeply problematic. I work with a lot of employees who are terrified of the implications of artificial intelligence and what it means and how it's gonna take their jobs and so on.

And the irony is they're, th- many of them are in a state of, paralysis. They relate with artificial intelligence like it actually is gonna make their life easier as opposed to they're gonna learn to master the tool so the tool works for them. But the more they stay in the kind of consumption mode with it, like it's gonna do things for me, it's gonna make my life easier, it's gonna give me like the shorter path to what I think I want, and I'm not actually going above it and telling it what to do, a skill that's very uncomfortable to go do, you're actually...

It's becoming a self-fulfilling prophecy. The, the thing is becoming more powerful than you, and you're, it will tell you what to do eventually. Kevin Kelly says there's only two options for the future state of work. One is you're gonna work for it or it's gonna work for you, and you get to decide, at least right now.

And if you're not making those kind of micro decisions every single day, committing to things, doing the hard thing, choosing to learn the hard way with AI, with options, with time, with everything, with relationships, with money, with food, with exercise. Like just pick the category. And this is one of the reasons why Men and Women in Discomfort to me is such a, a powerful community, is because we're building a whole group of people have aligned together on this really high, like way upstream idea of if we're gonna have a rule for how we're gonna navigate life, we're just gonna have the habit of choosing the hard thing.

And even if we don't understand the terrain that we're navigating, ju- just do the thing that's you resist. Do the thing that feels harder than you think you want to do it. And if you feel really bad about it, like terrible "Ugh, this is hard, ugh, I don't like this," that's actually the signal you're doing it right.

And I sound crazy to so many people. I recognize that. But I also feel a little bit like some, some crazy dude out in the wilderness that we're gonna look back on and go, "Yeah, I, there was something to what that, that old guy was saying out in the desert." And that's what I'm, I feel like I'm in tune with, and that's really positioning me poorly.

I just mean it like there's a group of people around the planet in this cultural moment who are going, "Oh, this, there's something here." And they're practicing it, and they're learning a capacity that again, I think it's a skill you're gonna learn. And I think it-- to trade those false promises is for something that's more true is to go, "Okay what am I going to choose?

What am I going to attend to?" To know upfront that there's no neutral state, that either I'm in paralysis and drifting away where something is gonna pick for me, or I'm learning the hard skill of choosing even when I get it wrong, knowing that I probably will get it wrong a lot. But it's not about right or wrong.

It's about the skill of choosing, the skill of deciding, and increasing the strength of those decisions over time

Yeah. The, I think there is this kind of fal-... We've talked about this before, but that it's related to I'm buying the book, I'm buying the course, and I feel some kind of sense of accomplishment or I'm making progress.

We talked a little bit before the call. It's like you're on this kind of scouting mission, and it feels like you're actually doing the exploring and making progress- ... but you're just scouting, coming back to base camp, scouting, coming back to base camp. Yeah, I haven't actually made any progress.

... But what I do think is interesting is what you're saying, there is no n- kind of neutral. You're drifting or people- ... will decide for you. At the same time, instead of building and practicing agency in choosing and in, at times stumbling forward, learning the hard way in that regard but you're also, by sitting in that indecision, by sitting in that trying to keep your options open as wide as possible you're practicing a different thing.

You're, you're- ... kind of building those habits and those patterns for stagnation in a sense. ... So even in that sense there's not a neutral. You have a practice, it's just- Yeah ... what are you practicing,

yeah, and I think that's why I think this whole season is one that it's really a conversation about how are you forming yourself as a person?

'Cause you're forming yourself as a person somehow. And even if that concept seems foreign to you, like I, I'm a, I don't form myself, that... We got a problem right there, friend. You, the, how you engage with whatever is in your world is forming you into something. Clay being formed into something.

And what's weird about this clay is you have hands on the clay if you want to. You can actually push the clay in certain directions such that in the world it's in it will, it'll form. And it is happening by your decisions, by your indecisions by your taking on more options or narrowing your options.

All of these are forming who you are, and I think this, this notion that it's somehow I'm at least a, a participant or I have some responsibility in the formation of who I am, that, that really is step one, to understand that. And then the question becomes, for our purposes, are you gonna form yourself towards what's easy or are you gonna form yourself towards what's hard?

And if you form yourself to what's easy you'll look pretty indiscernible from everyone else. That... If you're wondering what easy looks like, just look around. Easy is everywhere. Everywhere. And the people that stand out it's a-

it's so distinct, like that we start throwing crazy labels on them. Like they're w- like they're talented maybe, like there's something that got-- they were born with. And I think, wait, I talked about this in the past, like super elite athletes who get affirmed for "Oh, you're so talented," that how offended they often get because it so undermines how much work it took for them to be in their position.

I just saw this recently with Alex Hammond when he climbed the Taipei 101 thing. There was a little interview where there was, when he did free solo, everyone was saying like, "Oh, the reason he did that was 'cause he's a little on the spectrum and his hypothalamus is, doesn't fire like everybody else, and he doesn't have any...

His amygdala is less developed and he's less scared." And h-he's no dummy. He... Somebody asked that question, he laughed at it. He goes "Y-you don't think I get scared? Y- how about practicing doing a scary thing for 20 years and then guess what happens? You're still scared, but you do-- y-you've actually learned how to navigate it really skillfully."

I suspect there's lots of people who are looking at his extraordinary feat of climbing this skyscraper, this taller than the Empire State building. Because it didn't look like a mountain, they went, "Oh, that... It's kinda easy," right? Like it was kinda just a stunt or whatever. It's like it w- I couldn't watch without...

I was terrified, and I was just watching it on a screen. And again, th-that doesn't happen 'cause he woke up one day and decided to go do something. It happens because he practiced and practiced, and he became so rare that he becomes extraordinary. I watched the Australian Open final, men's final between Carlos Alcaraz.

He became the youngest all-time Grand Slam g- person at 22 and change, and he was going against a Novak Djokovic, who was trying to get his 25th Major, which is unprecedented. Again, like extremes, like young extreme, old extreme, and the entire conversation is around who, who either will be the greatest of all time or is the greatest of all time.

And in a sense, those examples are so unhelpful because they feel so far away. But I want you to locate yourself as a young Alex or a young Carlos, although Carlos is so young maybe that's a terrible example. Or the point is what position are you going to be in? What skills are you gonna take on?

How are you gonna form yourself? The hard way is the only way. It is the-- Learning the hard way is the most important skill you could learn, full stop. And this is validated even by guys like Carlos Alcaraz. He was interviewed, and one of the comments he made, or actually one, was this, "You guys have no idea what I'm doing when you're not looking.

All you're seeing is the performance. You're not seeing the practice." And this is th- learning the hard way is shorthand for learning the way to thrive in life, learning how to flourish. Not just get the benefits of flourishing, but to actually have the inner capacity to put yourself in a position where flourishing is a natural outcome

So what does that look like? What, w- we've talked about the, what we tend to do if we're pursuing that easy path, but what-

Yeah ...

what are those concrete things that we do to choose that hard way in these moments?

Yeah, so in a sense, every episode this season will tackle one thing at a time, and today, it was staying at a pretty high level to understand it, and then diving in around options.

And here's a... It's a simple one. Pick. Decrease your options. Time block your day such that you're committed to things at the cost of everything else that you're not gonna go do. If you have fourteen things on your to-do list, you don't have a to-do list.

You don't. You have an options list. Narrow the options. Pick one. Priority is a single word. It's not priorities. It's a singular. If only, if nothing else happens, this will happen. That is a narrowing. That is the kind of thing that people who learn the hard way do on a daily basis. Especially when you have leisure, you have the ability to pick a whole bunch of things in those moments, not because the world is pressing in and you have to...

You have a deadline and you're crashing towards the final. That's not what I'm talking about. I'm talking about you have so many options available, and you choose to have very few. That is the hard way. And if there's anything that happens between this episode and next episode for listeners, I just wish they would experiment.

They would experiment with just noticing how terrible it feels to have fourteen options available, and they all look beautiful, and you pick one, and you say no to the other thirteen. It is... it kinda wanna makes you barf. It kinda wanna makes you feel like I just, I-- It's not just fear of losing out.

It's actually knowing that you're missing out. But when you choose to miss out, the pleasure of missing out is only comes when you commit all the way through and you're doing that one thing and you experience on the other side of that one thing the thing that's only available to people who chose that one thing.

And that's that, that deep sense of satisfaction that you're actually in something substantive. You're not just living your whole life on this thin veneer of an existence. You're actually becoming someone. You're f- you're participating in the formation of who you're becoming. And that's the invitation this week is reduce your options by picking the one thing.

And then as you're in it, stick with that one thing, especially when you don't want to. And not only will you guys do it, I hope as listeners, I-- what I'm putting myself on the hook for is I will too. 'Cause like I mentioned at the be- earlier, like it's just we are so aflood in options. At the least recognize that's not a good i- that's not a good situation to be in.

And then work your way in the direction of narrowing, slowing slowing. Get to a state where you can pick the one and stick with it.

Men and women of discomfort is our membership community, and we are open to everyone. But keep in mind, our tagline is it's probably not for you. If we're wrong about that, or if you want to find out for yourself, you can find us at MWOD.io