(upbeat music) Hello and welcome to another episode of All The Hacks, a show about upgrading your life, money and travel. I'm Chris Hutchins and I started this show almost two years ago because I love doing all the research to optimize every aspect of my life. And I wanted a way to share that journey with you.

After the first dozen or so episodes, I knew this would be my full-time thing, but somehow it took me another year and a half until I was ready to go all in. Now, I am so glad that finally happened, but why did it take me so long to commit to something I knew deep down inside I was ready for?

Well, that is exactly what we're gonna talk about today. And I'm joined by the perfect person for the conversation, Matt Higgins. Matt grew up in poverty and dropped out of high school at the age of 16, before going on to graduate from law school and then become the youngest press secretary in New York City history during 9/11, where he led the effort to rebuild the World Trade Center site, before becoming the executive vice president of the New York Jets, and then the vice chairman of the Miami Dolphins.

Matt was also a guest shark on "Shark Tank," he teaches at Harvard Business School, and through the investment firm he co-founded, RSC Ventures, he's invested in some of America's most beloved brands. So what does all this have to do with me taking too long to go all in on this podcast?

Well, Matt just published an incredible book that I wish I had been able to read a year ago, where he shares his framework to stop hedging and unlock your full potential. It's called "Burn the Boats." So today, we're gonna talk about why too many of us are driven by fear, why we wait for the perfect moment to act, and why so often we subconsciously construct a safety net or plan B that actually holds us back.

But we're not just gonna talk about it, we're gonna lay out an actionable playbook to overcome all these hesitations and burn your boats, as Matt says. We'll also cover understanding your own motivations, overcoming fear, processing failure, managing crises, asking the right questions, and a lot more. So let's get into it right after this.

Matt, thanks for being here. - Thanks for having me, I'm excited, Chris. - It's funny, I read the front cover of the book before I opened it, before I dug into it, and it's like, you can unleash your full potential, all this, there's a lot of books that cover topics like that.

"Awaken the Giant Within," Tony Robbins, all this stuff. What made you feel like we needed another book in here, and what's gonna set this story apart? - That's a great question. Well, big picture, I don't think there are new ideas in the universe, mostly they've all been discovered, but there's new packaging.

And when I read a lot of business books on the subject, not disparaging anyone in particular, I do feel like they're written like reference manuals, number one, and by the third chapter, you've basically got the crux of it. They're very repetitive, and that's not how people learn information. I'm a storyteller by heart, was a journalist when I was a kid.

I know how to explain, articulate, package stories. And so I wanted to create a book that was very readable, that was a business book, but masked as a memoir, masked as a riveting historical fiction journey, and sort of break the genre to some extent, with the goal being you could read it from beginning to end in one setting, and be left with a feeling of infinite possibility.

So packaging, to me, I think is actually very important. Storytelling is very important. And I've accumulated a lot of wisdom through a lot of heartbreak and a lot of incredible opportunities, and thought that I had something special to share. - I think you're selling two parts of this short.

I think the idea of there being this plan B, that there are benefits from not having and getting rid of, I think is a unique perspective I hadn't read before. And so we're gonna get into that. And then I think the second is you said it's a business book.

I'm curious if this really is just for people running businesses, wanting to start a business, 'cause my perspective reading it was that it has a lot more broad applicability than just being for business people. - Yeah, that's a good point. Like, it doesn't quite know what it wants to be, but I would argue that business is just the tapestry, or the canvas, rather, and that at the end of the day, it's really just about anybody, which is everybody, looking to unleash their potential.

- I heard you say this is for people who wanna break out. They feel like the universe has a lot more in store for them but they keep finding obstacles. So let's just jump in. What do you think some of those common obstacles are that kind of hold people back from pushing forward?

- What I try to do with this book, and had in my head the entire time, is show, don't tell. Like, when I use that third person voice, Matthew, like, you're at the center of the journey too much here. You wanna show and illustrate rather than tell. And a lot of books, I think, just tend to lecture you, and then, therefore, it doesn't quite stick.

So that's a way of saying the boat, in my book, historically, is meant to be literally the escape route. That's how military strategists use it. Burn the boats is literally burning your escape route. In my case, the boat is meant to be a metaphor for all the things in our lives that hold us back when we're at the threshold of doing something great, something uncomfortable.

And a lot of that has to do first with internal issues that aren't really discussed. Certainly, I feel like they're not discussed at my level enough, and that's imposter syndrome. In my case, it was shame. The metaphorical boat that I needed to burn first was the shame I carried around from the stigma of growing up in abject poverty and taking care of my mother who died when I was 26, being a high school dropout, getting a GED.

There was all this shame that I carried that I didn't realize until life brought me to my knees that even though I had achieved a pretty significant level of success at an early age, objectively, I hadn't really scratched the surface of my potential until a bunch of things happened in my life that brought me to my knees.

I was stripped away, and we can get into this. And then I realized, oh, you haven't really done anything yet, right, like any kind of self-work. And so a lot of the issues that we need to do, the metaphorical boats for all of us are internal. - How does someone who maybe hasn't even thought about what those things that are holding them back are even begin to identify them?

Is there a process or questions you ask yourself to even start to understand that? - Yeah, I think self-awareness is the greatest arbitrage in the universe. We're sort of taught that we should go to Barnes & Noble and buy my book or go on YouTube, watch TED Talk, and no one ever emphasizes like, actually, the greatest upside in ROI you can have is self-awareness and reflecting what's going on inside you.

So the first question, even when I'm doing a deal and I find that a founder or CEO or entrepreneurs help resistant, I try to identify, what are you afraid of? Like anyone out there listening, if you find it hard to assess your flaws or your failures and reflect, the question I always say is like, what are you afraid of?

And the answers usually fall into these different buckets, and I'll just throw out a few. Usually it's stigma, it's some kind of judgment from a super authority, a parental figure or a spouse or a friend group that if I acknowledge some type of shortcoming or even an aspiration, I wanna be a musician, my dad's gonna judge me.

There is something that's getting in the way of somebody being reflective of their dreams, of their flaws, and it's usually something that was prosthetically installed externally, long sentence, but in other words, it's not that nature put it in there. I think nature wires us to be reflective actually, 'cause it's a way to protect ourselves, but nurture, your friend group, those parental figures, those people in your lives, over time they accumulate and they prevent you from wanting to look in.

So the number one exercise I go through with anyone when I'm establishing that rapport and we're trying to establish a relationship or do a deal, and I find that they under-index for self-awareness, I try to identify, like, what are they afraid to find out? - So let's say someone goes through this process, they're like, okay, one of the things for me I'll share is the first two jobs I had out of college I didn't like, so I was convinced for probably a decade that I couldn't be happy and make money, and so I was so afraid that I would either work a job I didn't like or have no money, that this entire optimization and savings journey really began from I need to find every way I can to save as much money as possible so I don't have to rely on a job to be unhappy, and over a decade, as I managed to do that saving, I also managed to realize, oh, there are other jobs, there are other things you can do with your life that will make you happy, but it took me a lot of work trying to figure out why do I think that I couldn't make money and be happy?

What is it? So it actually came to me, but it's not sure I knew what to do with it for years. So what does someone do if they identify the thing that is holding them back or the thing they're afraid of, and then what? - I don't know. That's for them to figure out, Chris.

I wanna get a tattoo eventually, now I'm putting this out there in the world, but I can't find the words that are lasting enough to wanna imprint on my body. If I had to settle right now, it would be to face everything. If you just simply acknowledge the fact that if you face everything, including the thing you identified as the thing holding you back, that is where.

So let me use myself as a case study. When I say that life brought me to my knees, I had had cancer when I was 32 years old. I had testicular cancer, and when I was diagnosed, I talk about this in the book, my first reaction was concealment, that once people find out that I have cancer, and I was worried about losing my right testicle, that's like a tremendous trauma to go through in 24 hours, right?

But I was actually more concerned about everybody around me was gonna think I was weak, and now's the time they're finally gonna take Matt out. I met my HR director on the corner of 57th Street because I didn't want anybody to see me in the office so I could change my paperwork, my beneficiary, should I die?

And then two days later, I was like, how am I gonna prove to everybody that I'm undefeated? And I was running the New York Jets business at the time, and there was a dinner with the coaches, and I decided to show up to that dinner, and sit down, everyone's looking at me, it's cringy, I have ice on my crotch, but I thought I was all tough, and I raised a glass and did a toast.

I said, "Hey, I wanna tell everyone what my new motto is." And I said, "It's half the balls, twice the man." And I said, "I just ordered dog tags," which I still have to this day. I tell this story because in my 20s, that was like, or early 30s, wow, that's so tough.

Look what you're telegraphing, right? It wasn't until later on when I got divorced, and my whole identity kinda crumbled, right? As this young kid who was able to do everything earlier, succeed earlier, you know, press, press, press. This was one thing I couldn't press through, and it was a public shame that I needed to own.

That's how I saw it at the time. But then I started reappraising everything, saying, why did I go back to work two days later, after I had cancer, and like, was gonna die? And why have I been behaving like the house is on fire? And I realized, it's like I never warned the death of my mother, and I never left that tiny apartment in Queens, you know, living in that Roach Motel, with no food, with eviction notices on the door, and Con Edison about to turn off the power, that I had never stopped living in that state of hypervigilance, despite the fact that I ran the New York Jets.

So what was I afraid to look at? I was afraid to look at the pain and suffering of that effort to try to save my mother. Once I had nothing left, because my identity had been stripped, and I had sort of gone into a depression, right, to an extent, that was I able to realize my behavior, right, to look at it for what it was.

And that changed the entire course of my career. So it's hard to say what you're specifically supposed to do, but I know what you're supposed to do is look within, and once you identify it, is to face it and hug it, and like embrace it, like almost with excitement.

When I realized your behavior makes no sense, because you think you're being chased, when you're no longer being chased. Once I realized the boogeyman wasn't behind me, then everything started changing about my behavior. - And are there things in your routine or your daily life that you now do differently, because you're in this new state?

- Oh, I mean, so many things. Like, let's just start as a leader, back to that story I just told you about, have the balls twice a man. Imagine you worked for me at that time, and you were dealing with something in your life, and you needed some space to heal, to mourn, to recover, but you know the boss literally just had a surgery to remove a testicle on his back at the office.

That would tell you, telegraph to everyone around you, that unless you are in a state as extreme as that, you better suck it up. So to answer your question, I have done a 180, and then I try to create an environment where people can surface the issues they're dealing with, because one, you make better decisions, and two, if people have space to be human, you get more out of them in the end.

So that's one example. And in my relationships, I tend to very quickly create space to be vulnerable and share details that maybe can be a little shocking, but it's to open up the permission to do that. But in every area of my life, I am constantly trying to refine my ability to be self-aware and be unafraid about what I'm gonna find.

I'm constantly auditing my motives. Like, why am I doing this? Even my own book, frankly, sometimes I say I wrote my book so I'd read my book, 'cause I'm like, wait, now I am not on brand. If I wrote it in a book, I gotta actually live to it or else it's kind of embarrassing.

So my book is now my accountability partner. I read every day when I stray from it. - Okay, so we've kind of talked about a little bit of what you need to do to evaluate yourself, understand what might be holding you back. If we look forward now, I know a lot of people who maybe they're not caught up in what's holding them back, but they don't know where to go.

They know they are destined for something, but it's not that they're being held back, it's that they haven't figured out what's their motivation, what are they good at, what could they leverage in their life or their skills to start a company, do something at their current job, anything. I know you talk a lot about this in the book, but what do you think people should do to try to figure out where their path should go?

- I have this dialogue with students oftentimes at Harvard Business School. You would think top of the world, right? You've made it, you're at Harvard Business School, your life has been de-risked, you'll always have a six figure job. And yet I find even at that level, people can sometimes be totally lost.

And it's because they're asking themselves the wrong question. They're asking the question of what do I wanna do as opposed to who I wanna be? So I go through this discovery exercise with everybody I meet and I say, when you imagine yourself the happiest, are you a creator or are you an executor?

You know what I mean? When you imagine the environment that you thrive in, are you alone at a desk or are you in an office? The who do I wanna be and how do I wanna spend my time questions are way more important than what do I wanna be?

I wanna be a lawyer, I wanna be a... I actually think we should be spending way more time meditating about context, environment, the cues that tell you a little bit more about yourself. For example, in this exercise, it's in the book, I was talking to a student trying to figure out what they wanna be.

And then in the series of questions, she had said, "Actually, I wanna be the one "who enables a brilliant visionary, "but I don't think I have it in me. "So I wanna be the one who uses my hard skills "to make somebody's dream come true." And I said, "Okay, we can work with that.

"Well, what kind of context do you enjoy being in?" And she said, her name was Rachel. "Well, I love the beauty industry "and I'd love to end up there." I said, "Oh, well, as luck would have it, "I'm good friends with Bobby Brown." Bobby Brown, admittedly, hates math. And she's about to launch this new company called Jones Road and finally go out on her own.

And she needs somebody, a quant, and to help her with that. And I picked up the phone, put it on the table, and I said, "If Bobby Brown answers right now, "this is what's meant to be." She did. And fast forward, Rachel ended up working for Bobby Brown and launching her new brand.

So I just say that as an illustration about what happens when you shift the questions to where do you wanna work, what company, to who do you wanna be? And I go through that in the book too, these kinds of questions that help you identify who you are as a person.

- I mentioned that some people might not know where they wanna go. And you mentioned a couple things I could talk about. You have an exercise in the book that I think people should buy and take. No matter where you are in your career, what about when someone has an idea of what they should do?

And this is gonna bring it back to the title of the book. You know, they're kind of wavering. For me, I started this podcast and when I did, I kinda put one toe in the water and said, "Let's see if there's eight episodes. "Let's run it for a year "before I kind of really jump into it." I think this is one of the biggest themes titled the book.

So obviously, it's one of the biggest themes. But how do people really get the buy-in and commitment in themselves? And what's kind of the research say about the way you plan and the impact it can have on the outcome? - Yeah, when I meet someone or a business owner or founder who the business is either failing or in some respects, it's failing them emotionally because it no longer satisfies their soul.

Few years in, when I do the post-mortem about like, "How did we get here?" What I often find, it's because they refuse to ask the right questions at the beginning of the journey. And there's a few reasons why. When we have a great idea at three o'clock in the morning, most people are so excited that they've had something that stirred them, especially if they're in a bad situation, that they are then afraid to subject that idea to scrutiny.

Because we also aren't taught to focus on opportunity costs, especially if we don't value ourselves enough. We don't wanna talk about opportunity costs. We instead focus on how do I implement this idea? And I think that's how most people find themselves in a bad position. So I do the opposite, right?

I totally focus when I have a big idea on opportunity cost. I try to project Matt Higgins three years from now and ask whether this idea is big enough, interesting enough, valuable enough to sustain me three years from now. That requires you to believe two fundamental things. One, if you're somebody who come up with a good idea, you can come up with an even better idea a week from now.

It's a little bit like real estate. Brokers will always tell you there's always a better house coming on the market next week. The same is true with somebody who's an idea factory. So don't be afraid to rule out your own idea. And then two, I go through the exercise of opportunity cost.

I try to imagine what could be better than this? What could be three years from now when I'm out of this situation? And the reason why that's so important is most people make relative decisions to the situation they're in to escape it. Most big decisions we make, and you see this in personal relationships when somebody leaves somebody for another person that rarely works out.

And same thing with a job. If you take a job just to leave the last job, that usually will leave you unsatisfied too. So the reason why this opportunity cost decision matrix is so important, 'cause it will help you figure out, am I running from something or running to something?

So I go through in the book, this exercise around opportunity cost to pressure test our own ideas. And if you do that, and you spend a couple of days or a week going through that exercise, you'll make a much better decision that's a sustainable decision. - Like many of you out there, I love Notion.

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So, whatever the occasion, download the Drizzly app or go to drizzly.com. That's D-R-I-Z-L-Y.com today. Must be 21 plus, not available in all locations. And you mentioned the idea of just leaving a job for another job. So, to go back to the, this isn't just about running a business. This isn't just about being a founder.

Ideas that came to my mind were deciding to quit your job to do something totally different. That isn't starting a company. Are there ways that you think people can process those big decisions and think about the things holding them back? So, let's say we've identified, okay, I'm not just trying to escape this job I don't like.

I've really found a thing I think I'm passionate about. I went through this myself over the course of 18 months with this podcast, but I think there are a lot of people out there who they have the idea. They're not being pushed away as much as they are being pulled, but they're just scared or there's fear about going all in.

Let's talk about going all in. Let's talk about burning the boat. Let's talk about why maybe going slow or having a plan B isn't actually helping you. Yeah, so we have our idea. We've done our exercise. We've pressure tested opportunity costs. It's an idea worth pursuing. We're ready to go.

And then we get stuck. So, what are the reasons people often get stuck? Obviously, one is fear. When people sometimes hear about the title of my book, "Burn the Boats," they presume I mean "Reckless Abandon," but the book would be called "Burn the Boats" with you in it, and it's not.

So, I am one of the most paranoid risk takers you're ever gonna meet, but how you synthesize risk and fear is everything when it comes to plan A. So, what do I mean by that? That those who are able to fully commit to their own dreams and ambition have done the work to process the worst case scenario at the outset.

So, I'm always going through the following exercise when I have a big idea that I wanna go all in on, and that is one, what's the worst possible thing that could happen if this does not work out? First question I ask, what would I do if the worst thing that could possibly happen happened?

How would I mitigate it? I have never asked myself that question and never had an answer to mitigate that is entirely within my control. So, what I find is mostly the reasons are not practical. They have to do with judgment and fear of being judged or fear of being embarrassed.

But to the extent to which it's, I started a new job and it ended up being out of my depth. That was my plan A. You know, you could always be like, I'll just go back and get that other job because we're primal creatures. We are already equipped with the ability to defend ourselves when our plan A doesn't work out.

But unless we pressure test that at the beginning, then the third question I ask, what's the probability that the worst case scenario will materialize? Usually the probability is actually very low because we could catastrophize if you pressure test it. And then the fourth question I ask is, what would I be willing to do to have that plan A?

What would I be willing to endure to end up having that work out? So, in the case of Harvard, when I taught at Harvard Business School, which was very uncomfortable to me, I'd never been in a classroom before, but I wanted this so desperately, the idea that I had performed well at Harvard and had left these kids with something that was five times more valuable than their tuition, which was the objective I set.

I was like, I would walk on glass to succeed. I would subject myself to endless ridicule, public scorn. I would come within an inch of my life to achieve. That's how much it mattered to me. And when I pressure test through those four questions, through that synthesizing risk, I was like, it's a no brainer to go on.

So why does it matter? Why does that decision matter? Because when we are pursuing really hard things that take a long time, you're gonna take incoming, external and internal, the voice in your head, people around you, that are gonna make you wanna turn back. So, if you haven't already processed risk, you don't remember.

And because you've done it at the beginning of the journey, you're like, wait a minute, I already asked myself how I would handle if this didn't work out, and I'm okay with it. It's the memory that you went through that risk synthesis operation, exercise rather, that sustains you. Let's talk about a little bit what plan B means.

Sometimes people think plan B means risk mitigation, but I already said plan A incorporates risk mitigation. You've already gone through it. What plan B and what the science shows is, plan B is not about de-risking anything. Plan B is a way for you to achieve your subordinate goal. So, let's use it to anyone out there listening who wants to be a musician, but they have a crappy job that they hate.

But you're like, you know what? My dad always said I shouldn't be a musician, but I don't care, I'm gonna tell him to F him, and I'm gonna go ahead and I'm gonna be a musician. I'm gonna work really hard until I get on that band. However, if it doesn't work out, I do have a plan B.

I'm gonna go work at Bob's Record Store, 'cause I'm always perusing the aisles, and he thinks I'm really smart. That's your subordinate goal, which is to get a job different than the one you have, right, in the music sector, but very different being a musician than working at Bob's Record Store.

And what the study and the science shows is that plan B is actually an alternative way for you to relieve the pain and discomfort of pursuing your goals. So, there are two ways to get that done. I can either win, succeed on plan A, or I can go for my lesser subordinate goal, which is gonna leave me unhappy.

And then the last piece of interesting research that came out of Wharton in 2014 was they found that just the mere contemplation of having a plan B, Bob's Record Store, is enough to ensure you will never be a musician. Just thinking about it. And what they also found in the research, just having that insidious thought of working in that record store is going to dramatically reduce your desire to ever be a musician.

So, it's two things. You won't succeed, and you won't care as much anymore. That was a lot to unpack, Chris. (laughing) Yeah, I'm just thinking, like, it's hard for some people, especially maybe someone like myself, where I'm like always thinking about all the outcomes, all the options, to not have a plan B.

But is having a plan B different than knowing that a plan B exists? There is. I love that you said that. That's such a smart way to put it. Having a plan B is very different than the peace of knowing a plan B is out there for you. And you don't need to return to it because you've already, at the beginning of the journey in pursuit of plan A, identified what it is.

Like, it does not need to be crystallized because you'll know you'll get a job somewhere, not Bob's particularly. But if I'm having dinner with a friend and I'm like, I'm going all in, I'm becoming a musician, and they're like, yeah, and if it doesn't work out, you could just go work at Bob's Records.

And it's like, oh, well, now that I know that's an option, I assume it wouldn't be fair to say, I can never become a musician again because I've now heard that there is a thing. Or is it more when you start to say, okay, yeah, that guy, he's right.

I could just do this. That's gonna be fine. I'm trying to think how do you, as a optimizer, thinking through all the options, still make sure you aren't putting your primary goal at risk by just thinking about them? - Well, it's a great question. And so studies showed when you did introduce the idea of thinking about, I think the difference is all about sequencing.

If you had that dinner with your buddy who was a little skeptical, like, hey, Chris, you're kind of delusional. You sort of suck too. Your guitar playing isn't any good. Unlikely, right? If you had yet to do what I said at the beginning of this conversation and have that risk synthesis process, right?

That would have been the first time that somebody was now intruding into your thoughts. And then you get defensive, like, well, I could always go work at Bob's, right? But if you had already done the beginning, like, you're not even hearing it. Like, it does not matter. You're fearless and you're impervious because you already are self-contained.

I already know what I'm gonna do. And I don't care what you say. You know what I mean? It's not registering. But if you hadn't already done that work on plan A, if it wasn't part of your plan A, you would be susceptible to it. So this can sound like semantics, but I'm 100% convinced it's not semantics because the research shows it.

But you asked a great question is how to delineate between having already once thought through it versus having it at the table while you're going after plan A. I'll give it to you in a practical setting. There's some stuff I put in this book that I can't read, that I cringe at.

It's so deeply personal. A couple of weeks before it got published, I was going for a walk and I was having a low serotonin moment. And I repeated on me, like, why did I put that in the book? Why did I put that in the book? Should I go change it?

And then I was like, wait a second. We already went through this, Matt, at the beginning of the journey. You put it in the book because you're pretty sure somebody out there who's reading it right now is depressed and hopeless. And they're gonna read between the lines of what you wrote in that sentence.

And it may change the trajectory of their life. You've already made the decision. That's the difference. And then I've already gone through, all right. So it gets published and amplified in ways that I didn't really intend. Like I'll live with it. But the benefit of helping somebody out there read that sentence is worth it.

So again, nuance, but not semantics. - And when I think about this idea of, okay, go all in on this thing. You can be impervious to the feedback that maybe it won't work 'cause you've committed. You've metaphorically burnt your boat. Does that necessarily mean you have to commit to the full goal all at once?

Or I'll give a concrete example that we talked about for two minutes before we got started was, I have this vision and this is the first time I think I'm sharing it on the podcast. So it's kind of fun. There's AARP, this thing that everyone knows, oh, my parents are retired.

They joined this organization and they have all these great things and they've created a community of reasons that you would join a membership program for something. I don't see something like that for the millennial who likes experiences. They're not gonna join AARP, though I have in the past said you can for deals, even as a not old person, retired, you could join.

But I thought, oh, what if I start something that could be a valuable membership that I hope people get value out of related to all the hacks? So it's an idea I have. I haven't gone all in on it yet, right? I haven't even said I'm gonna do it until right now.

But do I need to commit to, this is going to be a massive thing to effectively burn the boat, or could I say, hey, I'm thinking of starting this. Now I've at least created some public accountability. Or maybe I create it and I say, here's where you can sign up.

I haven't built it all out to everything everyone might want. Maybe only a handful of you listening wanna join with a few aspects of it. How much do you have to commit to your grand vision to have burnt your boat, so to speak? - Well, I would argue that everything you just said is not your plan A yet because you're still in the formation phase.

So I think we get to define when it becomes a plan A. It's about crossing the threshold of saying, I am going to do everything I can to manifest this. And you and the language you've used are not there yet. It's all about our personal comfort level with risk and commitment and where it ranks with your other priorities.

So we are allowed to play and toy. In the book, I talk about this. I go pretty far down the road before I decide whether this is the thing. And I don't mind having goals that are in parallel and sometimes in conflict, right? I became a lawyer who goes to law school, gets an offer from Scadden Arps, and then I'm like, "No, I don't want to be a lawyer." And then I never even took the bar exam.

Plan A and burning the boats is not about dogmatic, rigid, forcing yourself to fully commit to everything that comes into your head. But when you've decided, Chris, that you're doing this membership program, which by the way is a great idea, and I'll sign up right now without even knowing a single benefit because the way you hack everything feels valuable to me.

This conversation is already fun. So I'm all in already. Hopefully that escalates your commitment. But it is not your plan A yet. So it doesn't matter. - I've already decided. I've burnt the boat. I'm all in on all the hacks, right? Like it's my full-time thing. I left my company, job, everything.

This is it. Do you actually need to burn the boats on all the small projects in your life and commit to a plan A? Or is it really more a higher order thing for one or two projects in your life, your professional career, your relationships? How do I think about it on that spectrum?

- I actually don't render an opinion on the number of plan A's we can have because I think the joy of living, at least as I've identified it, is in the perpetual pursuit of these growth opportunities that stretch me, that make me uncomfortable, and they tend to be operating simultaneously.

What I do though is I try to consolidate my gains because if I'm jumping from thing to thing and then I look behind me and I see a sea of unfinished projects and a lot of hurt people who were like, "Matt, where'd you go? "You were so into this.

"What year ago?" That begins to chip away at my self-esteem, right? I'm not proud of my behavior. So I try to hold myself accountable to scaling and optimizing. Things get easier the third, fourth time you do it. But I don't think it matters how many plan A's you have.

It's really about once it becomes a plan A, how do you increase the likelihood you will be successful? That's all my book is about. How do I put the odds in your favor once you've identified this thing as a plan A? Not your only plan A, but a plan A.

You can have 17 plan A's, just zero plan B's. I'm having this conversation in my head of whether the mere existence of multiple plan A's is plan B's. I gave you the framework before, which is a fun question. A plan B is by definition a way to achieve the subordinate goal of plan A.

So that's how it becomes a plan B. That's why the musician and Bob's Record Store is a perfect way 'cause both give him a new job, but they're very different. So as long as you're 17 or your membership club, your podcast, they're like very hard things that require total, utter commitment.

For me, I think I try to have a few number of things because I just personally can't manage lots of projects at once. Which goes back to something you said in the book, you talk about how to figure out what you're good at and accept that you're not good at everything.

It took me a lot of time to process this and I'll shout out my time at Wealthfront. As a product manager, I realized there are parts of being a product manager that I'm just not good at. And I realized that not as early, but early enough. And I think it's hard for people.

So I'm curious if you have any tactics for people to realize it and accept it, because I think it's so easy to assume that if you're good at something, you can be good at everything. And it's very hard to be self-critical, but I guess both, how can you find it?

And maybe what are some things you could say to encourage people that learning the things you're not good at is actually a valuable thing to learn? There's a concept in land use and zoning that relates to property. And it's to ensure that property is always put to its best use based on the current context.

So it's called highest and best use. And to make that less abstract, a warehouse in Tribeca in 1920, the highest and best use of that warehouse was as a slaughterhouse. In 2020, Taylor Swift is hanging out there with her private elevator, right? Like the property changes. I look at myself like a piece of property that is always changing due to its context, except the context is not external, it's internal.

I am an amalgam of all the things I've accomplished prior to today. Oh, well, now I'm a guy who was on "Shark Tank." I know how to do TV. Now I'm a person who teaches at Harvard Business School. I know how to teach. Now I wrote a book. Now I'm an author.

I have things to say. I ask myself every single week, sometimes every day, what is the highest and best use of Matt Higgins now that he has accomplished whatever it is he did yesterday? Whatever it is I've now achieved through my trauma? Part of the highest and best use of me now is to share painful things that some people don't talk about because that's very valuable.

By focusing on the affirmative and asking yourself, anybody listening right now, what's the highest and best use of you, rather than be a negative of saying, you begin to cull the herd of opportunity and say like, well, I mean, I could do Excel, but I'm not that good at it.

And by the way, why do I wanna be? And say, right, I'm a good communicator and I can synthesize complicated information and I could operate a company, but it's not the highest and best use of Matt Higgins is to operate a company with 200 people, even though I've done it before.

So I don't know why people are afraid of this. Like, why do you wanna be good at everything? Don't you wanna be great at a few things? But besides, if you ask the question I just gave you, the answer will lead you to where you should be spending your energy and you don't have to make a value judgment.

There's no value in the statement I just gave about the highest and best use. It just is true. That's my number one piece of advice. - Sounds like stop reframing what am I not good at and just focus on what you're great at. - Yeah, and now as I say this, and you bring up a great point, I find it's one of the hardest things for founders to accept is those limitations because they don't know what it means to be a CEO, right?

When you're a founder, you suddenly go from an idea creator to an implementer to a capital convener, and then all of a sudden you run an operating business. So you believe that being a good CEO, good founder, is having the capacity to run an operating business and do everything.

And they don't realize that actually being a good founder, good CEO, is the ability to identify talent that's better than you at each position and to render yourself obsolete wherever you possibly can. But I find a lot of people struggle with this from an identity standpoint. They feel like they need to be good at it only 'cause no one gave them an alternative definition.

- Or even in the non-founder CEO world, I find that people often think that there's a prescribed path. You do a job, you do it well, and then you manage people doing it. And I have met countless people that have realized that the best use of their time is not managing other people.

And other people, similarly, are phenomenal at it, even if they aren't a master of the skill of their industry or whatever the people that they manage do. So if you're a designer, you might not be the best designer in the world, but you could actually be the best design manager.

- I find a lot of people feel, for whatever reason, they wanna be branded like an operator. They're insecure about not being an operator, which fundamentally being an operator or managing people is being a very good therapist. And a lot of people don't have the patience or the EQ to be a therapist.

And so therefore, you're probably not gonna be a very good operator 'cause it requires so much time and patience to get the most out of people. But I find that scenario a lot. People just get insecure about not being like an operator, an executor. - Interesting. I find that so many people think that management is the next step.

I'm excited when I hear stories of people that realize that wasn't the case and what they did. And Google was one of the few companies that created alternative track for someone to just be very senior, very highly compensated, but not be a manager. And I see that trend picking up at least at a lot of companies in Silicon Valley.

And I hope that continues to permeate itself through all industries. - It's possible to separate influence and authority from command control responsibility. And it makes sense 'cause most people are very bad managers. So it makes sense that not everybody was born to be a manager. - And so while we're on the topic of things that we might not be good at, let's put that aside.

But let's talk about when things don't go right. When you do fail, are there things that people should be doing? 'Cause look, once you've committed to a plan A, you've boarded the boats, you're on the way, it's inevitable that things will go wrong along the way. Talk about the fear to get started, the fear to commit, but what about the challenges that come along the way, processing those failures?

You wanna be a musician, you decide to go all in, you do your first gig, no one shows up, it's a disaster. How would you advise someone to process that failure and continue pushing forward? Or maybe understand when they shouldn't. - Yeah, that's a big reason why I wrote this book, because I have seen throughout my life the same fact pattern play over and over again, which I don't quite understand why the universe is wired this way, but the act of persistence is a tremendous predictor of future success.

The mere act of persisting and surviving another day will ultimately beget success, which doesn't make any sense, right? Like, what do you mean I just stay around another day, I just push through and then eventually I get what I want? But the answer is it's true. And so I talk in the book about the most successful people I've seen would break through success.

If I try to discern, like, what's the common fact pattern here? Come from all sorts of different fields, different walks of life. The common fact pattern I see is when they face a setback, they simply expand the definition of what success looks like to accommodate that particular setback. It sounds almost delusional, it's like, I'm so glad that didn't work out because I never would have hired Bill, and now that Bill's here, I'm gonna make a billion dollars.

And yet when they have a win, it enhances their self-esteem. So what's the point of saying that? It's very important how we process failure. One, accept the fact that the goal is to continue, is to survive. So how do I survive? How do I keep going? And the number one thing you need to do to survive is to preserve your sense of self-worth.

It's something we don't like focus on, but your number one objective when you have a setback is to ensure that particular failure does not become enmeshed with your permanent identity. So number one, my process is, I acknowledge that I failed, so I remain intellectually honest. Also by acknowledging it verbally and otherwise, it loses its power over you.

The fear of even acknowledging it is the thing that kind of is half the battle, and being able to be like, yeah, I failed, whatever. But then number two, I am not a failure. Like, I just refuse to be identified, and that's the point I made about these outrageously successful people.

It's like, it just does not penetrate their reality distortion field. So number two, I'm not a failure. Three, but what is a failure trying to teach me? How do I extract maximum value from this failure? Back to my point about survival and persistence, in the failure is the answers to your future persistence, your survival, and you have to mine it and sit with it for a bit.

And then the fourth piece is to never look at it again, once you've extracted value. And I'm not great at that. And again, I wrote my book, so I'd read my book. So anybody here saying, wow, that's great, but I can't do it, understand that I struggle with this too, but I know it's true.

So while I struggle with it, I remind myself that is the way to do it. But those four simple, easy steps, and then go forward. Back to our point about the musician, like, when should he give up? The answer is like, never. It's just like, find a different way.

Find a different way to be in the band. Maybe you're not the lead guitarist, but you're in the damn band. You know what I mean? And just like, never stop. That doesn't mean never iterate, never course correct. That's like, you have to do those things, but just never stop.

And that's why it's so important to have this plan A construct and to accept the idea of the way you're gonna get what you want is to not have the plan B and to have processed the risk at the beginning of the journey, because the way to be ultimately successful in life is to never give up.

I know it sounds so corny and it's in all the books, but there's a reason there are cliches, right? 'Cause they tend to be true. You just don't stop. - I have a specific anecdote from researching podcasting, which is someone always asks, like, how do you be a top podcast?

And I was like, well, I have one piece of advice that's very easy. There are 4 million podcasts. And if you filter the 4 million down by podcasts that have done more than 10 episodes ever and have published in the last 10 days, you delete 96% of podcasts. So it's like, if you wanna be in the top 5% of all podcasts that have been created, not the top 5% that are active, but of all, you literally just have to produce 10 episodes and keep going.

And that's it. So you're not wrong. - We don't wanna accept that for some reason. I don't know why. I mean, because it's really hard. And there are moments like I'm going through something right now. There's always moments when I think that can't possibly be true. It can't be that if I just stay the course and continue to make course corrections and refinements that ultimately I'm gonna get what I want.

No matter what, despite everything I'm saying right now, it gets bleak for me. And I cannot believe that statement is true. And yet I just forced myself to believe it. And in the end, it is always true. It's just, I don't know how it's gonna play out. Even my book, when you open my book, anybody out there who reads it, they'll tell you just a funny story.

I did a $200 million back during a pandemic. I knew that the industry would probably turn, but I thought I could do a great deal and I could get it done and I would learn public markets and maybe I could outrun the timing and I could just show how it could be done better.

Long story short. So that was the opening of my book. And in doing my SPAC, I had to will every part of this to existence, including the IPO. I IPO'd at the height of COVID and it almost fell apart and I had to just stay up all night and to get it done.

I didn't feel good, but I just kept working through it. I rang the bell the next day. Within two days, I had double pneumonia and my oscillator, the oxygen was dropping. I'm like, wow, now I may die because I did this, but I got it done. And then I got a deal done and on and on and on.

And then ultimately the market turned and the SPAC fell apart. That was the beginning of my book. Okay, I'm gonna have to acknowledge a little failure in the beginning, but the good thing is I have my TV show. I have a Shark Tank spinoff. I'm gonna open the book about my Shark Tank spinoff and tell everybody how I'm partnering with Mark Burnett.

I'm leveling up. It's the whole premise of my book. I'm gonna get that done. So I write that. And then the TV show gets canceled before it ever airs. My editor is like, I think we gotta rewrite the beginning of the book. And I'm like, no, I think that's the point of the book.

Like, this is how it goes. And you know what? When we look back, if I did a podcast with you three years from now, I guarantee you there's gonna be exponential value somehow that came from me knowing how to bring a company public. And two, my TV experience is gonna result in the next iteration of Shark Tank that I created.

It's just the way the universe works. But when you're in the middle of it and it's bleak, sometimes it all doesn't make sense, which is why you need the faith. But if you just burn the boats, it's gonna play out in your favor. With travel back on the calendar and my kid in preschool, I need an easy way to optimize my immune system and get some extra energy every day, which is why I kickstart my day with AG1 from Athletic Greens, and I'm excited to be partnering with them for this episode.

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I just wanna thank you quick for listening to and supporting the show. Your support is what keeps this show going. To get all of the URLs, codes, deals, and discounts from our partners, you can go to allthehacks.com/deals. So, please consider supporting those who support us. - And how do you go up against this as what you said, a paranoid risk taker?

You're seeing all these things fall apart. Sorry about that. - Thanks, yeah. Well, I'm just trying to practice what I preach and model what it looks like. - But how does being a paranoid risk taker play into all of this? - I spent a lot of time agonizing of whether I should or should not do this back.

All the things that could play out. Exactly what played out was on the list. So, I was able to go all in on plan A. Plan A is not a delusional belief that you're gonna get what you're entitled to. It's the utter commitment to the goal. The only way, that SPAC had any shot of becoming an IPO or getting a deal done is if I had fully committed to it.

If I had an ounce of plan B as I was going it, I wouldn't have gotten as far as I would have gotten. And the same thing with the TV show, it wouldn't even gotten remotely close. So, as a paranoid risk taker, it's especially important for me to have processed all the risk at the beginning of the journey because then I would have these intrusive thoughts that never would have enabled me to get it done.

They're not at all mutually exclusive. It's actually more important for a risk-adverse person to do what I'm saying and to go through that exercise and process everything. 'Cause when I was taking on water through both of those experiences, I kept remembering, you've gone through this, you knew this could happen.

Attack, keep going forward and don't be afraid. You already know you have the tools necessary to handle whatever happens. Earlier in the conversation, you talked about goal setting. You've just walked through some big projects you worked on. Is there a framework you use to set goals in your personal or professional life?

Yes, I think if you're gonna commit to a life of perpetual pursuit of bigger and bigger opportunities and you're gonna put yourself in uncomfortable positions, you could find yourself drowning or overwhelmed or have taken on way too much. So, I always say, this also helps me with processing risk and going all in on plan A.

I believe it's important to identify what can I not live without, right? If I lost everything, what do I absolutely need to maintain in order to have a degree of peace and happiness? And as you become more successful, your relationship with risk actually increases 'cause you have more to lose.

You get more afraid to take bigger swings. I find this with colleagues all the time, like, well, now I have the big job and the big salary, now I'm even more afraid to take on risk. And so, I think it's actually very important to define your needs as narrowly as possible the more successful you become and then try to let that base case not change.

So, I draw a hard line of boundaries around my kids, my spouse who's my best friend, a few basic things that I need. We're always saying like, what's the smallest apartment we could live in? So, I'm not afraid of everything going to crap. And so, that's how I set objectives.

And when I feel like I've taken on a lot, that something may fail, then I'm always like, well, it doesn't matter because I know what I need if everything were to go to hell. And I think people don't do that. People don't ask like, what's the minimum? They focus more on what they want, not what could they live with if they don't get what they want or what they have is taken away from them.

- You talked about things going wrong. You've had experiences in your life that have dealt with all kinds of crises from the biggest stage to lots of business operational things. Maybe talk a little bit about your experience dealing with big crises and how you manage that both internally and externally.

- Yeah, for those that don't know, I was the Press Secretary to the Mayor of New York on September 11th, 2001. And then I went and helped oversee the rebuilding of the World Trade Center as Chief Operating Officer. So I spent two years at ground zero from the moment that first plane struck the tower.

And so the most extraordinary, complicated and gut-wrenching crisis maybe in American history. And my first takeaway that I learned from that experience was how showing up is half of everything and how people get that wrong. They get that wrong in every context, right? CEOs, leaders, you flail. That most people are looking for just symbolically and actually for you to show up and identify that you're here, that you're in charge.

So whatever situation I find myself in, even in a personal crisis, I say, "Am I showing up?" And showing up personally means am I facing the thing that is the crisis, right? Back to my earlier statement, if I had one tattoo, it would be face everything. So showing up is number one.

Number two is back to what's the worst possible thing that could happen in this crisis and how would I deal with it if it played out? And what's the likelihood of that playing out? I ask myself those same questions when I'm in a crisis. And then three, I look for the silver lining very early.

This law of physics that every action has an equal and opposite reaction is very much on display in a crisis. No matter what happens in this world, when there is a crisis and something bad happens, a portal is gonna open up to a parallel universe where something good is happening as a result.

Sometimes when that involves pain and suffering, it's very hard to accept and you have to just wait for that to materialize. But when life or death is not on the line, you should give yourself permission to say, okay, I just lost my job, which is a big crisis, but what's the portal that just opened up to a parallel universe?

Oh, well, I have nothing to lose. Now I'm willing to go all in on being that musician, my plan A, right? Now I don't have to settle anymore for Bob's Record Store. And so I do think, again, not in life or death situations, but every time I have a crisis, I get excited by what's the portal, where am I going?

What's gonna happen in my life as a result of what just happened? And there's another way to say it. Rahm Emanuel said at Mayor of Chicago, never let a crisis go to waste, but it's another way of saying what I'm saying. But I do talk in a book too about one of the interesting things when you look about crisis and sometimes you assess how you performed, and if you admire how you performed, often the reason is because you had clarity of decision-making and you act decisively 'cause you had few choices.

A lot of my book is about how do you migrate the benefits of crisis decision-making in times of peace so that no one wants to have cortisol flowing through their stomach in order to behave effectively but there is something to be said for the clarity of crisis decision-making and applying it to everyday life.

- It brings up a good question. Let's take someone who's at a job, they don't love it, they're trying to figure out what to do next. Do you think the average person is spending too much time trying to make that decision or too little? - I think the average person is spending too much time looking to settle to escape the pain of the current situation and not enough time believing that the right situation is out there and confidently pursuing it.

I think the same is true of relationships too. We wanna relieve the pain of the status quo and therefore we settle and not enough time trying to identify what's the right situation. So we tend to repeat the same bad patterns, I believe. Most people fall into that trap and that's because you don't value yourself enough.

You either believe the right situation isn't out there or you believe you don't deserve it, especially true in personal relationships. You just like don't know or you don't think you're worthy. - Well, on the professional side, I feel quite amped right now. I already did the plan A, went all in on the macro idea of what I'm building here, but I'm ready to start.

- You already got your first customer right here and it was effortless and your acquisition cost was zero. - Just to be clear, I have had two listeners or readers use this feature on the newsletter. I think both of them said, I'll pay $100 a year for a membership, you just have to build it.

So technically Matt, unfortunately you are customer three. Huge shout out to customers one and two. - Chris, I have news for you. I'm willing to pay 400 for the premium membership. - Okay. - So I am technically still the first premium member as I have upsold myself. (laughing) - Tier two.

- See, this is what happens when we commit to plan A publicly on a podcast. - So I'm excited to do that. I guess I should probably commit myself to this even further and say, if you go to allthehacks.com/join, I'm gonna put up a page where anyone listening can join a membership that I will create.

And the one thing that I will commit to having in it now, there's not a lot of features, is I'm gonna do a once a month call just for members, Zoom call, you can join, ask anything, we can talk about anything. I'm not gonna record it. I'm not gonna put it out to everyone.

We'll at least do that. The goal in the long run is to build a real membership, to have perks and benefits. I have some crazy ideas on travel. I'll talk about them in that first Zoom call. But if you go to that page, I will set something up by the time this airs.

- Wait, can we use this as a case study though? 'Cause one thing we didn't get into is something I talk into my book about the loneliness of being on the bleeding edge and what happens when you have a revelation or an epiphany like you've had with this membership idea, which I think is fantastic.

But let's say I was neutral. What happens is the relationship between the magnitude of an opportunity and the amount of data there is to support it is inverse, which makes sense, right? If you have a really great idea and only you see because you're so early, there's not gonna be any data out there to support it.

And two, if you rely on your friend group or family group or whatever to validate it, they're not gonna be able to see what you see 'cause it's your epiphany. At the same time, those are actually confirmatory that it's a big opportunity, unless you're crazy or delusional, because only you are putting the pieces together.

And I think what happens is oftentimes where people sit where you sit, wait a second, why is there only AARP? There should be a membership group. What is it about being 65 that makes you wanna belong things? That's not true. I would love a group where I get benefits, right?

What happens a lot of times, Chris, is now a person will road test it with their peer group or their friend group. And if they surrounded themselves with people who are risk adverse, or maybe they don't have their best interest at heart, the idea dies with those groups. So I talk in my book a lot about, make sure that when you have a nascent idea that you one, cradle it, but two, consult agenda-less supporters or what I call pragmatic optimists, people who are wired to be optimistic, but pragmatic, so they can give you real data.

But it's really important to sit with this idea that when you have a big opportunity, a big idea, there isn't gonna be the data or the affirmation to support it in the early days, and don't let it die at that point. 'Cause the best innovations in life are gut sandwiches.

They began with intuition, like you just had, a little bit of data, AARP, the thing exists, but you're gonna launch this based on intuition and my early membership fee of $400. Last point on this, 'cause Chris is about to start this journey. My number one advice to you is opportunity arrives before the tipping point of evidence.

So don't be afraid. If you trust your instincts and your intuition, if it's a great idea, you'll figure it out the same way Chris is gonna figure out with his new membership group. Do we have a name? I mean, the whole thing's under all the hacks, so it's gonna be there.

We'll see where it evolves. I have ideas of everyone joining can be a sub-agent of a travel agency. People are gonna be able to build this with me. One other thing I'll add is a feature. I'm gonna float to all members, the upcoming guests. So you would have gotten a message that Matt's coming on, we're gonna talk about this.

I'm gonna let you guys also be a part in, what should we talk about with this person? What topics should we discuss? So I'm gonna bring you in as members to part of what we're building. So there's a feature ad right now for members of this already announced, by the time you hear it, membership.

Exciting, I can't wait. All right, awesome. We did some work today. Love it. So if anyone listening right now has a thing, whether it's a new career path, a new job, anything, my strong recommendation is to check out the book and maybe you can burn your own boat like I just did on this episode.

We're all in on a membership. We'll see where it goes. Where can people find anything about what you're working on? I know you've got some cool bonuses on the book online. Where should people go? Yeah, I have a website, burntheboatsbook.com. I tend to spend a lot of time on LinkedIn.

So find me there. If you read the book, I'd love to hear from you. Feedback is amazing. So Amazon, Barnes and Noble, Goodreads, wherever it is you spend your time, that would be great. Also tells me which themes I should be building upon and expanding upon. So thank you.

So leave a review for the book, just like I always ask everyone to leave a review for the podcast. I know it's really important. I will go leave you a review after this. Thanks for being here. Thank you. (upbeat music) I really hope you enjoyed this episode. Thank you so much for listening.

If you haven't already left a rating and a review for the show in Apple Podcasts or Spotify, I would really appreciate it. And if you have any feedback on the show, questions for me, or just wanna say hi, I'm chris@allthehacks.com or @hutchins on Twitter. That's it for this week.

I'll see you next week. (upbeat music) (bubbles popping) (bubbles popping) (bubbles popping) you