Chapter 1
Fired at the Rest Stop
The Power of Failure
“I'm about to get fired again.”
I was on the New Jersey Turnpike, a long industrial stretch of road connecting cloverleaves in Delaware to my home in New York City. Along the way are rest stops named after people you've sort of heard of. Clara Barton. Vince Lombardi. Richard Fenwick.
My wife, my dog, and I pulled over at the Richard Fenwick Rest Area. I'd just received one of those emails that puts a pit in your stomach. My wife Camille watched me scroll through the email in dead silence. After an eternal minute I glanced up with a deadened look in my eyes. She waited patiently, but quizzically.
It was Friday the 13th, October 2017.
My track record as a startup executive was discouraging. I'd now worked at four companies over the past 14 years and this would be the third time I was fired. My self‐esteem plummeted as I read the message. How fitting to be at a rest stop when my career was in the toilet. Again.
“I'm about to get fired again.”
I thought back on the 18 years since I graduated from the University of Virginia—failure seemed to be a constant theme.
I'd started a record label, moved to a farm in rural Virginia, and tried to become some kind of hipster media mogul. That didn't work.
I'd followed a girl back to New York. We got married. Then the marriage fell apart.
I somehow found myself in the world of high‐tech venture capital–backed startups. I'd thought getting into the C‐suite and working hand‐in‐hand with the CEO might translate to job security. What an oxymoron.
“I'm about to get fired again.”
What was the root of all my failures? I worked for incredibly successful companies, filled with incredibly smart, talented people. Yet, I was left with a sickness inside myself that created a sense of transactional competition and insecurity that I tried to cover up with the money I was making.
“I'm about to get fired again.”
On the New Jersey Turnpike, the email itself was seemingly innocuous. A note from my CEO saying “I hadn't realized you'd be out today. Can we meet first thing Monday morning?”
She wasn't a morning person.
“I'm about to get fired again.”
I was at an inflection point. My adult life up to this point was marred by struggle and dissatisfaction. I never felt I could get my feet under me. I never felt I was doing what I was meant to do. I always felt I was at someone else's whim.
There and then, in that rest stop parking lot, I resolved that this firing would be different. I can't quite describe the resolve I had. The determination that suddenly formed inside of me. But I had a certainty. A certainty that this was going to be the last time this type of situation happened to me. I wasn't going to wallow. I wasn't going to feel sorry for myself. I was sick of letting life happen to me.
I was going to take control and use this moment to transform. To rise above the chop and the froth and the turbulence that kept upending my life and find a new path forward. To catapult myself into the life I wanted to live. I was going to leap into the unknown and simply trust that I'd figure it out. Figure out how to support myself on my own terms. And figure out how to finally achieve true independence.
Getting Fired Still Sucks
Despite this parking lot revelation, getting fired sucks. That's obvious, and yet still surprising to so many of us.
As a child, I always viewed myself with nearly limitless potential. I had been good at school and gotten good grades. I got where I wanted to go.
The first time I was fired was back in 2010. I was sitting in an office discussing leaving Gerson Lehrman Group, realizing this wasn't really a choice, but an order. I was getting fired—and I was stunned.
The truth was that I was treated well in my departure from GLG. Alexander Saint‐Amand, the CEO at the time, was honest and direct while still being caring. He told me as much as he wanted me to stay at the company, there wasn't a department head that wanted me on their team. I was too surly. Too disgruntled. Always complaining. So there was literally nothing much he could do, and he was right. I had pushed myself out of the company somehow.
Each time you get fired you can lose a little piece of yourself if you're not careful. Even if you use the firing to reframe the next chapter of your life, it still sucks.
The second time I got fired was not as nice.
When I was asked to leave GLG, I found myself at another startup, with a big pay cut and in the throes of a divorce.
I worked there a long time and built it from nothing into something. Me and a bunch of other folks. But I was disgruntled again. Thinking I had contributed too much and controlled too little. And I'd lost respect for the CEO. So I tried to get him fired. I secretly met with an investor and shared my frustration. They said they'd look into it and then followed up to let me know they didn't think it was a good idea and they were going to stick with the current leader. Months went by.
So much time had passed, I thought I was in the clear. I thought I'd somehow avoided discovery. I even got promoted to Senior Vice President. I'd been at the company for four and a half years at that point and had an inflated sense of my own importance to the company and my job security. There's that oxymoron again.
Then one day, the CEO and I went for one of our typical Monday walks, but there was a notable difference in his tone of voice. About halfway through, I realized I was getting fired. And this time it was not a graceful exit, but the kind where they turn off your email and lock you out of every system and then tell you that you can't go back to the office and please return the laptop. The most embarrassing and painful way to get fired. I had a team of close to 60 but wasn't permitted to say goodbye to any of them, many of whom I'd personally hired and developed and who I thought of almost as family. I still remember the head of HR, a very nice person and still the best marathon coach I've ever had, meeting me at the Grey Dog Cafe so that I could give back the company laptop. It's hard to put into words the level of shame and embarrassment I felt. A deep darkness came over me back then and lodged itself somewhere in my psyche.
That time I did wallow. I smoked a joint and drove out to Jones Beach to look at the Venetian tower and lie on the sand and listen to “Let It Bleed” by the Rolling Stones. Trying to figure out where to go from there. And how to pick myself back up.
Those painful experiences prepared me for the signals I needed to look out for when I got fired from The Muse two jobs later. The shift in tone. The abrupt meeting. The “pack your shit and go” vibe.
So before we dive too deep into all the self‐help talk about how all this is just fuel for the fire and, in hindsight, how lucky you are to have all these terrible things happen to you, let's just acknowledge that it's a deeply shitty experience.
And if it has happened to you, I want you to know that you're not alone. And it doesn't mean you're a failure. In fact, getting fired is both a deeply educational experience and one you can draw on in future years. And it's much more common than you think.
We've run numerous studies within the Pavilion Executive community evaluating how long most startup executives last in their role. We looked at various social media profiles and worked to ascertain how long each person held their position. The results were astounding. In fact, most startup executives last less than 18 months in their job, and that number has been steadily shrinking over the previous years, particularly during the COVID pandemic.
Various other companies have supported the data with Gong, the well‐known revenue intelligence and call‐recording company, revealing a study showing that vice presidents of sales at startups last just 19 months.
This information is a big deal. It means there is far less stability than there ever has been. Greater opportunity for sure. But far less stability. I remember growing up and hearing about people who worked on the assembly line at the Ford Motor Company. There was a pension and a clear retirement plan. They even gave you a gold watch after 20 years. You'd start working right out of college or even high school, put in your two decades, and be in a position to think about what came next in your forties and fifties.
All that is gone now. People are changing jobs more than ever before, and the reality is that, particularly in the world of fast‐growth startups, and especially in sales and marketing, every day you set foot in the office or log onto a Zoom call, you are taking on great risk.
There are a variety of factors why. There's so much capital out there, and the pressure is high for every company to become the next unicorn, the next multibillion‐dollar valuation. Startups go through phases of growth faster than normal companies by design, so your skills might be relevant for one stage and not another.
And as we've seen from the COVID pandemic, people's tolerances for working in inflexible, overworked, unappreciated environments are low. So maybe our own patience wears thin quicker.
But again, none of those realities matter in the moment when you realize you're about to be fired. You just feel loss and shame and anger. But, if you're like me, you will learn to understand these feelings. You will learn that these feelings are temporary, and you will grow from these setbacks. You really will. I promise.
You can use this experience to emerge better, stronger, and more powerful. Throughout this book, I'll show you how I did it.
In fact, you may just end up where I am, with gratitude. Gratitude for all the people that fired me. Gratitude for the lessons they tried to share with me that I was too stubborn to hear. Gratitude that every single experience and failure led me here, to a place where I can truly enjoy my life and where I'm still relatively young enough to do so.
The Lessons of Failure
Failure had been such a constant presence in my adult life that it was worth breaking down some of the root causes. Something about my moment at the rest stop triggered a breakthrough for me. But why? What was it about?
I imagine if you're reading this, you can identify with this feeling of failure. This feeling of not living up to your potential. That something inside of you was trapped. And the frustration that things aren't turning out the way they were supposed to.
I've been there so many times. Pivotal inflection points in my life that were seared into my brain as representations of missed opportunity and unrealized potential. It started when I didn't get into Thomas Jefferson, the magnet school in Fairfax County, Virginia, for the best and brightest. Then, I didn't get into Princeton. I remember the thin envelope sitting in the mailbox and the breakdown it triggered. The feeling of being passed up. Passed over.
That feeling followed me to one of my bigger failures, my record label. What were the lessons? What were the reasons?
Failure of Pride
I failed at the record label because I had no idea what I was doing.
There were so many ill‐fated decisions, made from pride and ego. I thought I knew it all. I leapt from investment banking into the music industry with no contacts, no network, and no experience in the industry.
I'd had friends who were musicians. It was 1999. The dot‐com boom. Everyone was starting something. I'd start a record label. I'd help my friends become famous. We'd all live on a farm outside of Charlottesville, and we'd build a recording studio in the basement, and we'd make great records like the guys from the Elephant Six collective where Neutral Milk Hotel came from or Merge Records from North Carolina or the two legendary indie labels, Sub Pop, where Nirvana was first born, and Matador, home to Pavement, perhaps the greatest indie rock band of all time that stayed indie (this is a much longer discussion obviously and depends whether you think REM was an indie band, they certainly were at the beginning).
I had all these dreams of going back to Charlottesville and trying to reclaim some of the magic that was my last semester at the University of Virginia, perhaps the last time before these past few years when I was truly happy and carefree, and felt light and content.
What was really happening was some kind of wish fulfillment. Let's call it stubborn youth. Stomping my feet and saying I was going to be good at something because I said I would be.
Of course, the world said otherwise. The bands I picked to support were not very good. I wasn't as savvy with artist agreements, and, of course, I had no network to rely on to prop me up or support the work we were doing. I moved to Charlottesville but was too shy and nervous to approach the team from the Dave Matthews Band, Red Light Management, the biggest and most important music company in the area.
Instead, I rented an office, took bong hits in the basement of the farmhouse we had all rented, and subsisted on the leftover bagels the bassist would bring back from his job at Bodo's. We invented the “bagel salad sandwich”—a bagel with a bagel in the middle. We were dirt broke. Absolutely broke.
So broke that there were multiple times days before rent was due I had no idea where the money was going to come from. I took a job delivering Domino's and still remember the day I delivered a pizza to a kid skipping school. The total bill was $7.42. He gave me $7.50 and told me to keep the change. A professional low point.
I remember being alone and lonely. I remember being sad. So incredibly sad. Driving back on Route 64 from Charlottesville out to our farmhouse at 6:00 in the morning, bright sunlight, after staying up all night for no reason and listening to the song “Remember” by Air in my Volkswagen Jetta and feeling like there was a bowling ball on my chest. Like I couldn't even imagine what happiness was.
I call those years “the bad old days” for good reason.
But I did learn something. And that thing was work ethic and humility.
In fact, as I sat in the car years later at the Richard Fenwick Rest Area, I realized that in every failure I had taken away a kernel of something with me. That even though I had failed and failed again, I had made some kind of deposit in my ultimate character.
The record label taught me that pride and ego are not the requisite inputs for success. They were actually active blockers.
As you think about your life, your career, and your success, remember that nothing is owed to any of us. So much of what we get, we work for. And I don't mean through a nose‐to‐the‐grindstone, get‐there‐early, leave‐late type of hard work.
It's about working with humility. A sense of service. The world has much to offer us, and if we listen, we may learn from it.
Failure of Physics
Of course, sometimes the reality is that failure or the perception of failure is because of factors that are simply outside of your control in the first place. “Doing what you love” is not good advice because it ignores some obvious realities about the world. That's why we need a good perspective on the external realities that power success.
Let's dive into them, and let's think about a framework for evaluating potential paths to success.
I often tell people, “You can't outthink gravity.” What I mean when I say that is that there are certain fundamental realities and principles of the universe that persist no matter what. They are the rules. That's what physics is. The rules and principles that govern reality.
When thinking about my career, an old friend once pointed out a useful heuristic. There are three key elements to success: The first is what you're good at, the second is what you're interested in doing, and the third is where the market is moving.
Most people overweight what they're interested in and underweight the market and their skills. In fact, most people don't quite understand how what they want to do translates into professional activities in the first place.
I had wanted to start a record label. Largely because I love music and fell in love with the romantic idea of living on a commune with a recording studio in the basement writing and recording music. That's my passion and my interest. But that doesn't mean there's a market there, and it doesn't necessarily mean I was in a position to run a record label in the first place, even if the market for music was growing, which, in 1999, with the launch of Napster and MP3.com, it most certainly was not.
Misclassifying What You Love
Most people, for reasons that are often cultural and disconnected from the daily activities they perform in a job, misclassify their interests. They do this because they fail to break down the actual daily activities of a job and instead ascribe blanket euphemisms to entire functions.
People say, “I don't like sales.” Well, working in sales is a lot of different things. Saying it that way undercuts the possibilities.
Sales is about having conversations. Being interested and curious about other people.
It's also about competition and keeping score. About knowing exactly how you're doing. Outcomes and results. Sales is about repetition, consistency, and discipline.
So if none of those things are interesting to you, then yes, maybe you don't like sales. But perhaps you're not deeply considering the activities and the mindset that different functions require.
Outside of the record label, I've also started a number of bands myself. I learned how to write songs and found musicians who could play them better than I could. I released a few different albums under the name Lipstik and The Flying Change. I worked with my friend and producer, Paul Brill, who I'd managed during the label days. There's nothing like the thrill of having a simple melody and chord progression in your head and then months or even years later hearing that song recorded beautifully. That feeling of creation is at the core of my being. It's when I feel alive. When I, feel most human. There's nothing like it.
I still get to feel that joy of creation almost daily. And yet, I'm not in a band now.
Years later, building and running my own company, I found the same creation in activities as mundane as putting an HTML email together in Hubspot. Or coming up with a good idea and working with a team to execute.
The beauty of creation isn't exclusive to art, but can be found in all manner of activities in your life. So I would encourage you to think deeply about functions and industries that might not appear relevant on the surface, but might actually hold the promise of fulfillment within.
The Power of the Market
Perhaps one of the most critical factors driving professional success—and the thing that will paper over numerous other errors—is the market itself.
In many ways, the market is simply a proxy for the broader energy of the universe. The movement and flow of that energy propels great people, companies, and products along. If you can ride that wave, you can achieve success, often in spite of many other shortcomings.
The market is gravity. The market is physics.
The market is greater than all of us. It is the sum total of people's desires and wishes, and it determines, more than anything else, the success or failure of an endeavor. The market is everyone. The market is the universe. And to have a successful career, you can't fight the universe. You need to flow with the universe.
Now when we say a large market, typically we mean a large total number of potential customers. Of course, the most important factor is the number of total potential customers multiplied by the average amount each customer might pay. That tells you the total dollar opportunity available to you.
But a large number of potential customers is still the best way to get a big market for a bunch of pretty simple straightforward reasons. Perhaps the biggest reason of all is that you can experiment in a big market and still have an opportunity to succeed. In a small market, you might get a few things wrong and have exhausted all of your potential customer conversations before you even begin to discover your product, how to price it, or what you really want to sell. A large market creates a margin for error that lets you iterate. A large market gives you the chance to test and innovate and still have lots and lots of people to sell to.
And as you think about learning from failure and perhaps avoiding it in the future, think first and foremost about the markets in which you will operate. Because they have physics to them that you won't be able to outthink.
When you have product market fit, when you are swimming with the current, everything feels simpler, everything feels easy. I spent 7.5 years at a company called Gerson Lehrman Group selling information to investors that desperately needed that information. That company grew tenfold in the years that I was there, and I wasn't smarter or wiser than I am today. But because we had a product that people wanted and would pay for, all of our best ideas took hold.
And, thinking again of physics, many of the companies that I worked for later, did not have that same wonderful lift of the market pushing things along. When you don't have the winds of the market in your sails, everything is harder, everything becomes more desperate.
I spent 4.5 years selling leads to private equity investors that didn't have a lot of money, weren't particularly interested in paying for leads, and the leads we had to sell were the ones nobody wanted in the first place. The market itself was fairly small. There just aren't that many private equity firms out there that are operating effectively. And because we had a product that wasn't very good, we couldn't charge very much for it. And those realities are simple physics.
I realized thinking through some of the failures I'd experienced at all sorts of different companies, failures that manifested themselves as firings, so much of what I ascribed to my personal situation was simply the market.
We don't always realize that we are part of the economy, part of the broader global universal movement of energy. But we very much are.
Warren Buffett famously said, “When a management with a reputation for brilliance tackles a business with a reputation for bad economics, it is the reputation of the business that remains intact.”
Buffett is talking about physics. There are forces of failure that are in your control. And there are forces of failure that are out of your control. Assuming that failure is always personal can be a grievous mistake. The agency you have in that failure is one of market selection. Of companies with “bad economics” as the Oracle of Omaha would put it.
The trick is learning that simple fact. Learning how to analyze opportunity in the right way and understand the basic, fundamental physics of a market and consequently of the universe.
I started a record label from a farm in the middle of Virginia with no network and mediocre bands. And yes that was dumb.
But more importantly, I started a record label in 1999 when the Internet was emerging, when Napster was taking hold, and when kids in college began buying computers with CD burners in them.
I started a record label in 1999 when the way record labels work is that you put down tons of money up front for recording, manufacturing, and distribution, and, if you ever get paid back at all, you get paid back years from when you invested. We call those capital‐intensive businesses.
Physics.
Even if I'd had the best bands in the world, in the heart of New York City, I was entering a period of secular decline in recorded music revenue that would last for decades before artists and creators finally reset their economics and found a way to integrate streaming, merchandise, and live performance. And even then, a record label is still not the right way to capitalize on all of that.
Physics.
Failure of Mindset
But, there is something more important. The most important thing of all. And this is bigger than experience, bigger than humility, and bigger than physics even.
The biggest failure I realized as I sat in the car in 2017, was not about a lack of experience or knowledge or being in the music industry at the wrong time, or the live‐streaming industry, or any industry in particular.
The diamond created from those years of repeated setbacks was formed from the realization that my biggest failure had been one of mindset.
Something had taken hold of me over the last years that was now ready to be shed, like a snake finding new skin.
That old skin had a mindset of lack, of deficiency, of wanting but not having. I had been filled with a sense of frustration at who I was and what I'd become. And I'd been caught in a trap of thinking that this frustration itself was motivating. That by being extremely dissatisfied and constantly telling myself what I didn't have, that the things I wanted would magically appear. And even more importantly, that all of success lay in money but that I didn't have the right or the ability to set off on my own, particularly after the failure of the record label so many years before.
Because of that mindset, I'd been caught in a loop for what was approaching 15 years. The key elements of the early part of my career were a company that was incredibly successful, peopled with incredibly smart talented people, but that left me with a sickness inside myself that created a sense of transactional competition, insecurity, and the idea that money itself was the input to my happiness versus the output of my happiness.
If nothing else, my hope for you, dear reader, is that you don't suffer the same fate that I did. Namely, years and years of unhappiness under the mistaken assumption that unhappiness itself led to happiness.
In fact, the truth, for me at least, was the exact opposite. The thing that ultimately created my success was not an emphasis on what I didn't have. It was the joy of what I did have. It was the release in needing other people's approval and opinions. And it was the letting go of self‐pity and even the sense that I was a failure in the first place.
My entire epiphany did not happen in the rented Chevy Malibu at the Rest Stop. But what did happen was the beginning of that realization.
The Definition of Insanity
They say the definition of insanity is doing the same thing over and over again and expecting different results. And at the core of that moment in the rest stop was the emergence of a resolve to try things differently.
For years, I'd told myself that I was a failure. And that even though I was working for people I didn't always respect, I didn't have what it took to be a founder and CEO myself. Because I didn't know how to code, I couldn't build a software business as the founder. And if I couldn't build a software business, then every business by definition was a lifestyle business and not worth very much.
But sitting there at that rest stop, I had reached a breaking point of sorts. I knew that I just couldn't do it anymore and that whatever my fears were about the future, I needed to try something different.
No matter what happened, I needed to find a way to build something of my own. Something that wasn't subject to the whims and vicissitudes of founders and investors that often didn't have a clue as to what was really happening in the business. Something that emerged from the best parts of me. The parts that loved to give and to help and to serve, even if there wasn't a ton of money in it. Something that felt true.
If you've ever been pushed to the breaking point, if you feel like you've failed time and time again, take some time to truly reflect on it. Who were you in those situations and those instances? Were you focused on bringing out the best in yourself and bringing joy and gratitude to the world? Or was your mindset continually reminding yourself that you weren't good enough? That you hadn't done enough?
Because the first step to the life you've always dreamed of is actually quite simple. Give yourself a break. The constant reminders in your head of what you aren't and what you don't have are not helpful. They actively detract from your ability to find success and happiness.
Emerging from Failure
In hindsight, the truth was that framing all these life lessons as failures was part of the problem. To truly chart a new course in your life, you must let go of the narrative in your head that tells you you're not good enough and aren't doing enough.
You need to let that part of yourself go for a very simple reason. It doesn't help.
That's the key.
I remember running down the West Side Highway with my friend Scott talking about firings and failures. He commented, “I always thought you had an amazing career and was also so impressed by the different roles you'd taken.”
I instantly countered, “No, they've all been failures. I haven't achieved the thing you're supposed to achieve working for all these startups, which is a liquidity event. I haven't made it.”
He replied, “Does it help?”
“Does what help?”
“The constant disapproval of yourself. The constant negative energy you bring to every interaction. Does it make people want to be around you more? Does it help you at work to close deals or achieve your goals?”
And the answer, of course, was no. It doesn't help.
Even if you don't believe any of it. Even if you are convinced that deep down inside you really are worthless and a failure. The reality is that all of that doesn't help you get where you want to go. And telling yourself what you can't do or haven't done is a surefire way to ensure that you won't do it.
As Henry Ford said, “Whether you think you can or you can't, you're right.”
I'd reached that point in my life, finally, where after so many repeated setbacks, both real and imagined, I was ready to try something new.
That something new was straightforward and is something anybody can do, including you. I was going to take a chance, and I was going to start believing in myself.
Sitting there in that moment, the thing that shifted wasn't a business plan or some amazing new app I could create. It was the resolution, formed from years of setbacks and negative energy, that this time would be different. I would not give my happiness or my pride to others anymore. I was going to take a leap, based on belief in myself, and I was going to break the pattern that had been consistent inside of me since childhood.
Reframing Your Narrative
The reality, in hindsight, and writing this from years in the future when I've realized so many of my wildest and most extravagant dreams, is that the biggest failure of all was classifying my life as a failure in the first place. That was the critical flaw.
The path forward to not just success but to fulfillment begins when you reframe the story you tell yourself about your life.
The New Testament (I'm Jewish but there's wisdom all over the place, and I'll take it where I find it) says: “For to everyone who has will more be given, and he will have abundance; but from him who has not, even what he has will be taken away.”
A story of your life that frames your experiences and your setbacks as stones on a journey leading to fulfillment will change the flow of energy around you and begin to attract more success. Success breeds success, and abundance breeds abundance.
In 2017, I resolved that being fired from The Muse was not going to be a setback. Instead, I simply resolved it would be a springboard. That I would emerge from this experience more powerful and more confident, and that I would leap into the void of entrepreneurship and trust that I would land on my feet. I would bet on myself.
I decided I would discard the narrative that I needed to “regroup” or I needed to “nurse my wounds.” I wasn't going to take a vacation. I didn't need to stare at the ocean and feel bad or sorrow or self‐pity. While I knew I was human, and had depressive tendencies anyway, this time I would harness the certainty and the strength I knew was within me and I would use it to forge a new path, one where I made more of the rules, and one where I confirmed to myself that I was who I had always hoped and thought I was.
There was nothing exterior that needed to happen. All of the things that would later completely change my life and produce so many incredible results. All of that simply started within myself. And it started simply by deciding it was so. Deciding it was so and letting go of the story I'd been telling myself that I was a failure in the first place and that I wasn't capable of what I knew I was capable of.
The Path Forward
So how do you change your life? How do you reset if you feel like you keep running into a wall? Well, there's no simple formula. But for me the first step was resetting the narrative inside my head. Failures are experiences, and I learned something from every one of them.
Part of the ability to view the world through that lens is to have an appropriate perspective on time. One of the famous maxims in technology is that people overestimate what can be done in a quarter and underestimate what can be done in a decade.
If you take a short‐term transactional view of your life and your career, and feel a deep sense of pressure, anxiety, and urgency to do something amazing very quickly, then failure may well fill your field of vision.
I remember getting out of the University of Virginia and telling anyone who would listen that I needed to be worth $12.8 million by the time I was 28. I have no idea why I picked that number—it sounded big to me at the time. I was about 23 when I was saying that and the only thing that could possibly make me that wealthy was my record label if it somehow became something it was not. And it did not become that thing.
That sense of pressure—to be something amazing or to accomplish something amazing in such a short period of time was a contributing factor to my sense of defeat. It's a very good thing to want great things for yourself and to use tools and techniques, which we'll discuss to help you achieve them.
But the need—the need to have those things and to achieve that greatness in such a short period of time is a complicating factor.
I wrote in the introduction to “play a long big game.” If you are able to take a longer‐term view of your life and your contributions to the world, not only can you achieve something amazing and have greater happiness on a day‐to‐day basis but you can also create more space for serendipity and for wonder. A “small short game” is thinking about life transactionally. It's chiseling. It restricts you. It limits who you are and what you're capable of. Having a long‐term view, removing the need from your daily life, removing the grind and the frustration and the resentment, if you can do that, you can set yourself free.
There's a good reason for the clichés “Life is a marathon, not a sprint” and “It's the journey, not the destination.”
One of the keys to personal and professional success is very much to process and absorb the idea that the moment, right now, is beautiful and wonderful and no better or worse than any other moment. This moment as we know is all we have.
So letting go of need. Putting it down. Recasting a lack of having as failure and disregarding arbitrary short‐term thinking for more relaxed and easy long‐term thinking is part of the path to success.
As I thought about my next steps, my mind was no longer concerned with a “get rich quick” scheme. The energy around constantly trying to sprint to a milestone only to have that milestone disappear and evaporate with every firing had left me. I was spent. And as a result of being spent, I was able to let go. And not need anything from the moment save for what it gave me. If this sounds pretentious or mystical it's likely a bit of both. There's so much of Buddhism in true paths to happiness, and this is maybe some watered‐down version of it.
The next step was to use that experience. But use that experience to listen to the market and find something that aligned with the path of the universe. Work with the wind not against it. The third step was to take a leap. A leap of faith and of trust that I was capable of becoming who I'd always hoped to be and wanted to be.
Chapter 1 Tactics: Negotiating Severance
Before we wrap up and talk about how you can reframe lessons of failure and chart a new and different course for yourself, I want to make sure that I leave you with some very practical tips and tricks for your career that you can leverage.
There's a lot that's going to be wishy‐washy in this book and will require some deep mental and spiritual self‐evaluation. But in every chapter I want to make sure I also leave you with something super‐actionable and tactical.
One key element that has changed my life as a startup executive is having the foresight to pre‐negotiate severance before you take your next job. For most high‐growth companies, they'll pay you some severance when you're fired. But please understand that severance is not required to be paid. It is optional, and you'll have to sign a bunch of releases and other paperwork if you do get it. The market rate is typically three months of base pay for a vice president–level candidate or above.
However, at Pavilion, we coach our executives to first pre‐negotiate severance as part of your employment negotiation. And we coach people to target a minimum of 6 months of severance with a goal of 12, paid in one lump sum (vs. paid with payroll).
Many companies will balk at the very idea of mentioning severance in the first place. They'll try to play psychology with you. “Why are we talking about severance when you haven't even started?” Perhaps in the same way that a potential marital partner might balk at a prenup and employ guilt in that discussion.
We have talk tracks we can give you, and the happy benefit of them is that they're all true. Namely that the average tenure for executives is short, that you're taking a huge chance with your life by taking on a new role, and that this is simply the reality of what you need to do in the modern workforce.
But however you get there, do try and get there. Prior to my success with Pavilion, my biggest financial liquidity events all came from pre‐negotiated severance. It can give you breathing room to find your next job, and if it's pre‐negotiated, you can go to work with a little lighter step every day knowing that you've anticipated some of the negative outcomes and have properly planned for them.
If the company truly won't grant you the 6 month's severance, you can counter with a time‐based increase in severance starting at 3 months for perhaps the first 6–12 months and moving to 6 months or greater after having demonstrated tenure with the firm.
The more you can pre‐negotiate, the less anxiety you'll feel if you sense the winds are changing at work and start to feel unsteady. I learned this after getting fired from Axial and, in my last full‐time job before working on what would become Pavilion, I negotiated 12 months of severance on a $400,000 base salary. That $400,000 was effectively the seed capital for the business and gave me enough runway to get the business to a point where it could pay my salary within a few months.
So, yes, we'll talk about all manner of recovering from failure but if you're on an executive track, one thing to always target is pre‐negotiating six months of severance for any VP‐level job or greater.