I went looking for a better airline seat.What I discovered was the why behind every why in our life

You may know me as Mr. Upgrade, the guy who has spent thirty years getting people into better airline seats for a lot less than they expected to pay.

How a minor-league pitcher ended up there, and where it led next, starts like most good things in my life: with my dad.

A motto with no markup

My father had a saying he repeated so often it may as well have been carved over the front door: Bennetts don’t pay retail. He told me it was on the Bennett coat of arms. I never checked, and I never needed to.

Dad was a small-business man and a born researcher who didn’t take no for an answer. He would frequently take me to the library to pore over reference books you couldn’t check out, and taught me that every market has a wholesale side. I didn’t know it yet, but that was my first upgrade lesson.

A bonus instead of a bachelor’s

Some kids have to work for everything. Early on, I wasn’t one of them: I got A’s without studying, stood six feet tall at fourteen, and hit .900 in Little League, which sounds made up but isn’t.

In 1991 the Kansas City Royals drafted me straight out of high school. I was seventeen, with a 92-mph fastball, and they offered me a $90,000 signing bonus to skip college and go directly to the minor leagues.

I took it. My education, it turned out, was going to come from somewhere else.

Keep the change

Here’s something most people forget about the minor leagues: the pay is terrible. I made $850 a month, six months a year.

So when the Royals handed us a check for a full-fare coach ticket to spring training, over $600 each way, and told us to keep the change, they had no idea who they were talking to.

I was raised by a man who said Bennetts don’t pay retail.

The fares made no sense to me, either. Two one-way tickets cost more than a round trip, which bugged me the way a locked door bugs a locksmith.

So I went digging, years before Google or Expedia, and figured out how an airline really prices a seat. Pretty soon I was saving 25% a ticket, sometimes 50%, and my teammates were lining up to have me book theirs too.

Three hundred dollars twice a year doesn’t sound like much until you’re earning $850 a month. Then it’s a raise.

Three seasons in, tendinitis ended my career. I still throw as hard as I ever did, it just doesn’t get there as fast.

That was the day easy ended. The first time.

Thirty years at ten cents on the dollar

With baseball behind me, I went into the airline ticket business, and in August 1996 I started a newsletter called First Class Flyer. This August it turned thirty, the longest-running publication in premium travel.

It has lasted for a simple reason: we got people $30,000 airline tickets for ten cents on the dollar. Around 2001 my clients started calling me Mr. Upgrade, and hundreds of thousands of readers later, we’ve served seven million upgrades.

The strategy I’m proudest of is one I invented: it lets you book two Business or First Class trips on a single airline ticket. The first time people see it work, they ask what my teammates asked in 1991: wait, you can do that?

You can. On major airlines, with no gimmicks and no games.

The mindset behind the miles

Two decades ago, I coined a name for the thinking underneath all of it: The Upgrade Mindset (TUM). Readers tell me they get as much from the mindset as from the strategies, because knowing how to think about getting the best possible is what makes any strategy work.

Here’s a story I watched play out for thirty years. People would tell me, “Matt, it has to be United.” I’d come back with a better seat, at a better price, on a carrier they hadn’t even considered, and nearly every time they took it.

They never really wanted United. They wanted the best seat at the best price, and until that desire came first, they couldn’t see the door standing right in front of them.

Options fall out of desires.

I just didn’t have those words yet.

A lot of the mindset was contrarian. Around the same time, I started telling readers that chasing airline elite status is the biggest mistake travelers make, that free agents fly better, and that buying miles and points on sale beats juggling a wallet full of credit cards. People are only now catching on.

I also taught them that a ticket isn’t finished when you buy it. If a better fare or a better seat shows up later, you keep upgrading, and that idea, that nothing is ever done being improved, turned out to matter far beyond airplanes.

Along the way I’ve had the good fortune of traveling to 117 countries, all while flying the best airline seats in the world. People sometimes ask what drives me, and the honest answer is curiosity.

The kid in the library never left. He just started using airplanes.

Confessions of an upgrade junkie

Here’s what I’ve learned about people like me. When success comes early and easy, you never have to learn how to make it happen on purpose, so when life gets hard, all you have to fall back on is effort.

I had terrific upgrade instincts in travel. In the other rooms of my life, my relationships, my health, a body that used to belong to a professional athlete, I was mostly winging it.

Maybe you know the type: genius at the deal, stuck at home. For a long time, that was me, and it was never a character problem. It was a pattern I could run in one room of the house and not in the others.

The pattern doesn’t care which room it’s in. We do.

I was an upgrade junkie: relentlessly ambitious, always improving something, always onto the next thing. And for decades, I had what I now call premature upgrade syndrome.

Every upgrade runs on five steps (I’ll get to them in a minute), and the fifth is just do it. I’d run straight at step five, skip the four that come before it, and then wonder why so much of what I built had to be rebuilt.

As I see it, people fail for three reasons: they’re living in fantasy, they’re uninformed, or they’re not deliberate. My father made sure I’m rarely uninformed, so my misses came from the other two.

I like to say I don’t have a problem in the world.

Except that I’m impatient. And I bite off more than I can chew.

Like a lot of smart people, I also went guru to guru and method to method, borrowing one system for money, another for health, another for relationships. A hundred processes, or none; either way I started from scratch every time, and not one of them told me why I was stuck.

The engine that couldn’t (yet)

A couple of years ago, I poured my heart into the biggest project of my career: the world’s first upgrade engine, software that would automatically find people the best possible flight for their money.

The whole workflow ran on the upgrade process I’d been describing to my team from day one. There was just one problem: I’d never written it down.

The project was struggling. My team kept going in circles, and I kept telling them, a little louder each time, to just follow the upgrade process.

One day my assistant looked at me and said, “You’re Mr. Upgrade. Why don’t you write down the upgrade process for your team?”

I thought it was obvious. I honestly did.

I was dumbfounded that they couldn’t see it in the very project we were building, and even more dumbfounded that it wasn’t obvious in life. And then it turned around and hit me.

I knew the process. I just wasn’t following it.

Not everywhere in my business, not in my health, not in half the rooms of my life. It hit home with a conviction I’d never felt before, and I took her up on the challenge.

That was premature upgrade syndrome at its purest: I was building step five on four steps I’d never written down. The engine, in its first form, stalled.

Digging down

So I sat down to define the process I’d been using to book flights like a king for decades. I started writing it on a short retreat in Jeddah, one of those 117 countries, while the engine sat stalled.

What I found surprised me. I didn’t invent the upgrade process; I discovered it, the way you discover something that was sitting in plain sight the whole time.

For twenty-eight years I’d watched thousands of very smart people go after one thing, the best possible flights, and every one of them made the same five moves.

Baseline. Desires. Options. Decisions. Implementation.

Where are you? What do you want? What can you see? What will you trade? And then, only then, just do it.

You’ve run those five steps every day of your life, mostly without noticing. From one angle, that’s all there is to it.

From another, it’s endlessly sophisticated. If everything we do fits into five steps, then everything fits somewhere: our mindset, our emotions, our fears, our blind spots, each showing up differently depending on your worldview and where you are in the process.

I’ve spent the last two years mapping where it all fits and how the pieces interact. It’s astonishing, and it’s a much longer conversation than this page.

Two more things surprised me. The process is fractal, with five steps inside every step, like a snowflake, and that’s where it gets really interesting. And it’s universal: the steps that get you from coach to first class are the same ones that get you to a better relationship, a better career, a better business, better finances, and better health.

The subject was never travel. It was how anyone gets from where they are to somewhere better.

It was never about the seat.

And the deeper I dug, the further down it went:

• The stalled engine made me write down the process.
• Writing down the process led me to The Upgrade Formula: the process, the mindset, and the dynamics that act on both.
• The Formula led me to the Upgrade Paradigm, the paradigm that governs all others.
• And the paradigm needed a name for the study of all of it: Upgrade Science.

Remember the Upgrade Mindset I’d been writing about for twenty years? It had been one-third of the Formula the whole time. I just hadn’t seen the other two.

Everyone already has an engine

All that digging finally told me what an upgrade is. An upgrade is any move from where you are to somewhere better: a goal hit, a problem solved, a transformation in your health, your money, your marriage, your work. Different areas, same move.

Elon Musk has said the hardest thing in life is to be useful, and useful just means able to make something better. So upgrading is what we’re always doing, and it’s the hardest thing there is.

Your brain makes somewhere around thirty thousand decisions a day. Every one is a small try at better, and almost none of them is made on purpose.

So goes your baseline, so goes your life

The recent discovery I’m most grateful for showed up in my own bloodstream. For years my fasting glucose sat around 137, and every doctor called it borderline without ever explaining what borderline was quietly doing to me.

It stayed a number somebody else said, until someone suggested a glucose monitor on my arm. Suddenly my phone showed me my number every five minutes, and it got real in a way no doctor’s visit ever had.

Your baseline is everything.

Then the five steps ran in order:

• The monitor showed me my real baseline.
• My real baseline reordered my desires that same week. Health moved into first place.
• The new first place showed me options I’d walked past for years.
• The decisions practically made themselves.
• And the doing took six weeks.

The number at the end of those six weeks was 95, a 31% drop.

You can never decide against your highest desire, which means step four falls out of step two. We don’t have a discipline problem; we have a desires-conflict problem.

I didn’t find discipline. I reordered my priorities, and I stopped needing it.

Knowing what’s actually in first place for you is harder than it sounds. There’s a way to find out, but that’s for another day.

Add it up and I got my health back, a nervous system that had lived in fight-or-flight for years finally settled, and a clear enough head to bring a new product to market.

And I haven't been angry in months : )

Even talking with my team and family got easier: share the five words, and there are only five things to talk about.

Now boarding

This fall, my big upgrade is rolling out The Upgrade Formula: the models, playbooks, and upgrade maps I’m building to help people improve how they improve.

Then, once Upgrade Science and the Formula are launched, I’m going back to finish the world’s first upgrade engine. This time, with the process written down first.

I used to be an upgrade junkie. These days I’m turning into what I call a Deliberate Maximizer, someone who wants the best and goes after it on purpose, one step at a time.

I’m not all the way there yet. That’s sort of the point.

The reason you do everything

I’ve missed more upgrade opportunities than I can count. I’m an upgrade pilgrim, trying to make the most of life the best way I know how.

Nobody acts to make things worse, not even when it looks that way from the outside. Aristotle observed that every action, every pursuit, aims at some good. Every single one.

Which means upgrading isn’t only something you do. It’s the reason you do everything.

It’s the why behind your why.

Here’s to upgrading how we upgrade our lives.