Michael here. Tell me if this lands:

I knew something had gone wrong when I found myself considering a 6:10 AM flight with a five-hour layover in Atlanta and calling it "not that bad."

This is how the bargaining starts. First, you tell yourself the layover gives you time to answer emails. Then you tell yourself economy is basically fine because you are not soft. Somewhere in the middle of this, someone in a group chats texts that they're flying business class to Lisbon for 70,000 points and $94.

You do not want to hate this person. You may even love this person. Still, for one clean second, you want their phone to fall into a fountain.

Later, at the airport, you are holding a coffee that cost too much and tastes like the cup it came in. A man in Louboutin sneakers walks past you and into the Centurion Lounge like he pays rent there.

In your group chat, someone else posts an Air France selfie with the caption, "Points came through." Or one friend mentions Tokyo the way people mention dry cleaning. You ask what the flight cost, and they say the phrase now responsible for half the lifestyle confusion in America:

"Oh, I used points." Of course they did.

You begin to wonder: did you missed a door somewhere? Not a literal door. Nobody tells you there is a door. That is part of the trick. The door looks like a welcome bonus, a transfer partner, a company card, a rent payment, a lounge pass, a dining credit, a renewal fee, or a monthly benefit you forgot to use at a store you never meant to enter.

Still, it is a door.

And the question is not "Which card should I get?" That comes later, once dignity has left the room. The first question is smaller and more embarrassing:

Not real heaven, obviously. Airport heaven. The heaven with lie-flat seats, lounge showers, early boarding, warm nuts in a ramekin, and a person beside you who knows which card earns five points on flights booked directly with airlines and says it with the calm of a monk.

You want to be above wanting this. You want to believe a lounge is just a room with soup. But then your flight is delayed three hours in Newark (of all places), your phone is dying, your coffee tastes like regret, and someone else disappears behind a frosted glass door into climate-controlled mercy.

The points economy is not a scam.

It’s worse: it works.

That is the problem.

For a long time, travel rewards felt like a harmless side quest, a hobby for people with spreadsheets, airline blogs, and suspiciously strong opinions about Hyatts and Hiltons. You could ignore them. Let them say "transfer partner" at dinner and calculate cents per point while everyone else enjoyed the fries.

Then travel got expensive again.

Flights climbed. Hotels climbed. Fees multiplied. Cheap fares got harder to trust. Summer travel started to feel less like a reward and more like a stress test with boarding groups. Suddenly, the spreadsheet person did not seem eccentric. They seemed prepared.

I do not resent the points people because they are wrong. I resent them because they figured it out before I did. It’s not noble, but it is honest.

I thought I was good at travel. It turns out I was just employed by people who were good at reimbursing it.

Before entrepreneurship, I had the version of access many ambitious professionals get without naming it: corporate travel, a company card, status earned on someone else's budget. Airports stopped feeling like chaos and started feeling like a workplace with worse chairs but better lighting. I had the rhythm down. The booking window. The loyalty number. The upgrade list. The small, private pleasure of watching a system recognize you.

You do not think of that as privilege at the time. It's just another day at the office. Then you step out.

The company card disappears. The reimbursed flights, the automatic status, the invisible hand that had been smoothing the airport experience — all of it removes itself from your lower back. One day you try to book a summer trip and realize the system is speaking a language you used to understand by accident.

That is when the machine becomes visible.

The airline is no longer only an airline. It still has planes, pilots, routes, delays, unions, gate agents, and boarding groups. But one of the most valuable parts of a modern airline is its loyalty program.

That sounds fake until you sit with it. During the pandemic, major U.S. airlines used their frequent flyer programs as collateral because lenders understood something most travelers had not: the miles were essential. They were currency. The perk was the asset. The thing you thought was a thank-you was, financially, the point.

The airline sells miles to the bank. The bank sells status to you. The merchant pays the fee. The cash customer helps fund the rebate. Everyone calls this loyalty because "soft class warfare with lounge access" would test poorly.

Once you see it, the whole airport looks different. The lounge is a showroom for financial behavior. The boarding group is a receipt. The metal card is a tiny passport issued by a bank.

The points economy has a personality. It smiles at you, calls itself a reward, charges you $895, gives you a Saks or wellness credit you forget to use, and somehow gets you to defend it at dinner. It is charming, useful, annoying, manipulative, and selling you a story you've already agreed to believe. It opens doors. It also makes sure you notice the doors.

Amex raises the Platinum to $895. Chase pushes Sapphire Reserve to $795. Both swear the value is there if you just remember to use all the credits, which is how luxury became homework. Nobody dreams of a life where they remember to use a quarterly wellness benefit. And yet here we are, trying to turn a protein powder subscription into a lie-flat seat.

This is the premium-card bargain now. Pay a lot, organize your life around our partners, and maybe you come out ahead. Use the Uber credit. Use the hotel credit. Use the dining credit. Use the thing you did not want until the card suggested you should.

The card promises to simplify your life. What it actually hands you is homework with better branding. And nobody's canceling. Amex added a record 13 million new cards in 2024 — a 6.6% jump — and card-member spending hit $1.55 trillion. That was the year before the price hike.

That's heaven on earth with terms and conditions.

And still, the math can work. That is the irritating part. For the right person, the expensive card is a tool. Travel enough, eat out enough, push enough spending through the right channels, and it pays for itself and then some. For the wrong person, it is an $895 permission slip to pretend you live a life your calendar cannot support.

There is no moral failure in using the system. The system itself is another question — math that quietly decides who gets rewarded for spending and who just spends.

That is where Bilt gets interesting.

Then there is Bilt, the card that lets renters earn points on the monthly check they used to fire into a void. Its genius was not that it made rent glamorous. Rent is never glamorous. Rent is the money you send away every month so you can continue owning none of the walls around you. Bilt's genius was that it made renters feel like they were finally allowed to play.

If you have ever sent off a rent check knowing it bought you nothing but another month of owning none of the walls, you understand why Bilt landed. It did not fix housing or make landlords lovable. It just turned a dead payment into a door. And the trick is not to become a travel hacker or learn to say "transfer partner" without flinching — it is to start where your life already is, and to stop trying to break into someone else's heaven.

You do not need the Maldives villa or the $84 breakfast. Maybe you just need the wedding in Chicago to hurt less, or to take your parents somewhere without doing the math at the front desk, or one trip a year that does not feel like self-harm. That counts too.

This is also why the whole thing lands on such a specific nerve for young people. You have done everything right. You have the job, the degree, the ambition, the taste. Your group chats are full of flight deals and you know exactly what a good hotel lobby should look like.

What you do not have is margin.

The ladder that was supposed to be there is wobbling under you. Rent eats the raise. Homeownership keeps stepping back as you step toward it. Your salary climbs slower than the cost of becoming the kind of adult that salary was supposed to produce. The milestones that used to mean you were getting somewhere — a home, a family trip, a little breathing room — now arrive with dynamic pricing.

So when someone tells you they flew business class on miles, it does not register as travel advice. It registers as proof that there is another economy running underneath the one you are stuck in, where the same dinner, the same rent, the same groceries you are already paying for quietly produce a second currency. Where ordinary life, routed correctly, spits out upgrades.

That is why it gets you. It is a small workaround in a world where the main road feels blocked. It does not solve wealth inequality. It does not make housing affordable. It does not turn your salary into ownership. But it hands you something rare: a lever. And when you have spent years being told to budget harder, hustle smarter, invest earlier, want less, and somehow still end up rich enough to live like a normal person, even a small lever starts to look like grace.

The ugly part is that opting out does not make the system fairer. It often just makes you the person subsidizing everyone else's upgrade. The rewards have to come from somewhere. Merchant fees get baked into prices, so the person paying cash for dinner pays the same menu price as the person earning triple points — but only one of them leaves with a tiny piece of a future flight.

My sad Peet’s airport coffee is doing something in the system. It is either just coffee, or it is a fraction of someone's upgrade. The cup is still bad. The difference is whether you get anything back for holding it.

So the answer cannot simply be "ignore it." Ignoring the points economy does not make you pure. It makes you more expensive to yourself. The game is rigged toward people with good credit, steady income, and enough cash flow to pay in full.

The person who can float expenses earns points. The person who cannot gets fees. The person whose job sends them to conferences builds status. The person paying for a family emergency on a debit card gets nothing but the same high price. So yes, the system is unfair. But opting out does not punish it — it usually punishes you.

I do not just want to understand the points economy. I want in.

Please, St. Peter, let me into the lounge. Let me have the quiet room with the soup. Let me have the outlet that works, the shower during a layover, the boarding group that does not require me to fight a family of five for overhead space. Let me have the small, stupid dignity of not feeling punished by every trip.

I know this is not noble. I know a lie-flat seat is not salvation. I know airport comfort is a ridiculous thing to spiritualize. But that is partly why the desire is so revealing. Nobody wants to admit how much easier it is to be patient, generous, and calm when the system has decided to cushion you.

This is not about getting back something I lost. It is about wanting in — and that want is not embarrassing or rare; almost everyone outside the glass has it. The door opens easiest for people who already have room to maneuver, while the ones who could use the smoother path most — young, capable, doing everything right and still in the slow lane — have the longest walk to it. Heaven should have a door you can reach from where young people actually start, not one you can only reach once you have already arrived.

The door is not locked. You just have to pay a cover charge to get in.

That is different. More irritating, maybe, but also more useful. Locked means you are done. Monetized means someone built a tollbooth and called it loyalty.

So no, you are not locked out of heaven. But you may be standing outside a door that got heavier while you were busy living your life. The people flying better than you are not all richer than you. Some are simply using a system that quietly rewards them for knowing where to stand.

Heaven is not closed. It has just been turned into a rewards category. And it is worth asking why heaven needs a card reader.

You are not locked out of heaven, but now there’s a waitlist, a referral bonus, a transfer partner, an $895 annual fee, and a lounge agent who needs to see the card.

Feedback, thoughts, suggestions? Hit the reply!

Michael Wildes is the founder and CEO of Drive Phase Holding Company. After leaving a career as a professional pilot, he spent a year as Business Editor at FLYING Magazine, writing 330+ articles on aviation's transformation. Now he focused on building permanent-capital companies focused on long-term trends that compound over decades. Based in Arlington, Virginia.

Connect: mikewildes.com

Email: [email protected]

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