What Step 3 of the Upgrade Process looks like in action - and why this intelligence applies to everything
The Opportunity: You just got an alert. First Class seats on a premium carrier. Routes that typically cost $15,000 to $30,000 in cash. Available now using miles or points you already have – or use miles anyone can buy.
This is opportunity. This is what Step 3 of The Upgrade ProcessTM looks like in real life.
Big dreams come true when big opportunities are leveraged. Every success story is full of people who seized moments like this – not people who waited for perfect certainty.
That's Upgrade Intelligence in action. Let me show you what it looks like – in the travel world – and every other world in life.
What Step 3 Options Intelligence Actually Means
In the five-step Upgrade ProcessTM (aka The Anything ProcessTM), Step 3 is Options. Most people think expanding options always means more research, more analysis, more thinking.
Wrong.
Intelligent option expansion often also means taking advantage of great options, when you encounter them. For example, when you see spectacular premium space – First Class seats that cost $15K-$30K in cash available for a fraction of that in miles you already have or can easily buy – you can book it.
Lock it in with a confirmed ticket number.
Then cancel for free or a small fee if plans change.
Free or cheap cancellation. Zero or low risk. Maximum optionality.
And here's what happens next: The booking doesn't just preserve an option. It transforms your identity from passive to active.
Before booking: "I'm someone who dreams about First Class travel."
After booking: "I have a confirmed First Class ticket in 127 days."
That identity shift is where intelligence often lives.
The Core Intelligence Move
The pattern to understand: Book things with easy cancellation policies that transform uncertainty into momentum.
Most major airline loyalty programs let you cancel award bookings for free or a small fee.
You get a confirmed seat with a ticket number. But if plans change, you can cancel and get your miles back – often for free, sometimes for $25-$50. See the policy table below for specifics and always double-check with the airline directly.
What This Demonstrates: The power of a booking to create momentum, not just preserve options. The booking doesn't wait for certainty. The booking creates certainty.
This is the Intelligence Inversion: flipping from waiting for the right moment to creating the right moment through action.
Also Applies to: Hotels with free cancellation policies, refundable event tickets, and memberships that can be canceled.
Three Intelligence Applications
The Booking Backwards Move
Upgrade Reality: Change is the only constant. Planning around rigid constraints can result in suboptimal outcomes.
You know you want a major trip this summer, but you haven't locked in where yet. Then you see Business Class to a major European hub at 70,000 miles instead of the usual 250,000. Dates might work. Destination is spectacular. Free or cheap to cancel if needed.
The Intelligence Move: Book the flight first. Get your ticket number.
Decide later whether it's your destination or your gateway.
You've just locked premium transatlantic travel for 70% less than normal. Free or cheap to cancel. Low risk to explore. Maybe that city will become your destination. Maybe you connect to other cities. Maybe you spend two days there, then train elsewhere. I LOVE trains.
Notice what happened: You stopped the backwards approach (pick destination > find flights > pay premium). Now you're optimizing around opportunity (capture value > design experience around it).
Also Applies to: Booking refundable hotels before finalizing exact city/date, purchasing refundable concert tickets before confirming your schedule.
The Portfolio Intelligence Move
Upgrade Reality: Most people see one path forward. Intelligent people see multiple paths simultaneously.
You're booking that major trip. You have points across two different bank programs. All with transfer partners. All with different sweet spots. The same destination has premium availability through multiple programs. Different dates. Different pricing. Usually cancellable for free or small fees.
The Intelligence Move: Book all three. Different dates, different programs, minimal total risk.
Suddenly, you're not hoping one option works. You're controlling three options simultaneously. Your schedule shifts? You've got flexibility across multiple date windows. Your companion's availability changes? You've got options that accommodate. Cancel the ones you don't use for free or a small fee.
One trip. Three confirmed bookings. Low total risk. Exponential flexibility.
What This Demonstrates: Portfolio thinking versus single-path thinking. Your desires WILL often change. Having multiple bookings with easy cancellation is insurance against the only constant: change itself.
Also Applies to Career Upgrades: Multiple side projects while employed; test new direction without leaving current position. There's little commitment or downside when getting a taste for other options.
The Strategic Insurance Move
Upgrade Reality: Perfect outcomes are rare. Intelligence means eliminating downside while preserving upside.
You're waitlisted for the world's best First Class product. The cabin that gets written about. Odds are 50/50 it clears. Meanwhile, premium Business Class on the same route has instant availability. Cancellable for free or a small fee.
The Intelligence Move: Book Business as backup while waitlisted for First.
First Class clears? Cancel Business for free or a small fee. First Class doesn't clear? You've got confirmed premium travel. You've removed the downside (stuck in economy or paying through the nose for premium) while preserving the upside (First Class clearing). This isn't speculation. This is strategic optionality at low risk.
Applied to Business: Probationary employment periods; both sides can exit during first 90 days with minimal consequence.
More Advanced Options
The Flexibility Arbitrage
Not all constraints are equal. Intelligent people weaponize their specific type of flexibility.
Date-flexible? Book the same destination, three different date ranges, across three programs.
Destination-flexible? Book three different ones for the same dates. Cabin-flexible? Book Business Class as backup while pursuing First. All cancellable for free or small fees when using miles.
What This Demonstrates: Intelligence isn't generic optimization. It's the specific leverage of your unique constraints.
Applied to Health: Class schedule flexibility. Book three different yoga class times across the week with studios that have capacity and won’t be out of pocket if you’re a no-show; cancel the ones that don't fit your needs, keep the time slot that actually works best.
The Mayfly Response
Upgrade Reality: Exceptional opportunities are ephemeral. They often exist for hours, not days.
Premium travel availability appears. World-class products at a fraction of normal cost. Then they vanish like the mayfly – that tiny insect that lives for 24 hours.
The Intelligence Move: Immediate booking on ephemeral opportunities. You see it. You book it. You optimize later. Your hesitation costs more than any cancellation fee.
This works great with airfares. See our report on hold options published last month: The Option Optimizer’s Secret: How to Turn One Fare Into Infinite Possibilities. (Keep an eye out next month when we combine the previous month’s airfare options and this report's mileage award options - part 3 in this series.)
What This Demonstrates: Decision velocity often beats perfect planning. This is Upgrade Intelligence: knowing when to act instantly versus when to deliberate.
Also Applies To: Flash sales with easy returns in any other industry, limited-time refundable offers, and time-sensitive opportunities with low-cost exit options. Many do this with Macy’s and Amazon returns. We don’t recommend exploiting policies willy-nilly, however. Do unto others…
Why This Is Intelligence, Not Tactics
Here's the critical distinction: Tactics work once. Intelligence compounds forever.
Learning "you can cancel award tickets for free or cheap" is a tactic. Useful once. Doesn't transfer.
Understanding how to leverage cancellation policies across all contexts to create commitment without irreversible consequences? That's intelligence. Useful everywhere.
This is what Step 3 of the Upgrade Process teaches us: Options aren't just about quantity. They're about intelligence.
Most people expand options only through research. Research is good, but it’s passive. Research often delays action.
Intelligent people expand options through strategic bookings with easy cancellation that:
- Create momentum (accelerate commitment)
- Preserve flexibility (cancel if needed)
- Eliminate downside (free or cheap exit)
- Generate clarity (action creates information)
- Force alignment (turn dreams into deadlines)
Note: This intelligence doesn't transfer to everything. It applies specifically to situations with good cancellation policies. You can't apply it nicely to jobs or homes very well – the exit costs are higher and backing out hurts others. But anywhere cancellation policies exist? This thinking transforms how you operate.
That's why travel is the perfect laboratory for understanding this specific form of intelligence. The stakes are manageable. The cancellation policies are frequently generous. The results are measurable. And the lessons transfer to anything else with similar policies.
Award Cancellation Policy Cheat Sheet
Note: Always verify current terms before booking. AND keep in mind that most policies require you to cancel within 24 hours prior to departure. Be sure to double-check and not cut it too close.
The Bottom Line
You didn't just learn how to control $50K in premium travel at zero or little cost.
You considered what Upgrade Intelligence looks like in action. Travel is just the laboratory where it's often easy to see. Now go apply it wherever you can find good cancellation policies.
You may already do this to some extent. Hopefully you will leverage the approach more now.