Sixteen years ago a man that I worked with won a Nobel Prize. My boss’s boss’s boss’s boss wanted to send him a nice bottle of wine, and the task fell to me to execute. It was far more difficult than you’d expect.

• What bottle do you give someone on the occasion of winning a Nobel Prize? (And the instruction was a bottle, rather than a case)
  
• What if the gifter has one of the top wine collections in the United States? (They’re going to judge whatever you choose)
  
• And what if the recipient knows nothing about wine? (I asked his wife for his preferences and she told me he “prefers red… but I drink white.” Which of course told me that the gift needed to be two bottles.)

I wound up settling on a bottle of Château Lafite — a recognizable name so he’d realize it had value — from a particularly good year, so the person giving the gift would feel happy with it, as well as a bottle of Peter Michael chardonnay because white.

I’ve been tasked with gifting many nice bottles of wine over the years as thank yous to important people, as the guy in the office who ostensibly knows something about wine and as someone junior enough to be tasked with such things at the time. Back then I dreamed of being the guy important enough to be on the receiving end of such gifts.

What I never dreamed of, though, is being important enough to be flown first class. In 2002 I was already getting plenty of upgrades, and had been for several years. I was traveling in upgraded cabins internationally thanks to elite status and miles. But it never occurred to me that anyone would pay for me to travel up front.

Growing up I was a frequent flyer, starting around age 5. My parents divorced when I was young. I lived in New York with my mother and my father lived in California. At first he’d fly out to pick me up for visits (he would do straight turn transcons!) and later I’d fly as an unaccompanied minor. And I’d look towards the front of the cabin as I boarded and assume that would never be me in those seats.

• I’d certainly never pay for it
  
• How could it be worth it?

Years later when I started traveling for work midweek transcons in coach were nearly $2000 round trip The idea of paying for first was beyond my comprehension.

The cost of coach trips has come down, and in percentage terms the cost of flying first has come down even more. Part of that is a change in airline pricing philosophy, and part is a change in technology. Instead of just having full fare first class and possibly a discount fare bucket, airlines can price first as a specific upcharge to the prevailing coach rate.

That’s helped them sell more seats up front — Delta sells about 60% of its first class seats, American is closer to 50%. It used to be more like one in ten.

• That means far fewer seats for upgrades
  
• And more competition for the upgrade seats that remain

Planes are full and there are more elites, flying more miles — industry consolidation means it’s actually easier to stick with a single carrier for all of your travels and rack up higher status.

What’s more airlines aren’t just selling seats at time of booking, they continually upsell passengers. United for instance is known for selling upgrades to customers with the explicit pitch that they’ll take those seats away from people waiting for upgrades, and they make offers in the ‘tens of dollars’.

Delta’s new offer selling upgrades for miles instead of money (at very poor value) mean even more of those upgrade seats will disappear.

Yet some people have a very high upgrade percentage, and others have a very low upgrade percentage.

• This depends on the routes they fly
  
• And when they fly

While most flights are full, not all flights are full. And not all flights are full of business travelers, who are most likely to both buy premium cabin seats and also have higher status for upgrades.

• I mostly fly on Monday mornings and Thursday afternoons. Those are peak business travel times with the most competition for upgrades.

• I’m also flying hub-to-hub (such as Dallas Fort-Worth – Washington National) where there are the greatest concentration of elites.

• And I’m flying out of a home city on American Airlines with a heavy concentration of elites and premium fares.

• Not to mention that Austin has experienced the greatest traffic growth of any airport in the United States.

That’s the death knell for upgrades, although those are still doable on legacy US Airways routes to Philadelphia and Charlotte more than to cities like Dallas.

As a result my first class travel comes from,

• Clients who buy first class seats for me. It’s not the extravagance it once was. It doesn’t mean a $2000 roundtrip, it may be less than $200 more per direction. So where I once dreamed of being someone that would receive nice bottles of wine as gifts, and couldn’t imagine being flown first class, when someone has me out to work on a project with them or to give a keynote they’ll often just buy me the ticket up front.

• Confirmed first class upgrades. Since complimentary upgrades are hard, if I care about the first class upgrade I need to confirm it. That doesn’t just mean systemwide upgrades or mileage upgrades (American charges 15,000 miles plus a $75 co-pay even for top tier elites, rarely worth it). I don’t often buy the most expensive tickets, but I’m rarely able to buy the cheapest ones, so my fares are usually eligible for Business ExtrAA BXP1 confirmed upgrades. I just need to find flights with availability.

My upgrade percentage is low because upgrades are harder but also because when I care about sitting up I make sure it’s confirmed in advance now.

Folks with more flexibility about where and when they fly can do a lot better with upgrades.

1. Avoid hub-to-hub flying
   
2. Avoid flying between 6 a.m. and 9 a.m. on Mondays and between 4 p.m. and 8 p.m. on Thursdays and Fridays
   
3. fly on Saturday afternoons, Tuesday afternoons, and Wednesdays!

Do this and watch upgrade results skyrocket.