For my latest trip to Oahu, this time to surprise my father and take him out for his 80th birthday, I decided to fly Basic Economy. I’m here this week.
Originally, I planned to splurge on First Class for $1,600 roundtrip because the flight was on the Boeing 777 300ER, my favorite plane with solo first class lie flat beds along the window. But in the end, I could not bring myself to pay that much, largely due to my frugality.
We have had such a strong stock market in 2025 that part of me felt it was fine to treat myself. After all, I sold my old house for a profit in the first quarter of 2025 and bought the dip with about 80% of my home sale proceeds in March and April.
But just as I was about to purchase the First Class ticket, I realized something else. I had not suffered in a very long time, and the longer I go without discomfort, the softer and lazier I become. You should check out my growing one pack! So I decided to embrace some first-world suffering by booking not just Economy, but Basic Economy.
First class seats on Boeing 777-300ER to Hawaii from SF are my favorite, but I said no!
The Joy of Basic Economy
When I was about to check out at $460 dollars for standard Economy, United hit me with a $60 upsell to choose a window seat. That felt like a bait and switch. And upgrading to Economy Plus would have cost around $750, which was not appealing for only four extra inches of legroom, especially since I am an average five feet ten inches tall.
So, in true personal finance fashion, I rejected the upsell and booked Basic Economy for $360. With Basic Economy, you cannot select your seat, and you are limited to a carry on bag that fits under the seat in front of you. Based on what I read, I would not know my seat assignment until getting to the gate, which meant I needed to arrive earlier than usual.
We had to adjust our morning routine. Instead of leaving home at 8:15 a.m. to get the kids to school by 8:27 a.m., we left at 7:40 a.m. so I could drop them off at 7:53 a.m. and still comfortably make my 9:30 a.m. departure.
Despite the inconvenience, paying $360 felt completely worthwhile. You arrive at the same destination at the same time no matter what class you fly. I took most of difference between First Class and Basic Economy, and invested $1,100 of it into our Fundrise Venture account for my children.
I’m glad I did because Microsoft, Nvidia, and Anthropic forged a partnership that now values Anthropic at $350 billion. And Anthropic is a core holding in Fundrise Venture.
Winning the Basic Economy Lottery
The Sunday before my flight, I played basketball until ten at night hoping to tire myself out enough to sleep longer than one hour on the plane. It worked, as I ended up sleeping about one and a half hours on the four hour and forty four minute flight. Here were the main Basic Economy lottery wins.
First lottery win: can check in online
I received an unexpected text from United. It said:
“New perk for you. Basic Economy customers are now able to check in online and receive a digital boarding pass.”
This removed all the anxiety about needing to check in at the counter or gate. I expected a slow two step process, but instead Basic Economy suddenly felt identical to regular Economy and Economy Plus.
Second lottery win: short security line
United now uses the International Terminal for some flights to Hawaii. This meant the security line was about eighty percent shorter than a normal domestic line. I got through quickly and reached the gate at eight thirty seven for my nine thirty flight.
For context, I only spent 17 minutes from when I arrived at the airport to reaching my gate. With 35 minutes to spare before boarding, I treated myself to a twenty three dollar vegetarian tofu lunch box.
Third lottery win: landed early
The flight was on time and landed twenty two minutes early. My last four United flights had all departed late, so this felt lucky.
Fourth lottery win – the biggest one:
I avoided seat 51E, the dreaded middle seat. Because I arrived early, I asked the gate agent if he could change my seat. I requested any window seat since I love leaning against the wall for extra space.
He said he switched me to 46L but could not print a new boarding pass. That was fine by me. When I checked in again, he said the change did not go through. He tried twice before asking me to board and hope for the best while the line behind me grew longer.
I sat in suspense for more than twenty minutes. When they finally closed the door, I realized I had secured the window seat after all. That seat was effectively worth five hundred twenty dollars if I had booked Economy and paid extra for seat selection.
With the $160 saved compared to Economy, I bought poké from Tamura’s Market for my parents, sister, and me.
Basic Economy Is A No Brainer To Save Money
My seatmate also fit in her seat comfortably, something that is not always guaranteed in Economy. She leaned my way a a lot but it was fine. She was flying solo to Hawaii for her thirty fifth birthday.
I was tempted to use the hilarious “May I meet you line” suggested by billionaire investor Bill Ackman, but there was no need. We ended up talking naturally about her ten day plan in Hawaii, her move from Ukraine five years ago, how she enjoyed living in the Richmond District in San Francisco, and my grand plan to surprise my father.
The flight turned out to be one of my most pleasant travel experiences, especially since I had miscalculated the time difference due to daylight savings. I thought we had another hour in the air, so waking up from my nap and realizing we were landing early felt like an unexpected bonus.
Basic Economy ended up being the clear winner. And honestly, after this experience, I am not sure any level of income or wealth would make me regularly pay for First Class again. Paying for four First Class seats for my entire family feels even more extreme.
It is wonderful to be under six feet tall. Beyond the possible longevity advantage, it is great to fit comfortably in almost any seat and save money at the same time.
Basic Economy luxury, baby! I had to scoot to the right side because the middle seat passenger kept rubbing her right leg and shoulder on me, and I’m a married man. The window seat gives me an extra 3-4 inches to the right.
In Search For The Next Suffering Attempt
With this fortunate but ultimately failed attempt at suffering, I probably need to find new ways to toughen myself again. Maybe I should teach my kids tennis to save $160 an hour in private lesson fees and endure the occasional tantrums. Oh wait, I already do that.
Finally, I realize there is also a thrill component of Basic Economy that I enjoy.
Even though I expected to sit in the middle seat, it is never guaranteed. You could always get lucky and end up with a knee bashing aisle seat or you might get the dreaded middle seat. If you like to gamble or invest, there is a small thrill in not knowing. You might suffer or you might get lucky.
Do you feel lucky? I always do so I love to try.
Readers, what are your thoughts about flying Basic Economy? With the price so much lower, why would you not try it? And do you have any first world suffering ideas that could help toughen me or anyone else up and increase our appreciation for life? How much money do you need to make to feel comfortable paying for a First Class seat?
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