The tuition I pay for procrastinating

Back in March, I was surprised. With memory prices soaring, the new MacBook Pro somehow hadn’t gone up in price.

Apple’s memory upgrades have always been expensive. But this time, the usually greedy money-making Apple didn’t touch the price. That tells you how much margin it normally makes. It also meant an opportunity for my family, who needed a new Apple machine anyway.

MacBook Pros will definitely get more expensive later, so buying now is basically free money!

So I started nudging my wife to upgrade her MacBook Air (M1, 16GB RAM) to the latest MacBook Pro (M5 Pro, 48GB RAM), since Xcode was getting sluggish. Though for someone who works from home like her, a Mac mini might actually fit better.

Honestly, I was tempted too. I wanted to bump my M1 Max up to the latest M5 Max. But it’s still good enough, so I did a little I-don’t-need-to-upgrade meditation and put that very expensive thought to rest.

In the end, we kept waiting for the Mac mini M5 reveal, hesitating all the way to this month’s WWDC, only to confirm the Mac mini wasn’t updated. It probably won’t be announced until the new CEO takes over in September. But I figured any price changes would land around then too, so there was no rush.

Meanwhile, we did go ahead and buy something else that’s guaranteed to get pricier: a Switch 2. Now my wife plays Pokopia every day, happy as can be.

This past Wednesday, with a nudge from my wife, I finally beat my procrastination and asked a friend who works at Apple to order my wife’s MacBook Pro with his 15% employee discount. Between the time difference and a few things to confirm, it slipped to today before I actually placed the order.

When the receipt hit my email… wait. That’s not right. Why is it more than 20% higher than the price I saw before? A full $500-plus more.

Whoa. Turns out, just yesterday, Apple announced big price hikes, and the MacBook Pro got hit the hardest.

One day. I missed it by one day.

No way!?¹

But since anything can happen at any time, it’s not a big deal. I’ll just pay another expensive tuition for my procrastination.

$500 is cheap, honestly. History has repeated itself far too many times.

Today’s loss reminds me of 2017, when Bitcoin took another big tumble down to a thousand or two. I decided this was a golden opportunity and figured I’d park twenty or thirty thousand dollars in it. I painstakingly moved all my cash into a freshly opened crypto exchange and bought a tiny bit of ETH to test the water. I stared at the $1,800 on my screen, thinking I’d wait “a day or two” for Bitcoin to dip a little more, then go all in.

Then I forgot about it.

I even thought for a while that I’d already bought in, until the end of the year when Bitcoin shot up several times over and I realized I never actually had.

It wasn’t until Bitcoin climbed past $20,000 that I finally worked up the resolve to buy in again, by which point I’d already missed a 20-40x return.

Another time, Meta crashed to $88 over its metaverse misadventure. I’m no fan of how my old employer ran some things internally, but come on, it’s Meta! Even if the metaverse was burning cash, the core ad revenue was untouched. The price made no sense. I was all set to back up the truck. The old me would have done it without blinking. But I waffled, telling myself I had a wife and kids and no income, that I shouldn’t gamble like that anymore. I even asked a sharp investor friend, and she said let’s wait and see. In the end, I didn’t buy.

You can guess the rest. Watching Meta rocket from there to over $700, my heart bled. It’s been bleeding ever since, until there was nothing left.

Then again, anyone can play armchair quarterback. Hindsight is 20/20. Maybe I just remember the chances I missed and conveniently forget the calls I got wrong that cost me dearly, or the losses I dodged by hesitating. After all, I want to believe my judgment and taste are smart.

I’ve gotten plenty of things wrong too. During COVID, I was sure that with companies hurting so badly, the market would keep crashing, so I dumped all my stocks. I figured Ko Wen-je had a real shot at Taiwan’s presidency last time. Or that Trump wouldn’t get re-elected. Or that the MacBook wouldn’t go up in price until September.

That’s why my ADHD self doesn’t invest on its own anymore. I’ve taken myself out of the decision and automated everything into a mechanical index fund.

But buying a computer, I still have to do myself. Should I dollar-cost-average into laptops too?

Looking back from the third-person view of someone already paying 20% more, the right move is obvious. There was a real need, and I’d already predicted hardware prices wouldn’t drop for two years. So I should have just bought it all at once, the M5 Pro and maybe even the M5 Max, and “made” 20%. The moment you see it, you act. Right now. This second.

And even if my read is wrong, I won’t lose much. The odds of a MacBook dropping in price on its own, or going on a deep discount, are basically zero.

I keep thinking my judgment is right. What gets me is the procrastinating and the second-guessing, missing one chance after another.

So in a time of rising prices, even shopping works like a game: you only get the loot if you kill the monster.

Another way to look at it: because my wife’s MacBook cost 20% more, I got to write this post. And I’d gladly pay $10 for this post to exist. So really, I only lost $490.

Think about it that way, and I feel just a tiny bit better.