Woulda Coulda Shoulda: How to Deal With Regret in Real Estate

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Almost exactly a decade ago—June 17th, 2011 to be precise—a friend of mine published a post for a now-defunct, libertarian-leaning blog we both contributed to about a “totally decentralized P2P digital currency.” He noted that, “Having been up and running for about a year, Bitcoin has appreciated significantly against the dollar. To give you an idea, Bitcoin users say on the forums that one of the first ever transactions using bitcoins was to buy a pizza online. One year ago, that pizza cost the consumer B$10,000. After a year of appreciation, B$10,000 is worth roughly US$140,000.”

In other words, each Bitcoin was worth about $14. Had I decided to buy, say, $1,000 worth of Bitcoin at the time, it would be worth a cool $2,716,714 as of this writing, which, I should note, is right after Bitcoin lost about half its value over the course of a week or so.

Had I instead bought $1,000 worth of Bitcoin when 10,000 Bitcoin were traded for two Papa John’s pizzas in 2010 in the first-ever Bitcoin transaction, the value of my Bitcoin would be something close to $20 billion.

Instead, I bought none.

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Woulda coulda shoulda

Unfortunately, when I first heard of Bitcoin, I thought of it as what it was described as: an alternate currency. I just didn’t think of it as a potential investment.

I can’t say the same thing about the Dogecoin phenomenon, which skyrocketed 12,000% earlier this year. Back around 2017, I had considered taking some money and spreading it across various “altcoins” And I love memes, so had I done this, I would certainly have put some money into the meme coin. Unfortunately, I just never got around to it.

I also have plenty of such stories about real estate. One particular deal that was not to be still haunts my nightmares: 21 houses, all ’90s built, in relatively good shape, and performing. The price was only $1.89 million. Less than $100,000 a door!

I valued them at close to $2.6 million.

We went over asking at $1.95 million. The portfolio sold for $1.975 million.

Another time we made offers on two properties simultaneously: an eightplex in a really bad neighborhood and a five-unit apartment in Hyde Park, a really good neighborhood in Kansas City that was on the upswing. We got the eightplex, but then our bank pulled one of our credit lines, and we had to rescind the offer on the fiveplex.

The warzone property was an endless management headache that never cash flowed. We finally unloaded it (shockingly for a small profit) seven years later. In the meantime, prices in Hyde Park skyrocketed.

We lost out on a 150-apartment complex once as the seller decided to go with another, lower offer than ours because the other was all cash. Our offer was $2 million. The apartment sold for $2.8 million less than a year later.

Even a solitary house in Hyde Park that I lost out on still gets to me. We had the highest offer but got it in late (it was an online offer process). Our offer was $51,151. It went for $50,000. I don’t know how much the buyer put into it, but it sold for $203,000 later that year. And this was before prices in Hyde Park skyrocketed!

We are certainly not alone in this matter. A whole thread here on BiggerPockets is dedicated to deals that “got away.” It includes lots of lines like, “I could’ve held it, sold a few years later for $130,000+ more,” and, “I wanted to buy it, but I never followed up … He paid $200,000 and sold it for $440,000 two months later. I blew it.” And on and on it goes.

Even the likes of Warren Buffett have plenty of misses. For Buffett himself, that includes Berkshire Hathaway’s $7 billion investment in ConocoPhillips, which fell to just $4.4 billion, as well as using $443 million in Berkshire stock to buy Dexter Shoe. Dexter Shoe went up to $5.7 billion, which is nice. Unfortunately, that $443 million of Berkshire Hathway stock went up to $10.6 billion.

There is always regret

Get this clear in your head: If you are investing, you will always face regret.

There are no exceptions. In fact, you will have something to regret no matter what.

Either you should have bought before the runup or at the trough, or you should have sold at the peak. And even if you buy right, you should have bought more and earlier.

For example, a friend of mine did get in early(ish) on the Elon Musk-induced Dogecoin rocket ship to the moon. He put in $1,000 at around 2.5 cents and ended up making about $40,000. The first things he said after that?

1. “Should have bought more.”
2. “Should have bought earlier.”

Of course, at this point, it’s all just noise. There’s nothing that can be done about it.

Who knows? If I had bought $1,000 of Bitcoin at 39 cents, perhaps I would have had it all in Mt. Gox and lost it all when it collapsed. Or perhaps I would have been just like that guy in Britain who accidentally threw out a flash drive with $127 million of Bitcoin on it. Talk about regrets!

Indeed, even if you can predict the future correctly, that doesn’t mean you can capitalize on it. Peter Schiff, for example, correctly called the 2008 housing crisis, but his portfolio still lost 50% of its value. Michael Burry correctly called the housing crisis and made the right bet. Then he correctly called the GameStop short squeeze. But he sold out before the price really skyrocketed, costing him almost $1.5 billion.

Yet we assume we would always have capitalized just right on whatever it was we missed out on.

The key thing to remember is there will always be things to regret. It comes with the territory. If you don’t want to have anything to regret, then sit on the sidelines.

But then again, what could be worth regretting more than that? I have a friend who bought a second house in 2015 and then decided to “wait for the correction.” He’s still waiting, unfortunately. There are many such stories.

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Remember the wins

We’ve had some great wins investing over the last 10 years. One of our biggest wins was the purchase of a portfolio of 97 houses at a great price. In hindsight, we got pretty lucky. We really had no business being able to close that deal at that time.

Yet I think much more about the 21 houses we missed out on than the 97 we actually got.

For every story like the man who lost $127 million of Bitcoin, there’s one like the guy who bought $27 of Bitcoin in 2009, forgot about it, and then rediscovered it when they were worth $980,000. While I imagine that made him ecstatic, I suspect he reminisces about that much less than the guy who lost $127 million. And it’s not the difference in price that’s the reason.

Indeed, Tom Brady has won seven Super Bowls. Still, I suspect he thinks far more about the “Helmet Catch” that ruined his perfect season in 2007 than the last-second Vinatieri field goal, the second last-second Vinatieri field goal, the interception on the 1-yard line, or 28-3 combined.

Science backs this up. Studies have shown that “bad memories stick better than good.” We naturally think of our losses and not our successes. We need to actively fight against this tendency.

Regret is a choice

While it’s natural to have regrets, that does not mean it’s inevitable. In the end, regret is a choice.

There’s something psychologists call metacognition or “thinking about our thinking.” When we probe what we’re thinking and ask why we can interrupt the negative feedback loop of regret. We can even talk back to that voice in our heads to correct the record.

We can thereby force-feed ourselves the good memories and good deals we did get. This is why Hal Elrod recommends beginning the day with 10 minutes of affirmations (among other things) in his popular book The Miracle Morning. It may seem weird, but talking yourself up to yourself has been scientifically proven to be effective.

And what if you don’t have any real estate accomplishments yet? Or if your biggest regret is not having started? The first thing I would say is a quote I saw from BiggerPockets’ own Mindy Jensen, “Never compare your beginning to someone else’s middle.” We all start at the bottom.

The modern world is inundated with FOMO and other people’s social media personas—which are always cultivated to make you feel like they’re killing it—shoved in our faces.

It’s helpful to remind yourself that much of what you see is fake (often really fake!) during your daily affirmations. But furthermore, it’s not a competition. Don’t compare yourself with others, folks. It’s natural, but it doesn’t help. You need to actively push back against that as well.

Another quote I really like is an old Chinese proverb, “Every day is a new life to the wise man.”

This one I say every morning. No matter what mistakes you’ve made in your past—investing or otherwise—it’s done. It can’t be changed. And moving forward requires letting go.

Yes, you should learn the lessons from your mistakes, but not dwell on them. Understand before going in that you will make mistakes and miss opportunities. You will buy when you should have sold and sell when you should have bought. You will do the wrong repairs or get ripped off by a contractor or accept a bad tenant, or one of the infinite other possibilities.

It’s part of investing (and life in general). Accept it and embrace it.

Then make a choice not to dwell on those mistakes. And make a choice not to dwell on them again and again. This requires an active and continuous process of affirmations and metacognition in the same way your car requires oil changes and tune-ups.

Keep this routine up, and you will not fully banish regret. That is close to impossible. But you will push it to the sidelines and allow yourself to focus on the present.

Note By BiggerPockets: These are opinions written by the author and do not necessarily represent the opinions of BiggerPockets.