Sneaky sideways moves that strong chess players swear by are called “intermezzos,” or “in-between moves.” The American chess genius and unofficial World Champion Paul Morphy executed these many times in the New Orleans cafés where he won game after game in the 1800s. Morphy’s move seemed obvious. Why not just recapture the piece that was just taken? But then, BOOM. Morphy interrupted the sequence with a different aggressive move, throwing his opponent’s position into turmoil. Intermezzos are shocking. When Judit Polgár played one against another top grandmaster, he jumped out of his chair. Intermezzos are reminders that instead of looking far in advance, we should search for little surprises that no one else sees.

The futility of planning far in advance is nailed in one of my favorite one-liners, from the late comedian Mitch Hedberg: 

“Where do you see yourself in five years?”
“Celebrating the five-year anniversary of you asking me that question.”

Indeed, five-year plans fall apart when encountering the unexpected — like a global pandemic, for example. I think of five-year plans as five future me’s. I consider the overlapping risks and skills, while being on the lookout for surprises. “No plan survives first contact with reality,” according to co-authors of Designing Your Life, Bill Burnett and Dave Evans. The Stanford professors are proponents of what they call an “Odyssey Plan,” in which you imagine alternative plans for your life, with the thinking that even if the plan is unlikely to unfold in a predictable way, the planning itself will help reveal your values, desires and fears. They recommend creating three different five-to-ten-year plans: a primary plan, an alternative plan and one plan that you would undertake if money and the thoughts of others were no object. Their goal is to make you more open to possibilities, rather than be shackled by a rigid vision.

Chess demands that same mindset: Plan, but be ready to discard the plan at any moment. Our version of the proverb, “Man plans, god laughs” is, “Long variation, wrong variation.” When a chess master thinks ten or even five moves ahead, they often miss a reply on move one, two, three, or four. Mapping out a future many years away may require a sharp turn if your desires or circumstances change. Stay flexible so you can be aware of intermezzo opportunities all around you.

I won my first U.S. championship and international master norm because I saw an intermezzo. It was just a little rook move, but it was devastating, threatening a tactical motif known as a “windmill.” A windmill is a series of intermezzos that eliminate several enemy pieces, one after another. After winning the game and the title, some of my friends asked me how I was able to see so far ahead in such a high-stress game. But the real secret wasn’t how far ahead I’d seen, but how far sideways.

A time in my own life beyond chess when I should have made an intermezzo move was when I was looking to buy my first house. I was motivated to buy a home for all the typical reasons — for the first time in my life, I could afford the down payment, and buying a home seemed like checking off the first item on the American Dream list. Plus, the process of looking at houses with my boyfriend, now husband, was a blast. Even the modestly sized homes we were looking at were staged so beautifully; they all seemed palatial without the everyday clutter that plagues our real homes. And the fun part was imagining all the different directions our lives could take, depending on which house we purchased: the cafés and bars we’d frequent, the neighbors we’d meet, and the reading nooks and kitchen appliances we’d have space for. Who would we be if we lived in this house or that one?

After looking at about ten options, we settled on our top three: a slick renovated condo in a central neighborhood, a tiny house even closer to the center of the action, and a row home in South Philly, an area that boasted some of the best food and fun in the city. During the process, I seduced myself into thinking I had to choose one of these options. It was almost as if I was producing my own episode of House Hunters, where home buyers are shown exactly three houses before buying. We bought the house in South Philly. But at that time of my life, I was traveling constantly. I hadn’t decided whether I wanted kids, so who knew if this was my “forever home?” There’s a related principle for those on the fence between buying a home or renting. If you plan to live in a city for at least five years, it makes sense to buy. Any shorter than that, you’ll get crushed by transactional and moving costs.

Intermezzos don’t just delay a decision; they can improve it, while keeping what economists call “optionality.”

If I’d thought carefully about the different paths my life could have taken at this point, I might have held off on the big purchase and considered alternative paths. I could have found an intermezzo move. Maybe I could have traveled the world and stored my stuff in a unit. Or rented in a city where much of my work took me, like St. Louis, the capital of chess, or Las Vegas, the capital of poker. A great intermezzo buys you time, allowing you to return later to the crossroads that stumped you with more information. Intermezzos don’t just delay a decision; they can improve it, while keeping what economists call “optionality.” I didn’t see any of that. I was in the tunnel.

My friend Matt used the intermezzo delay when his life changed unexpectedly after being selected for jury duty. Well into his 40s by this point, he’d had earlier inklings that he wanted to be involved in the legal field but never took action. Then he was chosen as a juror for a murder trial in Brooklyn. Watching a passionate public defender struggle to gain the attention of jurors — who wanted to go back to work or who believed the defendant was guilty on sight — awakened a dream of a life where he’d be that lawyer. “I kind of assumed that would be the end of it,” Matt told me, “this idea that I would be a public defender in an alternative life.” But then the feeling didn’t go away.

Months later, the thought was still in his head. He had to do something. And it occurred to him that being a lawyer wasn’t one decision, but a series of decisions. Why not take an intermediary step while gauging his capability and interest? So he started to study for the law school admission tests that would gain him entry to law school. His intermediary moves gave him information: Each time, he was keen to get to the next step. He enrolled in Brooklyn Law School at age 48 for one heck of a life intermezzo.