When we commit to accomplishing a goal, we commit to the possibility of at least two kinds of failure - the possibility that we won’t get what we want, and the possibility that, if we do, we may discover that success wasn’t worth the costs. These costs include not just the time, money and effort we expended to reach our destination, but also the things we gave up in order to get there. The poet Robert Frost famously alluded to these things as “the road not taken”; economists call them “opportunity costs.”

A number of years ago, a physician called our office to inquire about our planning services. With his daughter about to graduate from a prestigious Ph.D. program, he and his wife were thinking about retirement. They had been proud to pay for their daughter’s private schools, Ivy League college, and graduate studies. But now it was dawning on them how much money they might need in order to stop working. His voice grew quiet as he said, “I wonder if we made a mistake?”

The trade-off between education and retirement funding may seem obvious, but this is one of the hallmarks of opportunity costs. What’s easy to see from the outside can remain nearly invisible to us on the inside, since our focus on what we want obscures other considerations. In fact, the more we desire something, the more elusive opportunity costs become.

That’s too bad, because the evidence says we’re terrible at predicting what will make us happy in the future. We focus too much on the potential upsides of our goals and overestimate the satisfaction we’ll feel in accomplishing them – a condition that psychologists call “arrival fallacy” – “the illusion that once we make it, once we attain our goal or reach our destination, we will reach lasting happiness.”

In our eagerness to succeed, pausing to ask questions about costs can feel counterproductive. Don’t a lot of successful entrepreneurs say they never would have started their businesses if they’d known exactly how much time and money were required? How many successful marriages and careers would have ceased to exist before they began if people had ruminated on the costs?

With “opportunity costs,” in particular, there’s an added level of difficulty. Embedded in the term is the question of “compared to what?” We need to know what other opportunities exist before we can decide whether there’s a better choice than the one we’re considering. Unfortunately, we often lack the awareness even to ask the question.

This was the point of the parable that writer David Foster Wallace once told the graduating class at Kenyon College:

Before the pandemic shutdowns, it was a given all over the world that people needed to endure long commutes to central business districts in order to sit in cubicle farms five days a week. Now, after two years of working from home, everything about that existence is being questioned and in many cases rejected - the commutes, the idea that being at the office improves work quality, even the number of workdays each week.

Just like the London commuters we discussed in an earlier article, The Importance of Breaking Good Habits, who were forced by subway repairs to find different, better routes, once the pandemic shutdowns forced people to experiment, they found other, more optimal solutions for themselves.

Absent completely upending our lives, is there another way to identify opportunity costs and find better solutions?

The financial-planning process can get us part of the way there. One of its chief aims is to evaluate trade-offs among different financial goals, quantifying them with time frames and dollar amounts to see whether the financial resources can cover them all. A popular metaphor for the process is the jigsaw puzzle, since the purpose is to figure out a way to fit all the pieces of our lives together, for both our present and future selves.

The planning process has a hard time competing, though, with the stories we tell ourselves about what our goals should be. These goals are shaped by societal norms – the water we swim in – and the scripts we learn early in life about what’s important, regardless of how we ourselves may feel about it. (How else to explain the choice so many people made pre-pandemic to live more than an hour from their office, forcing themselves to sacrifice the equivalent of twelve workweeks each year just to get to their desks?)

To combat our tendency to fall in line and make choices similar to what everyone else is doing simply because they’re doing it, we need more powerful medicine than logic and numbers. Even a cost-benefit analysis is probably not enough, since the exercise is typically a rationalization for what we want to do, with the cost side of the ledger never having a chance against the benefits side.

If we’re going to combat the stories we tell ourselves and try, at least for a moment, to account for our cognitive biases, we need to harness our emotions. We need to fight a story with a story, and one way to do this is to flip the idea of success on its head. Instead of asking what we'd like to achieve and stopping there, we should ask, At what are we willing to fail as a byproduct of that success?

This is not failure in the sense of a sacrifice made in service of later success such as the “fail fast” mantra of start-up culture. Nor is it failure in the sense of being willing to do something despite the risk of embarrassment such as, “I’m willing to play golf badly simply for enjoyment.” This is failure in the sense of falling short and failing to achieve something at all, irrevocably - the opposite of success.

It may seem unfair to call the things we choose not to do “failures.” If we didn’t attempt them in the first place, did we really fail? However, the Latin root of “failure” means “to trip, cause to fall,” which was used figuratively to mean “deceive, trick, dupe, cheat, elude.” To the extent that we trip ourselves up with stories about exaggerated benefits and negligible costs, it seems not only fair, but apt to call this kind of self-deception a failure.

Indeed, it often feels like failure when we realize later that we would have preferred a different path. As British psychotherapist Adam Phillips has noted, many people spend much of their lives ruminating on the other lives they might have led, often with regret. He notes, moreover, that success in one area of our lives may actually trigger these regrets:

My grandfather ran a successful bakery for more than two decades in a small Texas town. He was on the school board, owned several rental properties, and helped his three children go to college. These successes seem more than enough for one life, but underlying them all was a frustration borne of regret that he didn’t go to college himself. Though he might argue differently if he were still here, it seems to me, looking back, that his accomplishments fueled, rather than soothed his regret by hinting at other possibilities that a college education might have afforded.

If we’re up for the challenge of confronting opportunity costs and doing the work to compare different options, there are a number of potential benefits. We may discover, for example, that we can do more than we imagine if we allot less time to a primary pursuit in order to make time for another one.

In fact, allocating less time may, ironically, make us even more productive, as professor Robert Boice concluded, in studying the writing habits of his fellow academics over many years. As summarized by Oliver Burkeman in “Four Thousand Weeks, Time Management for Mortals,” Boice found that “the most productive and successful [academics] made writing a smaller part of their daily routine than the others, so that it was much more feasible to keep going with it day after day.”

There may be substitutes for what we think we want that could be even better. “Designing Your Life,” which we’ve written about before in What If You Could Test Drive Your Life?, argues that while we tend to believe there is only one version of our lives that will make us happy, in fact, there are likely many versions with which we could be content and even thrilled. To help imagine what these other paths might be, the authors suggest asking, What if the career or path you’re imagining for yourself didn’t exist - what else would you do then?

Perhaps you could plan to pursue different goals concurrently, or if not possible, then sequentially. Since you’re not stuck in an Aesop’s fable, you’re not limited to being either a grasshopper or an ant, and there may be a number of creative ways to configure your life in ways that allow you to address both your financial obligations and your passions.

At a minimum, if we’re willing to pause and question what we think we want by considering viable alternatives, we’ll know that we made a considered decision, using all available information, and be less prone to regret. We’ll also likely avoid the worst possible type of regret - that of finding out too late that we dismissed an opportunity that we could have easily pursued if only we had thought about it.

It’s a truism that we don’t change until the cost of remaining the same is greater than the cost of changing. Factoring in opportunity costs gives us the best chance we’ll have of changing for the better.