It’s never the right time. Here’s how to know when to act anyway

How to use The Secretary Problem to get unstuck

Sarah sat across from me, twisting her wedding ring. “I know I need to leave,” she said, “but the timing isn’t right. He’s got this big thing coming up. I just got promoted. The market is uncertain, and…” She trailed off, her voice heavy with the weight of an impossible decision.

Fifteen years later, she still hasn’t left. She now owns a home in the country with the person she wanted to leave. She’s as unhappy as she was 15 years ago—except now she’s even more stuck.

Sarah is one of the most talented people I’ve ever met. A preternaturally good cook whose talents are spent on a partner who’d literally prefer to eat a box of Cheez-Its (I’m not making this up).

A brilliant chemist who consistently thwarts her own advancement because she’s waiting for the “right time” to take the risk, to make the jump, to ask for the raise, to start her own company—to, basically, do anything besides what she’s been doing for the last two decades.

***

My guess? You’ve got your own version of Sarah’s story.

Your big move, your big decision may not be the same as hers. Your partner may actually like your cooking.

But we’ve all felt that stuckness when it comes to big decisions. Whether it’s leaving a job, starting a business, starting a relationship, ending it, or making that big move—I bet, just like Sarah, you’ve got a carefully curated list of reasons why now isn’t quite right.

Well, I hate to break it to you.

Waiting for the right moment is burning you out.

That feels counterintuitive, so let me say it again. Your continual attempts at finding the right time make your burnout worse.

But… Waiting for the right moment is actively not acting—how could doing nothing burn you out?

Before we get to the science: how many browser tabs do you have open right now? Chances are, somewhere between 5 and 30.

How do I know? In a 2023 study, researchers found that the average person has 1–3 browser windows open, each one with 5–10 tabs. The person with fewest tabs open had three. The person with the most? Four hundred!

Each of those browser tabs—each of those things you’ve left open to get to later—acts as a drain on your computer’s memory. They may feel like passive bookmarks, but your computer’s got to work to keep them open.

Same with any big decisions that you’re leaving open. Here’s why (and what to do about it):

The Science of “Later”

There are a gajillion blog posts, books, pithy instagram reels, and podcasts telling you that there’s no right time to do something, so you should just…do it anyway.

But why? What’s the science? How does delaying a decision for the “right time” worsen burnout? And how do you do it anyway?

Let’s break it down. There are four interlocking processes at work in your burnout.

Process 1: Construal level theory

We talked about the first one—Trope and Lieberman’s Construal Level Theory—in the blog post two weeks ago. A quick recap: the further away something is from us, the harder time we have conceptualizing it with any sort of granularity.

In Construal Level Theory, “further away” means any sort of psychological distance from you in the here and now.

In other words, trying to wrap your mind around the inside of your crazy uncle’s head during one of his Thanksgiving rants, or around life in Urumqi, or around you in 2040—all of these are similarly psychologically distant. And that means we have a hard time grasping them in anything but the abstract.

Process 2: Affective forecasting

That doesn’t stop us from trying, though! Gilbert and Wilson have done some spectacular research on what they call “affective forecasting”—that is, predicting how you’ll feel when something happens in the future. Even if we can’t truly construe something in the future well, we still have no problem thinking we can predict how we’ll feel when that something happens.

Chat, we’re terrible at it. And in two ways.

First, we overestimate how big the feeling will be—whether positive or negative (something Gilbert and Wilson call the “impact bias”). In one particularly fascinating study, they looked at professors up for tenure. Prior to their tenure decisions, these professors predicted they’d be much happier for much longer if they got tenure, and much more devastated for much longer if they didn’t.

But neither was true. The agony and the ecstasy both faded more quickly than expected.

Second, we don’t even get the direction of our prediction right all the time. “Unfortunately,” they write, “the conclusions that we draw in this way aren’t always right. Trysts are often better contemplated than consummated, and sweetbreads are often better the other way around.”

(Find me a better written line in the scientific literature…)

Process 3: The infinite elevator

Late last year, I also introduced the idea of the infinite elevator to explain why dating apps are such a cognitive suck.

Dating apps keep you swiping because what’s in front of you is an endless, unknown supply of “what if the next one’s better?” And it’s really hard to commit to someone, warts and all—no matter how few warts they have—if you’re constantly taunted with the idea of a wartless partner just a swipe away.

Infinity paralyzes us. The more choices we have (or imagine we have!) about something, the less likely we are to make the choice—and the more dissatisfied we are with whatever choice we make.

Process 4: Metabolic fuel consumption

In their 2004 Science paper, Sam McClure and his colleagues put participants in an fMRI to see which portions of their brains lit up when they were faced with immediate versus delayed rewards.

What’s really cool is, they found different parts of the brain lit up, depending on how far away in time the reward was. Immediate rewards were processed by the limbic system—the primitive part of our brains that’s shared with other mammals, birds, reptiles, amphibians, and fish; the one involved in emotion, motivation, and sex.

On the other hand, the further away a reward was in time, the more active the pre-frontal cortex became. That’s the part of the brain where complex decisions sit; its size and activity distinguishes humans from many other animal species.

And it’s the part of the brain that burns through metabolic fuel the fastest.

To quote Roy Baumeister: “We have a limited bucket of resources for activities like decision-making and impulse control, and when we use these up, we don’t have as much for the next activity.”

So, to put it together:

1. We’re terrible at imagining the future with any detail

2. Even when we try, we’re terrible at predicting how we’ll feel in that abstract future—overestimating the impact a decision will have on us

3. We’re always tempted by the next best thing, especially in the uncertainty of the future

4. And we handle all of this uncertainty using our pre-frontal cortex, which burns through metabolic energy like a dragon with reflux.

With me so far? Great.

Now let’s do something about it.

Adaptation and a little bit of math

First, an admission: I really hate the advice that’s supposed to come next. “Girl, do the thing.” “Do it scared.” All that. The stuff you’re expecting me to say.

I mean, yes. do the thing, and do it scared. It’s true.

I work really hard to live by that advice.

But I also hate it because it’s cheap and doesn’t honor the uncertainty, the mental energy, the risk that “do it scared” requires.

So, instead of just telling you that waiting for the right moment is burning you out, and instead of concluding you’ve just got to act, let me give you a four-step system to find the actual optimal moment to make a decision.

Before I do, I want to dip my toe into the research of hedonic adaptation. As Gilbert and Wilson’s findings imply, humans are super adaptable. Even big adverse health events don’t crush people’s spirits the way you might expect standing on the outside. It takes us a few months, but we’re immensely adaptable creatures.

(In the interest of balance, I feel obliged to tell you that some researchers disagree with this idea altogether)

Anyway, I bring this up because keeping it in mind has given me a remarkable amount of freedom about big decisions. My brain is way more adaptable than I give it credit for. As is yours. You’re way more resilient than you think. Even when you make “bad” decisions.

Your brain is a remarkable emotional safety net.

Now, with that freedom, let’s get you from stagnation to action, shall we?

The Secretary Problem

Imagine you’re hiring a new secretary.

Side note, what we’re about to do is called “The Secretary Problem” because that’s not sexist at all. Not altogether surprising since it was first popularized in the 1960s.

To make matters worse, it’s also been called “The Sultan’s dowry problem” or “The marriage problem”—because, well, the 60s.

Anyway, mid-century sexism aside, imagine you’re hiring for a new secretary. You’ve got twenty qualified candidates, each of whom you’ll interview. Here are the rules of the game:

• Once you interview a potential secretary, you can’t go back and interview them again. If you pass on them, they’re off the list and they find another job.

• On the other hand, once you hire a secretary, you’re done. Whoever hasn’t yet been interviewed is lost to you forever.

There’s one crucial difference between this problem and the infinite elevator problem, which we’ll use to our advantage later: there are a finite number of secretaries. It’s not like you’ve got infinite Tinder swipes.

Here, you’ve only got 20 secretaries to interview.

How do you pick the best one?

The answer is simple: skip the first 5 interviewees. Then pick the next candidate that’s better than the first 5. If none of them are, pick the last candidate.

In other words, your first five interviews are information-gathering. They form your baseline—in those first five interviews, you create a ranked set of potential secretaries. But you don’t hire any of them.

Starting in interview 6, you’re actually looking to hire. And your only rule is to pick the first secretary who’s better than any of the baseline ones.

Why five? Because 5 is the square root of 20 (rounded up).*

The math is super cool, but I’m not going to go into it. (If you’re interested, check out Bearden’s 2005 paper here).

That means if you’re only interviewing 9 secretaries, skip the first 3. Interviewing 64 secretaries? Skip the first 8.

That’s it. That’s the rule:

Skip the first √n secretaries, then hire the first secretary that’s better than any of the √n secretaries. And if no one is, hire the last one.

Applying the secretary problem to making a decision

OK, enough nerding out on math. How’s this apply to your big decision?

Let’s say you’re trying to find the perfect time to quit smoking. You’re aware that people who make rash “I’m going to quit tomorrow” decisions rarely succeed, so you want to be thoughtful and pick the optimal time for you to quit.

But when is that? Put the secretary problem to work for you:

1. Set 16 quitting deadlines over the next year. Put them on the calendar.

2. Don’t quit during the first four deadlines. Instead, reflect—would this have been a good day to quit? Were you free from big stressors that would have sent you back to the cigarettes? Or was it just a gorgeous sunny day and a cigarette felt good? Rank those quit deadlines. This is your baseline set.

3. And now, starting with deadline #5, quit on the first day that’s a better quitting day than any of the ones in the baseline.

4. If you haven’t quit by the time you get to deadline 16, then that’s the day you quit.

Remember, as always, that you’re never going to find the perfect moment (because it doesn’t exist). Instead, you’re finding the best moment, of all the ones available to you, to do the thing.

And then, friend, do the thing. Do it scared.

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Footnote

*The traditional solution to the secretary problem is slightly different. Instead of discarding the square root of n interviews, the traditional solution is to discard n/e interviews (where e = 2.71828…)—or, approximately 37% of the interviews. I like Bearden’s solution better because a) it’s more natural, and b) it requires discarding fewer interviews.