Margot keeps her CPA license in her wallet, behind her hospital badge. She has renewed it six times since she last signed anything with it. Each renewal costs a fee and two weekends of continuing-education courses taken at the kitchen table, and each year she gives herself the same reason: it is good to keep your options open.
Keeping your options open costs more after 40 than it did at 25. Each option kept alive needs regular upkeep: a fee, a lunch, a weekend, a yes to extra work. The upkeep comes out of the same limited time, money and energy that a real change would need. Past two or three open options, the upkeep alone can stop a person from using any of them.
Margot is fifty-one, and she was keeping six. Over one winter she closed four of them, one every two weeks. Seven weeks after the first closing she sent her first invoice in six years, and it was for the option she had spent the least to keep.
This post shows how to price the options you are keeping, which one to close first, and a six-line test you can run tonight.
The Price of Six Maybes
Margot runs finance for a regional hospital network. Her six open options were each opened for a good reason, and none of them was ever closed. Before she changed anything, she wrote down what each one had cost her in the previous ninety days.
- The license. The renewal fee, and two weekends of courses.
- The recruiter. A lunch every quarter with the search consultant who placed her in her current job eleven years ago. Each lunch takes an afternoon. The evening before, she updates a résumé that she then does not send.
- The practice. A consulting company she registered six years ago. It has a two-page website and has had one client. It costs a domain fee, an accountant’s fee for the annual filing, and an hour on most Sunday evenings that she calls working on the site.
- The teaching. A community college offered her an evening course in healthcare finance. She has moved it to next spring four times, each time with a warm email and a promise.
- The promotion. The chief financial officer is expected to retire within two years, and Margot is the internal candidate. She keeps the candidacy alive by saying yes to every extra project. The current one, a review of supply contracts, takes most Thursday evenings.
- The move. She and her husband talk about a smaller town on the coast. She keeps a property alert running and drives up twice a year to look.
Read down the list and nothing on it looks foolish. A license is insurance. A recruiter is a relationship. A company is a head start. Taken one at a time, each of the six is the kind of thing a sensible person keeps.
The trouble only shows when you add them up. Margot’s ninety days came to roughly sixty hours, a little over a thousand dollars, and a constant effort to stay presentable as three people she was not being: the candidate, the consultant and the one who might teach. She had built, without meaning to, a second job whose only product was the possibility of a third.
Before reading further, do the first half of the test that comes later. Write down the options you are keeping open right now, up to six. Next to each one, write the last thing you actually did for it, and when. Keep the list where you can see it. The rest of this post is about what that second column means.
A Game Designed to Make Options Disappear
In 2004 the researchers Jiwoong Shin and Dan Ariely published a set of experiments built around a simple computer game. Players had a fixed number of clicks to spend across three rooms, and each click inside a room paid a small amount of real money. The best strategy was to find the richest room and stay in it. Then the researchers added one rule: a room you stopped visiting would slowly shrink and then vanish.
Players changed their behavior at once. They spent clicks on rooms they did not want, just to stop them from disappearing, and they earned less for it. Shin and Ariely’s paper in Management Science reports that the pattern held across four experiments: when players were told what each room paid, when they had more practice, and when keeping a room alive cost them money directly. In another version a vanished room could be brought back at no cost, and players still worked to keep their rooms from closing. The authors’ last experiment pointed to the aversion to loss, rather than any wish for flexibility, as the driver.
A second study explains why the habit survives. Daniel Gilbert and Jane Ebert ran an extracurricular photography course at Harvard. Each student printed two favorite photographs and had to give one up. Some were told they could swap within a few days; others were told the choice was final. The students who could swap came to like the photograph they kept less than the students who could not, and only one of the students who could swap actually did. When a separate group read about a similar study and was asked which version they would rather join, about two-thirds chose the one that let them change their minds.
Put plainly, closing an option feels like a loss even when the option is worth little to you, and keeping it open quietly lowers your satisfaction with what you did choose. People pay to keep options open, and then enjoy their choices less for having paid.
Margot recognized herself in the second study before the first. She had renewed the license six times without once using it, and she had never asked herself whether she liked her current job, because a better one was always nominally available.
That reflex needs a name, because it rarely announces itself. Call it The Just-in-Case: the habit of paying to keep an option alive because closing it would feel like losing something. Whether you expect to use the option does not enter into it. The Just-in-Case never asks for much at once. A fee, a lunch, one more project. It asks often.
The Keeping Cost
Here is the idea in plain terms. An open option pays you only on the day you use it. Until then it sends a bill: some hours, some money, and some effort to stay presentable for it. The bill is paid from the same small reserve that using any option would need: the spare evenings, the savings you could live on for a while, the nerve to be a beginner in front of people.
Call that bill the Keeping Cost. At twenty-five it is small, because a young person’s options mostly keep themselves. The network is new, the skills are current, and nobody expects anything yet. After forty the Keeping Cost rises for two reasons. Each option takes more to maintain, because a credential, a relationship or a reputation now has a standard to meet. And the reserve it draws on is smaller, because a career, a household and often an aging parent have already spoken for most of the evening hours you think of as free.
That is why the number of options matters more than their quality. One option kept open is usually cheap. Six can absorb the exact hours and nerve that the best of them would need. Margot’s sixty hours went to good ideas, all at the same time, so that none of them got enough.
For about thirty years I believed money made freedom, and I chased it. I think about it differently now. Money buys options. Freedom is whether you can use them.
Freebound has argued before that the real job of money after 40 is optionality: the ability to say no to work that no longer fits. That still holds, and the appetite for options barely saturates the way the appetite for security does. This post is about the bill that comes with them. It is also a different problem from a backup plan whose parts all trace back to one employer, and from a job that renews itself because nothing is scheduled to end. Those are about the arrangement you are in. The Keeping Cost is the bill for the arrangements you keep beside it.
Every option you keep open is paid for out of the one you mean to use.
The First Ranking, Which Took a Month
Margot did what most careful people do first. She tried to rank the six by value, intending to keep the best two and let the rest go.
It took her a month and produced nothing. Every option looked valuable, and for a revealing reason: an option you have never used has never disappointed you. The practice could still become a firm. The teaching could still become a second career. The coast could still be the life she wanted. Each one was being judged on its best possible day, and none of them had yet had a real one.
By the end of the month she had a spreadsheet with six rows, eleven columns and a weighted score, and she had adjusted the weights twice to stop the promotion from winning.
This is the first attempt most people make, and the reason it stalls is built into the problem. Value is what an option might pay one day, and it cannot be measured until the option is used; upkeep is what the option costs now, and it can be counted from a calendar and a bank statement. So she started again with the number she could count. She ranked the six by upkeep, highest first, and decided to close them in that order, one every two weeks, until the cost fell to something she could live with.
This is not the same exercise as retiring goals you never chose. Margot chose all six, and each one was a good idea on the day she opened it.
The order mattered more than she expected. It meant that the first thing to go would be the thing she had been told, for two years, never to give up.
Two Weeks Without the Thursday Project
The promotion came first because it cost the most: most Thursday evenings, plus the low, constant work of being the person who always says yes.
On the second Monday in February she told the chief financial officer that she would finish the supply review but would not take the next project. She had rehearsed a longer explanation. She did not need it. He said, “Noted,” and asked about the review’s timeline.
Two things came back in the first two weeks. The obvious one was time, about six hours that had been going to the project. The other was quieter. She no longer had to be the candidate in every meeting, measuring each answer against how it would sound in a succession discussion. She noticed it first on a Wednesday, when she disagreed with a colleague in a meeting and did not spend the drive home replaying it.
The candidacy did not vanish. Nobody withdrew it. It simply stopped costing her anything, and that turned out to be what closing usually means: you stop paying the upkeep, and the option lives or fades on its own.
The Lunch Canceled by Email
The recruiter went next, two weeks later. Margot had expected this one to be easy, and it was the hardest, because the lunches were pleasant and the consultant was kind. Canceling felt like being rude to her own future.
She wrote a short email: she was not looking, she was grateful, and she would call if that changed. She sent it on a Monday morning before she could edit it again. The reply came within the hour and was warm.
What came back this time was attention. For eleven years she had kept a version of herself ready for a job she was not applying for, updated each quarter and rehearsed over lunch. With the lunch gone there was no reason to keep the rehearsal going, and she found she had more attention for the one option that would actually need a pitch.
I watched a version of this for most of my career, mostly in other people. They spent more time choosing investments than choosing the life those investments were supposed to support. The upkeep of a future was always easier to schedule than the future itself.
A Clear No to Next Spring
The teaching and the move went in March. The teaching took one email, the first honest one in four years: she would not be teaching the course, and the college should offer it to someone who would. The move took a conversation at the kitchen table. Her husband said, “So we stop driving up there.” She said, “We stop driving up there until one of us wants to live there.” They turned off the property alert that night.
By the end of March, four of the six were closed. What remained was the license, which renews each August, and the practice.
Looking back at the four, Margot noticed what they had in common. Each had been kept open on someone else’s calendar: the chief financial officer’s succession timeline, the recruiter’s quarterly cycle, the college’s term dates, the seasons of a coastal property market. None of them had a date of her own on it. The Just-in-Case had been running on other people’s schedules the whole time.
The Last Entry
You can price your own options in about ten minutes with a test called The Last Entry. It looks only at what you have actually done, because what you intend to do is where The Just-in-Case hides.
- List the options you are keeping open, up to six. Count anything you spend time, money or attention to keep available: a credential, a relationship you maintain for its usefulness, a side company, an offer you keep deferring, a candidacy, a place you might move to.
- Next to each one, write the last thing you actually did for it, with the date.
- Mark each last entry K if it kept the option alive (a fee, a lunch, an update, a polite deferral, a yes to stay in the running) or M if it moved the option closer to being used (a price quoted, a draft sent, a date set, a conversation with someone who could pay).
- Your score is the number of K lines, from 0 to 6.
A score of 0 or 1 means your options are mostly being worked, and the Keeping Cost is probably worth paying. At 2 or 3, at least one option is likely costing more than it returns; close the K line with the highest upkeep first. At 4 or more, the upkeep has become the plan.
Two rules keep the test honest. Closing means you stop paying the upkeep and nothing more dramatic, so an option can stay alive on its own, the way Margot’s candidacy did. And close one at a time, about two weeks apart, so you can see what each one gives back. An option you are moving forward on purpose, such as a deliberate tilt toward a second career, is an M line and stays.
Margot’s first score was 6. Every last entry was upkeep, including the practice, whose last entry was an hour spent editing a website nobody had visited. After the four closings her list had two lines, and one of them was an M.
Straight Answers on Keeping Options Open
What does keeping your options open actually mean?
It means choosing not to commit so that more than one path stays available later. In a career it usually involves ongoing effort: maintaining a credential, a relationship, a side project or a candidacy. That effort is the real cost of the option, and it is easy to underestimate because it arrives in small pieces.
Should I keep my options open?
Keep open the few options you are actively working on, and be deliberate about the rest. A useful check is the last thing you did for each one. If it only kept the option alive and moved it no closer to use, the option may be costing more than it is worth.
Why can’t I commit to a career?
Often because committing feels like losing the alternatives. Research by Shin and Ariely found that people pay to keep options from disappearing even when those options hold little interest for them, and that aversion to loss is the main driver. Seeing that the feeling measures the loss of the alternatives, and says little about their value, can make a decision easier.
What if I can’t commit to a job I already have?
Look at what you are doing to keep other paths open while you stay. If those efforts take the evenings and attention the current job needs, you may be getting the worst of both. Either commit to the job for a defined period, or move one alternative forward with a real step and a date.
Why do I struggle to commit to anything?
One common reason is that reversible choices feel safer. In a study by Gilbert and Ebert, people preferred decisions they could change, yet were less satisfied with what they chose when change was possible. Making some choices final on purpose can make them easier to live with.
What should I do if I have too many career options?
Count what each one has cost to maintain over the last ninety days, in hours and money, and close the most expensive one first. Closing simply means stopping the upkeep. Do it one option at a time, a couple of weeks apart, and notice what each closing gives back.
This is the eighth stop on The Leaving Path: too old to change careers → career reinvention after 40 → the transferable skills audit → a second career after 40 → a career change and your spouse → when a career change shows no progress → the hidden cost of success → you are here.
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Why This Painting
The Rijksmuseum’s description of this canvas is exact. Three girls from the Amsterdam Burgerweeshuis, the city’s civic orphanage: one reads aloud from a book, another listens, and the third is busy with mending. Thérèse Schwartze signed and dated it in 1885. A laundry basket waits on the left, and a cat sleeps on a bench on the right. The three share one hour, and only one of them is spending it on repair.
The Invoice in April
The practice was the cheapest of the six to keep. A domain fee, a filing fee and an hour on Sunday evenings: it had never asked for much, which is part of why it had never been used. With the Thursday evenings back, Margot rewrote the website as one page that said what she does and for whom. Then she called three former colleagues who had seen her do it, which is the short distance a first client usually comes from. One of them had a problem with a hospital merger.
In the first week of April, seven weeks after the first closing, she sent an invoice for twelve days of work. It went to the option she had spent the least to keep, and the first one she had given real time to.
The license renewal arrives in August. She has not decided what to do with it.
Keeping options open is not a mistake. It is a cost, and after forty it is a larger one than it looks, because it is paid from the same hours and nerve that using an option needs. Count the cost, close the most expensive option first, and give what comes back to the one you most want to use.
Every option you keep open is paid for out of the one you mean to use.
Read next → Why you have not left a job you could have left years ago
Most of the frameworks here come with a scored instrument: a worksheet you fill in rather than read. Reading one is quick. Filling one in is the part that changes something.
Open the pack →
