The thief who stole my travel wallet at the Barcelona train station must have been a high jumper. Before sitting down on a bench to organize my papers, I’d been careful to make sure no one was around. After the theft, I found an escalator behind the bench, but it was still hard to believe: the thief must have run up the down escalator and leapt over the wall the moment I put my wallet on the bench to set down my backpack. A medal-worthy performance, except that it happened to me.

I was a few months out of college and had worked a series of jobs to pay for the trip. Now, cash, travelers checks, credit card and rail pass were all gone.

I was able to replace everything except the cash, which should have made me happy. But I’d become attached to my “daily average,” the amount of money per day that I had left for the rest of the four-month trip. It was meant as a check on my spending to make sure I didn’t come up short at the end in Scandinavia. But when things cost less than expected at the beginning in Greece and my daily average began to rise, I was hooked.

As I made my way along the edge of the Mediterranean, the land of delicious food and wine, I stuck to greasy pizza, skipped meals, and would spend the first half of the day in each new place looking for the cheapest lodging to increase my daily average a little more. It might go up by just pennies, but as long as it rose, I was happy, glad to be winning the game. The loss of several hundred dollars at the Barcelona train station blew weeks of gains out of the water and meant I could never recover the average I’d had. Game over.

Then something marvelous happened: my trip got better. With a somewhat fatalistic air, I began to treat myself - a nice meal here, a better hotel there. If I couldn’t predict what might happen tomorrow, I might as well enjoy today. Nothing extravagant, and if I spent a little too much one day, I’d spend a little less the next. It turned out that I didn’t need a goal like the daily average to control spending, and I was able to eat and drink my way through the rest of the trip with money to spare.

There’s no disputing that goals help us. Would Van Gogh have dragged himself out of bed early every day to teach himself to draw if he hadn’t had a goal in mind? Yet while goals serve as useful tools, they bring problems of their own.

Accomplishing a goal can leave us feeling empty and surprised that “achievement doesn’t equal happiness.”

If the goals are too ambitious, they can be demoralizing and counterproductive, as Scott Adams, creator of the Dilbert comic, observed:

Goals can incentivize us to work against our best interests. Aiming for high grades can help us buckle down to study, but also undermine our education if it means we avoid rewarding but difficult classes in favor of easier ones less likely to dent our GPA.

A less recognized problem is that the path to achieving our goals typically requires us to adopt an entire infrastructure of choices and habits that become deeply entrenched over time. When it’s time for a new goal, we may need to retool this infrastructure or risk being held back by it. This was the problem with my Europe trip. The habits required to accumulate money for the trip didn’t serve me well once it was time to enjoy it.

Retirees face a similar problem. As one client told us, “Once you’ve spent a lifetime accumulating the resources to retire, it’s hard to turn around and start spending them.”

There are a number of potential explanations. Perhaps retirees who were motivated to save are more aware of the financial risks with retirement. Or, having more money to lose, they want to guard it more.

In our experience, the chief culprit is simply this: old habits die hard, and few habits are more deeply rooted and intransigent than the habit of saving money.

Those who embrace spending less than they earn tend to agree with Roman statesman and orator Cicero that "frugality includes all the other virtues." Saving for retirement is the prime directive around which they organize priorities about where to live, what to eat, and how to educate their children. It’s an admirable aim and one we’ve been praising since at least Aesop’s fable about the grasshopper and the ant.

The problem comes when trying to shift from this orientation as we move into retirement. Even if retirees accept that the purpose of saving money was to be able, eventually, to spend it, the habits supporting that purpose don’t go gently into the night.

What to do?

It helps to structure retirement finances to recreate a “paycheck” now that you’re no longer employed, and there are a number of financial strategies and products to help with this.

But structuring finances is the easy part. The bigger challenge is mindset. Habits that served us well are difficult to abandon. They’re familiar, comfortable, and even fun. Before my Europe trip, I enjoyed figuring out money-saving “hacks” like batching all my errands together so I could save money on gas by not having to drive as much.

Also, as we’ve written about before, much of our daily routines and identities are tied to our habits, so there are obstacles, real and imagined, to changing them.

We know it’s possible, though. The disruption caused by the theft in Barcelona is one example. We’ve seen similar effects with clients who became more willing to spend after experiencing an adverse health event or the death of someone close to them. The resulting sense of urgency and clarity of purpose can cause even die-hard savers to start planning their next trip or allocating money for other long-deferred goals.

It would be nice, of course, if it didn’t take a tragic wake-up call to jolt us out of habits that are impeding us. In our conversations with clients, we emphasize the opportunity costs of holding onto money too tightly and try to reframe spending as more than just consumption, but rather as an investment in their current selves. These conversations tend to help loosen the lid a little on spending habits.

But what if the problem with retirement isn’t about habits, but with the goal itself?

Retirement is still, in the scheme of things, a relatively new concept, derived from an industrial age of railroads and factories. According to Neil Pasricha, New York Times bestselling author of “The Happiness Equation,” some societies don’t even have a word for it:

If we are, in fact, in the midst of a fourth industrial revolution that promises to upend work and our social arrangements, it may be time to reassess the proper balance between time and money, work and leisure. Perhaps we need a different model for how to organize our lives, one in which the goals and habits we’re forming today can continue to serve us well and help us succeed for the rest of our lives.