Regret-Free Living

  Do you see what I’m saying? The problem of confronting overly delayed gratification and the resulting regret doesn’t occur just once, at the end of one’s life. Rather, it can occur at every period during your life, from the bookworm teenager who missed out on all the fun of high school by making too many sacrifices for the sake of a supposedly brighter future to the middle-aged dad who repeatedly skipped irreplaceable experiences with his own teens by constantly hustling for one job promotion after another. Sometimes people realize their mistake just before the window of opportunity closes—like when one’s children are getting ready to leave the nest—and sometimes the recognition comes when it’s too late to do anything at all about it except resolve to do better in their next life stage.

  The saddest, though, is when the realization doesn’t hit until you’re facing your own mortality, when it really is too late to change anything and all you can do is make peace with your past.

  For those of us who still have time to make changes and adjustments, it can be enlightening and even motivating to read or hear about other people’s deathbed regrets.

  Many of these are particular to each individual, of course, but if you listen to dozens of stories about people’s deathbed regrets, common patterns do tend to emerge. An Australian woman named Bronnie Ware, whose work as a palliative caregiver put her at the bedsides of patients with just weeks left to live, talked with her patients about what they wished they had done differently in their lives, and found five key regrets coming up more often than any others. As she describes in a popular online article and in a subsequent book, the two most common regrets are ones that are most relevant to my message.

  Her patients’ number one regret was wishing they’d had the courage to live a life true to themselves—as opposed to the life that others expected of them. It’s a regret about not pursuing your dreams, and therefore having those dreams go unfulfilled. If you ignore what you truly value in life and instead pursue a path that the rest of your surrounding everyday culture foists upon you, you risk having real regret at the end of your days. In American culture, which so often values hard work and earning money to the exclusion of other important values (such as leisure, adventure, and relationships), it stands to reason that people often come to the end of their days really wishing they hadn’t made this kind of sacrifice. As the old saying goes, “No one ever regrets not having spent more time in the office.”

  Along those lines, the second regret—and actually the top regret among Ware’s male patients—was this: “I wish I had not worked so hard.” That hits right at the heart of what I’m preaching. “All of the men I nursed deeply regretted spending so much of their lives on the treadmill of a work existence,” Ware writes. Women had this regret, too, but, as Ware points out, her patients were from an older generation, when fewer women worked outside the home. And when people say they regret working so hard, they are not talking about the hard work of raising children; they are talking about working to make a living to pay the bills and, as a result, missing “their children’s youth and their partner’s companionship.”

  Now, let’s take a deep breath. I recognize that all this talk about death and regrets in life sounds very depressing. I realize that by attempting to raise awareness of what you will eventually lose forever, I am handing you a kind of anticipatory grief. But believe it or not, thinking about impending loss can actually make you happier. A most revealing experiment with college freshmen shows why.

  A team of psychologists asked one group of young students to imagine that they would be moving far away in 30 days, and told them to plan their next 30 days accordingly: It would be the students’ last chance for a very long time to enjoy all the special people and places they’d come to like about their college. In short, the students were urged to savor their remaining time on campus. Then, every week that month, the researchers asked the students to write down their activities.

  By contrast, another group of freshmen weren’t told to imagine anything or to do any kind of savoring of their days—they merely had to track their daily activities. Guess what happened? As you can imagine, the students in the first group were happier by the end of the 30 days than the second group. Whether they did more or just managed to squeeze more enjoyment out of whatever they did on a daily basis, the mere act of deliberately thinking about their time as limited definitely helped.

  What’s the takeaway here? Being aware that your time is limited can clearly motivate you to make the most of the time you do have.

  We’ve all experienced some version of this effect when going on vacation in a new place. As tourists, we know all too well that we have only a week or however long at our destination—so we plan ahead to make sure we pack in as many landmarks, tours, activities, and other experiences unique to the place we’re visiting as we can. If we’re visiting friends, we make sure to spend plenty of time with those folks, and we try to savor every moment. In other words, we make a full and conscious effort to treat our time as the scarce resource that it is.

  Now, that’s usually very different from what we do when we’re back home, where we’re much more likely to take our hometown’s everyday, routine attractions for granted. It’s not just that we’re busy with other pressing, daily responsibilities, even though it is true that we are and it would be unrealistic to live your life as if you were always on vacation. But it’s more than that—it’s also that most people just have the sense that there’s no time urgency near home; they act as if they will always be able to visit that museum or that nearby beach or that friend some other time. As a result, we spend many of our evenings watching TV, and we fritter away our weekends. In short, when something feels abundant and endless, the truth is, we don’t always value it. But the reality, of course, is that the time you get to spend in each phase in your life is not that abundant, and it’s certainly not unlimited.

  Unlike some other topics in this book, the idea of having a finite number of phases with a finite number of days in each has nothing to do with money. Yes, the specific experiences you can have in each time period do have to do with money, but the reality and implications of these finite periods do not. Every person says things like “I’ve always wanted to hike such-and-such trail” or “I’ve always wanted to take my kids to such-and-such place.” Experiences like that exist on every budget. Let me suggest a simple tool to raise awareness of these phases in your life, in order to help you plan the experiences you want to have during your lifetime, and therefore to help you avoid excessive delays.

  Learn from Your “Time Buckets”

  Time buckets are a simple tool for discovering what you want your life to look like in broad strokes. Here’s what I suggest you do. Draw a timeline of your life from now to the grave, then divide it into intervals of five or ten years. Each of those intervals—say, from age 30 to 40, or from 70 to 75—is a time bucket, which is just a random grouping of years.

  Then think about what key experiences—activities or events—you definitely want to have during your lifetime. We all have dreams in life, but I have found that it’s extremely helpful to actually write them all down in a list. It doesn’t have to be a complete list; in fact, you can’t know right now everything you’ll ever want to do, because, as you know, new experiences and new people you meet tend to reveal unexpected additional interests that you’ll want to pursue. Life is all about discovery. And you will revisit this list later in life, too.

  But I’m sure you already have some ideas about which experiences you’d want to have at some point, some perhaps more than once. For example, you might want to have a child, run the Boston Marathon, hike the Himalayas, build a house, file a patent, start a business, volunteer for Doctors Without Borders, dine at a Michelin-star restaurant, attend the Sundance Film Festival, go skiing 50 times, go to the opera, take a cruise to Alaska, read 20 classic novels, attend the Super Bowl, compete in a Scrabble tournament, visit Yellowstone, see autumn in Vermont, take your kids to Disneyland three times, and so on. You get the idea. Be as creative as you want.

  Your list will be your own unique expression of who you are, because your life experiences are what make you who you are. Key point: As you’re making your list, don’t worry about money; money at this point is just a distraction from the overall goal, which is to envision what you want your life to be like.

  Then, once you have your list of items, start to drop each of your hoped-for pursuits into the specific buckets, based on when you’d ideally have each experience. For example, if you want to go skiing 50 times in your life, during which decades or five-year buckets would you like to have those ski days? Here, too, don’t think about money just yet—rather, think about the point in your life when you’d really like to have each experience.

  Some of these bucketing decisions will be easier than others. In fact, you probably already have a decent idea of some of the wonderful experiences you’d like to enjoy in your lifetime. As for your other “wish list” items, well, for example, you can always travel to a faraway place. But as we’ve noted, it’s always easier to travel when you’re in your forties or fifties than when you’re in your seventies or eighties. The point is, today’s the day to start actively and consciously thinking and planning for your years ahead.

  Filling Your Time Buckets

  As you time-bucket your life, you parcel out a single list of experiences into different and distinct time sections of your life.

  In general, using the time-buckets approach will make you begin to realize that some experiences are better done at certain ages. Mountain climbing and attending loud concerts, for example, are much more fun when you’re younger. Not surprisingly, the most physically demanding activities tend to fall on the left (younger) side of the timeline. You probably won’t be skiing much at 80. Yes, some people run the Boston Marathon in their seventies, and one exceptionally fit woman named Katherine Beiers completed the race when she was 85. But these individuals, of course, are outliers. And even for Beiers, the marathon at 85 was not her first—but her 14th.

  A Season for Everything: Time Buckets vs. a Bucket List

  As you go through this bucket exercise, you’ll come to see for yourself that there’s a season for everything. That being said, you might begin to sense that some desired experiences conflict with other experiences. Or you might realize that some of the activities you want to do won’t happen at all unless you begin to plan for them now.

  And just to clarify: This list is the opposite of the so-called bucket list, which is typically a single accounting of all the things you hope to do before you “kick the bucket,” so to speak. The more traditional bucket list is usually put together by an older individual who, when confronted with their mortality, begins to scratch out a list of activities and pursuits they not only haven’t done yet but now feel compelled to do quickly, before time runs out.

  By contrast, by dividing goals into time buckets, you are taking a much more proactive approach to your life. In effect, you’re looking ahead over several coming decades of your life and trying to plan out all the various activities, events, and experiences you’d like to have. Time buckets are proactive and let you plan your life; a bucket list, on the other hand, is a much more reactive effort in a sudden race against time.

  Now, you might notice as you fill up your time buckets that some experiences are more flexible than others. For example, you can still enjoy visiting libraries, watching classic movies, reading novels, and playing chess well into your old age. Taking a cruise can be enjoyable at just about any age.

  Still, as you start filling up your time buckets, you’ll probably see that the experiences you want to have in life don’t fall evenly across the ages. Instead, they naturally cluster during certain periods—taking on roughly the shape of the right side of a bell curve (see figure below).

  As long as you’re still ignoring the money factor, and still focusing primarily on your health and your free time, that bell will probably skew to the left—because you’ll want to have most of your experiences (especially those with physically demanding activities) when you’re at peak health to enjoy them, and before you’re constrained by the demands of parenthood. If your life plan includes children, the experiences you want to have with them will cluster a little later, probably creating a peak around your thirties and forties. Again, all that’s true even if you don’t take the cost of experiences into consideration.

  Experiences Clustered in Your Twenties vs More Traditionally Distributed Around Midlife

  Without the constraint of money, most of your experiences would optimally occur in your twenties and thirties, when your health is highest. But in reality, most people's spending is clustered around midlife instead.

  Okay. Remember, we’ve been focusing only on two key components of your time buckets: your physical health and your life’s dreams. We deliberately pushed financial concerns off to the side, because it’s always too easy to blow off our dreams by simply saying, “Sounds really nice, but let’s face it . . . I can’t afford that.” Focusing on money distracts from the hard truth that time and health are fleeting.

  But financial concerns are real, so read on to the next chapter, where we’ll talk about how to make sure you don’t miss the opportunity to spend your money while you still have time on your side.

  Recommendations

  If time-bucketing your whole life feels a bit overwhelming, just do the exercise with three time buckets covering the next 30 years. Know you can always add more to your list; just do it long before your age and health become a real factor.

  If you have children, think about your own version of the Heffalump movie: What one experience do you want to have more of with them in the next year or two, before that phase of their life and your life is over?

  8

  Know Your Peak

  Rule No. 8:

  Know when to stop growing your wealth.

  I recently celebrated my 50th birthday. I certainly had a wonderful time on that day, but it actually wasn’t the biggest party of my life. My biggest, best party happened five years earlier, after I had set out to plan the most memorable 45th birthday celebration I could afford. The idea was to bring together all of my family and friends from every stage of my life and to introduce them all to one of my favorite places on the planet: the serene and beautiful Caribbean island of St. Barts, where my wife and I had spent our honeymoon.

  Even though turning 45 is just a semi-milestone, I knew I didn’t want to wait until I turned 50 to have this experience: My mom was already old, and I wanted her to be able to fly in and to fully enjoy the celebration. (My dad was already debilitated and couldn’t travel, so it was even more important that my mom attend.) Plus my friends weren’t getting any younger, either! Who knew if there’d ever be another chance to bring all of these people together? That year was the right time bucket, and I was determined to make the party happen. I wanted to have this significant and unique memory for the rest of my life.

  Of course, this was going to cost some money. Fortunately, by this point in my life, through a bit of skill and a tremendous amount of luck in my work as an energy trader, I was doing well financially. But I know money is a concern for everyone, and many of the people I wanted to invite, including friends from childhood and college, couldn’t afford to fly to St. Barts and pay for a room in the secluded hotel I had my eye on. The people you share experiences with truly affect the quality of the experience—and nowhere is that more true than at a once-in-a-lifetime event. So I knew that if I wanted to have this kind of unique birthday bash, I was going to have to step up and pay for a lot of my guests to attend.

  Still, my wealth is finite, just like everybody else’s, and as I started running the numbers, I ran up against my limits. Having this dream celebration would cost a big portion of my liquid net worth. Was it really a good idea to spend that much money on just one week, no matter how amazing that week might turn out to be?

  We all face some version of this question whenever we consider a major purchase. Of course, the dollar amounts differ from person to person, often by orders of magnitude, but the core question is the same for all of us: What’s the best way to spend our money for maximum enjoyment and in order to generate maximum memories?

  Now, you already know some of my answers to this question: Invest in experiences that yield long-lasting memories, always bear in mind that everyone’s health declines with age, give your money to your children before you die instead of saving for their inheritance, and learn to balance current enjoyment with later gratification. But even though I’m a big believer in these principles, my 45th birthday party gave me pause: I had to talk myself over the psychological hurdle of spending a fortune on a single, weeklong party, no matter how memorable it would be. I had to tell myself again and again that I was never going to turn 45 again and asked myself when—short of my funeral, someday way in the future—I was ever going to be able to get all these key people in my life together again. Once I got over that psychological hurdle, though, I was all in, and I went all out, creating the best party my money could buy.

  The Party of a Lifetime

  I rented out the secluded beachfront Hotel Taïwana, on the white sandy beach of the island’s largest bay—all 22 rooms and suites. To house everyone, I also booked several rooms at the equally stunning hotel next door, the Cheval Blanc. I bought flights for dozens of guests. On top of all that, I arranged for boat trips and picnics and nightly food and entertainment: One evening was sushi-and-karaoke night, another was a night of old-school R&B.