Retirement often involves making important decisions with incomplete information when the stakes are high. You won’t have everything figured out on Day 1. More likely, you’ll arrive at your ideal retirement through a process of trial and error. You’ll make mistakes. That’s unavoidable. The important thing is that you learn from them. How best to do that?
Ray Dalio is an investment legend on par with people like Warren Buffett. He owns Bridgewater, the largest hedge fund in the world. Ray has a saying:
Pain + Reflection = Progress
In other words, pain is a good instructor and a strong signal. According to Dalio, success is nice, but it just causes you to do more of the same. You don’t learn much from it. Pain, on the other hand, has a lot to teach you. Whenever you make a mistake about anything, you feel some sort of pain. There’s a message in that pain somewhere. It’s hard to see while you’re going through it, but if you reflect on it once it’s over, you’ll probably be able to see what that message is.
As you experiment with retirement, write down these pain points and think about them. What caused the pain? What should I learn from it? What would I do differently in the future? If you do that, you’ll come out with a principle that relates to the people, places, activities or philosophy of your retirement. That principle is the progress in the equation above. It’s the newfound wisdom that gets you a bit closer to your ideal life and retirement. The more you experiment, learn and iterate, the better your odds of having a happy, meaningful retirement. In some ways, you might even learn to enjoy the pain as an indication of progress. Again, Ray Dalio:
“Encountering pains and figuring out the lessons they were trying to give me became sort of a game to me. The more I played it, the better I got at it, the less painful those situations became, and the more rewarding the process of reflecting, developing principles, and then getting rewards for using those principles became. I learned to love my struggles, which I suppose is a healthy perspective to have…”
I just finished watching the new Ken Burns documentary on Vietnam. During the war, Secretary of Defense Robert McNamara had commanders and soldiers in the field collecting vast amounts of data each day that was then put onto punch cards and fed into a mainframe computer for analysis. The hope was that by measuring hundreds of different variables—casualties, villages pacified, roads cleared—they could gauge progress and prove that we were winning the war.
In hindsight, there were many problems with this strategy, not the least of which was that the things they really needed to know—the state of Vietnamese politics, the loyalty of the people, the intentions of Hanoi—were almost impossible to quantify and thus weren’t being factored into the equation. An Army adviser summarized it this way:
“If you can’t count what’s important, you make what you can count important.”
When I heard him say that, it struck me that you and I do something similar when it comes to life in general and retirement specifically. There are things that really matter and that have a huge impact on our happiness and fulfillment. Things like our sense of purpose, the quality of our relationships and the depth of our experiences. Unfortunately, those things are nuanced and hard to both measure and manage, so instead we tend to focus on things that are easier to quantify like the size of our bank accounts, square footage of our houses or the number of friends we have on Facebook. There’s nothing necessarily wrong with those things, but they don’t form the complete picture obviously.
This morning I spent time reflecting on the types of metrics I use in my own life and how I can do a better job measuring the things that are important and not just the things that are easy to count. As a part of that process, I went back and re-read some of my past articles. If you’d like to do something similar, I’ll post links to those that were particularly helpful to me.
Jeff Bezos became the richest person in the world last week. In a little over 20 years, the founder of Amazon.com went from no money (or very little) to more money than anyone. Warren Buffett once called him “the most remarkable business person of our age.” That’s like Michael Jordan calling you the best basketball player or the Dos Equis guy crowning you “world’s most interesting person.” I’ve followed Bezos over the years and thought I’d share a few things we can learn from him about life and retirement.
You can accomplish a lot in a short amount of time. Someone once said that we tend to overestimate what we can accomplish in a year and underestimate what we can accomplish in ten years. Bezos started Amazon in 1995. That’s not that long ago. I remember what I was doing in 1995. I’m guessing you do too. In that short span he’s built a revolutionary company with hundreds of thousands of employees and transformed giant swaths of the economy. Most people spend about 20 years in retirement. I just went to the funeral of a friend who died at 102. He was retired for 40 years. That’s plenty of time to do some interesting things. No one expects you to start a billion-dollar company, but you don’t just need to ride off into the sunset either. Yes, you can relax and enjoy life, but you also have plenty of runway to take on projects or challenges that give fulfillment, meaning and purpose.
Be stubborn on vision, but flexible on details. That’s how Bezos describes the leadership team of Amazon. They have an uncompromising vision for the company, but they are flexible and willing to try new things to make that vision a reality. That same strategy works great when planning for and living in retirement. Know what you want out of life. Stay true to your vision and values, but when opportunities present themselves take advantage of them. Or when things don’t develop exactly how you anticipated they would, don’t be afraid to change up your tactics.
Experiment. Amazon Prime, Amazon Web Services, the Kindle, Echo and Alexa all started out as small experiments. Bezos and his team are constantly experimenting and making small bets. Some of those fail, but some are wildly successful. The more things they try, the greater the odds that they’ll hit on something big.
Take a page from that playbook. Don’t be afraid to experiment. I have a client who took up golf when he retired, but quickly realized it wasn’t for him. Rather than getting down when things didn’t come together as anticipated, he started experimenting with a bunch of different activities. What did he settle on? Beekeeping. That’s right, he now keeps thousands of bees, rents them out to farmers for pollination and packages and sells their honey. It’s now a huge part of his days in retirement and he would have never discovered it without a willingness to experiment. And while we’re on the topic of experimenting…
Be inventive. All of those experiments usually lead to inventions and innovations. The Amazon of today looks very different than it did at the beginning. The same should be true of your retirement. Don’t spend 20 years in a rut. Iterate, create, grow and evolve. That growth and change won’t happen automatically. You need to experiment and invent. As I said recently: You don’t find yourself. You create yourself.
Invest in yourself. The knock against Amazon from day one has been that it doesn’t show a profit. But the reason it doesn’t show a profit is because a) it charges low prices so it can gain new customers and grow the business and b) it reinvests every dime it makes back into the company to help it grow faster. All of those experiments, inventions and innovations cost money. The payoff has been huge, but it wouldn’t have happened without a willingness to invest in them. Warren Buffett once said that the most important investment you can make is in yourself. In retirement, you have time and money. How can you invest those in ways that enrich and improve you and your life?
Keep a “Day 1” mindset. Bezos works in a building named “Day 1.” It’s a reminder to him and his team that they always want to act with the same energy, focus and willingness to try new things that they had on Day 1 of the company. Someone recently asked him what Day 2 looks like and he said “Day 2 is stasis. Followed by irrelevance. Followed by excruciating, painful decline. Followed by death. And that is why it is always Day 1.”
We’re all going to die, so it will eventually be Day 2, but a life that has purpose and meaning is generally incumbent on keeping a Day 1 mindset as long as possible. It’s characterized by a willingness to take risks, try new things, build relationships, invest, act and work towards some greater purpose. In retirement, it’s tempting to ease off the throttle and orient your life around comfort and security rather than purpose and meaning. There’s nothing wrong with a little R&R, but keep your Day 1 mindset as long as possible.
Use a “regret minimization framework.” Before starting Amazon, Bezos had a great job at a wall street firm. All he had to do was keep showing up for work each day and he’d be set. But he saw how quickly the internet was growing and felt a pull to get involved. As he pondered the decision he wondered which course would result in the fewest regrets when he was 80. He called this his regret minimization framework (You can tell he is a computer science grad). He didn’t think he’d regret leaving a job, because he could always find another job. Leaving mid-year meant giving up his annual bonus, which was a big deal to him at the time, but he didn’t think his 80-year-old self would be concerned about it. He didn’t think he’d regret trying the internet business and failing because then he’d just get another job. The one thing he felt he’d really regret would be not trying and always wondering what could have been. It’s the old Mark Twain quote. We don’t regret the things we do as much as the things we don’t do.
So as you think about your life and how you want to spend it, use a regret minimization framework. What actions and decisions will result in the least amount of regret for your future self? Pursue those things. Yes, it might be scary, but it will ultimately result in the greatest level of happiness and fulfillment.
“Life isn’t about finding yourself. Life is about creating yourself.” – George Bernard Shaw.
When I was in college a friend of mine dropped out and said, “I’m going to move to Colorado for a year and try to find myself.” This totally made sense at the time. None of us had an overarching vision for our life or, for that matter, had the slightest idea what the future held beyond the current semester. If my friend could find the answer on a ski lift, more power to him.
The older I get however, the more I realize that George Bernard Shaw was right. You don’t find yourself. You create yourself. Nowhere is this more true than with retirement. Finding yourself implies a certain level of randomness and passivity. Be patient. Keep your eyes open. Wait for the puzzle pieces to fall into place. Maybe the life you want is just around the corner. Not only does that almost never work, but in retirement the clock is ticking. You don’t have the luxury of waiting to allow your dream life to gradually materialize.
If it’s up to you to create yourself, then you need to be proactive. As Teddy Roosevelt was fond of saying, you need to “get action.” You need to think like a designer or a builder. You need to test, experiment, iterate, be curious and try things. The goal is a well-designed life. A well-designed retirement. You take pieces like friends, activities, skills, wants, relationships and locations and you mold them into the life you want. Whatever you come up with won’t be perfect. There’s no “right” answer. But you’ll learn and grow from each iteration and gradually move closer to the life that feels like your true self. Not because you found it, but because you built it.
My U.S. readers have a chance to put this into practice right away. You have a long holiday weekend, starting today. How can you make the most of it?
“Get action. Do things; be sane; don’t fritter away your time; create, act, take a place wherever you are and be somebody; get action.” – Theodore Roosevelt
Have a great weekend!
There are so many things that sound great in theory, but aren’t always great in practice. Take retirement for example. No work. Loads of free time. Travel. Those all sound great (and most of the time they are), but I’ve had retirees complain about every single one of them at one point or another over the years. That’s why it’s so important to think about your plans and ask yourself this question before you enter retirement:
Do I really want this or do I just think I want it?
Another way to ask that might be “Do I want this in theory or in practice?” Ask it of every major item on your retirement “To-do” list. The only real way to answer that question is to experiment with your plans. In other words, you actually start doing things. Shocking concept! You need to take all the things you have planned for “Someday” and start experimenting with them today.
This is not a trivial exercise. It turns out that we’re pretty bad at predicting the things that will make us happy. Scientists like Dan Gilbert at Harvard have done research that proves this. So experimenting and doing the things on your list is a critical step to determine whether you’re on point or you need to go back to the drawing board.
And don’t feel bad if you don’t have things totally figured out. None of us do. That’s what experiments are for. Ralph Waldo Emerson once said:
“Do not be too timid and squeamish about your actions. All life is an experiment. The more experiments you make the better. What if they are a little course, and you may get your coat soiled or torn? What if you do fail, and get fairly rolled in the dirt once or twice? Up again, you shall never be so afraid of a tumble.”
Take those words to heart. Don’t wait. Get out of the lecture and into the lab. Experiment. Test. Refine. Who cares if it’s not perfect. Who cares if you get dusty or bloodied. You’ll learn from it and get better. Just start trying things. As you do, your brain will make certain connections, you’ll meet people that will be integral to your plans, you’ll develop skills you need, you’ll build confidence, you’ll sharpen your focus. None of that stuff happens overnight. You can’t flip a switch and have total clarity regarding your purpose, plans and priorities. It takes time. The sooner you start, the better prepared you’ll be to make the most out of your retirement years.
I’ve helped many people transition into retirement over the years and when I ask a new retiree how things are going, the response is generally positive. That said, retirement is a huge transition and there are always unexpected feelings or emotions that crop up. That doesn’t necessarily mean that there’s something wrong with your retirement. It just means that you’re normal. So don’t be surprised if you feel one or more of the following:
The Problem: I feel guilty.
This is surprisingly common and I’ve seen it manifest itself in two ways. The first is guilt if you’re not doing much or making the most of your time. You finally have some free time and you struggle with how to use it. You feel guilty because watching T.V. or running errands doesn’t quite feel like sucking the marrow out of life.
The second is guilt if you’re doing fun stuff that your friends and family aren’t doing because they’re still working. I’ve actually had clients hesitate before responding to me when I ask “What did you do today?” The answer is “I went golfing” or “We saw a matinee and then went for a walk” but they are hesitant to say that because they know I spent my day behind a desk. When prodded, they say they don’t want to make others feel bad or come across as boastful.
For the first type of guilt, don’t worry! You’ll get better at it. You control a much bigger piece of your time in retirement and that takes some getting used to. Work hard to do things that leave you feeling happy and fulfilled, but keep in mind that not every minute of your day has to be spent bungee jumping or traveling. Sometimes the best way to spend a day is binge watching House of Cards on Netflix.
For the second type of guilt, just allow it to pass. Don’t become an insufferable braggart, but don’t feel guilty about enjoying your life either. You worked hard and made good decisions. Enjoy your time.
The problem: I’m second guessing my decision.
Buyer’s remorse is a real thing. Chances are you’ve felt it if you’ve ever bought a house or had to make some similar big decision and feared making the wrong choice. It can creep up after retirement as well and cause you to question whether you should have retired in the first place.
I have a client who has been dealing with this lately and she shared something that I thought was really insightful. She said, “Whenever I second guess my decision, I focus on why I retired in the first place.” Her choice would have been to work for five more years, but two things happened: Her mom was diagnosed with Alzheimer’s and her grandkids were all at an age when hanging out with grandma was just about the best the thing ever. If she had stuck to her timeline and worked for five more years, there’s a pretty good chance that her mom may no longer be around and her by then teenage grandkids will have priorities other than grandma. In other words, she gave something up, but got something far greater in return. There are pros and cons with most decisions in life. Retirement is no different. Keep that in mind.
The problem: I feel disappointed.
Most of us have an idealized view of retirement. Add years of anticipation to the mix or a personality that enjoys the structure and challenge of work and it’s not uncommon to feel a bit underwhelmed after entering retirement.
The best way to avoid disappointment is to retire TO something rather than FROM something. If all you do is subtract things—work, obligations, commitments—you simply create a void in your life. That void can open you to self-doubt, regret, lack of purpose and boredom. Nature abhors a vacuum. If you take something out, you need to replace it with something else (e.g. travel, school, a second career, hobby, etc.). The goal is not to do nothing. That just creates a void. The goal is to do what excites you.
And test those plans out before you retire. I most often see disappointment arise when a person has prepared for retirement using all lesson and no lab. In other words, all of their retirement plans are in their head or on a sheet of paper, and they haven’t spent any time actually testing and refining those plans. Reality can’t compete with 40 years of idealized assumptions.
The problem: I feel like a fish out of water.
No matter how prepared you think you are for retirement, you will probably still struggle. It’s a huge transition. The routine you’ve had for the last 40 years is out the window. That can be a bit disorienting for many people.
When talking with a client recently, she compared retirement to becoming a parent for the first time. “Before becoming parents we read books, painted the nursery, sought advice from other parents and bought all the cribs, carriers and countless other things that parents need. We thought we were totally prepared. And then we had our first child and all that went out the window. Retirement is similar. As prepared as you think you are, you really can’t grasp what it takes or what it will be like until you’re actually living it. Your experience will be totally different than the guy next door.” Great advice. Yes, there are tons of things that you can and should do to prepare, but the battle is always different than basic training. Don’t get discouraged. You’ll figure it out and get better at it with practice. Focus on living the life that you want to live. Imagine your ideal life and then work backwards from there to figure out the most direct path to where you want to be. Focus intently on the things that matter to you and throw yourself into them wholeheartedly. That kind of focus and tactical thinking will help you rapidly flatten your learning curve and smooth your transition into retirement.
Remember that retirement is not a date on the calendar, it’s a life stage that will last for years. Think back to when you first became an adult. Were you better at it at 28 than you were at 18? Of course. The same will be true with retirement. It might feel a little awkward at first, but you’ll get better at it over time.