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.

~ Joe