When My Career Caught the Mail Truck

Intro: One of my friends told me that at 33, married with a baby, she’s doing some soul searching. She thought at some point that she’d be set and have figured out her career, but she’s realized that things never settle and it’s all journey. This makes her a little sad and confused. Here’s my response:

Willy Wonka: “Don’t forget what happened to the man who suddenly got everything he wanted.”

Charlie Bucket: “What happened?”

Willy Wonka: “He lived happily ever after.”

Charlie and the Chocolate Factory

I used to think that there was a way to win the game of life. I thought there was a general scheme to the world and if I just worked hard enough, things would work out awesomely. This worked for a while. If I worked hard at school, I would get into a great college. If I worked hard in college I would get a great job. I thought this is the way that life worked too.

That’s the way the world looks when you’re young. Everything is defined and there are clear goals. A few years ago, one of my favorite mentees, a young and chipper Duke grad, was looking for career advice. She asked me questions like, “What was the most important factor in your success?” and “What’s the most effective way to rise up in this organization?”

After I answered her questions, I said, “These are really great questions but they’re not the right questions.”

“What do you mean?” she said.

“You’re asking what I’ve done to be successful. You should be thinking about what you want to do.”

Regardless of what I told her, I always thought there was something magical about technology companies. It’s not just me that thinks this way. There’s even a British newspaper that refers to Google as The Chocolate Factory because the company seems so much like Willy Wonka’s. I thought that when I got the job as Head of Banking for AWS, I would reach a state of nirvana and finally be happy with life.

Don’t get me wrong—Amazon is a great company. There’s nothing better than a quarterly town hall led by Jeff Bezos where he talks about Amazon’s drone strategy or shows off the new Amazon Go store. Working there was one of my life goals, but once I got there I felt like the dog who had caught the mail truck. I looked around and said, “Is that all there is? Just a company?” When I talk to my friends make Managing Director at a bank or Partner at a law firm they have a similar feeling.

I should have realized that being part of a company or organization doesn’t change who you are. During my first week at Yale, I was in the courtyard of Silliman College⁽¹⁾Silliman College is one of Yale’s 14 residential colleges. These are like dorms on steroids. saying, “How crazy is this?! Everyone here is a Yalie.” I got some pretty weird looks that day because it’s so obviously true. But the crazy thing is that a year earlier, none of the freshmen was a Yalie. It made me realize that just getting into Yale doesn’t give you some sort of superpower, even though you’ve acquired some prestige from the outside.

So did catching the mail truck make me happy? I really enjoyed working at such a prestigious company and liked the admiration I got from others, but it didn’t make me happy. In Yale’s most popular class,⁽²⁾I took the online class, The Science of Well-Being, and wrote up some notes. Professor Laurie Santos teaches the difference between “What you think will make you happy” and “What will actually make you happy.” People have a good idea of what they think a great job will be: high paying and prestigious. But these are societal expectations that won’t actually make you happy. As Paul Graham says, “Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.”⁽³⁾Or as Steve Jobs said, “Your time is limited, so don’t waste it living someone else’s life.”

But the generic perfect job, like the generic perfect spouse, doesn’t exist. While there is no generic “great job” that makes everyone happy, there is a “great job for you.” Similar to dating, trying to go after the job that everyone else lusts after isn’t a recipe for success. You need to find a job that fits you. Professor Santos says that you’ll be happiest in a job where you can be your authentic self. That sounds very vague and generic but it isn’t. You can take a quiz to identify your strengths and find a job that leverages those strengths.

For me, I had another issue because I caught the mail truck in midlfe.⁽⁴⁾Here’s the dirty little secret of midlife. As Jonathan Rauch writes in The Happiness Curve (or for a shorter version check out The Real Roots of Midlife Crisis) catching the mail truck in midlife should make you really happy—but it doesn’t. It makes you look at all the things you failed to accomplish and how life could have gone differently. And you feel even worse because things, on the whole, are actually pretty awesome from an objective perspective. The good news is that things get better over time as you adjust to the new reality I’ve accomplished a lot in my career, but things were starting to change. I’m was now closer to retirement than to college.

To be happy in any stage of life you need three things: freedom, friends, and impact.⁽⁵⁾Of course you achieve these things differently at different lifestage. I like the idea that there are three things that you have in life: energy, money, and time. When you’re young you have energy and time but no money. In midlife you have energy and money but no time. As as you get onder you have time and money but no energy. In college it was easy. You had the freedom from your parents for the first time. Your friends were all around you. And, in a misguided sense of delusion, you thought you were going to change the world.

As you get older, you gradually get more freedom and have to decide your own path through life. It’s not like college anymore. It’s more like retirement planning. That may sound lackluster and boring but that’s because we think of retirement planning as merely a financial exercise. I’m thinking about it as a complete package. Once you have financial freedom to retire, what will you spend your time doing? As I wrote about in My Ideal Retirement Plan some people are lucky enough to make money doing what they love—seeing no difference between midlife and retirement life. But for the rest of us, we need to build up the retirement life that we want. This is important because retiring is the ultimate mail truck. You have the ultimate freedom to do what you want. But what do you want to do?

You’d think freedom would be an awesome thing. I mean, what’s better than having the ability to do whatever you want whenever you want? While that might sound great to some people, others (like me) think that being retired sounds a lot like being unemployed. Now I’m not saying that you need to be making a lot of money in your retirement, just that most people find fulfillment in working towards a purpose⁽⁶⁾This idea of working in retirement may seem a little odd to you and almost sacrilegious. You probably thought that the purpose of retirement was not to think about these types of things. But freedom without purpose can lead to anxiety. I remember reading Isaac Asimov’s Treasury of Humor in high school. Asimov wrote this book on vacation because he considered a three-week vacation in the Catskills “vacationing” hell on earth so he started writing a book. This of course was a bit irregular. He pointed out that the front desk of his posh hotel didn’t have a typewriter to lend him and thought the request quite odd. At the time I thought, “What an odd man who would rather work than vacation.” But now I realize that when I go on a “relaxing” beach vacation, I want to wake up early in the morning and get some writing done!⁽⁷⁾Steven Covey, in his book The Third Alternative writes about this idea. Covey says that most people only see two alternatives, “continue working” or “retire.” And by “retire” most people think about “retiring to leisure.” Instead, Covey say that we should focus on “retiring to purpose.”

Here’s an example of a great retirement plan from my friend Michelle, including the same factors of happiness: financial, friends, and impact. She hasn’t retired yet, but she’d been planning her retirement for over a decade.

1. Financial. Michelle had annuity investments that would spin off quite a healthy income for the rest of her life.
2. Friends. Michelle joined a knitting group and a golf group so she has a group of friends apart from work to socialize with.
3. Impact. Her son is starting a nonprofit to increase literacy for underprivileged kids. While Michelle doesn’t know much about the nonprofit world, she can use her business skills to help get this off the ground.

I’ve started my retirement planning as well. It’s not just about actually retiring as much as it is things today that I really enjoy. Here’s my retirement plan:

1. Financial. We are saving money and frugally planning for the future. We view money as an enabler to current and future financial freedom.
2. Friends. I’m realizing (and writing about) how important it is to spend time with friends and family. I’m making sure to spend quality time with my kids whether it’s watching a movie or playing ping pong. I’m also appreciating my friends more and am continuously humbled to have such wonderful friends.
3. Impact. I’m realizing that I can’t get all of my self-worth from my job.⁽⁸⁾I’ve learned from people like Michelle is that they separate “who they are” from “what they do.” At Amazon, there’s even a space in your personal profile labeled “What are you passionate about.” At Amazon, for a while, I put up a quote from the movie Say Anything, “When I was growing up, I didn’t want to sell anything, buy anything, or process anything. I didn’t want to sell anything bought or processed or buy anything sold or processed, or process anything sold, bought, or processed, or repair anything sold, bought, or processed. But now that I’m at Amazon, I enjoy buying, selling, and processing everything.” While I enjoy my job and have a great boss, I also enjoy helping out start-ups and being appreciated for my writing.

Planning your life isn’t really about your age. Let’s check back in with my mentee from the beginning of this piece. We met when she asked me how to be successful at her current job. After we talked over a number of years and across a number of companies, she realized that she wasn’t in the right field at all. She started with a job in IT, focusing on going to business school. To get more prepared for business school she moved from IT to a job in management consulting but realized that that job, and business school in general, wasn’t the right for her. So instead of going to business school, she’s following her true passion and she’s going to be a doctor. See what you can do when you acknowledge your true passions early!

I’m trying something new by ending this article with questions and exercises to help you build out your own skills. Tell me if you find this useful:

• Spend some time thinking about the things that really make you happy? How can you structure your life to do more of this?
• Take the quiz to identify your strengths. How can you use these strengths more at work?
• Fill out the Five O’Clock Club’s 40-Year-Vision and Seven Stories to see what’s really important to you and how you can get there.
• Instead of asking people “What do you do?” ask them “What are you passionate about?”
• When people ask “What you do?” give an answer that focuses on more than the way you make money. Tell them about your passions and how you’re committed to making an impact in the world.