My Ideal Retirement Plan

I know that money wouldn’t make me happy, but I still had dreams of being an early retiree. I dreamt of being that person who quit their job, moved to Hawaii, and sipped margaritas while I cashed my dividend checks. But as I got older, I realized that it’s not about the age of retirement but the quality of that retirement.

Let’s start with someone that I thought I’d envy. In 2004, I met a 30-year-old who had just sold his company to Amazon. He was a nice guy so my wife and I were trying to set him up with some of our friends. How could this go wrong? Who wouldn’t want a nice Jewish rich man who retired at 30? The only problem was that he acted like he was retired. He didn’t go out much, watched a lot of TV, and volunteered at some very noble charities delivering food.  Though he was rich, no one wanted to date him because he lived a very boring life.

Then there’s the person who I do envy. She’s been working at Microsoft most of her career with brief stints at other tech companies. She’s acquired some profitable stock options and she’ll be able to retire in a few years at 45. But she isn’t going to retire because she likes the work. Maybe she’ll pull back to spend more time with family, but work will become a choice, not something she does to pay the bills.

People often have more than one “job” even if only one of them pays the bills. They may say, “I’m an accountant but I make furniture on the side.” These are both jobs but only one of them counts in our society—the one they get paid for. After retirement, you can choose the jobs that you do and don’t have to worry about what you are paid for.

While she’s in quite an envious position, my friend Christine blew my mind. One day Christine got a cold call from a money manager.

He said, “Hi Christine, I’m Bob and I can make your life much better. I’m a licensed financial planner and can help you retire much sooner. My clients are able to retire 5 years earlier with my planning.”

She said, “I think you have the wrong person. I don’t need your services.”

He said, “Do you have someone else? Because I have great rates and a phenomenal track record.”

“No,” she said, “you misunderstand me. I’m a tenured physics professor. My job pays me enough to meet my needs. Unlike other professions, I can work at a job that I love for as long as I want without the fear of being pushed out.”

He said, “But wouldn’t it be better to retire early.”

She said, “Again, you’re missing my point. I have no interest in retiring.” And that’s why I envy Christine the most.

Retirement is the ultimate in financial freedom, but like money in general, it’s a means to an end. I love this quote from Tim O’Reilly, “Money is like gas in the car—you need to pay attention or you’ll end up on the side of the road—but a successful business or a well-lived life is not a tour of gas stations.”