The Heart of Money: When Should I Retire?

Question: I retired at age 55 and hated it, so I went to work as a barista—and love it. I am 73 now, and getting pressure from my kids, ex-wife, and a few friends to retire. Frankly, I don’t know what I would do with myself. I am fit and happy and would love to die of a heart attack while making a flat white. Economically, I could quit, but why?

Paul Sutherland: My definition of retirement is working when you want, how you want, if you want, and where you want. It sounds to me like you are retired already. I wrote the book 12 Steps to a Carefree Retirement and have studied retirement my whole career. So here are some thoughts:

1. Age is meaningless. I live in Uganda, where it is not uncommon to find 30-year-old grandmothers, and anyone over the age of 45 is considered old. When I lived on Maui, I got up at 4:00 a.m. to be in the office at 4:30 (9:30 EST, when the New York Stock Exchange opens). About three times a week, as I drove to work, I would see a biker heading in the opposite direction: an 88-year-old man who regularly biked from sea level to the top of the 10,000+ foot Haleakala Crater. Today, while picking up my 10-, 8-, and 5-year-old boys from school, accompanied by my 23-year-old son, I was chatting with a father who was picking up his 8-year-old daughter. I introduced my kids, and he said, “I have a 43-year-old son and a few kids in between my 8-year-old and him.” He was happy and laid-back. I’m sure you’ve met 35-year-olds who are dead inside and 90-year-olds still happily exploring every moment of life.

2. Hang out with people who love life and want to live forever. We become like the people with whom we associate. So, if you want to choose to feel old and run-down, then join the crowd that defines “retired” as “just waiting to die.” If you want to be young, then be active in the world of ideas: read, exercise, work, volunteer, do activities that are meaningfully important to you.

3. Never let your age be an excuse. I hear people of all ages, but mostly those over 40, wishing they had more options, saying, “I wish I had chosen a better job / got a different degree / saved more / got better investment returns, because then I could have the life I want.” I counsel that life lasts a long time, and there is no rulebook that orders which life events must happen at certain ages. Harland Sanders opened his first KFC when he was 62, Diane Rehm’s eponymous radio show was not syndicated nationally on NPR until she was 59, Charles Darwin published On the Origin of Species when he was 50, and Duncan Hines introduced his baked goods to the world when he was 72. I’ve met a 50-year-old woman who just started medical school, and I know an 88-year-old woman who still works a regular retail job. The latter is my mother, who calls the period in life after the children are grown the “My Turn” period. Today, thankfully, equality is becoming more mainstream and spouses can share the responsibilities of family, kids, finances, and career and not wait till the kids are gone to have a more balanced life.

4. Live ready to fail. Why don’t more people quit their job and go back to school at 50, become an artist at 60, or pivot toward a passion? Often this is simply due to a fear of failure, or of not succeeding. We find we reach “retirement” age never really having risked anything—we have safe relationships, safe work, safe 2.3 kids, safe schools, safe neighborhood, safe TV channels, safe friends, safe religion—and mostly never rocking the boat of our life or having an opinion with an edge. So, do the things you want to do! Why? Simply because you want to do them. If your kids, ex, or friends question your sanity, reply, “Why not?”

5. Aging is an adventure, and all of life is about connection. Every conflict, every pain, every tired muscle, and every relationship is an adventure. None of us, whether 16 or 66, knows what tomorrow may bring. The joy comes in seeing this unknown as an adventure. Focus your retirement years on connection. What connects you to your soul? What connects you to those you love? And what connects you to the friends you haven’t yet met (also known as strangers)? The happiest retired people I know experience a deep connection to one or more of these three things. Connection to others and to ourselves gives us meaning and purpose in our life.

I’m not sure that you owe anyone any explanation for how you spend your retirement years. But whenever someone asks me a question that makes me uncomfortable, I try to take a step back and examine what offends me and where the person may be coming from. Does your daughter worry that your barista job is taking time away from her children’s relationship with Grandpa? Are your friends worried about your health? Perhaps your ex is simply jealous of your extra income? It never hurts to consider things from someone else’s point of view, and it also never hurts to have a simple response when friends ask why you are working: “Why not?”