What retired millionaires say about wealth, regret, and what mattered

Executive overview

Most people assume wealth delivers happiness and erases regret. It rarely does. The millionaires interviewed here — across tech, consulting, aerospace, and retail — converge on a few consistent truths: relationships outlast money, regret clusters around time not spent with people, and the real work is learning to sell yourself.

Money reduces stress. Beyond that, its value depends on what you do with it.

What they said about money

• Reduces stress more than it creates happiness
• "Relationships are the currency of life" — better relationships, better life
• Money can buy things that create happiness, but not happiness itself
• Astronaut salary: $60–110k (civil service); private sector doubled or tripled it
• Goal once financially secure: spend it all before dying, give back to community

Regrets and what they would change

• Most common regret: not enough time with kids while building the business
• Not collecting enough names and contacts early in a career
• Not learning to sell earlier
• Not writing things down — ideas, plans, historical artifacts
• Several said they have no regrets; life worked out too well to second-guess

Advice to younger people

• Drop entitlement; expect setbacks and keep working through them
• Stop describing what you do — say what the client gains: "what's in it for me"
• Write stuff down, recruit a mentor, build a peer network
• Avoid people who are only out for themselves
• If you want to succeed without adversity, it won't happen — "prizefighters get hit"

Best and worst money spent

• Best: self-development, family experiences, paying for kids' education
• Building a home with emotional resonance outlasts material purchases
• Running a trade school and preschool funded personally — community investment
• Worst: unreliable vehicles (a Jeep no one wanted, a car lost to a hurricane)
• A 50-knot boat that nearly killed its owner; replaced with a 12-knot cruiser

Quotes they live by

• "A rising tide rarely lifts all boats — you still have to be good"
• "You can't look at the wake; look through the windshield"
• "If it is to be, it is up to me"