A former colleague in his forties was recently telling me about his future retirement plans, and it triggered this random recollection:

Last March I went to dinner with the investors of my startup to celebrate the closing of our A round. Over dinner and drinks, the topic of retirement came up via an offhand comment by one of the attendees. The comment stirred Bob Davoli, managing partner at Sigma Prime, to make a comment that went something like this (paraphrased): “I don’t really understand retirement. Do you think Michelangelo retired? Woke up one day and said: well, it’s time to hang up the paintbrush? If you’re passionate about what you do, why would you ever want to stop doing it?”

Bob’s comment made me recall my first meeting with a financial advisor, set up by my wife when I was 28 (and making more money than any 28 year old geek should). The advisor asked me: “So what age do you plan to retire?” I remember being both surprised and slightly annoyed. Why would I ever retire? I had been doing the same thing since I was 11 years old: writing code, creating software, having fun.

So if one of my boys ever approaches me after growing up to discuss their retirement, my advice will be simple: save money like you are going to retire, and then change careers to something that makes you never want to. And then I’ll go back to doing the same thing I have been doing since the age of 11. ;)

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