More Than Money
Issue #42
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More Than Money Magazine

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“In Person - Two Guys, Two Real Stories of Wrestling with Success”

Jason is a self-employed entrepreneur. David took early retirement five years ago, at age 44, when his technology company was acquired. The two had been college friends. They had drifted into careers and families far apart but later moved by chance to the same suburban Boston town. Each had worked hard and made a lot of money—enough to wonder what money and success are really about and to question the meaning of each in their lives.

They went to a discussion group for men with similar questions and were urged to express their goals, conflicts, values and questions around money and careers as honestly as possible. Jason and David decided to continue in that spirit by writing each other.

Below are excerpts from their correspondence, edited to disguise their identities and published here with their permission. The men ask questions rather than pose answers. We share their words to throw a fresh light on questions that many of us ask ourselves privately—and in the hope that their spirit of frank inquiry and reflection will be an example to others.

Dear David,

... On money, I want to earn 30 percent more than l did last year (that is, about $300K) with about the same time commitment. I want to take one week more vacation each year for the next 10. Alternatively, I want to have a new way of looking at life that makes a different income OK. In truth, I don’t like the thought of doing the same work for the same money for the next 10 years. That feels like a trap and a defeat.

But the problem is, I know in advance I’ll resist all the suggestions you make for how to break into some new mode. I want to be free, creative, bold, energetic—but my first response is to keep on doing what I’m doing and find reasons why anything else is a bad idea.

Like the idea that I could stop working. How does that make me feel? Several things. One is disdain for myself for giving up. I have to face it: my selfworth is tied very closely to my earnings. I’m afraid I won’t find anything else to give meaning to my life. Or I worry I won’t have enough money. My wife thinks I’m too money-oriented. She thinks my retirement goal of $1.5M net worth is too high. Right now, it’s $1.1M. Part of me wants to keep plugging till I hit that number, but then I look around at age 49 and realize, I do want to do greater things than I have so far, as measured by impact on the world, personal growth and satisfaction. I want to do different work than I am doing now. I want my wife and me to have some common understanding about the focus of our lives after our children are grown. So even though I’m stubborn about change, I want you to keep being tough on getting me to a better place. I am grateful for where I am, but I still have lots of fire to want to be the best I can be, not just good.


Dear Jason,

Is it $300K per year that you want? Perhaps thinking less about the money and more about what you really want could take you to a better place. I see money as a proxy. It can’t directly get me what I want most. I’m thinking back about gadgets and cars—the length of time they ‘thrilled’ me was remarkably short.

... I know what you mean about fearing you won’t find something else in life that gives you meaning. Since I left, it’s only been the support of my wife and family that’s led me to feel that my “non-work self”’ is important and loved.

... It sounds crazy, but my top question is whether I’m retired. Our net is over $1.5M (plus insurance), and we’ve adjusted our lifestyle to make that work. But I’m not at peace with that being enough, given my life expectancy of 90, kids in college, my Dad, who will likely run out of money, and a son-in-law who is unable to work (and grandkids in that family). Then there are my parents-in-law; we’re not even sure of their financial ‘legs’.

Also: what’s my financial responsibility to all that [extended] family? Money spent to help them could cause me to run out of cash late in life. Plus there’s a chance my wife could outlive me by 10 years, and I have first-line responsibility there.

So, despite what I said above, I feel I should go back to work. When I retired, I quit with no real idea about the future other than a deep and desperate need to get the heck out. I don’t regret it. I remember all too well those anxious talks when [my wife] would say my job was going to kill me! Whatever “goals” I had when I quit I have already exceeded just by getting back in touch with my family.

But it’s never so easy, right? I have this worry thing about money and am thinking I should start over somewhere. I do get some joy from work. On the other hand, I’ve felt like that before, and I know it can get old quick. Then there’s the emotional pull of having one’s self-worth tied to job and pay. It took me a long time to get over (and I still haven’t completely) missing the respect I got as a chief operating officer. Fact is, people treat you as your job. Most people cannot fathom how I would ever give up that role and the status and money that went with it.

I have to remind myself that most of the senior managers at the company had problems at home, which I saw as a consequence of mental and physical time away from their families —a frightening array of problems with kids, wives, affairs, divorce, drinking and more. I honestly can’t remember one person who worked at that level and had balance.

Oh yes, balance. I’m just not sure how to get over this question about having “enough” to retire. One way is just to have so much money that it’s a no-brainer. Another is to trust fate. Not my style to do that. But I want to try. I will say again that I’m blessed with my wife, probably the only person who could put up with what I’ve been describing. A lot is in flux, but she is my rock.


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