When I was 35, I was convinced that wisdom worked like a checklist. You need to work hard. You need to treat people respectfully. You try to pay your bills (this could be an entire column by itself). You raise your kids and save your money.

I thought that, eventually, somewhere around middle age, all the big questions would sort themselves out. Now, at 53, I seem to have accumulated more questions than answers—many of them still arrive sometime around 2:30am on a Monday morning.

It’s not that anything is wrong—quite the opposite. Business is weird, but good. My family is healthy. Life is generally kind. Yet, here I am, staring at the ceiling and wondering about things my 35-year-old self would not have expected to be wondering about at this stage of life. For example…

Am I building a business, or have I built myself a very demanding job? For years I thought growth was the goal. I needed more clients, more revenue, more opportunity. Now I find myself asking: How much is enough?

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