…my business coach taunted. I had been whining for the umpteenth time about why once again I couldn’t get around to fleshing out my latest entrepreneurial project. (A “business Will”/operations manual for solo business owners. Super-cool idea to avoid probate).

First distraction: escaping from NYC which was turning into an Orwellian dystopia – no thanks to decades of feckless local politics and COVID. Then, it was settling into my new home near Charleston SC. Setting up my remote law practice. My mother died. Her house of 40 years had to be cleaned out. Law clients needed contracts reviewed. I traveled a lot for family events.

“You’ve been making excuses for months,” he said. “When you really want to take action, you find a way despite the obstacles. But you’re letting the obstacles sidetrack you. Honestly, I don’t think you want to do this. The business project. The law practice. Any of it.”

I left that call chastened. But it was the “Gibbs-slap” I needed to ask myself:

Does my work spark the same joy it did when I started 25 years ago?

Is this still the path of useful service I want to follow for as long as I’m mentally sharp and physically able?

Am I truly free to explore new horizons while still tethered to what I’m currently doing?

And the answers were



And Hell No.

I’m an SBA award-winning business attorney

I was good – really good – at being a strategic advocate for entrepreneurs.  A powerful communicator and educator too, as an Entrepreneur.com columnist and blogger, podcast host, book author, and speaker with my own video channel. Multiple award-winner with a national reputation as an Influencer in entrepreneurship.

Yet I wasn’t happy. Not unhappy … but my enthusiasm had atrophied. I had proved I could transport my 25-year-old law practice out of NYC without a hitch. But my new surroundings (Trees! Birdsong! Beaches only 25 minutes away!), Southern hospitality, and slower pace gave me breathing room to remake my life in a new way. Which opened space for Divine discontent to shine through.

I had been on the high-achiever hamster wheel since I was a kid. Wellesley College graduate (with honors!). London School of Economics for grad school. Boston University Law School. 1st law job. 2nd, 3rd, 4th job. Started a NYC law firm with a partner. Went through “business divorce” 12 years later. Reinvented a solo practice which I maintained for the next 14 years. Never stopping to ask, Is this really who I still am and what I want?

If not now, when?

The Jewish philosopher Martin Buber tells this story in his Tales of the Hasidim:

A rabbi named Zusya died and went to stand before the judgment seat of God. As he waited for God to appear, he grew nervous thinking about his life and how little he had done. He began to imagine that God was going to ask him, “Why weren’t you Moses or why weren’t you Solomon or why weren’t you David?” But when God appeared, the rabbi was surprised. God simply asked, “Why weren’t you Zusya?”

That’s why I owe it to myself to get off the hamster wheel and explore these issues now. I can’t focus on “what’s next?” while I’m mired in “what’s now?”

Where am I being led? Rabbinical school? Choral music? Travel? A fresh use for my law license?

I have no idea. (Yet). But I can promise you this:

It’ll be a helluva journey.