For nearly half a century, my identity was topped by a piece of headgear: the Attorney Hat. It was a fedora of authority. As a divorce lawyer for over 47 years, I was the one who asked the questions to command the room, the one who smelled the traps, and the one who steered the ship through the choppy waters of “who gets the timeshare.” I was the professional navigator of other people’s chaos.
But retirement and the shifting tectonic plates of a long life have forced me into a different wardrobe. These days, I’m often “switching hats.” The irony is that while my titles have changed, my habits haven’t; I am still the man with the questions, only now, I’m often wearing the wrong hat for the job.
The accidental MD
Recently, a doctor client of mine contacted me after an illness. We discussed his case, but my brain decided it was time for a wardrobe change. I found myself leaning in to cross-examine his recovery.
I asked about his current health and the duration of his illness. It turns out that after decades of “fixing” lives, the instinct to heal outruns the billable hour. I may not have a medical degree, but at that moment, I was wearing the white coat, at least in my own head.
The home-front deposition
The most frequent hat-swap happens in my marriage to Lissa. I’ll describe a particularly gnarly situation in a mediation case of mine, expecting a sympathetic ear and perhaps a “That sounds difficult, Jeff.”
Instead, Lissa puts on the Chief Investigator Hat. She asks questions that challenge my tactical choices and force me to defend my reasoning. Suddenly, the roles are inverted. I am no longer the expert giving a report; I am the star witness for the defense, sweating under the desk lamp of her logic.
The “Dad, let us handle this” hat
Then there is the slightly itchy hat I wear with my adult children. For decades, the flow of advice was a one-way street. I was the Fountain of Wisdom.
Now, I find myself wearing the Student Cap. My children, who are adults with their own formidable opinions, offer me advice. Taking advice from the people who you taught how to tie their shoes involves admitting that the world has changed. My success in helping them become thriving independent adults means I am no longer the smartest person in the room. I’m just the guy who can’t find the “mute” button on Zoom (actually, I can at least do that much).
The humble citizen of Los Gatos
Finally, there is the Patient Citizen Hat. Living in Los Gatos, it is tempting to put the legal fedora back on when I see the Town Council wrestling with our traffic or the puzzle of the municipal budget.
Every time I’m stuck crawling down Santa Cruz Avenue, the old attorney in me starts looking for someone to sue. I’ve realized that Los Gatos traffic is a place where the “Statute of Limitations” refers to how many cars can make it through a green light before it turns red. Trying to get across town on a Saturday afternoon feels like a “continuance” that never ends.
But then I look at the complexities of fire safety in our hills or the delicate balancing act of funding community services, and I realize the “Defense” has a much harder job than it looks. 47 years in the courtroom taught me one immutable truth: you never know the strength of a case until you’ve seen the evidence you don’t have. I’ve made a conscious choice not to “armchair quarterback” the Council’s budgetary decisions without having reviewed the spreadsheets and the legal constraints they are balancing. It turns out that being a good neighbor sometimes means leaving the “Expert” hat on the rack and just wearing the one that says, “I’m listening.”
Conclusion
Switching hats is about the courage to be a “beginner” again. Whether I’m playing doctor to a doctor client, witness to my wife, or student to my children, each new hat offers a better view. After 47 years of being the man with the authoritative answers, it’s quite a relief to be the man with the inquisitive questions. I’ve traded the cross-examination for the conversation, and it turns out the view is much better from this side of the table.
