About
A lawyer named Shmiddy walks into a keynote…
Twenty-plus years building professional credibility is a long time to spend while everyone still calls you Shmiddy. I gave up fighting it somewhere around the second bar exam.
Friends have called me Shmiddy since I was a kid. It has followed me through two states, two bar exams, boardrooms, depositions, a film set, and a lot of stages. At some point I realized the nickname was not the thing undercutting my credibility. It was the thing making me memorable.
On paper I am an attorney and an executive. I have practiced law for over twenty years and served as Chief Legal Officer of a health and wellness company with more than $3 billion in lifetime sales. Contracts, negotiations, litigation, regulatory work, transactions, and the kind of executive decisions that keep you up at night. That is the part of the resume that gets me in the building.
The part that actually explains me
I went to law school married, with four kids, and paid my own way. Nobody recommends that. There was no five-year plan in that house. There was a very short list of things that had to happen this month, and a stubborn belief that if I kept building, something would open up.
Something did. Then something else did. And the pattern I noticed, looking back, was not that I had chosen correctly. It was that I had accumulated enough skills, enough relationships, and enough nerve that when a door appeared, I was in a position to walk through it.
Then I kept saying yes to things
I could have let attorney become my entire identity. Plenty of people do, and the profession quietly encourages it. Instead I started businesses. I invested. I got in front of a camera and acted. And I got deliberate about being funny, which turns out to be the most useful professional skill nobody puts on a resume.
None of it was a pivot away from the law. It was the same person collecting more options. The lawyer got better because of the comedy. The businesses got better because of the lawyer. The speaking got better because of all of it.
Why I talk about this
Because the question people get asked, over and over, from about age eighteen until they retire, is where they will be in five years. And that question has ruined more good decisions than almost anything else I can think of.
I am not on stage to tell anyone I have it figured out. I am on stage to make a case: build the skills, the relationships, the reputation, the financial breathing room, and the nerve, and you will have options when life does the thing life does. That is a better bet than a plan, and it is considerably funnier to talk about.
The rest of it
My wife and I have been married about thirty-five years, which either qualifies me to give advice or disqualifies me from ever giving it again depending on which of us you ask. Four adult kids. A growing pile of grandkids. I have done my time in Toastmasters. I still get nervous before I go on.
For the record keepers: licensed to practice law in Texas and Virginia. Named one of the Top 10 Corporate Counsel in the world at the 2024 OnCon Icon Awards. An official member of the Forbes Business Development Council since 2026, where I write for Forbes.com about leadership, meaningful work, and why serious people should not take themselves too seriously.
Attorney. Executive. Entrepreneur. Actor. Humorist. Husband. Dad. Grandpa. Not one of those was on a five-year plan.
The receipts
The award itself
Top 10 Corporate Counsel, 2024 OnCon Icon Awards. Winners are chosen from global nominations by peer and public vote, and there is no fee to enter, to be a finalist, or to win.