There’s an old saying, credited to so many people over the years that I’ve stopped trying to figure out who said it first, that the harder you work the luckier you get. I’d tweak it a bit. Hard work doesn’t make you lucky, but it puts you in the path of luck far more often than sitting still ever will. When I look back at the clients I’ve gained over my career, many of those relationships started with what looked like a lucky break: a referral out of the blue, a phone call at just the right moment, a chance…
Continue Reading The Harder You Work, the More Chances You Have to Be Lucky

That’s the thing, you walk out your front door and you have no idea what will happen. You don’t know who you’ll sit next to, who you’ll be introduced to, or whose path is about to cross yours for thirty seconds that turn out to matter more than a year of scheduled meetings. Most professionals treat this uncertainty as a reason to stay home, to skip the event, to send an email instead of showing up. I think about it the opposite way. The uncertainty is the entire value proposition. You cannot script who you’re going to meet, and if…
Continue Reading You Have No Idea What Will Happen, and That’s the Point

Early in my career I noticed that whenever I was avoiding a decision, it usually wasn’t because I didn’t know what to do. It was because I knew exactly what to do and didn’t want to do it. The hard conversation with a client about a case that isn’t going the way they hoped. Telling a partner their strategy has a problem. Cutting ties with someone who isn’t working out even though you like them personally. None of these require more research or more time to think. What they require is the willingness to sit in the discomfort long enough…
Continue Reading Most of the Time the Hardest Thing and the Right Thing Are the Same

I have watched people mistake civility for softness many times, and it is one of the more expensive misreadings a professional can make. Being kind to a colleague, a partner, or opposing counsel does not mean you have surrendered your judgment, your position, or your resolve. It means you have chosen a way of operating that costs you nothing and often buys you a great deal. The professionals who last are not the ones who confuse decency with a lack of spine. They are the ones who have learned that you can be warm in the room and sharp on…
Continue Reading Don’t Accept Kindness as Weakness

I ask a version of the question “what lights you up?” to younger attorneys, friends, and clients all the time. This is not what pays the bills, not what your resume says you’re good at, not what your parents or your professors told you made a respectable career. What actually lights you up. Most people don’t initially have an answer to the question because they’ve spent so many years optimizing for stability, prestige, or the next title that they’ve lost track of the feeling entirely. If you want a shortcut back to the answer, stop asking what you’re supposed to…
Continue Reading What lights you up?

Making the right decision feels like the finish line, but it’s really just the starting gun. I have watched attorneys agonize over which case strategy to pursue, which path to recommend to a client, as if the correctness of the choice itself was the whole job. It isn’t. The decision is only half of it. What happens after you decide, how you execute, how you communicate it, how you own it when it gets hard, is the part that actually determines whether the “right” decision turns out to have been right at all. You can pick the smartest option in…
Continue Reading Make the Decision Right

Dolly Parton passed away yesterday at 80, and by last night my feed was already full of thoughtful quotes her fans refer to as “Dollyisms, repeated so many times they are remembered. That happens with people who spend seven decades telling the truth in a way nobody minds hearing. You don’t get quoted that much by accident. You get quoted that much because you kept saying things that were simple on the surface and heavy underneath, and people kept needing to hear them.

The line of hers I keep coming back to is “Find out who you are and do…
Continue Reading Be Like Dolly: Find Out Who You Are and Do It on Purpose

We tell ourselves a story about limits, and the story is almost never true. It holds you back even when you have talent or are in the right circumstance. This happens because of people’s fears. Fear is clever that way. It rarely announces itself. It shows up disguised as “I’m just being practical” or “now isn’t the right time,” and because it sounds so reasonable, you believe it. You mistake the voice of fear for the voice of good judgment, and then you spend years living inside a boundary that was never actually there.

Nobody will tell you that the…
Continue Reading Fear We Manufacture

A few weeks ago I was standing inside a restaurant by the front door, waiting to be seated with my daughter and extended family in front of me. A man who looked like he might be homeless rode up on a bike, stopped, walked in, and came up quietly behind me. Before I even knew he was there, he put his hand on my shoulder and whispered, “Be the difference you want to see in the world.” I said the only thing that came out, “Exactly,” loud enough that my family heard it too, and for a second nobody quite…
Continue Reading Be the Difference You Want to See in the World

I learned so much from reading. Which sparks ideas. Try it. That’s really the whole thesis, and I could stop right there, but the old ad line deserves better than a one-sentence drive-by. Reading Is Fundamental was a public service campaign decades before anyone worried about attention spans and doom-scrolling, and it turns out the slogan undersold itself. Reading isn’t just fundamental to literacy. It’s fundamental to how professionals think, argue, negotiate, and eventually distinguish themselves from everyone else doing the same job the same way.

Books in particular do something a headline or a hot take cannot. A good…
Continue Reading Reading Is Fundamental, and Nobody Ever Told You Why It Still Matters

People love to talk about reinvention like it’s some kind of magic trick, like you disappear one day and come back as somebody new. That’s not how it works. You don’t need to become somebody else. Instead, get loud about who you already are. There’s a difference, and it took me years to see it. Reinvention means you have to dig past everybody else’s opinion of what you’re supposed to be before you find the version of you that is actually running the show. Learning how to get there isn’t instant. It’s a slow, deliberate education in trusting your own…
Continue Reading Never Normal, Never Sorry

That number should reframe how every professional thinks about a bad day, a lost case, a client who walks, or a deal that falls through. Attorneys in particular tend to carry losses like weight, because the profession trains you to believe that competence means winning, consistently. But the math simply doesn’t support that belief, not even for the best in the world at what they do. You can build a successful career by being spectacular in aggregate while being almost exactly average point by point. The players and professionals who last are not the ones who avoid losing. They are…
Continue Reading Fifty-Four Percent

There is a certain kind of professional who makes the whole thing look easy. The attorney who stands up and delivers the perfect argument without seeming to reach for it. The advisor who reads a complicated situation in seconds and somehow already knows the move. Watching people like this, it is tempting to assume they were simply born with something the rest of us weren’t, which is comforting because it lets you off the hook. It is also wrong.

What actually produces that kind of polish is not some innate gift, it’s repetition. The argument that looked effortless was rehearsed,…
Continue Reading Effortless Is a Myth