BusinessLawGuy's Blog

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 knew what to do with what had just happened. As I responded, he was gone, back out the door, back on the bike, back into the evening.

I will be honest that my first reaction was not gratitude, it was confusion. A stranger you don’t see coming putting a hand on you is the kind of moment that could have gone a very different direction, and I don’t think you get to skip past that part of the story just because it turned out fine. But it did turn out fine, and what was left once the surprise wore off was a sentence that has been sitting with me ever since, delivered by someone who had every reason to be asking me for something and instead handed me something of value.

The professional world runs on the assumption that change comes from the top, from the policy, from the person with the title and the budget. In practice, the culture of an office, a firm, or a courtroom hallway gets built one interaction at a time, by whoever decides to hold the door, give the credit, or tell the hard truth kindly instead of avoiding it. Nobody is waiting for permission to do that, and nobody needs a title to start. You do not need to run the company to be the reason a colleague has a better day than they expected to.

The same is true away from the office, waiting for a table with people who matter to you, which is exactly where I was when I heard it. I have no idea why that man stopped instead of riding past the restaurant. But he stopped, walked in, and said what he said. That is the whole lesson, and it doesn’t require a bike, a whisper, or a chance encounter to apply it. It requires deciding, in whatever room you happen to be standing in, that you are the one who is going to make it a little better, a little kinder, or a little more honest than you found it. Nobody is going to assign you that job. You have to take it.

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 book gives you the long version, the reasoning behind the conclusion, the mistakes the author made getting there. That is where ideas actually come from. Not from information alone, but from watching someone else’s thinking unfold across three hundred pages. You absorb a way of approaching problems, and one day it surfaces in a client meeting as an idea nobody else in the room had, because nobody else in the room had read that book. Magazines and blogs do their own version of this on a shorter timeline, but books ask more of you, and they give more back.

There’s a professional payoff here too, beyond the ideas themselves. Reading gives you something to talk about with people who are not talking about the same three things everyone else is talking about. Walk into a room able to reference something you read last month and you become memorable in a way that “how about this weather” never accomplishes. Clients remember the lawyer who connected their situation to something from outside the practice of law. It costs you nothing but the reading itself, and it pays you back in relationships and reputation.

None of this needs to be homework. Some of the best reading you can do has nothing to do with sharpening your professional edge at all. Pick up a novel, a memoir, something with no obvious application to your caseload or your quarterly numbers, and let it pull you away from work for an hour. That distance is its own kind of value, separate from whatever idea might come out of it later. So read the dense industry book if that’s what the moment calls for, but read the paperback that has nothing to do with your job too. Reading is fundamental precisely because it works on you in ways you can’t predict and can’t force. You just have to keep doing it and let it find you when you need it.

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 instincts over the room’s expectations.

For a long time I held back because I thought stepping outside the norm meant people would look at me differently. Then I had a realization that changed everything: Just like everyone else, I was never normal to begin with, so why was I performing normalcy as if it was a costume? People can only make you feel small about being different if some part of you still believe being different is a problem. I don’t. Being different is what makes us each interesting and unique.

Translate that into a career, a business, a boardroom, and the lesson doesn’t change. The professionals who are remembered aren’t the ones who followed the playbook the tightest. They’re the ones who looked at the playbook, understood it, and then wrote their own chapter. Every industry has its version of “the norm,” the safe lane everyone stays in because it’s proven and comfortable. But comfortable and forgettable are usually the same address. The entrepreneurs and professionals who you remember are the ones who got real with themselves before they ever pitched a room or launched a product.

I don’t believe in limits, and I don’t believe in staying in one lane, because life doesn’t hand any of us a lane to begin with. It handed me a wide-open field and a bunch of people standing at the edges telling me where the fence was supposed to be. I stopped listening to where the fence was supposed to be a long time ago. Whether it’s business, art, sports, music, or just how I choose to live day to day, I’m going after all of it, because that restless hunger to do more than one thing isn’t a distraction from purpose. For people like me, it is the purpose.

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 the ones who have made peace with losing and have built a system sturdy enough to keep producing excellent results anyway.

This was brought home in June 2024, when Roger Federer stood in front of the graduating class at Dartmouth College and told them something that should have felt deflating but instead landed as a liberating truth. Over the course of his career, he played 1,526 singles matches and won almost 80 percent of them. He hoisted 20 Grand Slam trophies, including a record eight at Wimbledon. And yet, across all of those matches, he won only 54% of the points he played. Yes, 54%. Barely more than a coin flip. Federer, one of the greatest to ever hold a racket, lost nearly every second point he played over the course of his career and still became one of the most decorated players to play the game.

What makes losing nearly every second point bearable, as Federer explained, is not a tolerance for losing so much as a discipline about what you do with it. He said that when you’re playing a point, it has to be the most important thing in the world, and it is. But when it’s behind you, it’s behind you. That sentence is worth sitting with because it describes a mental transaction most professionals never learn to complete. The lost point, the lost motion, the client who didn’t sign, the negotiation that went sideways — all of it demands your full presence while it’s happening and then you have to release it the instant it’s over. Federer’s point was that this mindset frees you to fully commit to the next point and the next point after that, with intensity, clarity, and focus.

I think about this constantly in the context of practicing law, because the profession is not built for forgiveness. You lose a motion, and it’s public. You lose a client, and it’s personal. You make a mistake, and it can follow you in ways a missed backhand never will. But the underlying mechanics are the same as they are on a tennis court. Replaying an unfavorable result over and over means you’re not fully present for the next thing. If you treat every setback as evidence of some deeper inadequacy you will eventually convince yourself that inadequacy is real. Federer won so much by being beaten on roughly half of every match he ever played, and he did it by refusing to let any single point outlive its own moment. That is not a tennis lesson. That is a career-long instruction manual, and it applies whether you are standing at the baseline or standing in front of a judge.

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, revised, and delivered badly a dozen times before it was ever delivered well. The instinct that read the room in four seconds was built by sitting through years of rooms that were misread. Ease, when you actually trace it back, is built on hard work and preparation that has been through enough repetitions that the labor itself becomes invisible. What you are seeing on the surface is the last five percent of a process that took time, being invested, and grit.

Here is the part that gets left out of most stories about grit. Putting in the work does not guarantee the outcome. You can prepare more thoroughly than anyone else in the room, argue the case better than you have ever argued anything, and still lose, because the other side had a stronger set of facts, or the judge saw it differently. Effort buys you your best possible version of the attempt. It does not buy you the result. Professionals who haven’t made peace with that distinction tend to treat every loss as proof that they didn’t work hard enough, when the truth is sometimes simpler and harder to accept: you did the work, and it still wasn’t enough this time. This is not the same thing as failure.

Perfection was never actually on the table, for you or for the person who makes it look easy. You want to reach the point where you’re just further along in absorbing the losses that come with doing hard things repeatedly, and better at not letting any single one of them define what you think you’re capable of. The standard worth chasing isn’t flawless work or guaranteed outcomes; it’s knowing you prepared as well as you could have, and having enough grit left over to show up fully the next time. That is the only version of mastery that actually exists, and it is available to everyone willing to keep doing the unglamorous part, the hard work.

Think of yourself as the patient. Your chief complaints include the same routine, the same vacations, the same everything. Your symptoms include days that are the same, vacations that are technically different locations but functionally the same trip, year after year, a vague sense that “someday” you’ll do something different, maybe right after this next busy season, and difficulty remembering the last time you thought about anything other than work, errands, and the next thing on the calendar.

This condition is common. It’s also quietly expensive. Not in dollars but in perspective. This sort of routine blindness doesn’t hurt physically, which is what makes it dangerous. You don’t notice what you’re not seeing.

When you do something different from your norm and get out of your routine you suddenly feel better. Nothing about your trip to somewhere new and doing things out of your “same old” travel routine is medicinal on paper. But something happens anyway – maybe you found new activities you love or even, gasp, disconnected from work long enough to notice the size of the world again.

Then you came home and rewrote your own prescription for the future including different kinds of vacations and different family trips. Not because the one new location you just went to is magic but because distance from the routine is what created the space to think clearly about what you actually want and need. The active ingredient is disruption.

You want to do this before you burnout, not after. Don’t look to the future or wait for retirement to do this because that date in your head has a way of moving, and you may never reach it. It you don’t break out of your routine now, the opportunities you lose are shared memories and a clearer sense of your own priorities. Try to break out of the same old same old and then repeat doing so as often as you can.

Warren Zevon was dying when he sat down with David Letterman for the last time in 2002. He had been diagnosed with terminal cancer just months before. Letterman, visibly moved, asked him if facing death had given him any special wisdom to share. What Zevon said was simple. He said he had always enjoyed himself, but that the enjoyment was more valuable now. He said you are reminded to enjoy every sandwich, every minute of playing with the band, being with the kids, all of it. Not a grand pronouncement. Not a theory of life. Just a reminder to actually be present for the good things while they are in front of you, because one day they won’t be.

Most of us, in business and in life, are remarkably bad at this. We close a deal and immediately move to the next one. We finish a hard project, exhale for about forty-five seconds, and open the next email. We hit a milestone and treat it as nothing more than a checkpoint on the way to somewhere else. We have conditioned ourselves to treat achievement as a transaction and celebration as an indulgence, when in fact it is the opposite. Pausing to mark a win, to look around at the people who made it possible and actually say something real to them, is not a distraction from the work – it’s the point of the work.

The best professionals I know understand that the small moments are not the gaps between the important ones. They are the important ones. The lunch where you laugh until your sides hurt. The Friday afternoon where the whole team sits together and just talks for a while. The client who calls just to say thank you. These moments are what make a career worth having. They are also what keep good people around you. People stay in relationships where they don’t feel invisible. They stay where they feel seen and valued.

Zevon’s insight wasn’t about mortality, even though that was the context. It was about attention. It was a reminder that enjoyment is a practice, not something that happens automatically when conditions are good enough. You have to choose to be present for it. You have to put down the phone, close the laptop, look at the person across from you, and let yourself feel the fact that something good is happening right now. Build that into how you work. Celebrate deliberately. Acknowledge the people around you with the same energy you bring to solving problems. So, the next time there is a reason to celebrate, don’t save it for later, eat the sandwich.

AI is not the threat to your career. The threat is the attorney down the street, the consultant across town, or the professional sitting two floors below you who has already figured out how to make AI work for them. That person is not smarter than you. They may or may not have more experience. What they have is a willingness to adapt, and in competitive professions, that willingness is currently worth more than almost anything else on a résumé.

The conversation about AI in professional services has been dominated by fear, but that fear is largely misdirected. The model that replaces the judgment of a lawyer or a seasoned professional does not exist. What does exist is a professional who can now do in two hours what used to take eight and have time left to actually think about strategy. That person is not being replaced by a machine — they are being made dramatically more valuable by one. The professional who refuses to engage with that reality is not protecting their craft. They are simply making themselves easier to pass over.

In the legal world specifically, there is an obligation that goes beyond self-interest. Clients hire attorneys because they expect competence, and competence in this moment includes understanding the tools that are reshaping how legal work gets done. Billing six hours for research that an AI-assisted attorney could complete in ninety minutes is not a sustainable model, and clients are beginning to understand that. The attorneys who will thrive are the ones who use AI to sharpen their judgment, accelerate their output, and deliver better work at a price point that reflects the reality of the market. The ones who cling to the inefficiencies of the past will be billing for time, which is not the same thing as delivering value.

This requires the same thing that every meaningful shift in professional life has always required: curiosity, a willingness to be a beginner again, and the discipline to actually put in the time to learn something new. The attorneys and professionals who built successful careers did it by adapting to new areas of law, to new client demands, to new market conditions. AI is not a departure from that pattern. It is the latest version of it. The only question worth asking right now is whether you are going to be the person who integrates it and pulls ahead, or the person who watches someone else do it and wonders what happened.

Nobody escapes the curriculum. Life keeps teaching, and it does not care whether you’re ready for the lesson. That is especially true in business, where the stakes are high, the pace is relentless, and the temptation to believe you have figured it out is both understandable and dangerous. The moment you stop staying curious and open, you stop growing. In a competitive environment, standing still is the same as falling behind.

The lessons don’t always arrive in the form you expect or prefer. Sometimes a trusted employee leaves, or a long-standing relationship sours, and you realize in hindsight that the warning signs were there all along. The difference between professionals who grow from those moments and those who don’t isn’t intelligence, it’s willingness. Willingness to sit with the discomfort of being wrong, to examine what happened without excuses, and to carry that understanding forward into the next situation. The lesson was always available. The question is whether you chose to receive it.

What makes life such an insistent teacher is that it will keep presenting the same situation in different packaging until you actually learn what it came to teach you. In my world, the attorney who keeps losing clients over communication issues and keeps blaming the clients hasn’t learned the lesson. Nor has the business owner who has cycled through three difficult partners and blamed each of them. At some point, the common denominator in your recurring problems is worth examining. That is not a comfortable conversation to have with yourself, but it is a necessary one. The professionals who are willing to have it tend to be the ones who build something that actually lasts.

The good news is that accepting life as your teacher doesn’t require perfection. It just requires a certain kind of intellectual humility that the best professionals carry with them throughout their careers. It requires the recognition that you don’t have all the answers, that the world keeps changing, and that there is always something more to learn. That posture keeps you sharp. It keeps you asking better questions, listening more carefully, and staying genuinely engaged with your work in ways that rigid expertise never allows. Life is going to teach you whether you want it to or not. You might as well be a good student.