BusinessLawGuy's Blog

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 to actually act. I’ve come to believe that discomfort is usually a signal, not an obstacle.

This shows up constantly for professionals because our training rewards being thorough, and being thorough can quietly become an excuse for stalling. A lawyer can always do more research. An accountant can always run more numbers. It looks like diligence and sometimes it is, but often it’s just a more respectable way of putting off the moment where you have to take a position with your name attached to it that someone isn’t going to be happy about.

I don’t think it’s a coincidence that the hard thing and the right thing line up as often as they do. The easy paths tend to be easy because someone else absorbs the cost of you taking them. Avoiding the conversation is easy for you and expensive for the person left guessing. Keeping the wrong hire on staff is easy for you and expensive for everyone covering for them. What I’ve noticed is that the right decision is usually the one where you’re the one who has to live and feel the discomfort up front, instead of quietly passing it downstream to somebody else.

None of this means every hard thing is automatically the right thing. Plenty of hard things are just hard. But when you already know what needs to happen and you find yourself stalling, it’s worth being honest with yourself about why. Most of the time it isn’t more information you’re waiting on. It’s more nerve. The professionals I respect most aren’t the ones who never feel that hesitation. They’re the ones who’ve learned to act despite it, faster than the rest of us would prefer to. So the next time you catch yourself circling a decision you’ve already made and know is right, ask yourself what you’re really waiting for.

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 the substance at the same time, without either one diminishing the other.

Inside your own office, this shows up constantly. The colleague who says thank you, covers for a teammate having a rough week, or gives credit generously is not the pushover in the meeting. Treat that person as an easy mark, and you will find out quickly how wrong you were. Kindness in a work environment is a form of discipline, not an absence of it. It takes more control to stay generous with people than it does to be sharp-elbowed, and the people who mistake generosity for weakness usually discover, too late, that they were dealing with someone who simply chose not to fight about things that didn’t need fighting over.

The same principle holds with business partners and the people sitting across the table from you in a negotiation. Being fair, being pleasant, and looking for the outcome that works for both sides is not evidence that you will fold when it matters. It is, if anything, a signal of confidence. The negotiator who needs to posture and bully usually does so because they are not sure their position holds up any other way. Kindness and firmness are not opposites. You can hold your number, protect your client’s interest, and still be the person in the room everyone would rather work with next time.

For attorneys, this lesson applies most sharply to opposing counsel. Professional courtesy toward the lawyer across the table, agreeing to a reasonable extension, being straight with them about scheduling, treating them like a person rather than an obstacle, is not a concession on the merits of the case. It is how the best litigators actually operate, because they know the case will be won on the facts and the law, not on who was rudest in the meantime. The attorneys who read that courtesy as an opening to take advantage tend to find out, once the discovery fight or the motion practice actually starts, that the kindness was never a substitute for preparation. It was simply proof that the other side didn’t need to be difficult to be effective. Don’t mistake someone’s grace for their limit. More often than not, it is their strength, worn quietly.

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 want and start paying attention to what you want.

That’s the tell. Losing track of time isn’t a small thing, it’s data. I’ve watched attorneys who drag through certain assignments come alive the second the conversation turns to the type of assignment they really enjoy. The task itself isn’t the variable. What lit them up was the differentiator. Most of us never stop long enough to notice the pattern because we’re too busy getting the work done to ask why some of it drains us and some of it energizes us.

You don’t need to have this fully figured out to start paying attention to it. In fact, almost none of us do, and treating that as a problem to solve immediately is part of what keeps you stuck. What you can do is start noticing, honestly, without judgment, which meetings you leave with more energy than you walked in with, and which ones don’t. Which projects you’d keep working on after hours without anyone asking you to. Which conversations you replay in your head afterward because you’re still turning the problem over, not because you’re anxious about how it went. Those are the clues. You collect them over years, which is what makes it hard to catch them, group them with prior similar thoughts, and process them, let alone to put them into action.

None of this means you quit your job tomorrow because a spreadsheet bored you. It means you start treating your own attention as information worth taking seriously instead of noise to push through. Careers get built one decision at a time, and the professionals who end up somewhere that actually fits are usually the ones who paid attention early and kept adjusting, not the ones who waited for a single lightning-bolt moment of clarity. You may not know yet exactly what you’re building toward. That’s fine. Just notice where you thrive, follow it honestly, and trust that the pattern will tell you if you make the effort to pay attention.

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 the room and still watch it fail because you never did the work of making it real.

This plays out in real life all of the time. Two parties may come to an agreement, a right decision, but then it’s left to sit there without the discipline of putting it on paper, and has a way of going bad. The professionals who consistently succeed are not the ones with the sharpest judgment in the abstract. They are the ones who understand that judgment without follow-through is just an opinion.

This matters just as much away from the office. People spend enormous energy trying to find the perfect choice, the perfect job, the perfect house, the perfect direction for their life, as if somewhere out there is a decision so obviously correct that it will execute itself. It won’t. I know people who made what looked, on paper, like the wrong call, a path nobody would have recommended, and made it work through sheer commitment and refusal to fail. I know others who made the objectively right call and squandered it through half-hearted effort thereafter. The choice you make matters less than what you do the day after you make it.

None of this means the decision itself is irrelevant. Do your homework, weigh your options, get the input you need, and make the best call you can with the information in front of you. But once it’s made, stop rethinking whether it was right and start putting everything you have into making it right. That shift, from evaluating the decision to executing on it, is the difference between professionals who talk about good judgment and professionals who actually produce good outcomes. The right decision is a starting point. What you do with it is the whole rest of the story.