Different decisions deserve different amounts of emotional energy.
I think we tend to overcomplicate things.
The older I get, the more I realize that one of the greatest skills in leadership isn’t making perfect decisions – it’s understanding what kind of decision you’re actually making.
Last week, a friend shared a framework with me that hit home and inspired this writing!
Some decisions are hats.
Some decisions are haircuts.
And some decisions are tattoos. Think about it.
A hat is easy. You put it on. If you don’t like it, you take it off and grab another one. There isn’t much risk. It costs very little to change your mind.
Haircuts have a little more weight. You may regret it the second you look in the mirror. Your buddies may give you grief for a few weeks. But eventually it grows back. Time has a way of fixing it.
Tattoos are an entirely different conversation. Those deserve thought, counsel, patience, and a healthy respect for the long-term consequences.
The problem is that I think most of us spend our days treating hat decisions like they’re tattoos.
We convince ourselves that if we make one wrong move, everything is going to fall apart. So instead of making a decision, we make none at all. We wait. We analyze. We ask five more people. We hold another meeting. We convince ourselves that we’re being responsible, when in reality we’re often just afraid.
I’ve done this more times than I’d like to admit.
I’ve spent weeks, if not months, thinking about a decision that, in hindsight, I could have tested in three days. I’ve delayed conversations because I wanted the words to be perfect. I’ve held onto ideas because I was trying to eliminate every ounce of risk before taking the first step.
Looking back, almost every one of those decisions was just a hat.
In business, I see this constantly.
A leader wants to change the meeting cadence but worries everyone won’t like it. Try it for a month. It’s a hat.
Someone wants to adjust pricing but fears the market’s reaction. Measure it. Learn from it. If you’re wrong, make another adjustment. That’s a hat.
A company wants to test a new service, experiment with a different process, or reorganize a department, but spends months debating something that could have been validated in a matter of weeks.
The irony is that many of the greatest breakthroughs don’t come from having all the answers. They come from taking action, gathering information, and being willing to adjust.
Action creates clarity. Waiting rarely does.
Now, that doesn’t mean every decision should be rushed. Some decisions deserve much more weight.
Hiring the wrong person isn’t a hat. I’d call that a haircut. It may cost you time, money, and energy, but you can recover. Promoting someone before they’re ready, investing in a piece of equipment that doesn’t produce the return you expected, or launching a new division that struggles out of the gate – those aren’t fun, but they aren’t permanent either. They require humility, learning, and course correction.
The mistake many leaders make is demanding tattoo-level certainty before making haircut-level decisions.
That certainty simply doesn’t exist.
Leadership has never been about knowing exactly how everything will unfold. It’s about making the best decision you can with the information you have, accepting responsibility for the outcome, and being humble enough to change course when new information presents itself.
Relationships work the same way. How many conversations have you postponed because you’ve convinced yourself they’re bigger than they really are?
You need to apologize.
You should call a friend.
You need to ask your spouse a hard question.
You need to tell an employee they’re capable of more.
You need to tell someone they’ve hurt you.
Instead, we replay the conversation a hundred times in our heads, imagining every possible negative outcome. Days become weeks. Weeks become months. Sometimes months become years.
I’ve learned that most of those conversations are hats too.
You can clarify your words. You can apologize if you said something poorly.
You can have another conversation tomorrow.
What you can’t get back is the time lost because fear kept you silent.
Now let’s be clear – there really are tattoo decisions in life.
Who you marry.
Who you choose as a business partner.
Selling your company.
Compromising your integrity.
Making decisions that affect your family, your values, or your reputation for years to come.
Those deserve patience. Those deserve prayer. Those deserve wise counsel and careful thought. The goal isn’t to become impulsive. The goal is to become better at recognizing the weight of the decision sitting in front of you.
Because the person who treats tattoos like hats becomes reckless.
But the person who treats hats like tattoos becomes paralyzed. Neither one is effective leadership.
One question has helped me tremendously over the years. Whenever I’m stuck, I simply ask myself, “If this goes sideways, how difficult is it to undo?”
That question has saved me countless hours of unnecessary overthinking.
If I can reverse the decision tomorrow, it’s probably a hat.
If it will take a few months to recover from, it’s probably a haircut.
If it changes the trajectory of my family, my business, or my life for years to come, it’s probably a tattoo.
Different decisions deserve different amounts of emotional energy.
The mistake is giving them all the same amount.
So here’s what I’d encourage you to think about today.
What’s the decision you’ve been sitting on? The conversation you’ve been avoiding. The opportunity you’ve been delaying. The idea you haven’t launched. The toxic employee you know you need to let go of. The boundary you know you need to set.
One day you’ll look back on this season of your life and realize there were a handful of decisions that changed everything. My guess is they won’t be the ones you lost sleep over. They’ll be the conversations you finally had, the opportunity you finally pursued, the boundary you finally set, or the apology you finally offered. Most of the things that shape our lives don’t begin with certainty – they begin with courage.
So before you spend another week waiting for perfect clarity, ask yourself one question: Am I protecting my future… or am I simply protecting myself from being uncomfortable today? Those are two very different things. And sometimes the only thing standing between the life you have and the life you want is realizing that what you’ve been treating like a tattoo… was really just a hat.
Ask yourself one simple question. Is this really a tattoo? Or have you accidentally turned a hat into one?
My guess is that by the time you finish reading this blog, you already know exactly what it is.