Sometimes having everything to lose requires acting like you have nothing to lose. Not recklessly, but with enough clarity about who and what matters most to act accordingly.
Tuesday morning I woke up worried about my daughter.
We had moved her back to Statesboro on Saturday, into a new house for another year of college. Moving is exhausting under the best circumstances, and the first few days had been rough. New house, school starting back, work, emotions, exhaustion, and all the little things that seem manageable individually but have a way of piling up on each other.
She was having a hard time, and I was having a hard time with her having a hard time.
This is one of the stranger parts of being a parent that nobody adequately explains to you. Your kids get older and increasingly capable of handling their own lives, which is exactly what you spent years preparing them to do. Then they actually do it, and sometimes every instinct in your body still says: go get your kid.
When we left Statesboro Saturday, we’d finished almost everything on the moving checklist. Furniture assembled. Stuff unpacked. Bed made. Clothes put away. The normal parade of trips to stores for things nobody remembered we needed until we needed them. There was one conspicuously unchecked item: something for the big bare wall in her new bedroom.
Her room has blues, whites, and lighter colors. There was also another conspicuous absence from the room: Dino.
His government name is Dinosaur Nugget Stevens, naturally.
Dino is her cat, but her new rental doesn’t allow cats, so he stayed behind at our house. Tuesday morning, somewhere between worrying about my girl and getting ready for my first calls of the day, I had an idea.
I fired up ChatGPT.
Between early calls, I uploaded pictures of Dino and started working through iterations of an oil painting. I wanted him lounging regally, paw in the air holding a wine glass, surrounded by blues and whites that would work in her room. Ridiculous enough to make her laugh, but somehow classy enough that you could hang it over a bed.
Several iterations later, I had it. A masterpiece, or at least the finest portrait of Dinosaur Nugget Stevens ever produced.
Then the plan escalated.
I uploaded it to Walgreens, scoured the internet for coupon codes because apparently my priorities have limits, and ordered a 24-by-36-inch print. To my surprise, it was available for same-day printing. About an hour and a half later, I got the notification that it was ready.
Now I needed a frame.
I had a rare full 60-minute opening around lunch, grabbed a tape measure, and headed to a local thrift store. I wasn’t really looking for art. I was looking for something approximately 24 by 36 inches whose art I could evict.
Found it.
I picked up the print and frame and made it home with about ten minutes to spare before my next call. During a Teams meeting, because multitasking occasionally produces something useful, I gutted what appeared to be a perfectly respectable piece of 1990s framed art and installed Dino’s masterpiece in its place.
By 2:00 it was sitting there ready to go, and I couldn’t stand it.
I knew she was upset. I knew I had this stupid, wonderful thing sitting in my house that might make her smile. I knew she could probably use a hug. I knew I could too.
So I looked at the rest of my calendar and did something that, depending on your perspective, was either completely rational or mildly irresponsible. I canceled three meetings.
They weren’t unimportant. They also weren’t urgent. I finished a few things that genuinely needed to get done, got in the car around 4:00, and headed south.
Three hours later I was in Statesboro, Georgia, attempting to sneak past a Ring camera while carrying an enormous gold-framed oil painting of a cat holding a glass of wine. This apparently looks exactly like what you would imagine an uninvited weirdo approaching a college house would look like. I scared the crap out of my daughter and her roommates.
She opened the door. I showed her Dino and handed over some additional care-package material from Mrs. Stevens. Then we hugged. A good, long hug.
We talked for a while. I hung the picture on the formerly bare wall and leveled it, because apparently driving three hours without warning to deliver a thrift-store-framed, AI-generated oil painting of a cat is impulsive, but hanging it crooked would be irresponsible.
She took me for ice cream. Her older brother met us there. We talked, laughed, and there may have been a few tears mixed in too. Then we hugged again, I got back in the car, and I drove three hours home.
After six hours of driving and a 1:00 a.m. bedtime, morning came pretty damn early.
What exactly was I risking?
Did I get a lot done at work that afternoon? No. Was the entire operation silly and kind of ridiculous? Maybe. Was I completely prepared for all of my meetings and deadlines the next morning? Not entirely. Did I miss discussions, context, or maybe even a decision in one of the meetings I skipped? Probably.
Does my wife, my daughter’s friends, and a statistically significant percentage of otherwise rational people think I’m crazy? It is decidedly so.
Did my favorite daughter need a pick-me-up? Yes. Did I need it as much as, or possibly more than, she did? Yes. Would the work wait? It would have to.
And that’s where this stopped being a story about a ridiculous cat painting.
Everything to lose
As I’ve gotten older, I’ve accumulated a lot more to lose. A career. A reputation. A paycheck. Responsibilities. A mortgage. 401(k)s. 529s. Car insurance. People who depend on me. Commitments I’ve made and people at work who quite reasonably expect me to honor them.
When you’re young, “nothing to lose” can be almost literal. You haven’t accumulated much yet. Taking a chance is comparatively cheap. Eventually you build a life worth protecting, and the natural response is to become more cautious.
You protect the career because it funds the life. You protect the reputation because it supports the career. You protect your calendar because that’s where the work happens. You worry about being in the room, staying informed, meeting expectations, keeping up, and not giving anyone a reason to question your commitment.
Some of that is called responsibility. Taken too far, some of it is called fear.
There is a difference between having something to lose and being afraid to lose anything.
That’s a distinction I’ve been thinking about a lot lately, particularly in my career. After enough years, experience gives you things worth protecting, but it also gives you risk capacity. You have scars. You have relationships. You’ve made mistakes and recovered from them. You’ve developed judgment. You’ve hopefully built enough of a track record to know that missing a meeting, questioning a decision, saying no, handing something back, or choosing a different direction probably isn’t going to cause the earth to stop rotating.
I’ve written before that heroes don’t scale. I still believe that. Organizations shouldn’t depend on somebody continually jumping in to save the day. Good leadership creates clarity, ownership, mechanisms, and people who can operate without waiting for the hero to arrive.
There’s a personal version of that lesson too. If leaving work for one afternoon causes everything to collapse, I’ve built something wrong. If my presence is required in every meeting where something might happen, I’ve built something wrong. If protecting my career requires repeatedly choosing it over the people the career exists to support, I’ve built something very wrong.
That doesn’t mean the work doesn’t matter. Mine matters quite a lot to me. I like solving hard problems. I like building things. I like working with good people. I take pride in being dependable and doing what I said I would do.
But work is one of the things that matters. It isn’t the thing that makes everything else matter.
Priorities are what wins when important things collide
Oliver Burkeman’s Four Thousand Weeks starts with uncomfortable arithmetic: an 80-year life contains roughly 4,000 weeks. His point isn’t that we should become more efficient at stuffing work into every one of them. It is that our time is finite enough that deciding what deserves it is unavoidable.
I find that idea both terrifying and strangely liberating, because priorities stop being the things you write at the top of a slide. Priorities are what wins when two important things collide.
It’s easy to say family comes first when family isn’t competing with anything. It’s easy to say your health matters when the calendar is empty. It’s easy to say people are more important than work when nobody important scheduled a meeting at 4:00. The test happens when choosing one costs you something from the other.
We spend a lot of time asking familiar questions at work: Who owns it? What are we trying to accomplish? Why does it matter? When does it need to happen? Where should the work live? How are we going to get it done?
They’re useful questions for running an organization. They’re probably more important for running a life.
Who are your people, and who gets your time when giving it to them costs you something? What are you actually trying to protect: your livelihood, your title, your responsibilities, your reputation, or simply the comfort of not disappointing anyone? Why are you working so damn hard in the first place? When does patience become inertia, or being dependable become always being available? Where do you want all of this to take you, not just professionally but as a person? And how should somebody watching you spend your time know the answers?
That last one is uncomfortable.
For me, a big part of the answer is my family. The work supports a home, education, opportunities, vacations, cars, groceries, retirement accounts, and all the other decidedly unromantic things that cost money.
But my family doesn’t just need what my job can bankroll. They need simpler things sometimes.
Sometimes my daughter needs her dad.
You show up for your people. Period.
The safety net
Maybe the point of building a safety net isn’t to spend the rest of your life staring down at it.
I’m not advocating blowing up your job and attempting to survive on love and vibes alone. Responsibility matters. Deadlines matter. Other people’s time matters. Sometimes you have to miss the thing you desperately want to attend because another commitment genuinely needs you.
This isn’t permission to be reckless. It’s permission to be deliberate enough about your priorities that, every once in a while, you can look reckless.
When you know your who, what, why, when, where, and how, some decisions become surprisingly easy. You can cancel the meeting, take the risk, say the uncomfortable thing, use the vacation day, go to the game, make the phone call, drive the six hours, or bring the ridiculous cat painting without pretending there are no consequences.
Tuesday afternoon I had plenty to lose. That’s exactly why I needed to remember what I wasn’t willing to lose sight of.
The meetings could wait. My girl needed a hug, and so did I.
Rabbit holes
- Oliver Burkeman, Four Thousand Weeks, on finite time and the limits of productivity.
- Derek Sivers, Hell Yeah or No, a useful filter for making room for the few things that deserve a wholehearted yes.
- Bronnie Ware, The Top Five Regrets of the Dying, a much heavier reminder that the scoreboard can look very different depending on where you’re standing.
