The Impossible Equation
You can't do it all. But if you're like me, you're still gonna try.
I have a life that’s too full. My cup keeps overflowing. And I’m terrified of eventually missing what’s running down the table leg.
It doesn’t happen overnight. At 26, I was a single dude living in Houston, no kids, no dogs, no “real” responsibilities (besides keeping myself alive). Blink and you’re 40 with a wife, 3 little boys, a house you built, a career, a passion for a thing that doesn’t pay you a lot yet, and a puppy (because why not?).
But I’m walking around with the same cup I had at 26. I’m still the same guy (at least when it comes to name, rank, and serial number). So how am I expanding my mind to fit all of this?
The Cup Is Overflowing
The real answer: I’m not.
I’m losing stuff. Moments. Memories. Whole years, it seems. Flashes of insight that I wasn’t quick enough to write down. And I can’t stop thinking about what living the life I’m living right now will cost me in the end. The life I keep opting into, day after day.
It’s the Impossible Equation. If you’re a working parent, you already feel the pinch. Needing to be in three places at once. Countless demands on your time and attention at rates that would be unfathomable to our ancestors two generations ago. We’ve spent decades dissecting “work-life balance,” like it’s a benefit a company can provide or some attainable state. It’s bullshit. The minute we could get email on our phones, the best we could hope for was “work-life integration.” Nobody has the playbook for that. Which is why most of us suck at it (myself included).
But there are others like me who see that whole picture and go, “Yeah, I see the partner and the kids and the mortgage and the day job and the cute puppy whose recent dump stunk my office up for an hour...But I have this thing I have to build. And I need to do it now.”
God help us.
Because it’s the dumbest time to build. And we’re going to do it anyway.
I’ve always had some outlaw in my way of thinking. Rebellious teenager energy mixed with a confidence that whatever moves I make, I’m gonna get away with ‘em. Chalk it up to rumored mafia connections a few generations back.
It’s my version of the pull to break away from the well-trodden path.
Despite my ancestry, my draw was never a career that ended in a cell or a cemetery. I always wanted to create things: first music, then books, businesses, and solutions to problems. Building my own thing to contribute to improving my little corner of the world, and along the way, freeing me from the “default mode” way of living.
And I’m looking at this dinky cup that I’ve been holding all my adult life. It certainly wasn’t built for this...not even if I’d upgraded to one of those 32 oz Erin Pub mugs that Villanova kids would obliterate after a night at the local Irish bars could it hold this.
On top of that, I’m not operating like I was when I was young and optimistic. I’ve seen too much.
Financial insecurity. Broken relationships. The loss of loved ones. The scars of interpersonal conflicts, traumatic experiences, layoffs, and health scares.
I don’t know about you, but my cup’s beat to shit. Hairline fractures are adding to the spillage. Memories I wanted to keep slipped out and pooled around the base of the cup. Ideas I had for my business - some really goddamn good ones. The important stuff is seeping out, too. I used to have every millimeter of my wife’s face mapped in my mind: now, I’m happy that I can remember her eye color.
The Permanent Guilt Loop
Theatrics aside, I’m in it now. I’m building my 2nd Act while working hard to ensure I don’t dynamite my current life. It means trade-offs I hadn’t thought about, skills I hadn’t cultivated, and mental disciplines I hadn’t fully developed.
Take my perpetual guilt loop as an example:
When I’m with my kids, I feel like I should be building. I’m watching my boys wrestle in the game room and take swings in the batter’s box, but my mind is racing. “I’m behind. The deliverables are stacking up. This is what’s jeopardizing my launch timeline. I still have to learn how to do X. Y didn’t configure properly, now I have to troubleshoot. HOW DO YOU MIGRATE YOUR CUSTOM DOMAIN TO SUBSTACK IN TIME FOR THIS NEWSLETTER??” I’m right here. And I’m miles away...missing memories.
When I’m building, I feel like I’m robbing my family. I’m writing this at a Starbucks 1.7 miles from my home. It’s a Monday morning on a day the kids have off from school. I could be snuggled up watching Paw Patrol, or making kids pancakes I promised I’d make for 3 days (and didn’t, I’m realizing as I type), or tossing the tennis ball with the pup. I’m right here. Advancing my dream. And I’m miles away...missing opportunities.
All the while, I’m going to war with the voice in my head.
“You’re missing the good stuff right now.” No, I’m nailing this newsletter.
“Your son is getting better at t-ball, and you’re missing that stage of evolution because you’re distracted.” Well, yeah, but when else am I going to do it? And what am I really missing? He’s on his butt, building a dirt pile at 2nd base while ignoring his coach.
The tension is always there. It’s like a cancer, slowly eating away at me. When I’m with my family and I haven’t launched yet, I’m thinking about the business. When I’m working on the business, I’m thinking about Michelle and the boys. It never stops.
It doesn’t matter where I am. I’m always in the wrong place. Building while parenting feels selfish. Parenting while needing to build feels like I’m pushing my dream further away. I can’t win.
But in addition to coming from gangster bloodlines, I’m also extremely stubborn. Which means I’m not giving up on any of it. So how am I, and all the others like me, supposed to keep going?
The Margins ARE The Business
People like us don’t get 4 hours of focused work blocks following our morning walk, workout, or cold plunge. We write ideas in the notebook between meetings. We type notes in the stands (on the rare occasions we’re not coaching). We sit in the driveway to get our thoughts down before dragging the groceries into the house.
This newsletter’s proof. I outlined the damn thing on Sunday afternoon, driving downtown to hit La Barbecue with some out-of-town family (which ended up becoming Terry Black’s after the La Barbecue brisket and ribs sold out. Sad, but TB’s is a solid consolation prize).
My 2-year-old was asleep in the back seat, pacifier in his mouth, sunglasses sliding off his nose. I was whispering a nine-minute voice note, which was interrupted by me yelling at (yet another) Austin driver who doesn’t understand right-of-way laws. When I got home, after the kids went to sleep, I dumped out the transcript and started hunting for ideas to structure what you’re reading. I’m writing it during this guilty Starbucks session.
This IS the system. The margins aren’t a consolation prize for people who don’t have the luxury of focus time. They’re where the work gets done.
The Fundamental Truth They Don’t Tell You
All the productivity advice lives somewhere between mediocre and irresponsible.
“Quit your job and follow your passion” means I’ll lose the house.
“I’ve made $8 million over the last 3 years” is irrelevant when I’m still trying to make my first $10k.
“You need to go all-in.” Sure, after getting the kids to school, working the day job, exercising, eating, taking the kids to practice, and going through the epic bedtime saga, I’m all in...on the 90 minutes a day I have to myself (because I wake up 90 minutes earlier than everyone else).
Here’s what people like us need to hear before we start:
If you’re going to build in this stage of life—as a working parent with young kids and a full schedule—THIS is the experience you’re going to have. The tension will always exist. The guilt loop is permanent. The margins are the system. Accept it or don’t build.
This is chosen suffering. We’re choosing to build under these life conditions. I’m not an idiot: I know it’s the wrong season. I should have done this shit when I was 29, but I didn’t. The flip side is wait until I have more bandwidth.
Well, my youngest is 2, so....a decade? Longer? I’m 40. My mom passed away at 56, and my grandfather was gone by 52.
I think about that every day. Fuck waiting.
But there’s a difference between choosing a worthy struggle and self-imposed suffering. It’s never more apparent than when I want the conditions to be different. “How fast could this thing launch if I could focus on it for two uninterrupted weeks?”
Doesn’t matter. The conditions are the conditions. Every time I let myself get frustrated that things aren’t different, I’m cutting open my flesh, dropping the knife, and reaching for the salt.
The Argument For Doing It Anyway
The above paragraphs are like taking little kids out to dinner in public. If you’re a couple contemplating kids, watch a full meal of parents wrangling toddlers before you make your decision. Like kids, you’ll never feel fully ready. I wrote this to scare off the people who aren’t ready. If you don’t have some serious resolve and have a willingness to take a beating (a la Tyler Durden not fighting back in the basement of Lou’s Tavern), turn away now.
But some of those optimistic couples will have kids soon. Just like plenty of you are saying, “Doesn’t matter. I’m doing it anyway.”
Good. If you’re going into this thing with eyes wide open, there’s a smaller chance of you getting knocked out of the race you’re about to run.
Because there are really, really good reasons for doing it anyway.
Anybody who’s watched the economy over the last two decades knows one thing for certain: we are all at risk.
If your company’s underperforming or the market shifts, you might get laid off.
If you got a new boss, you might be shown the door. If your job can be done by AI, it will be...and soon.
Building your own thing BEFORE you need it is great for two reasons:
1. It gives you sovereignty. If you do it right, 12-24 months from now, nobody can tell you which of your kids’ events you can or cannot attend. At the minimum, you’re building the life raft while you’re still on the boat.
2. It provides a value to the world that doesn’t exist yet (at least, not your version of it). All the world’s religions point to service for a good reason. We’re here to be useful.
Both are good reasons. Both are also necessary. Marry your desire for sovereignty with doing the most amount of good for the most amount of people, and you’re likely to solve the money problem at the very least. But if you can dial that balance in, your life’s ceiling goes way, way up.
So lean into the crazy-believer energy. Build in the margins. Try to make something of your own. Recognize it’s going to cost you something (or multiple somethings) you care about, and hold an honest accounting with yourself before you go into it. But go into it. Empty the cup of the non-essential (seriously, how much Netflix and Instagram do we all need to make it through a Tuesday?) and make room for the important stuff. Patch the cracks as best you can, and get on with the fucking thing.
Because the kids that you think about while you’re building?
They’re watching. They’re downloading your OS.
And they’re either watching you build someone else’s dream, or you’re modeling the path to building your own.