What do an Executive Assistant, nachos, Indiana Jones, and a hundred million dollars have in common?
They all starred in the newsletters that hit hardest this year, made lawyers laugh, made them rethink their businesses, and occasionally made them send me emails like “Jordan…were you talking about me?” (Yes. Probably.)
As we wrap up another year of running law firms, battling burnout, and trying not to take advice from random people on Facebook, here are the ten newsletter moments that stood out the most. Think of this as your own personal season finale for legal professionals, with way better jokes.
Here we go.
How to Win at Life (and Business) with an Executive Assistant
The time we said running a business without an Executive Assistant is basically playing life on hard mode. Batman has Alfred. Tony has Jarvis. Branson had Penni Pike. I have Audrey and Olivia. If you don’t have someone protecting your calendar and keeping you from scheduling a deposition during your dentist appointment, you’re doing this whole thing with Nikes full of rocks.
The big lesson was simple. Hire for judgment. Delegate decisions. Meet every week. And stop assuming you need to be the one who answers every email. You don’t.
Your Origin Story Is More Powerful Than You Think
The time we broke down how your origin story is actually your emotional superpower. Spider Man has the spider bite. The Ninja Turtles have the ooze. You have the reason you left Big Law, started your firm at your kitchen table, or decided to help the clients who remind you of yourself.
If people don’t know why you care, they have no reason to care about you. Your why sells more than any case result ever will.
Leading Your Team With Clear Intent Instead of Micro Management
The time we talked about leadership by intention instead of micromanagement. Batman doesn’t hover over Robin. Phil Jackson didn’t tell MJ how to dribble. The military uses Commander’s Intent so teams know the mission, not every step.
Tell your people what outcome matters, get out of the way, and let them surprise you. Leadership is not reading every email your paralegal sends. It’s telling them what good looks like and letting them get there without you breathing fire down their neck.
What Would You Do If You Won the Lottery?
The time we used lottery money to expose what actually matters to you. When you imagine winning a hundred million dollars, the stuff you’d keep doing is the stuff you’re aligned with. The stuff you’d immediately dropkick into the sun is the stuff you should be delegating or deleting from your life.
I realized I’d still coach lawyers, still write these emails, still hang with my family, still chase down great escape rooms. The question wasn’t about money. It was about clarity. Lottery You is honest. Listen to that version more.
The Best Books I’ve Read So Far in 2025 (and Why They Stuck With Me)
The time we broke down the best books of 2025 so far and why they stuck. From The Good Life to Being Mortal to High Output Management, these books hit because they weren’t just business books. They were life books. They forced us to think about growth, mortality, happiness, and leadership on deeper levels.
Plus, research says reading is the sexiest hobby a man can have, which continues to be proof that my wife is a very lucky woman.
Netflix, Nachos, and Neglect
The time we talked about Netflix, nachos, and neglect. Rest is good. Avoidance wrapped in melted cheese is not.
Everyone loves a good binge, but if you’re checking out because your systems suck, that’s not freedom. That’s survival mode.
We broke down the five systems that pull you out of the nacho trap. Intake that filters. Calendars that protect your sanity. Emails that stop being your to do list. Billing that doesn’t rely on you chasing people. Delegation that turns you from bottleneck to CEO.
An Ideal Month – 4 Weeks Repeated for Success
The time we laid out the 28 day Ideal Month. Instead of letting the calendar boss you around, we designed a month that actually works.
Anchors first. Infinity stones second. Everything else gets placed intentionally.
It’s Serena Williams training. It’s Luke on Dagobah. It’s me figuring out exactly when to work, when to read, when to exercise, when to be Dad, and when to go eat Chinese street food at a market because TikTok told me to.
The Hidden ROI of Office Culture
The time we talked about the hidden ROI of culture. The Ted Lasso lesson. The Chick fil A drive thru effect. The moment I finally realized that happy employees save you from mistakes, turnover, stress, and hiring your fifth receptionist in a single year.
Culture isn’t pizza parties. Culture is whether people feel respected, trusted, and appreciated. And sometimes pizza helps with that too.
Deciphering Losada’s Enigma
The time we dug into the Losada ratio and why negativity hits harder than positivity. Indiana Jones level mystical math or not, the point was simple. People remember the sting longer than the compliment.
Loss aversion is real. Three positives to offset one negative might not be scientifically perfect, but it’s emotionally accurate.
Start meetings with good news. Compliment publicly. Critique privately. And try not to undo a week of encouragement because you rolled into a meeting with the energy of a Sith Lord.
The Cost of Free Advice
The time we tackled the cost of free advice. Facebook threads full of strangers telling you to cold DM 4,000 people or pivot your firm to AI chatbots by Thursday.
Batman would never crowdsource Gotham strategy from the Joker. You shouldn’t crowdsource your business strategy from internet randos either.
Only keep advice from people living the kind of life you actually want. Ditch everything else like the yellow pages in 2025.
Wrapping It Up
This year’s newsletters had a theme. Build your life on purpose. Build your firm on systems. Lead with clarity. Protect your time. Increase the positive. Ignore the noise. Do the things you’d still do even if your bank account suddenly had an extra eight zeroes.
Until then, pick one of these ten lessons and apply it this week.