How I (Finally) Chilled (Way) Out and Leveled Up

The Before Times. The Long Long Ago.

April 2017. It's 11am. I've already been up for six hours. I rolled out of bed at 4:45am, opened the fridge, and cracked an ice cold Celsius wild berry. I put on my gym clothes and trademark sleeveless hoodie, grabbed my briefcase bag, and was out the door. It was morning but effectively the middle of the night. Nobody was out on the Boulevard of broken dreams. Even the night owls had gone home to bed.

I go to my office. The overnight security guard is still working the desk. Hi Gary. He cracks wise with that high-pitched, nasally voice, "Good morning Jon. Your boss must be a real asshole making you work these crazy hours." Me and Gary go way back to my Boies, Schiller & Flexner days (overnights).

I hit my office. I keep all the lights off and work in the still dark. I've got Mr. Suicide Sheep on a Bose speaker. These first couple hours are peak production and performance. Nobody is around to bother me. No phones are ringing. Nothing. I'm just crushing it.

Some guy sold one of his businesses and cleared about $12 million. But he's a psychopath and he can't sit still. Now he wants to get back into a related industry. The APA is extensive, has a ruthless non-compete, but also has extensive carveouts for certain of his other businesses. Real recognize real. So he called me because I'm kind of crazy, too.

I can only do work like this in the morning. Provision X. Carveout. Exception to the carveout. Chances of success under the relevant law. Possible exposure if it goes way south. Option tree. Mapped it all out. Clicked send. 8am and I was done. Just in time for the good coffee shop to open (hi Anns).

So I stroll down the street (with my hood up and characteristic scowl), briefcase bag in tow. I get to Ann's. I order a red eye and a Pellegrino (breakfast of champions). I do about an hour of light work. Emails. Allocating cases and projects. Checking upcoming deadlines. Marketing. Telling my haters on LinkedIn to go fuck themselves.

9am and I walk back to my place. I hit the gym for an hour or so. I shower up, get dressed, grab my travel bag, and punch in an Uber.

11am and I'm in the back seat of an Uber. En route to the airport. My phone is blowing up with emails and phone calls. There's some case emergency. Some new preliminary injunction hearing. Some state court brawler up near Tampa is on the phone screaming about sanctions (in your dreams). I'm waiting on a wire for $150,000. And I need that fucking money. Just another day in the neighborhood. I'm trying to review a draft of something on my iPhone. And that's fine, but the phone keeps ringing and interrupting me. There's a traffic jam getting out of downtown. The Uber driver is trying to make small talk with me. He probably thinks I'm an asshole because I said hi, thanked him for picking me up, talked with him for a minute or two, then had to switch into go mode. And it's all just too much. My heart is beating way too fast and I don't feel right.

I tell the driver, "Excuse me, sir, could you just take me back to where you picked me up? Please."

He's confused and has no idea what the fuck is going on. I say, "It's fine. I'll update the address so you can just take me back. And I'll tip you extra in case that somehow screws you over."

So he turns around and drops me off back at the front door to my building. I go into my loft, turn off my phone, and take a nap. I wake up a couple hours later. I turn on my phone. It's a shit show. 40 or 50 emails. A bunch of phone calls and text messages. Chaos.

I book a new flight for the early evening. I've got a couple hours. So I figure I'll beat rush hour traffic, go to the airport now, and just post up there at a bar and work. So that's what I do. Then I get on the plane, open my laptop right back up, and keep working.

I did this 12+ hours a day, 6 days a week for 5 or 6 years. Then things fell apart (the yams again).

My Son: My Second Great Teacher in Life

I did things one way for a long time. Sure, it was intense and sometimes chaotic. But I was the master of chaos. I was a machine. I naturally had a certain capacity. But I also had a system. I had a process. I was ruthlessly disciplined. I made it all work. But there was no breathing room. There was no margin for error. There was no real downtime. It was full go every day. Everything on the line.

Then my son was born. And, a couple hours later, he started having trouble breathing. So they took him to the neonatal intensive care unit and hooked him up to oxygen and IVs. So, on one hand, I have a bunch of hearings and litigation deadlines. And my colleagues are expecting me to call all the shots and make all the big decisions. Because that's what I had always done. That's the way I made it. And on the other hand, my newborn son could die.

I don't know what it was. Was it God? The universe? The infinite? Something up there in the ether talking right to me. And in that moment, I knew that everything had to change.

I was very fortune. They cleared my little guy to go home after about a week in the NICU. And from the very beginning, he has been teaching me all of the lessons that the grown me had so-far failed to learn.

Covid hit. And I was working from home. So I got to spend lots of time with him. At about 2 months old, he started to do this big smile, where he would break into a belly laugh. It was absurd. I got to be there for all of that. It was amazing. And when everybody went back to the world and their jobs and their offices and their normal lives, I knew I couldn't do that.

I had to find a way to work less so I could spend lots of time with my son. I had to delegate high-stakes shit and insist upon it. So when someone asked, "Are you sure you want me to handle this? You would do it better" -- not to seize upon that as an opportunity to take it back. Because then I could justify it. I could say: I delegated this. But you weren't ready to do it. So I'll just handle it. Then I can control it. Then it's exactly the way I want it. Then I know there won't be any problems.

But you never grow that way, not as a team. I remember the first time we had a preliminary injunction hearing in federal court and I wasn't the one who handled it. Breakup of a $200 million vape company? Ok, CP, it's yours. Take the squad. I'm working on strategy and analysis and hanging with my little guy. By far the best lawyer in that courtroom. He crushed it. Injunction denied.

Desiderata. There is a season for all things. Yes, it was swag as hell walking into a courtroom with 4 or 5 of my colleagues and smokin' a publicly traded company at an injunction hearing. And then saying, "You can pay now or pay more later. I don't care." That was the season and it was an epic one. And it will come again. But now it was time for me to step back a bit. Lay low. Be a dad. Learn other lessons.

Fast-foward. I'm in a Mexican standoff with a two-year-old. Me. Jonathan Pollard. I'm the negotiator. I'm the fixer. I'm the problem solver. I'm a certified world beater. And I can't get my two-year-old son to brush his teeth.

I'm not going to hold him down and force him. I'll never relate to my son like that. I'm not going to physically overpower to get him to do what I want -- because it might be expedient. That's not my way. Particularly given my own upbringing and being afraid of my dad until I was old enough and big enough to stand up to him. No way.

So I'm sitting on the bathroom floor. With a two-year-old who is very upset about brushing his teeth. But who also has a fairly limited vocabulary (because he is two). And not being particularly reasonable about the matter.

You have to understand: Up until right about that point in my life, my go-to reaction when people were unreasonable about a particular matter was "You'd better get the fuck reasonable in a hurry." Pretty much. I dealt with unreasonable people all the time. And I put them back in their place.

But the tables had turned. Hence the Mexican standoff. I deployed logic and reason. I attempted bribery. I tried humor. We took a break and then I tried again. I tried casually broaching the issue, "Hey buddy, let's go brush our teeth." My suggestion was met with a stern look of disapproval. Like he was saying: "Dad, did you really think I would fall for something like that? You realize I'm your son."

We start talking about Peppa. My son straight up stans Peppa Pig. I say, "Peppa brushes her teeth." My son doesn't believe me. I pull out my phone and frantically bring up Youtube and search for a video. BOOM. I'm in luck. The Brush Your Teeth with Peppa Pig Song. We watch it together. I say, "Well, if Peppa brushes her teeth, then I want to brush my teeth with her while I watch the video again." And NOW, my little guy suddenly wants in on the fun. So we brush together with Peppa.

How long would this new strategy work? Not long. Who knows. Who cares. Keep it rolling.

Some Things I Learned

It's impossible to explain all of the lessons I have learned over the past few years. But lessons work like this: You can know something conceptually and analytically. But you don't really know it until you've lived it. Then you know it in your bones.

There's more to life than work. You can do great work and still have time for yourself and all those other parts of life that matter. You can also make more money in less time. Re-evaluate your model and figure it out. But you might have to take some big risks -- especially if you already built something that got comfortable.

A team can't really grow and flex its muscles if only one person always gets that critical shot. You want a badass squad? The only way you get there is (again) by taking the risk. And part of that risk is trusting other people to step up and make that shot.

Don't argue with idiots. Don't go in for the extracurriculars. Don't waste your breath. Don't get pissed off over little things. Some people have real problems. Don't create bullshit problems for yourself. That's ungrateful. Just keep it moving.

Stop and smell the flowers. Take it all in. Relax. Chill the fuck out. The world is all sorts of messed up, but it's also pretty amazing at the same time. And we're all dying. Make it count.

JP