30 years without a real break
Hello Friend!
This is embarrassing.
In 30 years of working, I've never actually taken a break. Not once.
Not for my honeymoon, my kids being born, or even family funerals. I've been that guy, the one who checks email during Christmas dinner and takes calls in hospital waiting rooms.
Pathetic, I know.
But here's what finally broke me: A few months ago, I caught myself checking Slack during a phone call with my father. He was talking about chasing better health, and I was chasing notifications.
That's when it hit me. I'd become a prisoner to my own productivity.
So I'm doing something radical.
I'm spending the next five days with 12 men on a retreat in Vermont. When I say I'm going off the grid, I mean it.
Phone stays off. Kristine has the guide's emergency number and nothing more.
Even though I've had personal and professional freedom for ten years, it never occurred to me I should actually use it. But that's exactly why we're all in this community together. Chapter 2 of our life and work is a redefining moment... if we choose to lean into it.
Here's how I'm making sure this break actually breaks the cycle:
5 Things That Make a Break a Break
1. Merge, Not Catch-up
The problem: You return from vacation feeling like you need to cram five days of missed work into two days. That's not a break. That's borrowed stress with interest.
Try this: Set expectations upfront. I told my clients: "I'm taking five days off, and I will not catch up on past messages. I'll merge back in and add value moving forward." The world won't end. Promise.
2. Put Your Streaks in Timeout
The problem: Your productivity apps become prison wardens. You've got 47-day writing streaks and meditation chains that make you feel guilty for being human. Taking a break means disappointing your digital overlords.
Try this: Hit pause on everything. My most important goal is finishing book #2, but nothing gets written this week. I'm trading my scorecard for my sanity. The streak will survive.
3. Plan for Your Inner Saboteur
The problem: You do great for 24 hours. Then that voice starts: "Maybe I should just quickly check..." or "Am I being irresponsible?" Your brain will stage a coup.
Try this: Create a recovery plan. Mine includes deep breaths, the mantra "You're exactly where you need to be," and an accountability partner (I've warned the retreat guide I'll need backup). Expect the urge. Plan for it.
4. Build Your Moat
The problem: Even with boundaries, you'll worry about that client who might need you, that project that could implode, that friend having a crisis.
Try this: Weaponize your away messages. My voicemail and email specifically ask people not to leave messages… just reach out next week. I'm not hiding; I'm healing.
5. Own Whatever Happens
The problem: Murphy's Law loves vacations. The system will crash. The client will panic. Someone will quit. And you'll blame yourself for not being available.
Try this: Accept it now. Life will happen without me. Bad things included. I can only control my intentions, not every outcome. If something breaks while I'm gone, we'll fix it when I'm back. The cost of never unplugging is higher than any crisis I might miss.
The Brutal Truth
Here's what I'm learning before I even leave: The world doesn't need us as much as we think it does.
That client emergency? Someone else will handle it. That "urgent" project? It can wait a week. We create our own indispensability complex because admitting we're replaceable feels terrifying.
But it's also liberating.
We think people are watching our every move, but they'll hardly notice we're gone. We create these internal dramas and surrender to that voice saying "You're not doing enough."
But you are. I am. We all are.
Sometimes the most productive thing you can do is absolutely nothing.
Your coach,
Chris
P.S. If you're stuck in your life and work right now, let’s talk. And let's do that when I get back… rested, reset, and ready to help you build the freedom you deserve.
