The Ultimate Flex: Rest
One of the most powerful reasons to be your own boss is control of time.
But that same power is a double-edged sword—it assumes you, the business owner, are exceptional at managing your time. Not just for efficiency, but for resource allocation and, ultimately, profitability.
Otherwise, what’s the point?
Dialed In, Then Letting Go
Over the last two weeks, I’ve been incredibly focused—exceptionally productive, energized by the countdown to our long-awaited family trip to Hawaii. It’s been over a decade since Heather and I were last in Maui, on our honeymoon. And now we’re heading back to the Fairmont Kea Lani—with our daughters.
A full-circle moment that hasn’t even fully landed for me yet… probably because I’ve been so laser-focused on work.
Here’s what a typical day looks like:
I wake up around 6 AM and step into dad mode—getting the girls dressed, making breakfast, talking through dreams and snack choices. While they eat, I catch up on market updates or prep financial plans. Then it’s a quick walk to school with my oldest, followed by the preschool drop-off for our youngest.
By 9:00 AM, I’m on Zoom with clients.
Mid-morning to early afternoon is blocked for deep work—rebalancing portfolios, building models, and pushing forward on strategic planning. The calendar’s tight, the energy is high.
But earlier today, around 1 PM, I felt it.
That quiet internal knock that said: “It’s time.”
So I stopped.
Rest—Real Rest—Is the Ultimate Flex
Not the car. Not the watch. Not the account balance.
But the spontaneous power to say, “STOP.”
To pause. To breathe.
To step off the gas and still know you’re on the right road.
Marcus Aurelius wrote in Meditations: “If you are distressed by anything external, the pain is not due to the thing itself, but to your estimate of it—and this you have the power to revoke at any moment.”
Rest is my way of revoking false urgency.
Of reclaiming that power.
Stress + Stillness = Strength
In Deep Work, Cal Newport teaches us to master attention. But even deep work demands deep rest. Without it, the well runs dry.
Nassim Taleb, in Antifragile, says strength doesn’t just come from resilience. It comes from systems that gain from cycles:
Stress. Volatility. And recovery.
I’ve built my weeks with structure and discipline to avoid burnout. But the biggest freedom in being my own boss isn’t just in that structure—it’s knowing when to walk away from it.
Not to reject responsibility, but to embrace the bigger mission: life itself.
The Five Kinds of Wealth
Naval Ravikant reminds us: “Real wealth is not about money. It’s about freedom—doing what you want, when you want, with whom you want.”
That’s not laziness. That’s clarity.
Sahil Bloom takes it a step further. He describes five types of wealth:
- Financial
- Time
- Physical
- Social
- Experiential
Today, I’m choosing to invest in time and experience.
The memories we’re about to make in Maui…
That’s compound interest of a different kind.
Rest Isn’t a Break From the Plan—It Is the Plan
Right after this trip, I enter what I call my Client Surge—two focused months of proactive reviews, strategic planning, and meaningful conversations with the families I serve.
That kind of focused, high-impact work demands energy.
It demands clarity.
Which is why this pause isn’t an interruption—it’s part of the plan.
Rest is part of the rhythm. The inhale before the next exhale.
Take the Pause
So here’s my challenge to you:
Find confidence in taking your rest.
Whether it’s 15 minutes or a full day off—don’t wait for permission.
Rest isn’t a luxury. It’s essential. It’s how we refill the tank for what matters most.
What does rest look like for you?
What would it mean to pause—not out of weakness, but out of strength?
I’d love to hear your version.
And wouldn’t you know it—the first thing I wanted to do when I chose to rest…
Was write this.
It didn’t feel like work at all.
And that’s how I know—
I’m truly resting.