Confessions of a Chronically Overbooked CEO: Missing Meals, Milestones, and My Mind

From one business owner to another: I built a successful company, but nearly lost track of my life in the process.

Let me tell you a story. If you’ve been leading or running a business, it’s probably a very familiar one.

Once upon a very busy time, my wife had to schedule a formal meeting just to fill me in on our family’s life. I’m talking full agenda, printed handouts, strategic action items. She needed to know if we were still planning that winter vacation, when to book my parents' anniversary celebration, and how not to double-book me for a million things I’d already overcommitted to.

Spoiler alert: I didn’t have answers. Honestly, I barely had time to read the agenda. 

As a CEO, business leader, and professional "fire putter-outer," my days often felt like a speed dating event with my calendar: back-to-back meetings, surprise emergencies, a million "quick questions" that turned into 90-minute brain-drains. My work life had completely swallowed my real life.

Somewhere between chasing quarterly goals and managing client deliverables, I also missed the life I was supposedly working so hard to support. Soccer games came and went. Strategic planning meetings clashed with family dinners. I even stepped away during my cousin’s wedding ceremony to “clean up a mess” on a client call and by the time I came back, I’d missed the whole thing.

"It’s okay, Dad," my son said once. "You’re busy."

He said it casually, like it was just the norm, like it had never occurred to him that I might be able to show up. That I’d missed enough milestones that this was just how life worked. I laughed it off at the time, but later that night, it echoed in my head louder than any boardroom conversation I’d had that week.

When your six-year-old understands your busy season better than you do, it’s time to reassess. Business owner support shouldn't mean sacrificing the very life you're building your business for.

If that wasn’t enough, the hits kept coming. I once missed a team celebration, the kind of thing I used to swear I'd never let slip. One of our longest-standing employees hit their five-year anniversary, and I was stuck in a back-to-back investor pitch. I sent a Slack message an hour later that read, “Congrats!! 🎉” and it made me cringe the second I hit send. That moment should’ve been mine to honor. Instead, it became another calendar casualty.

You’d think that would be rock bottom.

But no. That came the day I found myself taking a budget call in an exam room, right as my wife and I were about to hear our baby’s heartbeat for the first time. Business on the phone, family in the room, and me? Caught trying to be fully present for both and succeeding at neither.

“Can you mute yourself for a second?” my wife asked.

“Hang on, they’re finalizing Q4,” I whispered.

There are low points. And then there are “finalizing budgets while hearing your child’s heartbeat for the first time” points.

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Why Delegation Isn't Just a Luxury, It's a Leadership Skill

Delegation isn't admitting defeat, it's recognizing that your genius belongs on the big stuff: vision, strategy, growth. Not in rearranging project timelines or tracking down missing invoices. Not in remembering birthdays or rescheduling meetings.

Great leaders understand that their value doesn't come from doing everything, it comes from doing the right things. Delegation is one of the most impactful strategies for CEOs who want to grow without burnout.

The Executive Support Advantage

When I think back to that 10-minute phone call with Morgan Pinnacle Group (MPG), I realize it was the moment everything started to change. It didn’t just save my schedule, it honestly saved me.

MPG was founded by people who have lived the chaos of entrepreneurship, felt the pressure of overcommitment, and deeply understand this struggle. They built it for leaders who know delegation isn't weakness, it's wisdom.

Imagine:

  • A full inbox... magically handled.
  • Business travel plans, client meetings, project timelines… managed.
  • Market research, CRM management, and client follow-ups executed so you never lose momentum.
  • Board decks, investor updates, and strategic reports polished and prepped before you even ask.
  • Strategic calendar blocks and streamlined systems keeping you focused on leadership, not logistics.
  • Special projects (the ones you’ve had on the back burner for months) finally moving forward.
  • A life outside your calendar... reborn.

You don’t have to choose between scaling your company and seeing your kids' soccer goals. You don’t have to sacrifice your health, your relationships, or your sanity on the altar of "doing it all."

You just have to choose to delegate.

Small business support, business owner support, real work-life balance, it’s not a pipe dream. It's what happens when you have the right executive support in your corner.

-Jason M., Founder and CEO

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