I used to think being busy meant being productive. I was wrong.
In my years as a CIO, I'd show up to work with a mental checklist of 47 things. By noon, I'd have touched 30 of them. By 5pm, I'd completed maybe three. I'd leave exhausted, wondering where the day went.
Then something clicked. I realized my calendar wasn't working for me. It was working against me. I was constantly reacting instead of directing.
Let me break this down.
The Problem With Having Too Many Priorities
When everything feels important, your brain goes into survival mode. Decision fatigue kicks in. You bounce from task to task like a pinball, losing mental energy with every switch.
Research shows that task-switching increases the time needed to complete work and reduces the quality of outcomes. It's like trying to boil ten pots of water on two burners. You end up with lukewarm water everywhere.
Here's what I've learned after moving from software developer to CIO to running my own businesses: the executives who rise fastest don't work harder. They work with intention. They schedule. They protect their time. And they treat their calendar like a contract with themselves.
Schedule Everything (Yes, Everything)
This is my first rule: whatever gets scheduled, gets done. Whatever doesn't get scheduled doesn't exist.
I schedule my morning walk. I schedule the Netflix episode I want to watch. I schedule sleep. It sounds extreme, but it works. Think of it like this: if you don't tell your calendar what to do, your inbox and everyone else will decide for you.
According to Harvard Business Review research, timeboxing ranked as the most useful productivity technique out of 100 methods studied. That's not a small sample. That's a clear winner.
The discipline of scheduling personal tasks, like going for a walk or watching a show, does something powerful. It creates boundaries. It reminds you that rest isn't a reward. It's fuel.
My 90-Minute Weekly Weapon
Here's the thing nobody talks about: most leaders spend zero time planning their own careers and lives. They're so busy executing that they forget to strategize.
Every week, I book 90 minutes with myself. Just me. No distractions. No Slack. No email.
During this block, I dive into strategic planning for three areas: my career, my business, and my personal life. I review what's working. I spot what's not. I adjust.
This single habit keeps me ahead of everything and everyone else. It's like having a weekly board meeting for my own life. Most people never do this. They wonder why they feel stuck.
The 5:15 AM Advantage
I wake up at 5:15 AM every day. Not because I'm a masochist. Because those early hours are mine.
By 8:30 AM, I've already invested in my health and my profession. I've hit the gym, done my reading, and worked on something that moves my career forward. Before most people check their first email, I've already won the day.
This system became my secret competitive advantage. It's what allowed me to level up from software developer to CIO. And eventually, it gave me the freedom to become a corporate dropout, running multiple small businesses while spending time on activities that align with my purpose.
The Burnout Connection
When you feel overwhelmed by priorities, your brain perceives threat. Cortisol spikes. You stay in reactive mode. Over time, this chronic stress erodes your relationship with work and your outlook on the future. That's the definition of burnout.
But here's what scheduling does: it restores a sense of control. Research consistently shows that perceived control is a major driver of workplace wellbeing. When you own your calendar, you own your energy. You shift from reactive to proactive. And that shift alone can prevent burnout before it starts.
A Simple Path Forward
Start with one change this week.
Block 90 minutes on your calendar for strategic planning. Protect it like a meeting with your CEO. Then, pick three personal activities you normally skip, like exercise, reading, or rest, and schedule them too.
You'll feel the difference within days. Not because you're doing more. Because you're finally in control.
If you want help building a system that works for your leadership career, let's talk. Book a call at https://book.drdegnan.com.
Until next week!
—Oliver
