I started as a solutions architect. Within 15 years, I became a CIO for Fortune 100 companies. Each promotion took about 15 months on average.
Solutions architect. Chief architect. CTO. SVP. CIO. CEO.
That's the trajectory. And none of it happened by accident.
Here's how it actually worked. I stopped thinking about Monday through Friday, 8 AM to 5 PM. I forgot about the 40-hour workweek entirely. Not because I was grinding myself into the ground. Because I had found something I loved.
I spent weekends experimenting with new technology. Early mornings before the office opened. Sometimes evenings. I would get my hands on emerging platforms, test them out, and prepare pitches for leadership.
When they bought in, I volunteered to lead the implementation.
I got really good at pitching new solutions for one reason: I wanted to get my hands on them. I wanted to be the one building the future, not just watching it happen.
Then something clicked. I realized I couldn't do it alone. So I got obsessive about finding top talent and getting out of their way. My job became creating the platform for their success.
That visibility compounded fast. The promotions followed.
Why This Matters for You
Let's cut to the chase. You're not going to level up to executive leadership by doing your job from 9 to 5 and hoping someone notices. That's not how it works. Never has been.
Research backs this up. A meta-analysis across over 100,000 employees found that proactive personality, the tendency to take initiative and influence your environment, is a significant predictor of career success, including salary, promotions, and subjective career satisfaction (Zhang et al., 2022). The people who move up are the ones who act before being asked.
But here's what I've learned working with hundreds of leaders over the years: you can't just work more. You have to work smart.
Managing Your Availability and Energy
This is critical. In my LevelUp System, I teach that sustainable career advancement requires managing two resources most people ignore: availability and energy.
You need to excel in your current role first. That means showing up focused, delivering results, and building credibility. That's non-negotiable.
But alongside that, you need to carve out availability for initiative-taking activities. Projects that allow you to step into new responsibilities. Efforts that move the needle for the organization.
Here's the twist: those activities should align with your passion. Professionally and personally.
Think of it like when you first learned to ride a bike. At first, everything takes effort. But once you love it, you don't count the hours. You just ride.
When your initiative work aligns with genuine interest, you can do it before work, after work, on weekends, even on vacation. I never considered it work. It was exploration. It was fun.
The Three Pillars of Executive Readiness
You want to level up to executive leadership quickly? You need to demonstrate three things, actively, every single day:
Executive Thinking. This means seeing the bigger picture. Understanding how your work connects to organizational strategy. Anticipating problems before they surface.
Executive Execution. Delivering results, not just completing tasks. Building systems that scale. Creating outcomes that matter.
Executive Leadership. Developing others. Building teams that succeed without you hovering over them. Becoming the platform for their success.
All three go hand in hand. You can't skip one and expect the others to carry you.
What Doesn't Work
On the contrary, here's what won't get you there.
Exerting yourself mentally and physically every day without reserving energy for strategic planning. That's a recipe for stagnation. You become reactive instead of proactive.
Simply putting in the time and hoping for the best. Hope is not a strategy. Visibility doesn't come from attendance. It comes from impact.
And since we're talking about leveling up, I'll share this: I had several advisors along the way who helped me stay in executive leadership. Getting there is not the same as staying there. Getting promoted is one thing. Succeeding and thriving at that level is another challenge entirely.
The Burnout Connection
Here's something most career advice ignores. When you try to level up by brute force, by grinding harder and longer at work you don't enjoy, you burn out. You deplete your reserves without replenishing them.
But when you channel your energy into passion-driven initiatives, something different happens. The work feels lighter. The hours feel shorter. You actually gain energy from the process.
That's sustainable momentum. That's how you climb without crashing.
Your First Move
If you're serious about leveling up to executive leadership in the next 15 months, stop waiting for permission. Start identifying the initiatives that align with your passion and move the needle for your organization. Then volunteer to lead them.
And if you want someone in your corner who's been in the trenches, who's lived this path from solutions architect to CIO, let's talk.
Book a discovery call with me at https://book.drdegnan.com and find out exactly how to level up to executive leadership in the next 15 months.
Until next week,
Oliver
