Dr. Oliver Degnan

Time to leave corporate life? Read time: 4 minutes I left my CIO role after 20+ years in the trenches. Thought I had it all figured out. I didn't. Here's what nobody tells you about making the jump. The Reality Check More people are ditching corporate careers these days. I get it. You sit at your desk, stare at your screen, and wonder if this is all there is. Maybe you've been passed over. Maybe the politics finally broke you. Maybe you just want out. So you start dreaming about becoming an...

When Everything Is a Priority, Nothing Gets Done Read time: 4 minutes 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...

Forget About 40 Hours. Read time: 5 minutes 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....

Feeling Disappointed All the Time Read time: 4 minutes Something weird happens when I start working with a new executive. They walk in frustrated. Angry. Disappointed. But when I ask them what's wrong, they can't quite explain it. It's like trying to describe a smell you've never encountered before. Since 2018, I've worked with over 500 corporate leaders in my role as a fractional CIO and executive advisor. Many of them showed up with the same confusing mix of emotions. Discouragement....

Stop Asking for Permission to Succeed Read time: 4 minutes From kindergarten through college graduation, we're conditioned to raise our hand. Ask permission. Wait for instructions. Follow the rubric. Then we enter the workforce, and nothing changes. We're handed an employee handbook, a job description, and an unspoken rule: stay in your lane. Here's what I've learned after 20 years as a CIO: the professionals who rise fastest are the ones who stop asking for permission to succeed. The...

10 Ways to Guarantee You'll Stay Burned Out Read time: 4 minutes I've watched hundreds of executives try to escape burnout. Most fail. Not because they're lazy or stupid. They fail because they're doing things that feel right but don't actually work. Here's what I've learned from 20+ years leading teams of 1,600+ people: burnout isn't about being tired. It's a defect in your relationship with your environment and your outlook on the future (Degnan, 2025). So let me break down the ten most...

Too Much On My Plate: The Executive Priority System That Saved My Sanity Read time: 4 minutes Some time ago, the SVP of Engineering walked into my office looking defeated. "Everything's a priority," he said. "The board wants the new platform yesterday, sales needs custom features, and security found vulnerabilities that need immediate patches." I recognized that look. Same one I had fifteen years ago when I was managing 47 "critical" projects simultaneously and sleeping four hours a night....

The Two Words That Expose an Insecure Leader Read time: 4 minutes TL;DR I’ve seen too many execs puff up by calling people “my VP” or “my project manager.” It’s not ownership, it’s insecurity dressed as power. This red flag screams they won’t develop you because they fear you’ll replace them. Flip the script: Spot it early, and build teams where growth means everyone levels up. Here’s how to spot and fix immature leadership without the drama. Spotting Immature Leadership I was in a meeting...

Your Executive Job Search Is Failing Because You're Not Leading It Read time: 4 minutes TL;DR: Stop blasting your resume everywhere and attending random networking events. The executive job search is a leadership activity that requires a strategic approach. Use the 911 Method: identify your top 10 target companies, map paths to decision-makers, deliver 9 pieces of value, 1 pitch about yourself, and 1 clear ask. Those who commit to this system land roles in weeks. Those who revert to the...