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 executive consultant. Or a business owner. Or both.
Then you get a certification. Build a website. Print business cards.
And nothing happens.
That's when reality hits. Corporate life is a team sport. You had sales, marketing, operations, and admin all working together so you could collect a paycheck every two weeks. Now? It's just you.
I learned to stop thinking of this as a solo journey. You need a team around you. The difference is that you're now 100% accountable for the outcome. No pointing fingers upstream or downstream. Just you.
The Age Advantage
Here's what might surprise you. Research from MIT and the U.S. Census Bureau found that the average age of founders of the fastest-growing companies is 45 (Azoulay et al., 2020). Not 25. Not 30. Forty-five.
Your experience isn't a liability. It's your greatest asset.
But experience alone won't pay the bills.
What You Actually Need to Do
Before you hand in your resignation, do these three things:
Build relationships now. Your corporate network becomes your first sales pipeline. Those cross-functional relationships you've been building? They're gold when you're on your own. Don't wait until you're out the door to start nurturing them.
Learn the language of sales and marketing. You need to understand terms like "top of funnel" and "closed-won." Your financial freedom depends on it. It's like learning the language of stock markets. You just have to start watching and listening until it clicks.
Master closing. This is different from networking. Different from marketing. Different from everything you've done in corporate. You need to get really good at asking for the sale. And I mean really good.
The Biggest Mistake Highly Educated Dropouts Make
We know a little bit of everything. Give us a problem, we'll give you a solution.
But that doesn't work in the open market.
You need to pick one problem you're going to solve extremely well. And stick with it. If you diversify too much, nobody knows how to buy you. Think of it like this: a plumber who also does electrical, roofing, and landscaping? Confusing. A plumber who specializes in fixing old pipes in historic homes? Clear.
Get crystal clear on your positioning.
The 12-Month Plan
Once you've got the basics, map out your next year. Commit to taking one step forward daily.
Here's my approach: I schedule everything on my calendar. Not just meetings. Everything. If it's not on the calendar, it doesn't exist.
Start with a low-risk experiment this week. Offer a small pilot service to a few potential clients. Practice your pitch. Measure the feedback. Adapt. This build-measure-learn loop turns the abstract idea of closing into a real, repeatable habit.
The Burnout Connection
Here's what most people miss. Leaving corporate doesn't automatically cure burnout. In fact, going solo without proper systems can make it worse.
Burnout isn't just exhaustion. It's a breakdown in your relationship with your work and your future outlook. When you're alone, without a team, without clear positioning, without sales skills, that relationship deteriorates fast.
The key is building sustainable systems from day one. Not grinding harder. Building smarter.
Quick Wins to Get Started
Stop thinking you can do everything yourself. That's a recipe for failure.
Build a team. It might be a social media expert, a sales and marketing person, someone who can book appointments. AI can help in some areas. But you can't be a one-person show forever.
The corporate dropouts who succeed? They treat entrepreneurship like the team sport they learned in corporate. They just build a different kind of team.
If you're feeling stuck, you're not alone. Most people in their 40s and 50s reevaluate their options eventually. The question isn't whether you should leave. It's whether you're prepared when you do.
Want weekly strategies on career success and avoiding burnout? Subscribe to my free newsletter at https://read.drdegnan.com
—Oliver
