My Corporate Exit Story: The Plans, Pivots, and Surprises

After 25 years of corporate jobs, I decided to step off the corporate ladder and leap into the entrepreneurial unknown.?

My transition plan looked flawless on paper - strategy documents, market analyses, and financial projections were all neatly organized in color-coded folders. Because that's what two decades in corporate leadership teaches you, right?

Spoiler alert: Reality had other ideas. Here's my rollercoaster ride of surprises – the good, the bad, and the "why didn't anyone warn me about this?"

1. Breaking Out of the Financial Services Box

All of my career was in financial services despite trying to switch industries a few times. So? I had assumed my consulting clients would continue the pattern.

But suddenly I found myself working with biotech startups and nonprofits, each new client bringing new challenges and perspectives, and finding immense satisfaction in that.

2. Freedom to Fail (Without Taking Anyone Down With Me)

One unintentional wrong move and your entire team's bonuses could get impacted or de-rail a key company priority. So I took carefully calculated risks and often dropped failed ideas after the first try.?

Now? I can experiment wildly, fail spectacularly, persist, and fail again, and the only person feeling the impact is me.?

This newfound freedom led to some unexpected wins – like joining NYU's faculty (after enough rejections to wallpaper my home office) and landing a spot in a bestselling book.?

3. Money: The Emotional Rollercoaster

Let's talk about the money thing. That steady bi-weekly paycheck was more than income - it was a security blanket.?

Intellectually I knew it was gone, but my emotions took a little longer to get used to this new paradigm.?

On top of that discomfort, I discovered that pricing my own services was an entirely new game.?

"What's your rate?" blasted open my comfort zone walls. I hemmed and hawed and didn’t learn how to be unapologetic about the value I bring to the table for months.?

4. Why did no one warn me that you get a lot more rejection as a consultant?

After years on Wall Street, I thought I had a thick skin, but turned out I had to grow another layer of toughness.?

What I did learn is that rejection isn't just about hearing "no" or being ghosted - it's about turning those "nos" into opportunities for refinement.?

What seemed like setbacks at the moment became stepping stones to building something more valuable and sustainable than my original vision.

Looking back on these two years, I'm filled with gratitude for my journey so far.?

To the clients who trusted me, to the amazing professionals who've become part of my network, and to my former colleagues who cheered me on - thank you.?

Here's to embracing the unexpected turns that lead us to exactly where we need to be. And to the new surprises that await me - after all, I am still only in the beginning.

Click here and subscribe to the Leading with Data newsletter.

Every Friday morning, I'll email you 1 actionable tip to accelerate the business potential of your data & make it an organizational priority.