Leaping Without Looking: Trading Two Decades in IT for the Unknown World of eDiscovery

Leaping Without Looking: Trading Two Decades in IT for the Unknown World of eDiscovery

Twenty years. That’s how long I’ve been in IT, for 13 of those the manager with the spreadsheets, the metrics, the carefully calculated risk assessments. The guy who could quantify anything and always had three backup plans.

Today, I’m walking away from all of it to become join the world of eDiscovery. My legal background? Zero. None. Nada.

When the Universe Starts Screaming

A friend mentioned an opportunity at their small eDiscovery company. Past-me would have immediately listed why this made no sense: no legal experience, no industry knowledge, starting from scratch in my late 30s.

But then the synchronicities became impossible to ignore. At lunch the day after he mentioned it, KERA Think episode on happiness. The next morning The Hidden Brain episode “Taking the Leap” randomly autoplayed during my commute. I immediately devoured “The Happiness Files.” Then came “Unreasonable Hospitality” – a book about going beyond what’s expected, what’s safe, what’s reasonable.

When Your Tools Tell You to Stop Using Them

The irony still makes me laugh. My Kolbe score (7-6-3-5) labeled me a “Stabilizer” – someone who should “avoid chaos” and believes “it’s better to miss an opportunity than to make a mistake.” My Cultural Index called me a “Craftsman” who “dislikes confrontation and may avoid it in favor of following the status quo.”

Yet both assessments revealed I was burning energy trying to be someone I wasn’t. I was forcing myself into increasingly aggressive behaviors and faster reaction times that went against my nature. The very transformation my current organization was going through was driving me into exhaustion.

For the first time in my professional life, I had a bone-deep certainty that transcended any spreadsheet: I needed to make this change.

Choosing Myself First

For eighteen years, every decision filtered through its impact on my team, the organization, the five-year roadmap. Will this create stability? What about knowledge transfer? Succession planning?

This time, I chose differently. This decision was solely for me.

I gave a month’s notice - enough time to wrap up projects, document everything, ensure a smooth transition. The team will adapt. The systems I’ve built will stand (or they were built wrong). But if I stayed, I know I’d be the one who crumbled.

The New Unknown

After two decades of expertise, I’m becoming a beginner again. Project management in eDiscovery – a field where my knowledge starts at zero. The company is small, they’re excited about my tech background, seeing potential where others might see inexperience.

No safety net of accumulated expertise. No falling back on “how we’ve always done things.” Just a willingness to learn.

The Art of Starting Over

Past-me – the Craftsman who needed “clarity and established policies” – would be terrified. Current-me is exhilarated.

Sometimes the biggest risk is playing it safe. Sometimes twenty years of experience in one field gives you exactly what you need to succeed in another – even if you can’t see the connection yet.

I’ve learned: you can’t make a leap like this alone. I leaned hard on several friends throughout this process – for advice, for encouragement, for the occasional reality check when my doubts crept in. They listened to my fears, validated my instincts, and reminded me of my worth when I couldn’t see it myself. I owe them everything.

To anyone standing at their own cliff edge: the data can only take you so far. Sometimes you have to leap without looking. And sometimes, the best thing you can do is let the people who care about you help you find the courage to jump.