August 20, 2025

5 Smart Ways to Reinvent Your Career — Without Starting From Scratch

Hello Reader

Welcome to Level Up Weekly newsletter, where I leverage 19 years in Stanford tech to help emerging leaders think strategically, build influence, and execute with confidence - so you’re seen, heard and valued where it matters most.

The Career 'Mistake' That Doubled My Impact

"Sometimes the biggest leaps forward start with a step back."

💡 Today’s Glance

1. A bold career risk that felt like a step back—but became a launchpad
2. 5 steps to test your career leap without burning bridges
3. A reflection prompt to help you spot what’s quietly holding you backThe Wake-Up Call

That’s what I told myself when I left my corner office for a cubicle.

It wasn’t an easy decision—far from it. I had a stable marketing role at a tech company, a comfortable salary, and the respect of my peers.

But something wasn’t clicking.

You know that feeling when you’re good at what you do, but can sense there’s something else out there? That’s where I was. Every morning, I walked into my office and felt a growing disconnect between where I was and where I needed to be.

A Risk That Felt Like a Mistake

I wanted to build the technology, not just market it. But switching paths seemed impossible—until a friend managing tech support offered me an unexpected path.

So I did something that felt absurd at the time: I asked to join the tech support team.

The catch? If it didn’t work out, there was no going back.

Even the CEO pulled me aside to say, “You’re making a huge mistake.”

Discomfort Is Temporary. Growth Is Permanent.

Those first few weeks were humbling.

My hands shook during support calls.

I spent nights poring over technical manuals.

Every day reminded me what I’d given up.

But slowly, things changed.

I saw patterns in customer issues others didn’t. My marketing lens became an advantage. That shift led me to QA, then product management—a role that finally blended my past with my potential.

That “mistake” became the foundation for everything that followed.

5 Steps to Make Your Bold Career Move

(Without blowing up your life)

1. Run a personal audit

Where do you feel most energized? What drains you?

Score your current role from 1–10 across satisfaction, pride, and energy. Look for patterns—not just problems.

2. Give yourself permission to explore

You don’t need a master plan to start.

Follow your curiosity. Skim job boards. Talk to people in other roles.

You’re gathering clues—not committing yet.

3. Design low-stakes experiments

Volunteer for cross-functional projects. Shadow someone in a different role.

Small experiments give you data and confidence, without forcing a leap.

4. Name what you’re afraid of

What’s really holding you back—title, income, perception?

Write it down. Then ask:

• “What’s the worst that could happen?”
• “What’s the cost of staying stuck?”

5. Exit gracefully

If you decide to go, close the chapter well.

Leave documentation, support your team, and express appreciation.

A thoughtful goodbye opens doors for the future.

You’re Not Stuck—You’re Just Early

The most powerful career shift doesn’t start with quitting.

It starts with better questions.

When I look back, that “mistake” wasn’t a misstep.

It was the reset that gave me everything I have now.