No Regrets, Just Lessons: What Some Women Tech Executives Would Tell Their Younger Selves

The Pax8 Beyond conference kicked off with the Women in Tech Networking Event. This year, four accomplished women tech executives took the stage, sharing their candid insight, hard-earned lessons and real-world advice for the next generation of women leaders.

This year’s panel at the Pax8 Beyond conference featured four powerhouse executives: Jennifer Roy, CEO of Nucleus Networks; Lisa Williams, director of partner development, global partner solutions at Microsoft; Deon MacMillan, chief people officer at Pax8; and Carrie Schiff, chief legal officer at Pax8. The answers from the women on stage weren’t just vulnerable—they were tactical. And they offered something that’s often missing in leadership content: an honest reflection on what it means to lead boldly before you feel ready, all while maintaining a life outside the boardroom.

In an industry obsessed with outcomes, these women remind us that growth often starts with a pause.

Fearlessness Comes Late, But It Doesn’t Have To

When asked, “If you could give advice to your younger self, what would it be? “Roy, this year’s recipient of the Pathway Women in Tech Award, didn’t sugarcoat her answer.

“I wish I had been more fearless from the start of my career.”

For the first seven years of her journey, Roy admitted she played small, worrying about perception, holding back ideas and waiting to be invited instead of claiming space. Now, more than a decade in, she’s realized that fearlessness is a muscle. And that delaying its use only postpones the impact you're capable of making.

Her story isn’t uncommon. Many women in tech admit they spent the early years of their careers focused on proving they belong rather than trusting they do. But the message here is clear: Waiting for confidence to arrive can delay your influence. Sometimes, the best move is to act while still afraid.

‘Regret’ Isn’t the Right Word

Microsoft’s Williams offered a counterpoint.

“I try to live my life with no regrets. But if I could go back, I’d remind myself to keep the student spirit alive.”

Her message wasn’t about mistakes. It was about mindset. That early career pressure to “know everything” can cut off curiosity, and curiosity is a growth engine in any role. Especially as those in the channel chase AI integrations and where the tech evolves fast and partnerships evolve even faster, adaptability is non-negotiable.

The subtext is clear: Regret doesn’t build careers. Openness does.

The Leadership Lessons No One Writes into the Job Description

But what makes the panelists’ reflections so powerful is that they are more than aspirational. They are actionable, too.

Yet, if we read between the lines, a pattern emerges. The most successful women in tech tend to reflect with compassion for their younger selves, not shame about what they did not know or opportunities they missed. They refuse to dwell on regrets. Rather, they reframe their actions as directional signs:

• “Ask for the raise earlier.”
• “Speak up even if your voice shakes.”
• “Your ambition isn’t too loud. It’s simply surrounded by people who need to adjust their volume.”

This isn't about rewriting the past. It’s about mentoring the next generation through hindsight.

Why This Matters in the Channel

Women of the channel often experience the stakes of every decision more sharply. Saying no to a promotion, pivoting too late, not negotiating hard enough. These are the moments that can sit heavy on the heart and have a career impact years later.

But when leaders like Roy and Williams share their self-talk from the other side of success, they create a new leadership script. One where fearlessness isn’t something you earn through tenure, but something you practice early and often.

And that’s especially critical in today's social climate, as channel organizations rethink leadership development, equity initiatives and retention strategies. These aren’t just feel-good stories. They’re blueprints.

From Reflection to Action

If you’re a leader in the channel today, ask yourself: What would it take to make fearlessness a first-year skill?

Could you:

• Normalize “stretch roles” for early career women?
• Build mentorship models that go beyond coffee chats and into decision coaching?
• Reframe feedback not as correction, but as confidence-building?

The stories we tell ourselves about who we were shape who we believe we can become. By sharing these stories publicly, these women in tech aren’t just owning their path. They’re lighting it for someone else.

And maybe that’s the real power of hindsight. Not just to understand your journey, but to make someone else’s just a little bit braver.

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