What I Wish My 25-Year-Old Self Knew About Work, Growth, and Leadership

If you could sit down with your 25-year-old self and tell them what’s coming, what would you say?

As I've reached my mid-forties, I marvel that so much time has passed (and experience gained) since then. At 25, I was just beginning my career, full of ambition and assumptions about what success should look like. I didn’t yet know how winding the road would be.

I imagine my younger self might be surprised by a few things:

• You think B2B tech is riveting? Especially transportation and logistics?

• You started your own business? Didn’t see that coming—but it makes sense.

• I love that you’ve stayed close with people from every job you've had.

• You finally got that promotion. And then another and another.

• Life’s about to throw some wild plot twists your way. Some of them will knock the wind out of you. Others will take your breath away (in a good way).

• You live in a different city, work in a different field, and have a totally different title, but your values? They’re still there. They just look a little different now.

But if I had to pick what I most wish I could go back and share, it wouldn’t be the job titles or the career moves. It would be the lessons I’ve learned along the way and how they shaped how I lead, work, and live.

1. Fighting change only prolongs the discomfort.

When things start to shift—whether it’s a job, a team dynamic, a life circumstance—our instinct is often to resist. In my experience, however, change doesn’t go away just because we ignore it. Growth begins when we stop clinging to the old way and lean into what’s next.

2. Trust your intuition.

Overthinking has its place, but your instincts about people, opportunities, and direction are usually more accurate than you give them credit for. If something doesn’t feel right, it probably isn’t. And if something lights you up? Pay attention.

3. Safe isn’t always smart.

Some of the best things I’ve done in my career didn’t feel “safe” at the time. But they were right. The calculated risks—the ones guided by clarity, not ego—have always paid off in growth, even if the outcome wasn’t what I originally expected.

4. Leadership is built, not born.

I used to think leaders just had “it”—some innate confidence or charisma. I’ve come to see that the best leaders are the ones who actively build the mindset, skills, and self-awareness the role demands. It’s not about being perfect. It’s about committing to ongoing growth.

5. Grit is powerful, but it’s not everything.

Pushing through can get you far, but grit without support, perspective, and resources can lead to burnout. Resilience isn’t about doing everything alone—it’s about knowing when to ask for help, when to rest, and when to recalibrate.

6. Ask for what you want.

I can’t count how many opportunities came my way only after I clearly, confidently asked for them. Being vague to avoid stepping on toes or waiting for someone to notice isn’t a strategy—it’s a delay that can lead to frustration all around. Clear is kind. Direct is powerful.

There’s more, of course. There always is. But if my 25-year-old self could internalize just these few truths, I think she’d feel more grounded, less anxious, and more prepared for what’s ahead.

She might also be proud. Not just of what I’ve done—but of who I’ve become while doing it.

And maybe that’s the real question worth asking.