The Journey: #52 Stop Playing Small

As we close the year, I’ve been thinking a lot about the choices that shape our careers; the bold ones and the quiet ones. And the truth is, for a long time, I made the quiet ones. The safe ones. The comfortable ones. The ones that didn’t require me to be seen too much or want too much.

I spent years playing small.

Act 1: Marketing: When growth felt effortless

In my early career, Marketing Kristi, opportunity seemed to find me.

Fresh out of college, I landed in advertising with the charming title Ad Master (yes, that was real). I bounced from promotions to events and eventually into SEO, all within my first company. When I moved to agency life, I was quickly promoted to Manager, leading a team of ten. From there, The Knot, Crain’s New York, an eCommerce leadership role… one step naturally followed the next.

I was progressing quickly, but without much discomfort.

I didn’t have to fight for a seat at the table.

I didn’t have to ask for bigger opportunities.

I didn’t have to raise my hand and risk a “no.”

It was growth, but it wasn’t brave growth.

Act 2: When ambition got real

Then came Customer Success and everything changed.

Progress wasn’t automatic. It wasn’t guaranteed. It certainly wasn’t linear.

Every move required proof, a pitch, and some form of exhausting negotiation.

Once I reached VP, I stayed there. Across multiple companies. Not because I wasn’t capable, but because the leap from VP to C-Suite requires something deeper than great work.

It requires vulnerability.

It requires voice.

It requires being willing to want more, publicly.

And that was uncomfortable.

The year I stopped shrinking

When I joined ClientSuccess in 2021, I decided to do it differently, so before I even started, I shared my goal with our CEO: “My ambition is to become a CCO. I want to earn that opportunity here.”

Saying that out loud felt scary. But it also felt honest.

I began operating like the leader I was aiming to become, not just the one on my business card. I tracked my outcomes, stepped into cross-functional leadership, and focused on organizational impact. I made my work visible.

As my first anniversary approached, I prepared to make my case.

But I didn’t have to.

In March of 2022, Dave Blake promoted me to Chief Customer Officer, live, on air, during our virtual CSM Summit. I'll never forget it, the coolest career movement.

I was ready to fight for it, but I didn’t need to, because I had shown up boldly from the beginning.

And that moment has defined the last four years of my career, some of the most fulfilling and impactful work I’ve ever done.

All because I stopped playing small.

A reflection as the year ends

As 2025 comes to a close, I want to leave you with this:

Where are you still shrinking?

Where are you waiting for permission?

Where are you letting comfort or fear decide for you?

We often think ambition has to be quiet, that wanting more might be seen as too much.

But here’s what I know now:

The world won’t expand for us unless we show it how big we’re willing to be.

An invitation for 2026

If you’re ready for your next chapter, here’s a starting point:

10 Ways to Stop Playing Small

1. Share your goals with the people who can help you reach them

2. Keep a visible record of your contributions and outcomes

3. Take on work that ladders up to the company strategy

4. Put yourself in rooms that stretch you

5. Practice speaking in terms of business impact

6. Ask for opportunities sooner than you feel “ready”

7. Build relationships with leaders who see your potential

8. Say no to work that keeps you comfortable instead of growing

9. Revisit your development plan every quarter, not annually

10. Celebrate progress, not just milestones

You don’t need a new job to start acting like the future version of yourself. Just a new belief.

Let’s make this real

If you’d like accountability, reply to this email with:

What’s the bold move you’re making next year?

The one that feels a little audacious. The one that scares you just enough. The one you know you’re capable of ... if you stop playing small.

I’ll be in your corner the whole way.

Cheers to bigger rooms, bigger bets, and bigger belief.

2026 is waiting, and it has your name on it.