The Journey: #19 The Difficult Departure

When I joined this particular company a few years ago, there wasn’t much in place. No team, no structure, no clear strategy. Just a blank slate.

So I built.

I wrote every job description. I interviewed and hired every single team member. I created the career paths, the processes, the onboarding programs, the playbooks. I rolled out the technology, mapped the customer journey, and established how we’d partner with customers at every stage.

I aligned with cross-functional teams, drove new initiatives, and, maybe the hardest part, spent months educating the company on what Customer Success actually meant, and why it mattered to every single person, regardless of role.

This was the most foundational work I had ever done. And it wasn’t just about systems and strategies, it was about people.

I watched my team grow into themselves. I saw them rise into new roles, earn promotions, gain confidence. We celebrated professional milestones and personal ones. Birthdays, engagements, babies, new homes. We also faced hard moments, layoffs, loss, burnout, and everything life throws your way when you're trying to be a full human and a high-performer.

And then, one day, I knew it was time for me to go.

The reasons were complex, and the decision was mine. But leaving a company is rarely just a career decision, it’s an emotional one.

What no one prepares you for is how much it hurts to leave a team you built. A team you love. A team that trusted you.

It was one of the hardest exits I’ve ever made. But I wanted to do it the right way, not just for the company, but for the people.

Here are four things I did to make sure that when I walked away, I wasn’t burning bridge, I was building legacy:

1. I made myself replaceable. I documented everything, our strategy, our operations, our rituals, and the why behind it all. Leadership isn’t about being the hero; it’s about making sure the work can outlast you.

2. I had honest, personal conversations with everyone on my team. I didn’t want anyone to find out from a mass announcement. I wanted to say thank you, to reflect with them, and to remind them how proud I was of what we’d built together.

3. I asked for feedback. I wanted to know where I had helped them, and where I could’ve done better. It wasn’t about ego. It was about leaving with humility and taking those lessons with me.

4. I stayed connected. Because the job may have ended, but the relationships didn’t. I still cheer for them, support them, and keep in touch, because that part was always real.

I’ve since built other teams. I’ve moved on. But that team will always hold a special place in my heart. And I know I’m not alone.

So if you’ve ever had to make a difficult departure, whether recently or years ago, I see you.

It’s not easy to walk away from something you poured yourself into.

But you can leave with grace, and still hold on to everything that mattered.