Don’t Ask Me “What’s Next”

When you spend most of your career working on something you're deeply passionate about, something that checks all the boxes of your core competencies, the end, even when anticipated,  is harder than ever imagined. 

It's even hard when you know you are ready for the end, and when you're confident that you can move one and even confident that you will succeed.

It's just kind of brutal… and taboo to talk about?

But I'm here right now.

I built and scaled CITYROW for over a decade. It was amazing and challenging in all the right ways. It was my identity, my passion project. I poured everything I had and rallied everyone around me into it. It grew and grew, and then it didn’’t. The last couple of years were stressful, to say the least, and we finally “sold” the business in 2024.

Even though I knew the end of that chapter was coming. Even though I knew it was going to be hard to disentangle my identity from the business, moving through the transition is still, almost two years later, really, really hard.

I'm navigating it. And I’ll be fine, but it still sucks.

After CITYROW, I quickly launched my book Making Waves and immediately started doing incredible consulting work with friends. I have projects I'm excited about. And yet, I'm still in this messy in-between.

Because here's the thing about reinvention and moving the thing that was your entire life to the next: it's not just about finding the next thing. It's not about finding a job.

It's about sitting in the space where you're no longer defined by this one thing, but not yet clear on what the next thing is.

I realized I had to just sit in this. Sit in the gunk. Intellectually, rationally, knowing that great stuff is ahead. Yet knowing that at this moment, it sucks.

I hate when people ask, "So what's next?"

That brings me to today.

After finishing and launching Making Waves, my collaborator on the book, Leanne Shear, and I would catch up regularly. We're both in this transition from our companies to consulting, to figuring out what's next. And we had this conversation over and over about where we were both sitting. And the discomfort there.

We'd be on the phone for 60, 90 minutes just talking about what it felt like to be in this space and how we were handling it and also what creative project we were going to work on next.

And then finally one day, we were like: this is the project. This conversation. This is interesting. And, we should invite other people into that conversation.

So, after months of work, we're launching Step Into Next.

It's our conversation about what's happening right now. About chapters that have ended - whether it's a career, a business, a relationship, a phase of life - and navigating into the next phase. Or just the time it takes you to get to that next phase. Job. Career. Relationship. Whatever.

It's hard. It's really vulnerable. It's really challenging.

And that's what it's about.

We're not pretending to have it figured ou and we’re certainly not offering a blueprint or a framework or five steps to your next chapter. Because frankly, we don't think there is one.

There's no single path. It's about taking one step in front of the other. Walking YOUR labyrinth. Saying no to some things, yes to others. Not knowing but stepping anyway. And making mistakes along the way.

I hope you'll listen.

And if anything resonates, you're not alone. It's hard for all of us…and I’m starting to think maybe that’s part of it…