Last month, I spent a week in the Alps with a group of business owners, hiking and having deep conversations that had almost nothing to do with business.
And one thing that came up again and again, in different forms, was grief.
Grief for people lost, relationships that had ended, chapters of life that had closed.
And underneath a lot of that, without most of us naming it directly, was grief for the version of ourselves who started what we’re now running.
Sitting with that loss feels indulgent when there’s a business to run. It felt indulgent to me too, for years.
But you can’t reinvent anything while you’re still grappling with who you used to be.
I’m grieving pieces of my own business right now
Because I’m doing it right now. Grieving pieces of Screw the Cubicle, the business I’ve run for 13 years, even as I build whatever’s next.
That brand name has 13 years attached to it. Leaving corporate, starting over, the years of press and recognition that came with being the person who made that leap and built something out of it.
It was a huge chapter of my life, maybe even the biggest turning point I’ve had. And it’s just not fully who I am anymore, 13 years later.
There’s a version of me that was the corporate escape story. People trusted me on that, relied on me for it, and for a long time I was available for anyone who needed that particular kind of help.
Saying no to that now, even to people I’d truly love to work with, is its own kind of grief.
It’s my own grappling with being a person, in work and in real life, who’s used to saying yes to people who need her.
That was part of an identity I built a long time ago. And I’m not that person anymore.
Not everyone follows you into the next chapter
Some of that has meant losing people.
A chunk of the audience who’s known me for one specific thing might not follow me into the next chapter, and I have to let that be okay.
Trusting that what I built isn’t lost. It’s just becoming something else, and the right people will find their way to the next chapter of my work. I don’t get to control who stays.
I only get to keep being honest about where I actually am.
This is the actual work of reinvention
When you outgrow something you’ve built, you’re not just changing strategy.
You’re saying goodbye to a version of yourself you counted on to show up a certain way, and stepping into a version of you that haven’t fully met yet.
That’s the part that feels scary. That’s also the actual work. Grieving her, understanding who’s taking her place, is what makes room for the next chapter to actually fit.
What are you grappling with, when it comes to who you used to be? And how does that show up in how you’re trying to reinvent your business right now?
