Identity Shift

From Book Coach to Tech Founder

A few weeks ago, I had the pleasure of meeting Natasha Giuffre for one of her 100 coffee dates. The whole idea felt fun and intentional, and I was genuinely honored to be her 77th conversation.

She opened with a question that delighted me:

“Are you doing what you want to be doing when you grow up?”

My answer came quickly and with so much joy: yes. I really am.

From there, she asked what I’m building, what exactly TellaDraft is, and I found myself sharing the real behind-the-scenes: how I’ve gathered advisors, hired a dev shop, learned a new vocabulary, and built an entirely new set of skills this past year. And that’s when she asked the question I hadn’t fully answered for myself yet:

“Do you see yourself as a tech founder?”

This time, the answer wasn’t as certain.
I told her honestly: I’m working on it.

This past year, I’ve worked intentionally on becoming the woman who can hold the responsibility of starting something new and something potentially very big. It requires capacity, clarity, and a level of internal strength I didn’t always have. The mindset work has been just as important as the product work.

And then Natasha shared her reflections. Here she is, in her own words:

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“Heather is a writer turned tech founder.
Which sounds like a simple career pivot until you think about what that actually requires.
It’s not just learning new skills or changing industries. It’s accepting an entirely new identity.
We talked about what it takes to make that shift. Not the tactical stuff. The internal work of letting go of who you were and becoming someone new.
Because here’s the thing about identity.
We cling to it. Even when it doesn’t fit anymore. Even when we’ve outgrown it.
I’m a writer. I’m a lawyer. I’m a marketer. I’m a founder.
These labels become armour. They tell us who we are when we’re not sure ourselves. They give us permission to exist in professional spaces.
But they also trap us.
What happens when you want to be something else? When the identity you’ve spent years building starts to feel too small?
You have to kill the old version of yourself. Not literally. But you have to let go of the story you’ve been telling about who you are.
Heather went from writer to tech founder. That’s not just a job change. That’s releasing one identity and claiming another before you’ve fully earned the right to call yourself that new thing.
The space between identities is terrifying.
You’re not the old thing anymore, but you’re not quite the new thing yet either. You’re in this weird limbo where you don’t know how to introduce yourself at networking events.
Most people never make the leap because they can’t tolerate that in-between space.
They’d rather stay in an identity that doesn’t fit than risk the discomfort of not knowing who they are for a while.
But that’s where growth lives. In the uncomfortable space between who you were and who you’re becoming.
Heather made the jump. Not because she had it all figured out. But because she was willing to be uncertain about her identity long enough to build a new one.
Maybe that’s the real skill we don’t talk about enough.
Not reinvention. But the ability to sit in the discomfort of not knowing who you are while you figure it out.
Thanks Heather for making me think about the identities I’m still clinging to that might be too small.”

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I learned more from this conversation than I ever expected. It was one of those rare moments where someone holds up a mirror and you finally see yourself clearly, not just who you’ve been, but who you’re becoming.

And it made me realize this Substack is changing too, because I am changing.

You’re going to see a major shift here in the coming weeks as I step fully into my founder identity. We’re launching a new writing group, a new challenge, and a new workbook for the new year. First Draft Friday is wrapping up its final session, and something fresh and exciting will take its place.

And of course, the TellaDraft MVP is a major focus for 2026, a huge milestone that feels both thrilling and humbling.

I’m grateful for Natasha’s questions, her perspective, and the timing of it all.
And I’m deeply grateful for everyone walking alongside me on this journey.

There’s so much more ahead.

If you want to write your business building book in 2026 and test TellaDraft, join my Skool. Its free! You can join it here.