The First Time I Didn’t Perform
For years, I was a Porsche surrounded by Hondas. I made myself smaller, slower, more digestible. Then I started a company and had to stop performing.
There’s a moment in every founder’s life when “entrepreneur” stops being a job description and starts being a mirror. Not the flattering, ring-lighted kind, but the harsh, bathroom-at-2am version that asks: who are you when there is nothing to fix, no script to follow, nobody to impress?
This is the story of the first time I chose to build something from scratch instead of inheriting a role. And maybe more importantly, the first time I stopped performing and started choosing.
Recently, I walked away from a corporate executive role with an idea that barely made sense to anyone who knew the high-achieving version of me they’d spent years watching.
Inheriting an identity is still work
For years, I was excellent at inheriting.
I could step into an existing system and make it run smoother. I scaled organizations through significant growth by reading the room, decoding power dynamics, seeing what the “right kind” of a leader looked like, then shape-shifting into it with unnerving precision.
The work was still hard. The nights were still long. My nervous system still paid the price. But there was comfort in the constraint. You can get very far in life by becoming world-class at upgrading someone else’s blueprint.
Many “successors” do exactly this: they gradually internalize the norms, values, and expectations around them until the inherited role feels like their own.
That was me. I was a successor in spirit. My talent was optimization, translation, and polishing. I was the person you brought in when something already existed and needed to be grown, modernized, or rescued.
I knew how to win in that game. Which is why walking away from it felt less like a pivot and more like a death.
Here’s what I didn’t know about leaving: the grief isn’t about the paycheck or the title. It’s about not knowing who you are without the organizational infrastructure that told you you were valuable.
The first time you build from zero, you meet yourself
Building something from scratch is marketed as freedom. No boss. No precedent. No, “this is how we do things here.” Just clean white space and infinite upside.
What most people don’t tell you is that white space is loud.
I spent the first three weeks staring at blank documents, paralyzed by questions that had nothing to do with go-to-market strategy:
What do I actually believe is valuable?
Who do I want to serve if no one is watching?
What pace is sustainable for my body, not just my ambition?
Naming my offer felt like naming myself. Pricing my services meant testing my own worthiness. Choosing a niche forced me to confront what I was actually afraid of: being “too much” for people who were used to the polished, corporate version of me.
Research shows that the early-stage grind is not just about acquiring skills but about identity work: integrating who you’re becoming into your sense of self. That process is messy, full of tension, and loaded with self-doubt.
I’ve spent my entire life being told I’m too fast, too direct, too intense for the people around me. A Porsche constantly surrounded by Hondas. For years, I made myself smaller, slower, more digestible. I performed the version of myself that wouldn’t make people uncomfortable.
Starting consulting meant I had to stop doing that. And it turns out, dismantling a lifetime of people-pleasing patterns while also trying to sell consulting services is a mind-fuck.
Entrepreneurship as identity work, not just strategy
There’s a clean, LinkedIn-friendly version of entrepreneurship: clarify your ICP, build your funnel, choose your tech stack, ship consistently.
Important, yes. But incomplete.
Underneath the decks and spreadsheets, this is the identity work:
Reconciling the part of you that craves safety with the part that craves autonomy.
Letting old titles die without proof that the new ones will “work.”
Allowing yourself to be seen as you are now, not as the highlight reel of your past life.
This is why certain tactical decisions feel disproportionately loaded.
I spent weeks trying to name my Substack. Not because the words were complex but because I was renegotiating my entire professional identity. “How to Boss AI” finally landed and felt bold and direct - very me. But it also felt risky.
Would people take me seriously? Would they think I was too casual, too much?
The truth is, I was afraid of being myself in public.
That’s the work nobody warns you about. Studies on founders describe this as the ongoing effort to align what you’re building with who you believe yourself to be, while the market and your own history pull you in different directions.
On paper, it’s a business model question. In your body, it’s “Who am I if I’m not that anymore?”
The end of performing
For many of us, entrepreneurship is the first time we stop performing a pre-written identity. You realize how much of your previous “confidence” was actually costume design: the right brand, the right logo on your email signature, the right implicit script for what people like you do next.
When you no longer have those props, you have to figure out what’s actually yours.
For me, the shift looked like this:
I stopped using consultant speak. I started writing the way I actually talk - raw, stream-of-consciousness, with profanity and run-on sentences and vulnerable admissions that felt risky to share publicly.
I chose to build my company around what I actually believe: that AI adoption isn’t a training problem, it’s an identity crisis. That companies struggle with AI not because of the technology - they struggle because addressing the identity fracture that happens when people’s sense of professional value gets threatened by automation is uncomfortable work that most organizations avoid.
That’s what’s happening to employees right now with AI. And nobody’s talking about it.
So I built a consultancy that does. Not through endless training sessions or tool implementations, but through a “trojan horse” model: I enter through immediate operations work to build trust, then expand to the strategic identity work that actually moves the needle.
It was the first time I built something that might disappoint people who were invested in the high-achieving, always-on, people-pleasing version of me. It was also the first time the work felt like a reflection of my own values instead of a performance of someone else’s.
For founders in the in-between
If you’re in that muddy middle - no longer who you were, not yet who you’re becoming - you’re not failing. Your identity is catching up with your decisions.
The first time you build from scratch is often the first time you see yourself clearly. Not as the heir to someone else’s story, but as the author of your own.
I’m still learning how to be the author. But at least now I’m writing in my own voice.
And if it’s true for the founder, imagine how true it is for the employees you’re trying to lead through the transition to AI.
A note for leaders reading this
If you’re a leader thinking about AI adoption, you might be wondering what founder identity work has to do with your transformation initiative.
Everything.
Your people are resisting AI for the same reasons I resisted leaving my corporate role: not because the work is hard, but because it threatens an existing identity.
When you roll out new AI tools and wonder why adoption is slow, your high-performing analysts are asking: “Who am I if AI does the work I built my career on?” Your middle managers are thinking: “What’s my value if automation handles coordination?”
The same question I was asking myself: “Who am I if I’m not the corporate executive who optimizes other people’s systems?”
The difference is, as a leader, you can’t just tell people to “be more adaptable.” You have to create the conditions where they can safely reconstruct their professional identity without losing their sense of worth.
This means starting with their current expertise and showing them how AI amplifies it, not replaces it. It means making space for the grief and uncertainty that comes with change, not shaming people with completion lists. It means treating adoption as an ongoing identity negotiation, not a one-time training event.
That’s the work many companies skip, often leading to challenges in AI adoption.
Key Research Cited
Founder Role Identity: How Founder Role-Identity Affects Entrepreneurial Transitions
Authenticity Work: The evolution of founder identity as an authenticity work process
AI as Identity Change: Real AI adoption means changing human behavior and self-concept
Author Spotlight
We’re so grateful to Anna Levitt for allowing us to share her story here on Code Like A Girl. You can find her original post linked below.
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Thanks for your support @Elena Calvillo at Product !
Grateful to be featured here – this piece hit a nerve I didn't expect. Identity work is the part of building that nobody teaches you how to do.