✨ The Phases of a CEO Life
Leading, letting go, and what comes next
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Lately, I've found myself in a liminal space. Not at the beginning, where everything feels thrilling and urgent, but also not at the end—whatever that is supposed to mean. I'm somewhere in between: reflective, slower, perhaps wiser, but undeniably more uncertain. In this in-between, I've been asking myself harder questions about identity, impact, and the silent evolution no one really prepares you for when you take on the CEO title.
We tend to mythologize leadership as a peak to reach. What we rarely speak about is how that peak isn’t singular—it’s a series of elevations and descents. The CEO journey isn’t linear. It's a cyclical, deeply human experience. You start with a fire, you build something, and eventually, you must confront your own evolution—or risk becoming the bottleneck in a company you once birthed with love and fury.
This newsletter is an attempt to trace those natural phases—of leading, growing, reflecting, and, when the time comes, letting go. And just like people move through stages of life, CEOs move through seasons of leadership. These transitions are not just strategic; they're emotional, existential, and deeply personal. And often, the toughest phase is the one no one trains you for: the one where you begin to step back.
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🌱 The Four Phases of a CEO's Journey
1. Ignition Phase – The Founder as Creator
This is the era of adrenaline. You’re a builder, a dreamer, and a doer. The Ignition Phase is marked by rapid motion—ideas come fast, execution is scrappy, and you wear every hat. You’re likely pulling all-nighters, balancing burn rate with gut instinct, and measuring success through product launches and early traction.
But while this phase is exhilarating, it can also be isolating. Founders often mistake busyness for progress. Leadership is reactive, and the identity of the company is indistinguishable from your own. At this point, the biggest risk is burnout—and the greatest gift is clarity about what your company needs from you next.
I discussed busyness vs. progress with Marco Mendoza in Episode 3 of The First-Time CEO podcast, and why it’s important to not fall in love with your business. (Marco also is a badass marketer and hilarious, it is a very fun episode!) Check it out on YouTube, Spotify, or Apple Podcasts!
2. Expansion Phase – The CEO as Architect
As the company grows, so must the leader. The Expansion Phase is about systems, teams, and scale. You're no longer the only decision-maker. You build structures that allow others to succeed. Delegation, strategic clarity, and culture become your daily concerns.
Many first-time CEOs struggle here. It’s the shift from doing to guiding, from controlling to trusting. You start to notice your decisions echo further and that misalignments can multiply fast if not addressed early. This phase often requires the most personal growth—it’s where good founders become strong CEOs.
Tune in to Episode 9 with Iryna Savytska (Ukrainian president Zelenskyy knows about her startup!) to learn how she lost two years of her life as a CEO because of a decision to be a nice girl: YouTube, Spotify, Apple Podcasts.
3. Reflection Phase – The CEO as Philosopher
At some point, things stabilize. You're not constantly reacting to fires. The team operates with relative autonomy. You have time to think beyond this quarter's OKRs. It’s here that a deeper introspection begins.
You might ask yourself: What do I want from this company now? Am I still the right person to lead this next chapter? This is the point where internal alignment becomes as important as external performance. CEOs in this phase wrestle with identity and fulfillment. And it’s often here that the seeds of transition begin to form.
In Episode 10 with Jacques Anderson, who stepped away from her $29M-backed startup to become a leadership coach in Human Design, she shared that “when a whisper becomes a scream, that’s when you know it’s your calling.“ Learn more about the reflection phase and soul/business alignment with Jacques on YouTube, Spotify, Apple Podcasts.
4. Transition Phase – The CEO as Steward (and Then, Something Else)
Eventually, a time comes when your role needs to shift—or end. This might be due to personal evolution, investor pressure, market demands, or simply the feeling that your highest value is no longer operational. This is where letting go becomes an act of leadership.
But transitions are rarely clean. Stepping back can feel like erasing your fingerprints from something sacred. This emotional complexity is often described as “Retirement Syndrome”—a psychological state where departing leaders struggle with loss of identity, influence, and belonging.
Growth is always uncomfortable. Evolution and transitions are expansion, and therefore somewhat painful. It was one of the topics of my discussion with Kirk Marple in the very first episode of Season 1 on the transition from CTO to CEO. Check it out: YouTube, Spotify, Apple Podcasts.
What’s surprising is how little we talk about this openly. Especially in tech, where fast exits and big acquisitions are glamorized, we forget the human side of leaving. Behind the headlines are people navigating grief, doubt, and the need to reinvent themselves after being “CEO” for so long that they forgot who they were before.
🔍 Golden Findings
Here are some insightful resources that explore leadership transitions, succession, and the evolving psychology of CEOs:
CEO Succession Trends (2024): This Conference Board report analyzes 2024 data on CEO transitions and shows why earlier succession planning leads to more stable post-transition performance.
When Power Changes Hands: HBR explores the politics and psychology behind CEO succession and how internal dynamics can derail even the most logical transitions.
The “Letting Go” Paradox: From BoardSource, this guide offers communication strategies for transparent leadership exits and why silence around transition can create cultural fractures.
"The Identity Crisis No One Warned You About" by Deb Boulanger
In this LinkedIn post, Deb Boulanger shares her personal journey of leaving a corporate leadership role and the ensuing identity challenges. Her reflections resonate with many leaders contemplating or undergoing similar transitions.
🧭 A Practice: Find Your Phase
Leadership doesn’t come with a roadmap. But reflection can point us to where we are—and what we need next.
Ask yourself:
How do I spend my energy? Building, managing, reflecting, or planning succession?
What excites me most right now? Vision, systems, meaning, or renewal?
Am I building toward something—or preparing to release it?
Do I feel more like a creator, a manager, a steward, or a philosopher?
Don’t rush to label yourself. Let the answers emerge. And then ask: how can I lead from where I truly am?
🧩 #CEOCheck
What phase of leadership are you in right now? Are you entering, building, reflecting, or transitioning? What support do you wish you had in this moment? Hit reply and tell me where you are—I’d love to feature anonymous responses in a future edition.
Until next Sunday,
Victoria
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