“To everything there is a season, and a time to every purpose under heaven.” — Ecclesiastes 3:1
In Episode 4 of the Founders’ Battlefield podcast, we explored one of the most under-discussed truths in entrepreneurship: timing. Not just timing in the market, but the deeper, quieter knowing of when to push forward and when to pull back. When to hibernate in silence, and when to step boldly into the sun.
These are not just business tactics. They are spiritual rhythms. They mirror the rains, dry spells, planting seasons and harvest. They’re closer to how we read the land before sowing, or prepare our granaries before the long rains arrive.
Founders who learn to listen to these seasons often outlast the storms. Those who don’t, either burn out in the heat or drown trying to swim against a flood.
Every founder eventually confronts this paradox: the same hunger that fuels our hustle can also be our undoing. I know this because I’ve lived it. There were seasons I believed I had the Midas touch. Everything I built turned to gold. And I kept building more, bigger, faster. Until the gold began to crack. And I was left clutching the illusion that I could bend time, when in truth, the season had changed and I hadn’t.
Instinct is a founder’s greatest compass. But instinct is forged in stillness. You won’t find the signs in a case study. You find them in heartbreak, in the sudden loss of a contract, in the quiet boardroom, in the moment your body says it’s time to stop.
I’ve stood in that moment, piloting a 747 of dreams midair, hundreds onboard, and realising I hadn’t factored in the clouds gathering around us. They weren’t obvious at first. I thought we could navigate the political turbulence. But we didn’t. And we couldn’t land.
In Kenya, we don’t speak of spring or winter. We speak of long rains, dry months, planting and harvest. These cycles carry emotional weight. We know the smell of the soil before rain. We know when the air shifts.
As founders, we must learn to read our own ecosystems. The pressure to always be “on” can be seductive. But the wisdom to pause is often the most powerful act of leadership.
In the podcast, Khalhani Sichangi, a young Gen Z entrepreneur, spoke of that pressure to always be building and visible. But he also shared the importance of discernment. Not every moment deserves noise. Some demand silence. He called it strategic hibernation-a deliberate withdrawal to preserve mental clarity and energy.
Teresa Njoroge, whose social enterprise was born from a season of personal injustice, reminded us that stillness can be redemptive. Her time in prison taught her to regroup in silence, to build slowly with purpose. “You can’t thrive out of season,” she said. “Knowing your time and your season is survival.” For her, blossoming wasn’t about reclaiming who she was, it was about who she had become.
Then there’s Olive Gachara, whose arc from fashion to media to consulting reminded us that not all pivots are born of pain. Some are born of readiness. Her journey wasn’t linear, it was intuitive. She said something that stayed with me: “Even growth can exhaust you. You must learn to flow, not force.”
There’s something deeply spiritual about these conversations. They reminded me of Viktor Frankl’s words in Man’s Search for Meaning: “When we are no longer able to change a situation, we are challenged to change ourselves.” Many founders are not trapped by the market. They’re trapped by a refusal to evolve.
This ties into something I’ve been reflecting on from David Brooks’ theory of Adam I and Adam II. Adam I lives for résumé virtues, what we build and project. Adam II lives for eulogy virtues, who we become when no one is watching. The cycles of hibernation and blossoming aren’t just career decisions. They are invitations to shift from Adam I to Adam II. From external success to internal grounding.
I’ve had seasons where everything collapsed. Contracts pulled, investors vanished, employees questioned everything. Family needed more than I had to give. In those moments, I didn’t retreat in defeat. I retreated to redesign. I recalibrated.
Not every founder gets this timing right. Some push too hard and break. Others wait too long and miss the rains. But those who master the rhythm? They plant when the soil is ready. They rest when the sun is harsh. They harvest with humility. They’ve learnt to read not just spreadsheets but the weather of the soul.
So I ask you, fellow founder: is this your season to blossom or your time to hibernate?
Only you know. And if you’re truly honest, you probably already do. The hard part isn’t knowing. It’s obeying that knowing. Sometimes the signs are loud. Burnout, financial strain, spiritual misalignment. Other times the message is subtle. An unease. A still voice. A restlessness that doesn’t go away.
You don’t need to explain it to anyone. Just trust your season. Trust yourself. And when the clouds break, when the soil softens, when your roots feel strong again, step into the sun.
And that, perhaps, is the beginning of real greatness.
The author is a serial entrepreneur, founder of Seven Seas and Ponea Health and the creator of Founders’ Battlefield.
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