A Letter to My 20-Year-Old Self: Journeying Through Life’s Seasons

March 14, 2025

13 March 2025: Spirited Women Sundowner at EABL HQ, Nairobi, Kenya

Dear 20-year-old Waithera,

As I sit here at 49, surrounded by the tapestry of life I’ve woven over these decades, I’m writing to you across the expanse of time. If you could see me now—mother to three incredible sons aged 25, 18, and 17, navigating divorce and finding love in a new relationship, leading digital marketing initiatives across Africa—would you recognize yourself in me? Would you be proud of the woman you’ve become?

I know right now you’re dreaming of following in Mom’s footsteps to become a lawyer. That dream is beautiful—hold onto its passion, but not its precise shape. Life has other plans for you. The liberal arts education you’ll pursue instead will give you something more valuable—versatility, critical thinking, and the ability to see connections where others see divisions. And that MBA you’ll complete by 2001? It will open doors you cannot yet imagine.

The Women Who Shaped Me

Your mother—with her legal mind, unwavering principles, and tender heart—is planting seeds in you that will bloom throughout your life. The way she balances professional excellence with family devotion will become your north star. Her lesson that integrity is non-negotiable will guide your business decisions when the stakes are highest.

And your grandmother, whose name you carry? Her legacy flows through you in ways you don’t yet fully comprehend. The strength that enabled her to build a life of dignity despite the constraints of her time will resurface in you when you face your greatest challenges. The values she instilled—family first, unwavering work ethic, treating everyone with fairness—these will distinguish you in boardrooms and beyond. When colleagues later call you “The Digital Diva,” know that this blend of grace and grit comes directly from her influence.

The Highs That Shaped Me

That first role at AT&T in the United States will be your foundation, teaching you resilience and strategic thinking. When you eventually return to Kenya and join Capital FM, you’ll feel the thrill of being ahead of the curve, understanding digital transformation before most others.

Your time at Coca-Cola will expand your vision beyond borders, showing you how to think regionally across Africa. You’ll begin to see patterns and opportunities that transcend national boundaries.

But your greatest professional joy will come at EABL and Diageo. Leading the creation of DigiTribe—the first in-house digital creative team for Diageo in Africa—will feel like watching your own child take its first steps. That recognition at the Pride of Africa Awards in 2021 will bring tears to your eyes—not from pride, but from the realization that your vision has helped create something larger than yourself.

Launching ke.thebar.com during a global pandemic will be both terrifying and exhilarating. As the first D2C e-commerce platform for EABL, you’ll watch it become a lifeline during lockdowns, understanding what it means to lead through crisis.

Your work in responsible marketing will bring a different kind of fulfillment. Reaching over 17 million consumers with moderation messages will remind you that business can be a force for good.

And beyond work? Founding the Second Chances Foundation, advocating for dignified cancer care in Kenya, serving with the Rotary Club—these contributions will nourish your soul in ways that professional achievements alone never could.

The Battle That Redefined Me

In 2012, at the height of your career success, three words will change everything: “Stage 3 cancer.”

The diagnosis will come like a thunderclap on a clear day—breast cancer, aggressive and already advancing. In an instant, boardroom strategies and digital campaigns will fade in importance. The treatments will test the limits of your physical endurance. There will be days when simply standing requires all your strength.

But here’s what you’ll discover: you are immeasurably stronger than you know. From this diagnosis will emerge your life’s motto: “Hope, Fight, Win.” These aren’t just words; they will become your blueprint for survival.

“Hope” will manifest in setting future goals even on your worst days. “Fight” will mean advocating for your own care and researching treatment options. “Win” will redefine itself daily—sometimes victory is completing a full workday, other times it’s simply managing to laugh with your children despite the pain.

This journey through cancer will transform your understanding of time. You’ll develop a heightened awareness of how you spend each day, who you spend it with, and what truly deserves your energy.

Your illness will also clarify your purpose. The Second Chances Foundation will be born from your firsthand experience of Kenya’s cancer care gaps. And the most beautiful revelation? Surviving cancer will strip away your fear of professional risks. After facing death, what’s intimidating about proposing an innovative strategy that might be rejected?

Today, your scars tell a story not of weakness but of resilience. Your experience as a patient informs your leadership style—more empathetic, more focused on what truly matters, more willing to challenge broken systems.

The Guides Along My Path

Your journey won’t be a solo expedition. At AT&T, your manager Beverlee will take a chance on you, giving you responsibilities beyond your years. At Coca-Cola, a regional marketing director from Nigeria, Patricia will teach you to navigate corporate politics with integrity.

At Diageo, you’ll find not just mentors but sponsors—executives who advocate for you in rooms where decisions are made. One particular leader (Jane Karuku) will challenge your thinking about digital transformation, pushing you beyond conventional approaches.

These guides will give you the confidence, courage, and conviction to go against the grain when necessary. Remember to thank them. Remember to pay it forward. And remember that seeking guidance isn’t weakness—it’s wisdom.

The Valleys That Taught Me

Your mid-twenties to early thirties will bring periods of profound self-doubt. After the initial excitement of your early career, you’ll hit plateaus that feel endless. You’ll question your choices, wondering if you should have become that lawyer after all.

Between 27 and 32, you’ll experience what you’ll later recognize as a “quarter-life crisis.” The expectations you placed on yourself will collide with reality. The timelines you set will prove arbitrary. This disillusionment will feel like failure, but it’s actually the beginning of wisdom.

What I Would Change

If I could guide you differently, I would tell you to trust your intuition earlier, especially regarding digital marketing innovations. I would encourage you to seek mentorship more actively and diversely.

I would urge you to prioritize your wellbeing alongside your ambitions. The burnout you’ll experience didn’t have to happen, and it might have helped you detect health issues sooner.

I would remind you that vulnerability is not weakness—sharing your struggles creates connections that achievement alone cannot. And most importantly, be gentler with yourself during transitions.

The Comfort You Need Now

So what would I tell you, my 20-year-old self, as you stand at the beginning of this winding path?

First, know that the emotions that feel all-consuming now are temporary visitors, not permanent residents of your heart. They will pass through you, teach you, and leave.

Second, understand that the timeline you’ve mapped for your life is an illusion. Some achievements will come earlier than expected, others much later. Some of your greatest contributions haven’t even entered your imagination yet.

Third, trust that your liberal arts education and early MBA will serve you far better than the law career you envision now. Your ability to integrate different perspectives, to see the human stories behind the data—these will become your superpowers in the digital age.

Fourth, believe that your voice matters. The platforms you’ll gain will amplify your perspective in ways that create meaningful change.

Fifth, honor your body. Before cancer teaches you this lesson the hard way, recognize that your physical health is the foundation upon which all other success depends.

Finally, remember that the values your mother and grandmother instilled—family first, integrity always, fairness to all, hard work without complaint—these aren’t old-fashioned limitations. They’re timeless principles that will distinguish you in a digital world often lacking in human connection.

To Those Finding Their Way

As I share this letter with our future leaders, I see in your faces the same questions, doubts, and hopes that lived in me at your age. Know this: The confusion you feel now is not a sign that you’re lost; it’s a sign that you’re finding your way. The disillusionment you experience is not failure; it’s the beginning of a more authentic vision.

In my journey from that ambitious 20-year-old to the Digital Diva of today, I’ve learned that life’s path rarely follows a straight line. Instead, it spirals—sometimes bringing us back to similar challenges but with new perspectives, sometimes launching us into territories we never planned to explore.

The leader you become will be shaped not just by your successes but by how you navigate your failures, not just by your achievements but by how you face your darkest hours. Trust this process. It is making you not just the professional you aspire to be, but the human being the world needs.

With love and faith in your journey,

Waithera Kabiru aka The Digital Diva