hey you👋🏽

Welcome aboard Wandering the Grey, a newsletter dedicated to vulnerably unpacking stories in life, work and play. I’m your captain on this ship and I will bring you semi-tasty treats every two weeks.

Who are you and why should I care?

I’m Tobi Ogunnaike, and after spending five years working as a Software Engineer in Big-ish tech, I felt disillusioned and unfulfilled. I realized I didn’t enjoy writing code or being hunched over a lonely, dark screen for many hours a day. Yet, I had told myself various fallacies and fables to keep going. To persist on the path despite the nagging voices within that poked, prodded and jabbed. The voices that kept saying “you know this isn’t why you’re on this planet”. After hushing and shushing for years, I eventually mustered the courage to leave.

I didn’t want to look back on my dying bed full of regret saying “I wish I had the courage to live a life true to myself”. Not the one prescribed by society’s singular ideas of prestige and success.

I spent a lot of time introspecting and asking uncomfortable questions about the stories we tell ourselves about work. Why are our ideas of ambition and success so narrow? Why did I ever want to found a startup? Why did I and so many friends find it difficult to leave jobs that were lining our wallets but draining our bodies and souls?

Was I living life on the terms I wanted? Or was I merely following scripts that were embedded in me?

These questions led to essays which people seemed to love. I got text messages from old friends, LinkedIn DMs from strangers and old coworkers, email responses from people halfway across the world. I talked to a wide range of people: incoming interns that were already fearful of what work might be, and seasoned executives who had seen and done it all. People felt seen and I felt less alone.

So I vouched to keep writing. To keep authentically exploring and probing within because that’s how we connect the most with others. I set sail on a sabbatical to explore where my writing and other creative exploits could take me. I committed to surfing the uncertainty. This is all one big experiment.

A little bit more about me: My journey into tech wasn’t traditional. Because I liked pain and torture, I studied Chemical Engineering in college, then worked in a cool biotech startup that’s making dairy products (ice cream, cheese, yoghurt) without cows. They’re brewing milk proteins much in the way insulin is made industrially. Before that, I worked at a solar power non profit and a chocolate factory. I lived half of my life in Nigeria, and the other half was equally split between England and America. So I call ⚽️ both football and soccer. Sue me🤷🏽‍♂️.

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Vulnerably unpacking stories in life, work and play.


Tobi Ogunnaike
Unpacking big ideas on life, dreaming of new stories of work and yearning to blend more play into our lives.