Archive - Wandering the Grey

🤑💰 unshackling myself from golden handcuffs

What do you do when your money becomes a prison? Is it worth chasing $$ if you're gonna be depressed and wealthy? Are you flying first class on a…

Dec 7, 2022 • Tobi Ogunnaike

introducing—buttahbasted, the series

first drizzle of my written album for 2024 summer

May 16, 2024 • Tobi Ogunnaike

🌸 seduced in condesa

In this place, her mellow music starts to work its magic. Her mosaic of maverick and melody appeals to the marrow in my bones. When the beat kicks, it…

May 23, 2024 • Tobi Ogunnaike

Seize the Pause: Turn Your Layoff to a Sabbatical

Part-Time Internet Celebrity, Michelle and I are launching Turn Your Layoff to a Sabbatical next month — a live, cohort-based course to help people…

Mar 1, 2024 • Tobi Ogunnaike

I don't know where home is

My autocorrect is trapped in a bloody battle between warring worlds. When I text on my phone, Colonel Spellcheck searches through my words looking for…

Nov 29, 2023 • Tobi Ogunnaike

so you're a writer now?

People think I just sit down and essays happen. I have this beautiful affliction where words, ideas and thoughts visit me unannounced and demand that I…

Dec 20, 2022 • Tobi Ogunnaike

how I feel about where I am

"It’s Tuesday morning in a new city and the ring announcer presents the day’s main event—a no-holds-barred brawl between 'Doubt' and 'Faith'."

Jun 24, 2023 • Tobi Ogunnaike

the stories we tell ourselves about work

First, a little tease. After five years of working as a Software Engineer in Big Tech, I unclipped the shackles, dusted my big boy boots and left…

Nov 1, 2022 • Tobi Ogunnaike

I became a nomad🥲

adios san francisco?

Oct 30, 2023 • Tobi Ogunnaike

let's get to know each other 😬

Oct 29, 2023 • Tobi Ogunnaike

🌴🏖 sober sabbatical: scene one, take one

A number of you have flattered my ego by asking for regular updates on my personal journey.

Nov 22, 2022 • Tobi Ogunnaike

sick of seville

I'm convinced the universe has conspired to put me through wild experiences because it knows I will write about them. Behind the screen, the puppeteer…

Nov 1, 2023 • Tobi Ogunnaike

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