Welcome to Wandering the Grey

Hello hello! I’m Tobi and this is where I share travel stories from my sabbatical, and creative works of fiction, prose, and poetry.

Regardless of the format, I love depicting scenes — taking your senses on a ride and rewarding them.

A little backstory

In December 2022, I left my high-paying, unfulfilling job as a software engineer for a sabbatical. I spent years agonizing over that decision. So I threw a sabbatical party to celebrate the courage. Then overnight, a one-way flight ticket to Barcelona spiraled into a thirteen-town tour across Europe and South East Asia that rejuvenated my spirit. Those sad droopy shoulders received CPR and learned to stand tall again.

In 2023, I published a lot! You heard stories about me surviving street dogs in Koh Samui and being ambushed in Seville. I created and published “Untethered”, a digital magazine featuring essays from myself and five other nomadic creatives. After six months of solo travel, I questioned where home was. My friends shared their own stories too — one left tech to become a painter and masseuse, another was a graphic designer who had been nomad-ing for four years.

These days, I’m back in San Francisco working on an upcoming short-story collection (shhh, whisper it!) and consulting as a technical writer.

Why You Should Subscribe

If you’re like me, you already subscribe to too many newsletters. Your inbox is teeming with spam, bad news, and annoying nudges from email marketers. I’ll make my pitch simple for ya.

Instead of those bad vibes, I’ll provide

• 🏖️ an escape: funny, evocative, vivid stories from my six-month solo trip across the world—from Bali to Barcelona, from Lisbon to Kuala Lumpur

• 🥁 ear candy: spoken voice essays for those days when you’ve exceeded your daily screen time and want to hear an actual human…speak

• 🥘 stews to savor: tales about meals I ate abroad that start with food, but end up with a zoomed-out reflections on culture or life

• 🪞a mirror: I explore the authentic, messy bits of work-life like burnout, the cost of ambition, dealing with golden handcuffs, and grappling with my identity as a writer —many of these experiences could reflect your own

• 🤗 a chance to connect: I offer free thirty minute calls to connect with subscribers all around the world

what readers are saying?

From Tiago:

Thoughts and reflexions from Tobi’s left brain wrestling the right brain in a flowing, melodic, poetic and brilliant narrative which is quite entertaining and honest.

From Virginia:

Top notch writing and delicious descriptions.

From Katie of Bonesick

Every piece Tobi writes makes me think, makes me want to join the discussion. I love his luscious way of describing his experiences and the corners his brain is willing to sniff. It’s a lovely little breather from the humdrum. I feel like I’m on sabbatical myself.

From Jillian:

Obsessed with your newsletter babe. You’re such a talented writer. It’s like flowing down Russian river on a tube without any fluid friction.

If you choose to support my work by becoming a paid subscriber, you’ll have my undying, eternal gratitude.