Hello ☺️

Welcome to my space.

I’m Tobi, and I’m levitating off a leap of faith. In December 2022, I left my high-paying, unfulfilling job as a software engineer for a sabbatical. A one-way flight ticket to Barcelona spiraled into a thirteen-town tour that broadened my lens and rejuvenated my spirit. This newsletter shares the triumphs, the struggles, the sumptuous meals, the underwhelming tourist spots👀, the doubts, and the worries of a wandering man. 

My dream is to build the next phase of my career in a way that aligns with my values—creativity, autonomy, and authenticity. For the rest of the year, I'll be writing from my wanderings around my old city, San Francisco. 

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.

Subscribe to Wandering the Grey

Vulnerable reflections on travel, food, and work from a former Silicon Valley engineer pursuing a creative career. Escape and reflect with a wanderer.


Former Silicon Valley engineer pursuing a creative career.