Amit Jotwani

Amit Jotwani

We’ve been on the road for 10 months now, with a two-year-old in tow.

We’ve been on the road for 10 months now, with a two-year-old in tow.

A lot of friends and family have asked why we did this, how we did this, and what it’s been like. So I thought I’d share our experience—what led to it, how it’s going, and everything in between. More importantly, I want to write this down for ourselves, for when the memories fade. Maybe, just maybe, it’ll be something our daughter can look back on—a reminder to take a few calculated risks while you can, while health and finances allow it.

We’d been talking about doing something like this for years. The fairy tale scenario of packing everything up into storage and taking a few months, maybe even a year, to travel through Europe and Asia. But the thought of leaving everything behind—the life we built, the city we loved and called home for over 10 years, New York City—was daunting. Someday, we’d thought.

Why?

In Feb 2020, I had a stable career at Amazon, doing work I enjoyed as part of the Alexa developer education team. After four years, the monotony started to set in. I could do the job with my eyes closed. I even remember telling Deepti that I’d thought about taking a break in 2020 after my four-year vesting period.

Then COVID hit, and like everyone else, our plans shifted. Leaving didn’t seem right at the time, so I stayed on for another year and a half—until vaccines rolled out and a semblance of normalcy began to peek through.

Then, to our delight, we became pregnant. Priorities changed again. What we wanted shifted. Life changed again. But that dream of traveling stayed. It just got a little more complicated.

Leaving Amazon

By the fall of 2021, after over five years at Amazon, I was completely burned out. I knew I needed a break. Deepti and I talked about it for months—should I leave now, or wait another year? I was mentally drained, and the idea of welcoming a baby while feeling that way didn’t sit right with me. So, just before our daughter was born, we decided I’d leave Amazon. The timing lined up with the holidays, so I spent those last couple of months doing things that brought me joy, resetting, and getting into a better headspace before she arrived.

Did I leave too soon? I don’t know. Walking away from paternity leave wasn’t easy, but it felt right at the time. Hindsight always has the unfair advantage of wisdom. The goal isn’t to make the “right” decision, it’s to make the best one with what you know at the time. And in that moment, it was the best decision.

I took time off to soak in parenthood. Spending time with Deepti and the baby. Looking back, those are still some of our favorite memories. Hard, for sure, but something we look back on with a smile—and maybe a few tears. It’s incredible how the first few months of parenthood push you to your limits. It’s like a test of endurance, patience, and the determination to give everything to this new life you’ve created.

Side note: We can never appreciate mothers enough. Watching Deepti go through what she did—it was eye-opening. We always say “respect your mother,” but you don’t truly understand until you see it up close. What happens to their bodies, the mental and physical toll. It’s something that makes you sit up and say, “Wow.” Kids should always, always respect their mothers.

A Turning Point

After about six months, I decided to get back to the startup world. A few false starts with startups followed—none of them felt like the right fit for the kind of people, culture, and work I wanted. Then, a year later, I was part of the Retool layoffs. That was a first for me in my career. Life has a way of humbling you, sitting you down, and teaching you to be more present, to appreciate, and to be grateful.

I decided not to go back to a full-time role just yet. Instead, I took on freelancing and consulting projects. Thanks to the supportive network I’ve built, opportunities came my way more easily than expected. I felt grateful and lucky for that.

Then, our apartment building was bought out by NYU hospital, and our lease wasn’t getting renewed. With no reason to stay in New York, and our daughter not in school yet, it felt like the perfect window to make this trip happen. We packed up, put everything in storage, and hit the road.

Suddenly, everything aligned. A lot had changed—personally and professionally. And it finally felt like the right moment to do what we’d been dreaming about for years.

The plan was to get back to NYC in six months.

Jan 2024: Take off!

We decided to travel in a way where we always had a base. We started with Dubai, where Deepti’s family is, then moved to Delhi, where my family is, while traveling around India. After that, Bangkok became our base while we explored Southeast Asia. Now, we’re in Lisbon, using it as our home base while we plan to travel through Europe.

One of the best things about this journey has been how much time Zuni has spent with her grandparents and family in India and Dubai. She’s picked up so much Hindi, which has been incredibly gratifying. Hearing her speak and respond in Hindi brings a joy that’s hard to describe. So many priceless memories have been made with family along the way.

Bangkok

Bangkok, for us, was a surprise. It’s incredibly kid-friendly. The malls have everything—co-working spaces, gyms, restaurants, and amazing play areas for kids. We planned to stay for a month but ended up staying for five.

The apartments we stayed in were fantastic—play areas for Zuni, pools, and even a bowling alley in one place.

Thailand, especially Bangkok, was an amazing experience. The people were kind, the culture was welcoming, and the city exceeded our expectations. But there were downsides. The pollution was tough. Zuni started coughing more often, and we eventually had to get an air purifier. The time zone also made it hard to stay connected with work and family in the West. Late-night calls became exhausting.

Would we go back? Absolutely. Would we live there long-term? Probably not. But it was exactly the reset we needed. Traveling with a toddler isn’t easy, but the memories we’ve made are worth every challenge.

I’m writing this from Lisbon, after 10 months of traveling through Dubai, India, Thailand, Cambodia, Vietnam, Singapore, and now Europe. All with a two-year-old in tow. It’s been a mix of challenges and rewards, but every place has taught us something new—about ourselves, about the world.

…to be continued