Ready. Set. Go!

(This post was jointly written by Tyler and Makenna — we’re still sorting out a “single voice” for this blog so it’s largely written as split voices for now)

We have quite a few people signed up for blog post updates who only know Tyler, only know Makenna, or don’t know either of us but found this blog after a few social media posts. To kick it off, we figured we’d share a bit more about ourselves from our perspectives.

Q: What inspired the trip?

Tyler: I did a short(ish) stint of travel right after undergrad. It was ~14 weeks long across the eastern edge of Australia, Bali, Italy, Ireland, and Iceland. I had never traveled internationally solo before, but I knew I wanted to see something new. I ended up loving every week of that trip and ever since then, I’ve been wanting to do it again. I distinctly remember a bunch of Europeans and Australians at the time looking perplexed that I was only taking off ~14 weeks between graduation and starting my first job. Most of them were taking 1-2 years off between high school and college. It didn’t take me long to realize why they were all such strong advocates of trying to pull it off for a full year.

Makenna: A big inspiration for this trip was Tyler - there is no denying that. I don’t have a long list of international destinations that I have traveled to, but I certainly have a heavy dose of wanderlust and curiosity. Studying abroad or traveling post-undergrad was never something I could swing so for many years I was looking for another way to make that happen. It was no more than a month or two into dating that Tyler told me he would like to take time off from work to travel full-time. I think my exact response was, “can I come with?” and for the next two years we had both very lighthearted and serious conversations about what taking the time off would entail. I would like to think that Tyler started the idea, but I really moved it into action (I’m a bit persistent once I have my mindset).

Q: Why now?

Tyler:

TL;DR — why not now? I’m very fortunate and blessed to be able to pull this off physically and financially, and it’s as good of a time as ever to take a step back to reflect on what I want out of the next 10 years of my life. I don’t have any dependents and have nothing but green lights in front of me if I examine if there’s anything genuinely holding me back.

Longer answer – I graduated undergrad, landed a job at Amazon in a reliability engineering group, ended up specializing in chaos engineering, focused heavily on my career, got promoted a few times, blinked… and all the sudden I turned 30 and was ~20% of the way through my career. A few more years from now I might have kids in the picture, the world dynamics might not permit me to travel, or maybe I simply won’t be as lucky in my ability to pack up and leave for something new. In other words, it's now or never; time to seize the day.

Almost everyone I spoke to about this early on more or less said “you should totally do this”, “do it now”, “you won’t regret it”, etc. Not all of them had done something similar, but many of them expressed that they wished they had when they could (e.g., they have kids now and that complicates the picture). Makenna was also all in on the trip and supportive of doing it together.

Lastly, ~7 years ago, I remember my first week in Sydney on my post-graduation trip with vivid memory. I remember the boat blasting a song (“Call on Me” remix by Ryan Riback) when a multi-day excursion filled with backpackers was pushing back to head to the Whitsunday Islands. I remember how cool it was meeting other backpackers right after checking into my hostel and doing the Bondi beach walk in Sydney. I remember loving that trip and “thriving”. All that said, I barely remember the day I found out I made L7 (“level 7” / Sr. Manager) at Amazon (< 1 year ago). If you’re familiar with Amazon career paths, it’s a bit of an outlier to go from L4 (college hire engineer) to L7 (sr. software dev manager) in 7 years, and while I’m proud of that achievement (it was a big deal for me), it was an eye opener for me to realize which memories are engrained in my head and which ones aren’t.

Makenna:

Well, Tyler really took the good answer there, huh? In all honesty, our answers will align on this one which is necessary when you are making a life change like this! For better or for worse, if you work in New York, it is easy to get sucked into the career vortex. Working long hours, skipping holidays, and answering emails and slacks on vacation is a fairly common norm, especially for Tyler and me. And while this behavior rewarded us from a career growth perspective, it started impacting us personally. Suddenly our weekends were about recharging for the work week or squeezing in a few hours of work to get ahead of next week. The "workaholic" banner started to become more apparent and when we had a realistic conversation about how we would balance the careers we wanted and being present parents in the coming years, all of a sudden dedicating time for ourselves quickly dissipated from the priority ladder.

So was timing perfect, yes and no, but it rarely ever is. To Tyler's point, we are both in an incredibly rare and fortunate position. We have friends and family who support us wholeheartedly in our endeavors to explore, and we both were able to find careers in our 20s that could support us from a fiscal perspective. All arrows were pointing to go and we just had to muster up the courage and make the jump!

From a practical perspective, in 2023 we took a hard look at the calendar and asked ourselves what are our plans looked like for the next year? next 3 years? next 5 years? We looked at our investments, counted our paychecks, looked at our age (only getting older here), and figured out what life milestones we were aiming for and found the sweet spot – ready or not, it was time to go!

Q: How was it leaving your corporate job?

Tyler: About as smooth as it could have been. I've been talking about doing this informally for several years now. I even had some coworkers who would occasionally tease me about "Tyler keeps claiming he's going to pack up and travel the world at some point."

I semi-officially locked it in about ~8 months before my last day at work. I was completely transparent with my manager and VP to make it as smooth of a transition and outcome as possible for myself and my team. They were both wildly supportive (thanks again Vivek and Derek 😄).

Logistics aside, this was the first time I was leaving a company. I interned with Amazon (twice!) and joined full-time after graduation. I had moved internally within the same broader organization, but I hadn't yet walked away from a company and certainly hadn't walked away from 20+ people that I had been working with every day for the last several years.

That said, we're writing this blog post a few weeks into our trip and I feel 100% confident in my decision to leave. I miss my coworkers and colleagues, but I don't feel "disconnected" or like I couldn't reach out tomorrow. I'm optimistic we'll stay in touch. There will always be more work to do — I'm not too concerned about getting back into the groove of a job at some point (though that day is not today).

Makenna: Without sugarcoating it, this was the hardest hurdle for me and I'm thankful Tyler gave me the space and support I needed because I was definitely an emotional roller coaster. Within the financial services space, a sabbatical is not very common. Unlike some industries that may embrace individuals taking time away from their careers for personal reasons, murmurings around the financial services industry are this could put a real dent in one's career trajectory (yikes!)

Even though Tyler had informally socialized our leave quite a bit more, once we had locked in our departure date, I gave formal notice at work first. My notice was as well received as it could be. I was fortunate to be working on a very close-knit team; we almost knew too much about each other's personal lives in the best way possible. Now that this secret that I was keeping was out, it lifted a bit of weight off my shoulders. Over the notice period provided, I was able to have a smooth transition, and my last week was filled with colleagues providing sincerity and support; I was even surprised to get a few "I did this when I was younger too, and I wouldn't trade it for the world". That provided all the reassurance I needed that I didn't totally just dig my metaphorical career grave.

Q: Who packed more?

Tyler and Makenna: We have a shared answer on this one. It was Tyler. He packed an 80L backpack, a 40L backpack, and a 15L backpack. It’s all Osprey systems so they work nicely together, but he was hellbent on bringing accessories like a yoga mat and mini travel yoga blocks.

Note (from Tyler): My shoes are also 2-3x the size of Makenna’s shoes, especially the hiking shoes!

Q: What’s the most non-essential item packed (from each other’s perspective)?

Tyler: After 3+ years of dating, I just learned that Makenna has an eyebrow brush that she uses. I didn't even know that was a thing. She packed it, but it's small enough that it's possible I wouldn't have noticed for another year unless I saw it while we were packing.

Makenna: For someone who can't touch their toes, packing a yoga mat and yoga blocks seemed a bit much. But it's not in my backpack, and it's not my personal goal, so my hands were tied.

Q: When/how did you start planning?

Tyler: We are supposed to be planning? Oops. We'll elaborate on this a bit later, but I can share an anecdote that one of us found funny:

I was insistent on traveling in a freeform manner; Makenna loves an itinerary and plan, but when I was reminiscing on my post-grad trip I liked the "go where the experiences take you" mentality that I remembered. Makenna begrudgingly tried to support this as best she could.

Spoiler Alert: We are already 2 weeks in and during some downtime on a ferry ride I was scrolling through my old notes on my phone and came across a note titled "Post Grad Travels" from ~7 years ago. Coincidently enough I had jotted down a few notes under the "Lessons Learned" section. One happened to read, "Planning is important. Winging it takes a ton of effort". Makenna promptly rolled her eyes at that one. I guess you could say I had to learn this lesson twice.

Makenna: No comment lol

Q: Where are we going?

Tyler and Makenna: The path isn't fully known right now. We have packed for a mostly warm climate range so that is one of the leading factors when we plot out our route. We also have 5+ weddings/life events over the next 12 months that we are doing our best to plan around.

Q: What do we think we’ll miss the most about “normal” life?

Tyler: Friends and family! We're hoping that as many people as possible will collide with us along the way. Knowing we wouldn't see the people we love being around every day was the hardest part of "walking away" from work, NYC, etc. We were fortunate to see a lot of friends and family before we left, but we'll certainly miss everyone over the next 12 months.

Makenna: I am a big homebody so I think not having a space of my own will toughest. Luckily I packed a few non-essential comfort items that give me my sense of home so I'm hoping those will do the trick.

Q: What did you pack in your bags for a year?

We’ll have a more detailed post on this at some point (including notes on what we think was worth it, what wasn’t, and what hurts the most when lost in transit), but high level:

• Tyler: 80L Osprey Farpoint backpack, 40L Osprey Farpoint backpack, 15L Osprey daypack
• Makenna: 70L Osprey Trek Fairview, 32L Cotopaxi Mente Daypack