Nomad - The Making

Why and How we planned Nomad

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In the summer of 2021, my spouse, Sesh, and I both quit our Silicon Valley jobs and started a hiatus from our professional life. We expect the hiatus to be less than a year. We are spending the next 6 months of this time on Oahu in Hawaii, and have relocated here recently.

We’ve planned this hiatus for close to 4 years. It started with a desire to spend time off the beaten path, voraciously traveling and immersing ourselves in new environments and communities. The largest barrier, the reason it took us a long time to execute on the plan, was feeling ready, at the same time, to leave our jobs.

From the beginning then…

Sesh and I both grew up in a traditional urban household where education, and productivity are highly valued. We’ve been on the proverbial treadmill since high school, always having a target destination that we have worked toward. We both enjoyed excelling at reaching these destinations - strong high school performance, good college degrees, graduate school, jobs in exciting product companies, promotions at said companies, taking on larger responsibilities and more complex work and so on. We enjoyed this enough, and were reasonably successful, that at no point did we feel like we were suffering under the burden of any expectations, external or our own. But now that we had gone through the process of setting a goal, and meeting it, a dozen times or so, it started to feel like we were in a rut. We observed the pattern that was forming of taking on goals that are largely widely prescribed to people in our age group, and meeting them, and then going to the next goal.

After almost a decade of working as professionals, we felt like it was time to shake up any prescribed recipe, and spend some time deeply deliberating what we wanted to do with the rest of our years.

The travel vector

To aid with ideation, we thought of immersing ourselves in new experiences that will awaken parts of the mind that do not get stimulus in our daily routine. The best way to do this was to travel to lands that will surprise, challenge and inspire us. We were thinking about spending a few months living in a new region (not the USA or India). Europe, particularly around the Mediterranean, was top of our list given the accessibility to diverse cultures in an easily traversable region.

The go-within vector

Leaving the prescribed path meant that we had to create our own, and have a deliberate reasoning for whatever we chose. This reasoning would help us stay on the path, and steady us against the currents pushing us back into the rut we were trying to leave. For this, we knew we would want to spend a lot of time going inward and honing in on our individual and joint interests and values, and together make a commitment for how we were going to spend the rest of our life. We are also pretty detail oriented, and hands-on, and felt like we would want to engage in deep research and maybe even some hands-on building or prototyping for ideas we came up with. This meant we would need a lot of time available, to be as thorough as we would like to.

How to leave our jobs

After the first 5-6 years of working as software engineers, we knew how to keep our day to day job engaging and challenging, so we continued to grow and learn. This meant however, that we had no time or energy left for other deep explorations into our own thoughts and interests. We were certain that if we had to make the most of Nomad, we could not be working full time. We also decided early on that Nomad would have to be long enough that it felt like a real reset, and not an annual vacation. This quickly led us to the conclusion that we would have to quit our jobs.

This was the toughest hill to climb, and for a long time we just coasted along hoping the right moment would show itself. From the time we started discussing Nomad, Sesh and I changed jobs 4 times between us (company, team or role). We found ourselves in this beautiful weave pattern where he would find a new challenge to take on, and we would put Nomad on hold for at least 6 months while he explored it, and in those 6 months, I would find something new, and it would go on. This is not at all unusual, and on more reflection, we realized that our experience has been that something new and exciting is always 6 months away at our kind of jobs. Tech companies are adept at ensuring these carrots exist, so we stay on and continue to work, and our lifelong training to chase anything that feels like a forward and upward trajectory also ensures that we go after these carrots.

After doing hard time in this weave, we realized this pattern, and finally felt comfortable leaving the upcoming (significant) carrots on the table. It felt like we jumped out of an elevator between floors, and we couldn't be happier with this decision. Every 6 months that we waited, were 6 months spent away from taking control of our future, and making deliberate choices of where we spend our time.

Budgeting

Financial planning was an important part of taking a hiatus. We came up with a lump sum $ amount that we felt comfortable spending on Nomad, based on our income and risk tolerance. We had agreed to begin Nomad when we crossed that amount in savings (plus an emergency fund). We are mild to moderately savvy in personal finance, but make up for our lack of savvy-ness by being largely risk averse, and maintaining a fairly simple lifestyle. We’ve saved 40-60% of our income from the start of our careers, and started investing a few years ago, so we had reached the goal we set pretty quickly after we started planning for Nomad. The way we planned to use the money was to adjust duration and type of activities to stay within budget, depending on the location that we picked.

The two-body power

As you read this you will see that I use “we” everywhere instead of “I”. It’s not at all that my spouse and I are one mind or in agreement all the time. It is, however, true that we thought about Nomad as a joint venture from the beginning. We have similar enough interests that we felt like we would be able to make a plan that meets both our needs.

Planning something off the beaten path is hard enough alone, and I’ve heard it be referred to as a “two-body problem” when you have to do it with a partner. While it took time for us to meet on the same plane to execute Nomad together (finding a time that worked for the both of us), I think we found a two-body power, once we were able to get on the same plane. We were able to motivate each other, refine ideas together, and share the burden of planning and execution with each other. It required willingness on both sides to let go of some of the control we might have liked to hold on to. It also took some faith in the process that I like to call the “magic beyond our comprehension” that can enter our life when we relinquish some of this control.

Adapting

So now we were in 2021, and a few things had evolved since we started planning Nomad. While the career weave I described above was happening, we had let life go on. We now had a baby, and a puppy. We were also in the middle of the COVID pandemic, with a lot of uncertainty on how the world will change. We adapted by making a few safe choices with regards to location.

• We decided to stay in the US. This allowed us to have reliable health insurance for the family, and prevented any churn from international borders closing down due to the pandemic. The US is a known territory, which we felt comfortable in.

• We still wanted to travel away from San Francisco, and ideally travel a few times to experience the benefits of being nomadic (to be challenged, surprised, inspired).

• We were going to take the hiatus in the second half of the year, and thought it might be a good idea to find a warm place where we can skip a cold winter.

• We love nature, and have felt healing and inspiration every time we’ve spent significant time in nature. So we decided to optimize for access to nature.

Looking at all this criteria, there were a few places in the southern US that would work for us. However, once Hawaii made it into the list of candidates, nothing else really matched the allure. We have visited Hawaii before, and the access to nature and relaxed atmosphere made us fall in love with it. We were looking up properties to buy in Hawaii at the end of that trip many years ago!

With the new life situation we were in, we also had to adapt for activities we would engage in. We largely wanted to spend time going inward. This was possible anywhere, unaffected by the pandemic. We also wanted to spend time outdoors, strengthening our bodies. Hawaii provides ample opportunity for doing this. Lastly, we now also wanted to use this time to build a deep bond with our baby, and enjoy watching him grow from baby to toddler.

To accommodate all these plans, we picked the island of Oahu, which has a diverse landscape, and many family friendly amenities and activities. We also had not visited Oahu before. We picked a few different neighborhoods - one on a mountain plateau, one near a beach, one on backwaters, and one in a residential area close to the Honolulu city center. We will be staying in long term rentals in each of these neighborhoods during our stay here. The neighborhoods provide diverse scenery, communities and access to activities.

Now that we’ve started our adventure, I will be writing more about how we’ve decided to spend our days balancing time spent on our various goals, how Hawaii welcomed us, and periodically on what we are doing while here.