At an end-of-year gathering, a friend reminded me that I said I’d share some of my experience from the sabbatical. Unfortunately while I intended to post one of these per month, I’ve been mentally stretched thin trying to figure out life and career the last few months.

This post roughly covers the lessons we learned from searching for a job (and turning down opportunities) in Singapore - followed by the experience of what re-joining the labor force has been like. It is a long one so buckle up!

[#coronaperspective I drafted this two months ago, but let’s just say that plans have been disrupted… Considering that I’m again spending a lot of time thinking about career and life choices, and that we’ve been back in the Bay for exactly one year now, it seems appropriate to dust it up as I reflect on that struggle again given the new circumstances following the Covid-19 pandemic.]

Uncertainty Angst

We celebrated the arrival of 2019 on our South African friends’ boat. Although somewhat adrift and unclear about what our next move was, I didn’t mind the uncertainty. In fact, I thrived in it: the humidity induced sweat, the constant salty hair, the sun kissed skin, meeting new people every day, living at the rhythm of the tides - what’s not to love?

Maybe let’s ask Olivia - here is an excerpt of what she wrote during that period:

I want out of this humidity that steams the meat right off my bones. I want to be able to take a walk when I need to clear my head, I want my alone time back, I want it so bad I could cry. I want to wear city clothes and drive my car. I want to take a proper shower in a proper bathroom. I want to figure out my life, preferably with decent Internet.

Faced with an uncomfortable and borderline miserable partner just barely 6 months after our wedding, an action plan was needed. Thus it was agreed that we would aim to settle in a new place with some reasonable job prospects by June 2019.

The Singapore Compromise

With that goal in mind, we dusted up our attempt at rationally identifying where we might seek adventure next: a matrix of potential destinations vs. Must-Haves and Nice-to-haves that we based on the best and worst places for expats.

Our criteria made it hard to find an all-out winner, and thus we needed a compromise. Vancouver and New-Zealand scored the best; however, being Canadian and having frequently traveled to NZ for work, I pushed us to try something ‘different’: Singapore. And just like that, we had a destination that we could now start planning around.

[#coronaperspective It’s fascinating to see how some of these countries have responded to the pandemic so far: not only in their varying levels of success, but also their treatment of foreigners. I’ll try to keep an eye out on attitude shifts towards immigration/expats and travel in general]

We still had some wanderings planned: a stopover in Oman, a visit to the newly minted nephews in London, and 2 months at a horse barn in Sri Lanka. Still with the destination set, the weight of the uncertainty was lifted; and immediately replaced with the stress of job hunting. When you already have a job, and are working in an area where engineers are sought after, jobs seem to fall on your lap: recruiters, in-mails, word-to-mouth. It’s almost like you barely have to stretch your arm to pluck one. But here we were, 9 months out of the job market and in a new country without any contacts. Where do we even start? We still had 2 months to go, but we wanted to get a head start and searching online.

Virtual Job Search

At first, searching for jobs seemed like an easy task: enter a few keywords in LinkedIn, find an interesting position, upload a CV and voilà! Unfortunately, for all the simplicity that LinkedIn brings, it has turned job searching into online dating: companies sift through 100s of applicants -each boasting about their amazing accomplishments- and never get back to you. LinkedIn also comes with the caveats of most social-networks: everyone seems so happy and successful with their lives (careers), and there you are wondering whether your life decisions have failed you. Suffice to say that after four weeks my self-esteem was at rock bottom.

Olivia didn’t fare better, and in some respect things were even harder for her. While there were a few technical job openings that could be a good fit for me, there were far fewer interesting marketing jobs for someone with her background, and most required regional experience or product-specific knowledge.

After a month and 60+ applications, only a couple of companies got back to us. We clearly needed a different strategy for this to work. In hindsight, these were the 2 most important lessons during this time:

• Starting the search soon made sense, but it wasn’t worth wasting valuable time during the trip for it
• People in Singapore value in-person relationships; we needed to be there to stand a chance

In Situ Job Search

Singapore is humid and hot, but compared to the last 6 months, it was paradise: clean, air conditioning, delicious and varied food, and ubiquitous (I miss that word) public transportation.

We email blasted friends and ex-coworkers and asked for introductions, and we began our in-person networking phase. I often had 4 meetings a day, with at least one leading up to another connection or meeting. It felt like we were finally getting some traction.

Alas, it was proving hard to turn these meetings into proper interviews let alone offers. A friend would later explain that I needed to adjust my expectations regarding timelines: his last job hunt took 5 months from first meeting to offer; definitely not the pace we were used to. Still, there were a few leads that were exciting: a position with large consulting firm focused on future of mobility research, another in an autonomous driving startup, one helping open a new office for a large engineering consulting firm, and the last as an entrepreneur-in-residence with a VC firm.

The 2-Body Problem

I had pushed hard for Singapore, and I really wanted it to work out. But the gap between what we hoped for and the reality we were facing was slowly taking its toll.

We were starting to realize that getting work Visas was not going to be a slam dunk. Based on what we learned from different blogs and government websites, we expected that with our backgrounds it should be straightforward. However, it turned out in practice that most companies have to deal with quotas, and despite having applied for an independent visa (i.e. we wouldn’t require sponsorship), we were told by many of them that it still counted against their quotas and therefore they were hesitant about considering us for jobs.

Salaries were another factor we were quickly finding out was going to be an issue. On the one hand, living in Singapore can be cheap (eating at hawkers markets, no need for a car); on the other hand, enjoying life in Singapore is expensive (eating at nice restaurants, renting in nice neighbourhoods, traveling to nearby countries, and pretty much everything else). For most expats this is a non-issue as they are on generous relocation packages. For us, especially when comparing to our earning potential back in the US, it was becoming increasingly difficult to ignore the money we would be leaving on the table.

Home Sweet Home - aka Whiplash

The best way to describe how I felt during my first 2 weeks back is whiplash: we lived in 4 countries (well, cities), pondered different career choices, traveled 10,000 miles to the antipode, yet we ended up renting a place barely 3 miles from our previous one.

It’s now been one year since we’ve been back, and when I look back, it has been a wild upwind course with four distinct legs.

Yet Another Job Hunt

After spending almost 3 months job hunting (virtually and in-situ) in Singapore, the prospect of re-starting from scratch was daunting. Fortunately I didn’t have to worry about visa issues this time around, but the fact that it constantly came up reminded me of the realities of restrictions on immigration, even in so called ‘high-skilled’ jobs.

The only thing I was certain of is that after 8 years of working on different aspects of electric VTOL aircraft, I wanted to work in a different industry. Most of my network seemed to have moved on to autonomous vehicles, which although interesting, did not attract me enough as it felt too close to the eVTOL world (both on the technical front as well as the unrealistic timelines & hype.) After 2 months of dozens of emails, phone calls, and interviews, I ended up joining a finance company as a data scientist …

My Corporate Hell

On paper, working in finance ticked a lot of boxes:

• Sufficiently different industry to provide exciting new challenges,
• Tons of learning opportunities about the inner workings of financial markets,
• Competitive compensation,
• Prospect of an international career (there are a lot more financial hubs than tech centers),
• and the cherry on top: the role was within a smallish innovation team working closely with an amazing group of Stanford professors!

Alas, what sounded like the ideal job soon collided with the realities of being a cog within a large corporation: insane bureaucracy, multiple layers of management (I was reporting to 4 people), and lack of an exciting mission. I also quickly realized that the role was not what had been advertised. Instead, I was going to be a technical product manager (or at least what 3 of my 4 managers wanted) navigating corporate politics to obtain access to data, all to ultimately implement a column on a trading dashboard. Of course it was going to be powered by ‘AI’ (aka linear regression), but did I really want to spend two years of my career building this?

By now I had spent 6 months thinking about and searching for my next career move, and after finally picking a job, I was miserable. I know that’s a strong word, but I mean it: I gained 15 lbs and some nights I was so confused and sad that I cried: How did I end up in this situation? Why couldn’t I be as happy or successful as all of my peers with their amazing looking titles and achievements on LinkedIn? Should I have stuck to one industry and just climbed the ladder? Maybe I should go back volunteering in Mozambique? Or if I just stick with this job for one or two years then I can spring to another job and I’ll be happy then? Maybe I should at least wait 6 months to get my end-of-year bonus (50% of my comp!)?

I had spent too much time during our travels knowing what it’s like being happy to have the patience to be unhappy: I turned in my resignation after 8 weeks - what a contrast to my previous job tenure of 8 years!

[#coronaperspective It would have been interesting being part of that company during the crazy volatile markets - then again, I’m glad I don’t have to get all my market transactions approved… ]

7 Knots

Olivia made us go through an exercise back on the sailboat where we scored what mattered to us in life:

Looking back at that, it doesn’t come as a surprise that these were the three things I “learned about myself” during my short tenure in “wall street”:

1. I care a lot about the product I’m building: it needs to be exciting, technically difficult, and I want to do it alongside inspiring people that I can look up to.

2. The job I really wanted was the one that the professors had: the opportunity to contribute to a multitude of projects across a variety of industries (they all consulted with multiple companies).

3. My travel bug had not been satiated: I needed a job that either included a lot of travel or that would give me the flexibility to do so on my own time.

The job hunt was back on, but this time, instead of going through LinkedIn, I reached out to my network and let people know that I was considering consulting work. Within 4 weeks, I had lined up 2 projects, and a couple of months later I had found a good rhythm working with 4 companies across different industries: small satellites, maritime shipping, delivery drones, and autonomous vehicles.

Things are [#coronaperspective were] going well: I’m refreshing my technical skills and learning how all these companies were tackling different challenges, I’m feeling the same excitement I felt in my early days at Zee, my clients are happy with my work, I don’t have to deal with commuting most days, and I am averaging 60 hour weeks and loving it (whenever I get bored or stuck on one project, I switch to another.)

It’s not all rosy though: figuring out how to create an LLC, dealing with taxes, negotiating consulting rates, keeping track of hours and invoicing, juggling multiple laptops, etc. But (there is always a but?), there are really two things that are nagging me:

• I don’t have a seat at the table, a say in the direction of any of these companies, or a sense of ownership: this is slightly frustrating at times especially given the time I spent working on product and business before leaving KittyHawk.

• I am working so much that I don’t have much time for traveling and I’m risking burning out.

Sailing Away [#coronaperspective Running Aground ]

I made my peace with the first issue of not having a say. I figured that if I felt strongly enough about one of the companies, I’d just join full-time. Still, I needed a way to take advantage of my ‘independence’ as a contractor and avoid burning out.

I looked back on our year traveling, and I decided that what made the happiest is spending time on and around water. My DiveTheData collaborator and I submitted a couple of grants to expand the project, and I found a sailing boat that was willing to take me on as a crew member to cross from New Zealand to French Polynesia and get involved in some coral gardening there. This was a dream plan: I’d work 60-hour weeks for 6 months, then take 2-3 months to go sailing and diving. And to top it all, the plan is Olivia-approved!

I told my clients of my upcoming travels and started winding down projects with the goal of taking off mid-April. But just like sailboats run aground in the muddy waters at the channel edge, this all came to a sudden stop with Covid-19. At first, I was hoping it was a flood tide, i.e. that at worse this is a momentary delay while the water rises and things return to normal. But 2 months in, it’s obvious that this is more of an ebb tide: travel restrictions will take a while to lift and the job market has changed significantly that it’s unclear whether I can rely on easily finding consulting work.

When we were aboard Galaxy, we often had to wait days for tides and winds to sync, and that never bothered me because, unlike Olivia, I wasn’t worried about when we were disembarking and what we were doing next. The situation is now reversed, and I have a better understanding for how she felt and I hope I’ll be able to internalize her wisdom on the matter:

Galaxy couldn’t care less about what I want. Maybe it’s because she’s been focused on giving me what I need instead. Time to stop and digest momentous life changes undertaken all at once. A chance to face my fears and find my edges. A view of the horizon, and what might lay right behind it.