2015 and 2016 could not have been more different.

    2015 was mostly spent living out of a carry-on bag, traveling from Estonia and Berlin to Tokyo and Taipei helping run trips for, and building, Hacker Paradise.

    It was great. Wanderlust: satisfied.

    2016 found me receiving an H1-B visa, moving back to the Bay Area, and obtaining honest-to-goodness employment. Different.

    Here’s how becoming sedentary and employed has turned out so far, relative to expectations.

    The Good

    Basically, stability.


    My partner Mari1 and I are (at long last) engaged! After 5 years of being together, we’re back to living together and have a place in Bernal Heights that feels like our own. We’re so domestic we even got an L-shaped couch and the kind of mattress they advertise on podcasts.

    There’s something very warm and comforting in having a good sense of who you are going to spend the rest of your life with. Mari has been an anchor, making the disruption in other parts of my life that much more manageable.

    Friendship & Community

    It’s also been rewarding to be able to engage and re-engage in meaningful friendships. One of the toughest parts of traveling full-time turned out to be meeting new people every month (great people, mind you) and forging friendships with them. At some point, the task became exhausting. I yearned for the comfort of spending time with the sort of friend that already knew my jokes were overly-complicated and terrible and would laugh anyway, if only on the inside.

    I’m still not 100% back to feeling integrated or satisfied with the depth of my relationships back in San Francisco, but compared to full-time travel, the improvement has been remarkable and the last few months of 2016 felt much better than the months prior.


    I joined Opendoor in September. Part of the motivation of being an employee was to have co-workers I would learn from & enjoy working with. This came true. Another part, which I was more surprised to learn, was that “Growth Engineering” - a term I would have thought ridiculous back in college, and as a sell-out-sort-of-a-thing-to-do, is actually quite engaging and satisfying. It feels like I’m doing behavioral economics research again, but with higher stakes. I’m very grateful to Remi Gabillet, for first identifying this role for me.

    Opendoor has easily met expectations in terms of the company’s growth, the quality of my coworkers, my faith in the executive team, and my ability to have an impact as an individual contributor joining a 150+ person company.

    The Bad

    There’s no better crutch for procrastination than employment.


    A problem that I’ve seen a fair bit with engineers and especially founders in tech is this mission-at-all-costs mentality. Like political operatives on a critical campaign or soldiers in the middle of a war, it’s easy to say “this thing I’m part of is more important. I can postpone [personal thing that I should get done] for now, because if we win we can always deal with it later.”

    And then the mission comes to an end and we’re stuck figuring out that we’ve got to find a way to do our own laundry and maybe go to the gym more often and our last annual check-up was in the last decade. Maybe you deal with it, but often you start hoping and searching for another mission to come along because it’s easier and you don’t have to do boring, mundane things like take care of yourself.

    One of the reasons for deciding to get a job rather than starting another company was that I could use the superior work-life balance to get the rest of my shit in order, and avoid getting caught in the mission-at-all-costs mentality.

    That hasn’t really happened.

    It did, a little bit, at Sprig. But at Opendoor, working harder and staying longer has been too gratifying, too tempting to be easily avoided, and I found myself slowly falling back into using mission-at-all-costs excuses2.


    As a result, I’ve definitely gained some weight (something that did not happen while traveling and eating at restaurants full-time for a year and a half). I’ve ignored a doctor’s note to start watching my cholesterol. I missed a dentist appointment. I bike to work but have failed to follow a regular gym schedule.

    I also have yet to deal with setting up some nuances relating to my Health Savings Account. I have an accident claim from a rental car that got broken into that has been pending since September.

    I planned to set concrete mental health goals around building resilience and good habits, and meet with a therapist regularly3. Still TBD.

    Instead, I’ve reverted to occasionally staying up way later than I should and then being less productive at work the next day - essentially a high-school version of myself but with more severe impact to my productivity, given I’m not sixteen anymore.

    My lifestyle has me eating less healthily and drinking more than when I was traveling, on “vacation”.

    I find myself easily falling into many of the typical privileged-engineer-at-a-legit-startup-in-the-bay-area traps. It’s funny but also a little disappointing, since I was well aware of (and caution others) against this kind of self-neglect. I’d rather be making new mistakes.

    All in all

    Some good, some bad. As far as new year’s resolutions go, I’m going to need to make sure to be hitting the original goals I had in mind when I moved back to San Francisco.

    2017 Goals

    Sleep Maintain a healthy sleep schedule (7+ hours of sleep and in bed by 1AM, 95% of the days of the year).

    Exercise Do something (bouldering, gym, or other form of exerfise) 3+ days a week, 95% of weeks except vacation. Reach and maintain target weight of around 10 pounds less than Jan 1st, 2016.

    Mental Health Build mental resilience (either follow a book or hire a therapist by Jan 30; create a growth plan; follow said plan).

    Physical Health

    • Schedule & attend follow-up physical by Jan 30; follow recommendations.
    • Schedule & attend dentist appointment by Feb 30.

    Writing (AKA, other interests)

    • Publish a 500+ word piece once a month, including receiving quality feedback from friends.

    Fingers crossed.

    1. I have to say I’m pretty stoked to stop explaining why I use “partner” and just saying “fiancee”. 

    2. More caveats: Opendoor is a great place to work and if I haven’t tried convincing you to join yet, ping me. 

    3. I assume that by 2017 this is not a controversial position. To be explicit: I’m not in any particular trouble, other than the sort of typical garden-variety depression and anxiety you’ll often see in ambitious over-achievers. You don’t wait until you’re overweight to start exercising; you shouldn’t wait to be struggling emotionally to work with a professional to build resilience and maintain mental health. 

    Published: March 10 2016

    Giving back to open source projects you benefit from is one of those obviously-good-in-theory-confusing-in-practice ideas, like eating healthy or being carbon-neutral.

    Many services - flattr, bountysource and gratify, among others, offer widgets that developers can put on their projects to encourage subscription donations. None has been a breakout success.

    There needs to be a fast and straightforward tool to empower an engineering manager to say “sure, let’s do it.”


    Here’s how it would work.

    Dependency File

    Most projects I work on these days have a file with a list of package dependencies - Gemfile for ruby, requirements.txt for python, package.json for node, and plenty more.

    List of Dependencies

    Piggybacking on package managers files, Dependonate would take a project’s dependency file and generate a list of direct and indirect projects. Each of those projects can then be parsed to see whether their Readme file includes links to any of the popular donate options (flattr, bountysource, gratify, paypal, etc).

    Actionable Next Steps

    Finally, Dependonate would open up the various URLs that would make donating as registering and entering your credit card on the services above, the lists of desired projects to contribute to having been auto-filled.

    Dependonate would also generate a pretty report for the company to put up on their website as proponents of Open Source, somewhere near the engineering hiring page.

    Hit me up if you build something like this, or if your company would be up for donating through it.

    I found myself planning a series of flights for Hacker Paradise, flying from Tel Aviv –> New York –> San Francisco –> Tokyo –> Tel Aviv with a few days of flexibility for when to take each flight. I spent about half an hour on Skyscanner and Google Flights, and couldn’t find flights for less than about $3,000. Which is a lot. At roughly the same time, Vlad from Flystein reached out and offered to help Hacker Paradise participants book flights. So I tried the service out.</strong></p>

    Flystein Homepage

    What’s Flystein?

    Glad you asked. Flystein, it turns out, is what a value travel agent looks like in the “digital age”. Instead of making money by taking a percentage of your booking fare from airlines, Flystein helps you find the cheapest possible fare online that meets your needs and then charges a flat fee for doing so. You then book the flights yourselves, via links & booking instructions Flystein provides.

    Taking money for providing value. Who knew.

    How did it go?

    I gave Flystein my itinerary and neurotic set of flight cost preferences.

    My flight itinerary

    A day later, they came back with flights totalling $1934. A ~$1,150 difference between a “reasonably competent” online flight shopper like me and a bona fide flight expert.

    Proposed Routes

    How did things get so much cheaper?

    Throwaway Ticketing. My Tel Aviv to New York flight includes a roundtrip flight back to Copenhagen in February. I’m probably not going to take it, but who knows. Also, who cares – it was $200 or so cheaper than the equivalent one-way flight. I would have never known to check.

    Hidden City Ticketing. My San Francisco to Tokyo flight included a day-long layover in Tokyo and then continued on to Hong Kong. I, however, never made it on the connecting flight. One day, Hong Kong, one day.

    The Economist has a good write-up of the hows and whys and economics of flight hacks. The point is, you can save a considerable amount of money on flights if you know what to look for and are willing to dedicate the time required. Or you can use Flystein.

    How was booking?

    Mostly fine. One of my flight legs was expired by the time I looked (you have to book quickly) and I ended up calling British Airways, only to be told that I needed to pay thousands of dollars more.

    So I let Flystein know. After cursing about British Airways for a bit, Vlad found a flight that worked perfectly only a few minutes later. The new flight cost a whole $20 more.

    The whole booking episode could have been avoided if I had the ability to go full “travel agent” and just given Flystein permission to book on my behalf. It turns out there are legal reasons why doing so is not trivial, but they’re on it.

    Was it worth it?

    Flystein saved me over $1,000. Research fees for a trip like mine cost <$100 (a simpler flight starts at $49). So, yes. 90%+ of the savings for near 0% of the frustration in finding & booking flights. Value….but what if they don’t find anything? Fair question.

    It’s possible you’ve already found the cheapest rate you’re going to get. Flystein has a beat-my-price option where you only get charged if Flystein actually saves you more than their fees.

    Flystein. Use it when booking flights of non-trivial complexity (international flights over $500). It’s a thing.

    Published: August 01 2014

    I’m putting Estonia on hold - still excited to go there, and hoping to do so in April or May, once it warms up again.

    In the meanwhile, I’m heading to Costa Rica to help facilitate Hacker Paradise a 12-week digital retreat. The location has all the benefits of nomadism (cheap, beautiful location with delicious food and friendly people) while bringing together a small community of hackers working on individual learning, contracting or their own companies.

    Here’s how it happened: Casey Rosengren, a Penn classmate and fellow Penn Hackathon organizer, was doing the whole travel-and-freelance thing and did some work for a boutique hotel that was down to give Casey the entire place for a couple of months, leading to the creation of Hacker Paradise. I saw one of Casey’s posts about the place, and offered to come help.

    In short: I’ll be hacking by the pool in Costa Rica until November if you need me.


    PS. Care to join, either for the whole 12 weeks or for a shorter trip? We’re keeping a couple of spots open.