Getting Better

Fits & starts

Hey, it’s 2020 now! Cue things about resolutions and intentions and bettering selves. This year I intend to drive for more clarity and intentionality with what I put out to the world and how I spend my time doing it.

At work, most of us try to optimize how we spend our working time using a tool called Clockwise. It enables you to set preferences for how & when you like to work, automatically scans everyone’s calendars for meetings, and automatically reschedules those meetings to give each participant as much “focus time” based on their own preferences. On the surface, it’s wonderful for creating meeting block periods without having to think about arranging my day, and some of my colleagues thrive in long periods of deep focus.

But I barely use the focus time as Clockwise probably intends. Being at home, even in a relatively bare spare room / office space, I’m constantly distracted by my personal life: my wife, our things, my new puppy, my Nintendo Switch, my Apple Music library, Wikipedia, trees, cars driving by, a lightning strike of an idea, snacks.

For a while this frustrated me. I had thought working from home was the ultimate path to deep focus and productivity: no commute, no distractions by coworkers, no proverbial watercooler to seek out gossip (though I do enjoy my kitchen), no weird internal IT rules that prevent me from running my work computer the way I want. But I still find myself distracted, often by my own bullshit, which results in a very fits-and-starts style of work through much of the workday. Twenty minutes of deeply focused writing or backlog admin might be suddenly interrupted by my own desire to update my near-perfect playlist to cook to. Alicia might suddenly be having an awful symptom flare-up and I now suddenly need to make lunch and find her medication. Having a puppy isn’t quite like having children, but it’s certainly tested my ability to context switch on a dime to avoid pee stains all over the house.

I’ve very recently learned to accept this reality of working. It’s okay to get distracted by life. It’s okay to feel a little bored trying to improve how teams design products after hammering away at a product requirements document for a bit. It’s okay to stop and cuddle with my wife or a dog because that provides me so much more joy and fulfillment than how much time I can put into staring at a laptop screen.

I can still be quite intentional even if I’m bouncing between the many things in my life in fits & starts. An optimally-placed three hour block of time to write a song or a strategy document won’t solve for me being clear in what I’m looking to do and why; I can be comfortable working ten minutes here, ten minutes there, as long as I know why I’m doing it.

On Work

An extremely good problem to have

I just ended my one-year expat assignment for my company. I’m back in the US, most likely for good — so long, massive weekend farmer’s markets and cheap healthcare; hello political malaise and smartphone convenience.

While I was in Berlin, my job was very specific to the European market and required a deep embedding into European office culture. A lot of the standard corporate tropes apply — abundant meetings, open office environment, good-and-bad stakeholders to manage — but knowing how to navigate the interpersonal relationships and cultural nuances of an office is best done by immersing oneself in that office. Doing the same job from remote is, in a 8,000+ person company, difficult to sustain.

So now I’m in transition. Still at the same company, but looking for something to take on next as I phase out of my current responsibilities.

This has led to a very interesting phenomenon: a whole lot of teams seem to want me. I have spent roughly 30% of my last week simply meeting new people and learning about other problem spaces going on within the company, to see if they are interesting and impactful for me to take on.

While in many parts of both the US and the larger world people are constantly finding themselves out of work, struggling to make end’s meet, I’m having no less than 6 unique jobs thrown at me (disclaimer: all at the same company) with a crazy amount of enthusiasm.

This is an extremely good problem to have, and something I have weird feelings about.

  • I don’t love saying “no” despite having to do this a lot in my job. This is that same problem, but at a meta-level to product management — for the roles I don’t take, it’s: “Sorry, I don’t find your problem interesting enough to take a full-time salaried position to go solve.”
  • I’ve underestimated how many interesting product management problems there are at a Big E-Commerce Company. It calls into question why I spent over 3 years in largely the same space — doing different things, in different markets (and spending a full year living in a different market). But could I have been even happier by looking for these opportunities earlier on? Why aren’t some departments more proactive about showcasing their problems & solutions to attract people?
  • How firm of a decision do I really _need_ to make? If I pick a role that I like on paper and end up disliking, how easy is it to recall these same opportunities I’m currently being presented with?
  • Consider the bargaining-chip aspects of my position. If so many people want me, can I make them fight for me? How much of _that_ am I willing to push for, as opposed to simply being happy in my next position?

I realize these are extremely first-world questions to be asking. I am in an amazing position. But decisions are hard. And while it’s probably all going to be fine regardless of which path I take, I desperately want it all to be fine.

Originally published at on August 26, 2018.

On Work

Eight months, in an office

10 months ago, I was living what I thought was a dream: working remotely for a decently-buzzed tech startup where I was the lead product guy. I could work in my underwear, start and end whenever I wanted, have free reign to work and travel wherever I pleased.

Then in May, said startup laid me (and pretty much everyone else) off with a week’s notice.

I had seen this coming for almost a year for various reasons I won’t get into — but what did surprise me was the ease of getting back on my financial feet. Those of us who got laid off were offered a new job pretty quickly by Wayfair, an e-commerce giant also based in Boston. So that’s where I ended up.

Eight months later, I find myself finally in my element again. The first three months in this job were total culture shock: I was uncomfortable around so many people, all of them wanting to talk to me all about the work and nothing but the work. I was frustrated with having to commute to an office at all, let alone walking down the street like I would regularly do in New York.

But over the last few months, I figured out a rhythm to make it work for me. It’s certainly not a perfect situation — but then again, what job is, really? — but I’ve had some time to reflect about being in an office again.

(Disclaimer: this is primarily about the experience of working in an office environment, particularly after a stint in startup culture, and is in no way intended to be a reflection of the work I do, or my employer, at all.)

Wayfair employs thousands of people and has an office right next to Copley Square in Boston. When you walk into the office for the first time, it’s hard to not feel like you’re part of something massive, given just how many people are flocking to the Copley Plaza complex between 8 and 9am. You’d think one of the stores in the Copley Plaza Mall was having a blowout — nope, these are just Wayfair employees trudging into work.

After a few weeks, though, the awe of big company size and impact turns into drone-like fatigue…especially as wintertime sets in. Droves of sleepy, freezing employees passing through subway turnstiles, huddling underneath half-broken umbrellas and avoiding puddles of slush (and being forced above ground to avoid MBTA construction), just to stare at a PC screen and talk in corporate-speak.

Simply having to be at the mercy of weather sucks. When I was working from home, if it was snowing out, I could just stay inside. I technically have the facilities to work from home in my current job, too — so it can be frustrating to eschew all this technological capability just to be present in the office culture. Wayfair has offices in several locations around the US and Europe; I can’t tell you how many times I questioned my battling of snowstorms to get into the office, only to sit on calls with my Berlin colleagues all day.

That said, if you’re stuck on calls all day at home, you might never leave the house. Get this: working in an office forces you out into the world. This is something I completely took for granted as a remote worker — I would occasionally run out to a coffee shop for a while to get stuff done, but nothing was more comforting than parking it on my couch for 9 hours straight save bathroom and lunch breaks.

Speaking of which, when you begin to compare home-work and office-work life, tiny subtle details start to surface about your lifestyle. For instance, The cost of your utilities start to become something you scrutinize monthly — I drastically underestimated how much I was spending to run electricity and heat during the ’14-’15 winter while working at home. Finding food to eat in an office is a really hit-or-miss thing, depending on where your office (or home) is located. I have the benefit of being right near Copley Square, where food trucks and solid restaurants abound. My last office job was in an awkward part of East Cambridge, MA, where our best culinary options were in a mall food court. At home, you’re really at the mercy of your grocery list or what (if any) restaurants are nearby; back in NYC, this wasn’t a problem, but in quieter parts of the world, this could certainly be a drawback.

Everyone who Product Manages knows the difficulty of trying to herd cats — oops, I mean colleagues — toward a shared product vision, and this difficulty is only amplified when doing it from afar. Being in the office ensures presence from everyone who matters, including my/yourself. I find myself more productive overall, simply because I had face time with colleagues working on projects with me — and no at-home distractions, like my guitars or my television. I can also use my commute to unwind and/or focus on things I’d never be able to focus on given those distractions. I’ve started writing again simply because I have over an hour of “free time” on the train every day.

Working in an office can be painfully social. To avoid talking only about the work, you need to find common interests with your colleagues: in Boston, it’s generally assumed that this is Boston sports. If you’re not actively following the Bruins/Pats/Sox (or worse yet, following another city’s team) you’re already at a disadvantage. I’ve come to develop a personal brand around music snobbery, pop culture savvy and a more casual tone, which people seem to appreciate outside of my general apathy for sports.

Once you figure your general vibe out, though, working in an office can be delightfully social. You actually start to make friends and engage in social conversations and outings you never would’ve had sitting at home or in a coffee shop all day long. Sure, there’s spontaneity involved with serendipitously meeting new people at your local coffee shop, but there’s something equally spontaneous in the side conversations that happen at work. My aforementioned music snobbery may manifest itself during a discussion of weekend plans, which may lead to a colleague/friend to check out a band with.

And what happens when the work gets to be too much, and you find yourself stuck at the office all day? Isn’t that the beauty of working wherever you choose? What about those giant cultish companies who directly incentivize their employees to spend all waking hours at the office, or even sleep there?

Well, so, you can just leave. If there’s more work to be done, and your company has a VPN, you can catch up on work at home after having a lovely dinner at a reasonable hour with your significant other. I’ve come to realize (again) the importance of balance — not necessarily the lofty, unattainable “work/life balance” construct of 9–5, but finding a personal balance where I’m challenging myself and working hard, but not burning myself out and still finding time to reflect and find fulfillment elsewhere in my life.

Certain parts of the tech/startup industry paint office culture as a thing of the past, rendered unnecessary by new collaboration technology. Fully-distributed organizations are popping up everywhere, promising uber flexibility and balance. I admire these companies’ ability to embrace technology to try and bring more happiness to their employees — though it is certainly not perfect either. Remember that distributed companies (or remote work at all) is a fairly new concept, far from perfected by any one organization — and the larger the company is that you work for, the harder it is to adapt the necessary processes and technology to enable that flexibility.

All in all? I certainly don’t hate everything. My commute is sometimes frustrating, as can be the work, but that’s part of dealing with everyday life. I genuinely like quite a few of my colleagues (both in and outside of work), which after being remote for a while is quite refreshing. And I’ve achieved a balance that, at least for now, I’m happy with.

The question I now find myself asking more frequently is: where does this go? Do I advance up the food chain of a strong brand with its corporate quirks, or do I keep my hand in some things that could result in more personal freedom? What will ultimately make me a better, happier person?

Well, how many licks does it take to get to the center of a Tootsie Pop?