Categories
On Work

When work is fun, but it still burns you out

Right to it: I quit my job. I took a new job at a smaller company called Abstract, which builds a design system and collaboration toolset for product design teams. This is a job I have sought for years – not specifically this one at Abstract (since the business is only about two years old), but one that actually truly ticks all the boxes:

  • Small company, but not too small
  • Growing and relatively well-established in its niche
  • Thoughtful culture and approach to how it works – not one about obliterating the competition, working hard playing hard, you get the idea
  • Flexible to life situations, including the possibility of remote work
  • Compensation that reflects the value I believe I provide, without the noise of “benefits” I don’t truly need or value

It was a really hard thing to walk away from my job. Wayfair did have many of those boxes ticked. Those boxes also had big, painful asterisks associated with them which ultimately burned me out, despite having most recently been working on arguably the best team I’ve ever worked with on the most exciting product I’ve ever worked on.

But I also was getting no more than two or three hours at home by myself before my brain compelling me to fall asleep. Those 2–3 hours were usually zombie-like. My wife and I would haphazardly throw a dinner together – which is critical to do given my wife’s celiac disease and other food intolerances – and stare mindlessly at the TV most nights while we ate in near-silence. When she spoke for more than fifteen-or-so seconds, I would get short and my head would throb. Not because I didn’t want to listen to her for hours – because I did – but because my job had worn me out.

If I was lucky enough to spend those few hours with my wife, I had to be careful not to spend too much time with her, because I needed to sleep. I wanted eight hours of sleep, but realistically got six-and-a-quarter hours on average. (I know this to be true – my watch told me.)

Most people seem to get this amount of sleep regularly. I got stuck in a routine where I would be so tired on a Friday evening that we’d go to bed by 10pm, and then sleep in on Saturday morning. Then, my weekend routine of sleeping in to catch up gradually ceased because I couldn’t wake up later than 6:30am.

Waking up during the week was always the same routine: shower, dress, coffee, smoothie, read email, go. On most days I would wake up Alicia at steps 1 or 2, purely by accident. The “go” part could be anywhere from 45 to 75 minutes, depending on timing and other unpredictable things.

Virtually everything at home suffered as a result of all this. My wife’s mental health, my mental and physical health, our relationship in multiple ways, our willingness to travel, the cleanliness of our apartment, the diversity of meals we ate, the enjoyment we felt eating those meals in our unclean apartment. We constantly talked ourselves out of doing countless things because it felt like too much work after all the work we had each put in: me with basically nothing but my job, her with struggling to move her health and solo business in the correct direction.

The weirdest part about all this to me is that this all feels so first-world. I still had weekends, I still have a relatively nice apartment with meaningful flaws I could ignore, I make quite a bit of money, I have a life partner that I really truly do love.

Also, tons of people live like this. Literally every Monday was rife with colleagues of mine – mothers, fathers, driven 24-year-olds – half-asleep on the first day of the week. I have a neighbor who commutes and hers is thirty minutes longer than mine. I genuinely don’t know when she spends time with her children. Colleagues of mine often arrive home only to put their children to bed; sometimes I’m receiving emails from them after this time, clearly indicating they’re back at work.

By the way, this is not an indictment of my previous employer. This is on me. I truly enjoyed my time there, I tackled some really interesting product and organizational problems, and most of the people I work with are amazing people. I would happily work with or for several of them again in a heartbeat.

But what kind of life was I building for myself? What happens when roughly 80% of the interaction I have with my life partner are over text messages? Is this part of what leads to half of married couples divorcing? What kind of life is spent feeling mostly like a zombie?

A shitty one. And I’m fortunate to no longer feel like I’m building one of those.

I start on Tuesday. This will be good.

Categories
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 tonedeafcolorblind.com on August 26, 2018.

Categories
On Work

Adventures in remote desktopping

or, the obfuscation of ecosystem


I love working on an iPad Pro. It’s the device that I find myself wanting to continually pick up, and the device on which I seem to get the most done — not always finished products, but the best and most fully defined ideas I can usually bring to reality. That goes for many aspects of my life: personal projects to cultivate my relationship with my wife, writing and producing the bulk of songs, writing and communicating and planning product ideas and larger initiatives for my job, writing this blog post.

My job is doing product management which, while a very complex and multi-faceted job, is essentially reading, writing and talking. Hey now — the iPad is amazing for that. I’ve got Slack, Outlook, the Google Suite of apps, my writing and task management apps of choice loaded up, and that makes up about 90% of the job.

The other 10%? Fairly technical stuff locked down to company-owned devices. I’m diagnosing issues with complex operational products, testing features, writing SQL queries, reading code — stuff that would be insane for a large public e-commerce company to leave open.To do this work, I am effectively locked into a Windows PC. At least it’s a massively souped-up quad core Windows 10 PC, but…it’s a PC. Stuck between the Google and Office ecosystems. Locked down by IT administrators. This PC is a laptop attached to an enormous dock connected to two Dell monitors in a corner of a big room, neither of which I use or maintain a consistent connection to said enormous dock. Because PC laptop keyboards seem to be all-encompassingly awful, I have a separate, wired external keyboard and (also wired) mouse which still hurt my hands to use, just slightly less so than the laptop keyboard.

All to do about 10% of my job. Possibly less on some days.

Meanwhile, the iPad just sits there, next to said collection of heavy, bulky metal objects connected by many thick cables, waiting eagerly for me to return to the other 90% of my job.I was recently thinking about why I bother using the PC at all. I don’t mean this to undervalue our IT department, but what does it mean to be a primary working machine in the first place? Can I just pretend that my primary work machine is my iPad Pro, and the PC is just a novelty device that I bring in as the big guns?

Or, could I rely on VNC/remote desktop access for the few things I need the PC for? For a long time, I honestly forgot this was a thing: you could access your desktop computer, in its entirety, from another device.

Turns out Microsoft Remote Desktop on iOS isn’t half bad at all — and since my work machine runs Windows 10, it’s all tablet friendly (thanks Surface) and my sensitive work stuff translates nicely to a 10.5” tablet. I can tap to execute a script, or open a Chrome bookmark, or run a POST request in Postman, or…open a 80MB Excel worksheet.

I have three main gripes with this approach, which keeps me occasionally reluctantly returning to my PC:

  • iOS’s stock keyboard doesn’t seem to like unicode quotation marks — ‘ and ‘, but not `’`. I find myself copying-and-pasting quotation marks around SQL queries, which can become annoying.
  • Since Windows uses different conventions for key commands, and you’re accessing Windows via an iPad, sometimes basic key commands are hard to get right. The basics (Select All + Copy + Paste) work fine, but Windows-app-specific ones do not. I sometimes find myself needing to use a combination of hardware keyboard and Microsoft RD’s built-in software keyboard just to reopen a recently closed tab in Chrome-within-Windows.
  • Google Slides and Sheets (not Docs) are pretty terrible on iOS, so I sometimes need to use Remote Desktop for that. It’s sometimes actually more effective than the native app.

Temporary sanity

I’ve drastically undervalued remote desktop access, and now have an even deeper appreciation for both my iPad and Microsoft’s investment in the iOS ecosystem. It is now even easier to do my job from anywhere, even if that job is locked into certain systems and processes for various reasons.

Originally published at tonedeafcolorblind.com on May 22, 2018.

Categories
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?

Categories
Getting Better On Work

On Maker Overload, or why I’m okay with not solving all the problems

Following up on this, which was dead on. In the words of indie darling Courtney Barnett, sometimes I (want to) sit and think, and sometimes I just (want to) sit.

I’m a product manager, which means I spend virtually every weekday (and some weekends) doing two things: solving problems and making things happen to ship good, need-fulfilling products. Anyone who does product management can obviously break this up into many more buckets of duties, glorify it, debate its role in larger business culture, whatever — but that’s essentially what we do.

Sometimes I think I want to build something on my own — I wouldn’t be surprised if most PMs also get this urge. Thanks to a handful of tools that now exist, virtually anyone with Internet access and some spare time can build anything in a matter of hours or days. There’s a lot of people who create their own products on their own these days, using free or cheap existing tools, then publish them on sites like Product Hunt and write about them on Medium. When I read all these posts about “makers” making “products,” I react in a few ways.

First, curiosity, then a little bit of envy.

I love that we now have technology and platforms available for anyone to turn some idea into a packaged product in a matter of hours. Some of the problems people have solved are incredibly niche — I would never have thought of them. Sometimes I wish I had.

Then, jealousy-fueled anxiety.

Why aren’t I identifying those problems? Why can’t I be making those things? What do those people have that I don’t? What do I need in order to build amazing profitable things myself? WHAT AM I DOING WITH MY LIFE??!!?!!?!!!

Then, a ramble.

Hours and hours on Product Hunt. More things made by more people. Curiosity and anxiety on subsequent repeat.

Then, I’m tired.

I burned myself out worrying about other people’s problems instead of solving my own or those problems which I care about.

Why did I do that?


We used to have information overload. Then people rebranded this as #content in an attempt to legitimize it. Now, if the content wasn’t enough, we’re in maker overload. New startups and new people announcing new products being announced almost every hour on the hour. Call it a lovechild of social media and freelancer culture, both powered by the good ol’ Internet — now everyone can have their own voice, so there’s millions more voices, all yelling incessantly over each other for top placement on your Twitter feed. All so you try the hot new products they each built on their own.

What is the impact of all those new products? Sure, it’s huge in aggregate — if anything this is proven by how much pundits are talking about Product Hunt. But what value does each individual new solution to a problem have in the scheme of things?

Product management is really all about solving (the right) problems and enabling the people around you to solve them. Some of the “products” I come across solve problems that aren’t relevant to me at all, but because everyone is posting and writing and tweeting and retweeting about them I run into them anyway. Some of these products don’t solve any problem at all — they generate a problem of their own and attempt to solve it, even if the average person didn’t even need to recognize that as a problem in the first place. Some of those products are really just repackaging the exact same #content that other products already contain, only presented in a slightly different way. Just this year there were 50 products launched, all featured on Product Hunt, that repackage existing tools and content that already wasn’t too hard to find with a bit of Googling. Some of them are totally redundant with each other.

Tools and resources, for designers and developers, all day errday.

I’m not saying this is inherently a problem —and definitely not the fault of Product Hunt — after all, competition makes the world go ‘round. But is this really what makers want to be known for?

Maybe so, or more likely those makers are just trying to make some money or followers. This isn’t new — companies have been making redundant products for the sake of staying competitive a long time — but now that the Internet has enabled for a product to get noticed and hyped in a matter of hours, there’s too much noise to be continuously making products that don’t matter in the scheme of things. It only adds to the information overload, except under the guise of something meant to solve a problem — so people who read about this product (especially those who religiously follow communities like Product Hunt) are inclined to take them more seriously than your standard clickbait. When they do, the maker gets noticed for a day, then just like clickbait, it usually gets lost in the ether of the Internet. Some makers then keep trying to optimize their offering and market fit until something sticks.

Perhaps “maker culture” in tech has also gone the way of the pop music industry.


But that’s not necessarily a bad thing. I’m not suggesting that people stop building things for my own sake. Eventually you might happen across a brilliant solution to a truly challenging problem. Making things to satisfy urges or curiosities, make money, or to grow a personal brand is not inherently problematic — it does, however, create envy within others who aren’t sure they have those same needs. Especially when some of the most “popular” of those products made are redundant with each other or debated incessantly as to whether or not they’re dead.

I thought building my own things was what I should be doing with my life, but it turns out all the product overload is toxic for me. I get into a vicious cycle of anxiety and regret and forced ideation around problem spaces that really don’t need solutions at that moment. I don’t personally build things constantly to satisfy some inner need, but I also don’t want to build a career out of making things that follow trends.

I solve problems all day, some of which are incredibly rewarding (like those that make my fiancée happy) and some of which are incredibly dull or frustrating (solved typically between the hours of 9am and 5pm, but even those are sometimes challenging and/or rewarding). In a world where an app can launch and die in a matter, and much of the writing about said app is about whether or not it’s actually dead, I don’t want to come home every day and keep doing the same thing — it only stresses me out more. My catharsis is writing songs or posts (like this). Sometimes I want to just watch something mindless or live vicariously through someone else.

And that’s probably why I go on Product Hunt for hours on end. Now I understand the appeal of reality television.

I came into 2016 thinking that I wanted to launch a product, and now that I’m understanding myself better in 2016, the less I feel a need to do that. I have a day job, I better satisfy my curiosities via music and writing, and I don’t have any immediately-obvious solutions to problems I care about. It’s more important to me to be with the people I love and be reflecting and thinking about those problems I do want to solve. If you think you need to be launching products for the sake of launching products, take a minute to think about the merits of doing so. Don’t be a maker just because everyone else is.


Did you enjoy reading this? Feel the same way about maker and product overload? Nice. I’d love a like or share if you do, or you can follow me on Twitter. Thanks!