Category Archives: review

2023 Year in Review: interviewing for jobs with a baby on the way

Our daughter set the pace for the entire year. Even before her birth! We needed to prepare for her arrival. It turns out that babies don’t take up much space, so our 1-bedroom apartment was fine for the year. But kids require lots of support items, so we needed to buy and install storage. This consumed much of my free time from January until her birth in May.

We bought a ton of furniture from Ikea, assembled the furniture over the course of a few weeks, got a bunch of freebies from “buy nothing” groups on Facebook, got some more donations from my sister-in-law, did a deep cleaning, read books, and I’m sure a ton of other things that I’m forgetting.

The actual birth went smoothly. We had already been a few days prior: my wife had contractions so we went to the hospital. They told us that she was having contractions but she wasn’t ready yet.

The day before the birth, my wife experienced discomfort and pain all day. She insisted up and down that she was not having contractions. Finally around 11pm, she was in pretty constant pain. I set up a Google Form with a single button, “I’m feeling it now,” and I had her click it whenever she felt the sensation. I looked through a few rows of the spreadsheet and saw that she was having contractions every 3-5 minutes and we called a car to take us to the hospital.

Birth went smoothly. Doctors were great. I’m embarrassed to admit that when I saw her little head for the first time, I thought to myself “Holy shit! There’s a PERSON in there.” Obviously I knew that! I saw all the scans. I saw my wife’s belly. But the reality of seeing a new human being screaming and crying on your wife’s chest in bewilderment really drives the point home.

And then they plopped her on my wife’s chest and the baby started screaming. I remember reaching my hand down and resting my hand against her little back to comfort her. She was so upset from the birth. I knew so little about her experience that I didn’t know what would help.

The beginning was a struggle. Feeding was a struggle, swaddling was a struggle. The sleep deprivation was abominable. She’d sleep soundly all day and then scream for 6 hours in a row. But it was my daughter, so I just loved her and rolled with it.

Recovery care is absolutely baffling to me. They encourage you to get as much sleep as possible. But your baby wants to be fed every 1 to 3 hours around the clock. She doesn’t know what day and night are. You also haven’t worked out feeding yet with your baby, so she’s angry and screaming around the clock because she’s hungry. So your sleep is already ruined. On top of that, a nonstop parade of nurses and doctors come into your room with no coordination, robbing you of what little sleep you might otherwise get. I’ve had problems with insomnia my whole life. I’m an extremely light sleeper and I have trouble getting back to sleep when I’m awoken. However I literally fell asleep in the middle of a conversation with a nurse.

At one point, I wanted my wife to get 3 consecutive hours of sleep for the first time in 3 days, so I coordinated with the nurses to put our child in the nursey for the first time and don’t send anyone into the room. Then I went for a walk and thought to myself, “I’ll just get coffee at the first place that I see.” And then I walked past a Blank Coffee and thought to myself, “I’ll just get coffee at the second place that I see.”

I do want to credit the nursing staff with showing us the fundamentals of taking care of a baby. Their tips on feeding were helpful, and walking through swaddling and dealing with diapers with nurses was really helpful. I just wish they either (a) cared whether you got sleep, or (b) stop suggesting that rest was important. Telling us that we should sleep and then preventing us from sleeping was infuriating.

My wife’s mother stayed at an AirBNB for over a month to help us, and her help was crucial. She arrived fresh between 6am and 7am and held the baby, which allowed us to get an extra hour or two of sleep a day that we otherwise would not have. This made a huge difference in our morale and effectiveness. Having healthy home-cooked meals every day was a tremendous help. My wife and I each got 2ish nights in the AirBNB so that we could try to catch up on sleep (but our sleep schedule was so obliterated by that point that we still didn’t sleep that well).

I took 6 weeks off in the beginning. I’m using the remainder of my parental leave now. I’m so grateful that I have the time to appropriately bond with my child. It’s wild that our laws don’t ensure some minimum time of parental leave. 6 weeks barely felt like enough, I can’t imagine the women that have to return after a few days (or even a few weeks) still healing from literal physical trauma of birth or c-section delivery.

And I love my child so much. She’s so smiley and loves babbling with me and my wife. Her laugh heals me. Seeing her develop small new skills and capabilities makes me so proud of her. Sure there are bad parts. She cries sometimes, she gets sick sometimes, she sleeps badly sometimes, she’s destructive sometimes. But she calms down, gets better, learns how to sleep again, and things are just things. She’s wonderful. I’m truly in a new phase of life.

Learning how to interview and finding a new job

When I found out my wife was pregnant last year, I was at the end of a 2 year period of working for myself. I was having fun and the business had some income, but even without the baby I probably would have cut it off at that point. It was a no-brainer with the kid: I needed to find a real job again.

So at the end of the year I hit Leetcode, polished my interview skills, updated my resume, started applying for jobs, and found WOW THIS IS A REALLY BAD TIME TO APPLY FOR JOBS! It was at the same time that all of the FAANG companies were laying people off. So every company was flooded with more high-quality leads than they’ve had for a while. Or maybe ever had!

I also discovered that if you tell a recruiter that you have a child on the way, they don’t reply to your emails anymore. I wanted to be up-front about this, but quickly learned that I needed to wait until I had an offer letter in hand before mentioning it for the first time.

I still managed to get some interviews, and bombed a few interviews before I realized that my interview skills were out of date.

For a very long time, many companies copied how Google interviewed. Google likes hiring generalists (and when they say “generalist” they mean “people who know the specific skills that are taught in a 4 year undergrad computer science program”), so they set algorithmic coding challenges that you can complete in any language. I mainlined coding challenges when I was in college and got pretty good at them. Plus, I worked at Google for 4 years, and asked hundreds of interview questions in this style. So I’ve always interviewed on the assumption that the coding challenges were enough. This served me well from 2007 until 2016, when was the last time I had interviewed.

I was dismayed to discover that smaller companies in 2023 hire specialists! Maybe many did before this too. But most of the small companies I interviewed at before 2016 did the Google-style interview questions. They don’t want you to ramp up on their tech stack as a strong generalist. They want you to know their stack and hit the ground running as an expert. This is probably what they should have been doing all along (and again, I’m sure many companies did this all along). But I never ran into it, even interviewing for startups previously.

I had a few failed interviews. One was for a tech reason: I interviewed for an editor startup and did well on their generalist problems, but bombed the React coding exercise. I’ve never worked professionally with React in any meaningful way. Google Docs’ stack predates React and they wouldn’t have used it anyway, and Etsy forbade React on their buyer frontend until around 2020 because of the performance hit. I made some progress on the problem but didn’t get far enough, and they wanted their tech lead to come in as a React frontend expert. Fair enough!

I interviewed with Notion, and the guy asked me to design the database schema for a calendar app. Historically, I design database schemas using my patented 3 step process: first, I draw a few schemas that feel wrong. Then, I put the work aside for a bit and help teammates or go for a walk or go to lunch. Then, I come back to the problem a few hours later or the next day and discover that my subconscious made some progress on the problem. Maybe I need to iterate again but I’m much closer than I was a few hours ago.

This is an insanely bad approach for an interview, where you need to bang out a plausible schema within 45 minutes. Usually it took me at least 4 hours, sometimes over a day! I had some additional communication problems with this guy; to shortcut the discovery I asked if the app was like Google Calendar. I then probably burned 10 minutes of the interview designing with Google Calendar in mind only for the guy to keep telling me, “no, it’s simpler than that” until by the end of the interview I was ready to scream, “why didn’t you just say <<no, it’s not like Google Calendar, you’re basically designing a digital wall calendar with shareable meetings>>?” But I wouldn’t have gotten a good database design by the end of that interview anyways, so it’s not like the time made the difference.

After these 2 interviews, I regrouped and realized that I would need to pick the set of skills I wanted to work with and double down on them. I focused on polishing my interview skills for different types of technologies: pub/sub frameworks, different database technologies and their common design techniques and their tradeoffs, microservices vs monoliths, etc. For the previous few years I had mostly worked with Golang and cloud-managed Kubernetes, and was very API-heavy. So I looked for roles that satisfied that. When I got an interview with Hinge, I had no problem clearing their bar because I knew their stack and could talk comfortably about all layers of it.

Working for Hinge has been pretty great. It’s a growing company under Match Group, which is a little weird sometimes (I’m not always sure what to respond when I talk to vendors or insurers and they ask, “what company do you work for?” because the correct answer can be either). But my immediate team is full of sharp hard-working people. Our manager is really thoughtful about constructing good meetings, and he has warmed even my Grinch-like “we don’t need any meetings” heart. And they seem happy with my work; I’m going to be a tech lead next year even though I spent a good chunk of this year on parental leave.

And no time for anything else

Work and family take up almost all my time now! Sometimes I find some time to play video games, but not as much as I would like. I’m often too tired to read at the end of the day. My wife and I took like a 4 month break from watching any TV series together because the logistics and timing were just too complicated.

Part of that is the complications of living in a 1 bedroom apartment. Whenever the baby sleeps, we basically need to stop moving and be quiet. I bought it 7 years ago, so moving isn’t as easy as just renting a new place. Our building is getting heat pumps installed soon (“probably by November,” we were promised last year), and whenever that project is finished we will sell this place and buy a larger place. We thought about moving earlier, but babies don’t make a lot of space and I didn’t want to sell with a large construction project looming. Plus so few things are on the market right now because of interest rates. So this year, we will be going through the hell of selling this apartment, buying a new apartment, and moving into a larger space.

And that’s about all! For 2024 obviously parenting will continue to be my primary project. I want to shake off this dad bod that I’ve accumulated, and we will be moving into a larger space.

2020 year in review: living in interesting times

TL;DR: Holy shit.

Health

First, the pandemic. I have not contracted COVID-19 and I don’t know anybody who died from it. I know people who were infected by the virus, but they’ve all turned out okay. I’ve been lucky so far. I was tested in December because I had a fever and a cough. Thankfully the test was negative. There’s also good news on the horizon: we’ve reached the end of the beginning. The vaccines have started rolling out this month. I just need to hold on until phase 5, and then everything should start to return to normal.

I remember when the first cases were reported in New York. I looked up the infection and death rates from the virus, plugged them into a spreadsheet, dragged the calculation down for 2 months, and then immediately texted my girlfriend to suggest that she buy a few weeks of groceries as soon as she could. About 5 days later, everyone else joined me in feeling like this. There were hour-long lines at Trader Joes, and the local convenience stores were completely out of everything. It’s hard to emphasize how quickly everything shut down and sold out. News articles from the morning were hilariously out-of-date by the afternoon. Companies were revising and re-revising their policies on a daily basis. I know workplaces that went from “we’re open hell-or-high-water” to “we’re shut down for the remainder of the year” in the span of a few days. I’ve heard of several workplaces that took the following approach:

  • Monday: “We’re working from the office.”
  • Tuesday: “You can work from home if you want.”
  • Wednesday: “We’re going to work from home for the rest of the week.”
  • Thursday: “Please work from home tomorrow so that we may deep-clean of the office.”
  • Friday: “We’re shut down indefinitely.”
  • 9 months later: “We’re still closed.”

New York was crazy at the beginning of the pandemic. I felt afraid whenever I was outside. We knew that SARS-CoV-2 is highly contagious, but we didn’t understand its properties. People heavily emphasized washing hands and wiping down groceries, and there were suspicions that masks might make spread worse (on the theory that masks would trap the virus in front of your mouth or nose). I remember walking through grocery stores and holding my breath as I went through aisles with a lot of people. I remember moving out of the way and holding my breath as I walked past people on the sidewalk.

I saw a video by Jeremy Howard demonstrating how to convert t-shirts into masks. I felt a little better with masks on. That weekend, I sewed my own. After that, I began a long process of finding masks that work well with glasses. At this point, I have a good feel for what I need in a mask. Strong nose wire and large enough to cover my face. Adjustable ears. Either black, or a fun pattern. It’s worked out well so far.

Besides the pandemic, my health was pretty good. My weight almost stayed consistent during the year. I see that I ended last year at 201.0, and today I was 204.2. I’ll take that, given how severely the pandemic has restricted my normally active lifestyle. It could have been worse. My girlfriend deserves a lot of credit for my healthy eating habits. She’s a strong advocate for leafy greens and having balanced meals, and she challenges me when my eating habits slip. The pandemic did not help my exercise at all. I barely got around the city this year. I biked to Queens and Manhattan a few times, and I’ve tried walking as much as possible. But mostly I stayed put. I’m excited for the reopening because I’d like to take advantage of things like bouldering gyms for cross-training.

My mental health has remained good, which is a miracle consider that I’ve been tethered to my apartment. It hasn’t been perfect: I feel more irritable and cooped-up in general. But I’ve adapted to staying in my apartment. I miss a lot. I’m excited to go out again. I’m excited to eat at restaurants and go to museums again. I’m going to visit my family when I can.

I left my job at Etsy. See the Career section for the story. This had a noticeably positive impact on my health. I’ve slept more every night. I take long walks during the day. My step count is up on average. I take the time to cook healthier lunches. I’ve been exercising more, and I was already running 3 or 4 times a week.

Career

As I mentioned in the last section, I left my job at Etsy in November.

The reason was simple: I had always wanted to start my own software development company. Every time I got a stock grant, I would ask myself, “Do I want to work until my next one?” It was a convenient amount of time to consider. Normally I was granted stock every 3 months, but now that I had been there for 4 years (and some boring details with the stock refresher program), I got about the same amount but every 6 months instead. So I asked myself, “Do I want to do this job for another 6 months?”

My specific job was no longer better than the alternative of working for myself. I highly recommend Etsy as a place to work. It’s growing quickly, they have a good mission, the people are phenomenal and kind, and it has a positive impact on the world. I personally just ended up in the growing pains of a medium-sized company on the cusp of becoming a large company.

So what happened? For about a year and a half, I worked on adding GraphQL as an internal API layer within Etsy. I’m proud of the work that I did. I was given an incredible amount of latitude to design and build the support for it. It’s some of the best engineering that I’ve ever done. Adding an entire API layer to a medium-sized company is hard, but we successfully launched, got some people using it, got some wins, and were growing it. Yet there were serious staffing challenges on the project. At the beginning of 2020, we were 2 engineers and were promised 2 more would be added. The 2 promised headcount vanished at the beginning of the pandemic, and the other engineer was unable to work for vast swaths of the year. Consequently, I worked alone for most of the year. It was too much for me. Working on a growing an API layer and working by myself was burning me out. Taking a 6 week break and working on another team didn’t shake this feeling for me. Problems like this are difficult to fix. Hiring takes months. Onboarding and ramping up takes months. So this was a problem that would take roughly 6 months to fix.

I want to emphasize that Etsy is a great place to work. I would work there again. If you don’t work there, you should seriously consider it. They pay well and the work is meaningful. My situation was an edge case. A lot of Etsy’s practices were developed while it was a small or a medium-sized company. But make no mistake: it is rounding the bend to being a large company: It just entered the S&P 500. Sometimes it takes scale and growth to uncover problems. Things that worked at the smaller scale break when the company is three times larger. I encountered one of these growing pains, but it’s the kind that the company will learn how to avoid over time.

So I’m setting out on my own. I’ve been inspired by the stories that I’ve heard on the Indie Hackers podcast. Unlike many, I am so fortunate that 2020 improved my financial footing. My expenses went down and my savings went up. Accordingly, I’m in the best position of my life to start a new business that can be successful. I started a company called Jaunty, Inc. using Stripe Atlas.

I’m waiting for the IRS to issue my EIN, which will allow me to set up a business bank account and have fully-separated finances. But the IRS is currently backlogged. In fact, the IRS won’t even respond to the question “has it been issued yet?” until I’ve been waiting for 45 days, and I’ve been waiting for 30. Accordingly, I’ve been trying to learn skills that I can reuse when I can have separated finances.

I spent about a month having conversations with people who run small businesses. I had two goals for these conversations: first I wanted to get a sense of the challenges that they face. These might be my problems soon. Second I wanted to see if there were obvious problems that I could solve. It would be nice if I could build services to help small businesses. The responses had many similarities: lots of people had trouble getting users in the door, lots of people were uncertain how to market or identify traction channels that would work for them, and their problems were often hyper-specific and hard to generalize across all of them. These conversations helped me understand that just identifying a problem doesn’t help that much if the problem isn’t concrete. Sure, companies “need help,” and often have trouble making decisions, but this isn’t an actionable problem to start from. It’s a problem in an abstract sense, not a concrete one.

I had a really exciting conversation with a product manager that my friend connected me to. He helped me understand how product managers view idea creation and validation, and gave me a good mindset for validating whether a concrete idea would be useful or not.

Then asking myself, “What could I make without spending much money?”, I spent the month of December trying to set up a free newsletter showing the math behind business advice. My idea was that each post would have interactive tools embedded, and explain the intuition behind why the advice would work. I ended up with 15 subscribers over the month, but I had trouble promoting the newsletter. I got more subscribers by asking for help than I did by promoting the issues that I wrote. Someone described the newsletter as “circling around a good idea without quite hitting it,” which I think was accurate. My girlfriend identified the disconnect, which is that it’s probably suited for a more visual format like video, since the verbal explanations are dense but the visuals in the posts helped. It’s possible that I could have also gotten more traction by continuing to get advice and iterate, but I’m less excited with the idea now that I’ve lived it. Writing weekly blog posts powered by 600+ lines of code each is difficult.

I vastly prefer how I spent November over how I spent December. Building and promoting a newsletter was comfortable. Talking directly with people was awesome – I learned a ton quickly. It helped me understand their day-to-day.

I think that the newsletter is a nonstarter, so I’ve been examining the hosted GraphQL market over the past few days. After all, the very first thing that I purchased for my newsletter was hosting on Vercel. This is a great match for my recent work experience, and I think that I can provide real value to companies here. There’s no obvious single winner in this space, and I think there’s room to create a niche business. Of course, I don’t want to reach out to people around the holidays, so I’ve just been researching for the past few days. In the new year, I will start having active conversations to get a better picture of what people might want in a solution. I found the talk “Your first 60 days” to be really inspiring, and I’m going to try the approach it outlines.

Hopefully, I’ll have some good news to report in the new year. I expect that I will be able to try and fail at 3 ideas during 2021. Hopefully, one of the three will start to get some traction, and I will be able to get some revenue. My 2021 goal is to to rent out a tiny private office. If I learned anything from the pandemic, it’s that I need a separation between my personal space and my work space.

As a coda, this blog was actually pretty successful this year. I had 207,000 page views this year, which is easily a record for me. That’s not a lot by viral internet standards, but it’s a lot for me. The viewers predominantly came from two posts: Why are we so bad at software engineering? and DuckDuckGo is good enough for regular use, which had varying degrees of popularity on Reddit and Hacker News. Because of the traffic from these posts, most of my other posts got hundreds of views from people clicking around my blog for more content.

Personal life

My personal life went pretty well during the pandemic. In a lot of ways, I feel guilty that my life went pretty well in a year with so much misery.

My girlfriend moved in as NYC shut down. She’s still here. It was challenging at first – we went from “we get dinner once during the week and spend the weekends together” to “we are in the same space 24 hours per day indefinitely” It was a lot. But we’ve made it work. A few things helped this: routines, clear expectations, making sure we were meeting each other’s needs, and having a good apartment layout. Having three rooms that block sight lines has really helped. It’s been nice cooking with someone every night.

Besides, that, social interactions were infrequent and often strange:

  • My sister got married in the park, and we hosted (just) the two of them for dinner afterwards.
  • I went for a few walks around NYC with friends.
  • My friend’s house flooded unexpectedly. My college friends and I spent the day helping him throw away his ruined stuff and shovel all the mud out.
  • We visited my girlfriend’s sister’s family for a short getaway.

This is the complete list of in-person interactions that I have had since March. I know that pandemic shaming is fun, and I definitely didn’t reduce my social interactions as much as some, so I’d be fair game for that.

Besides that, I’ve experimented with video chats with varying degrees of success. My college friends and I have a video game night every Friday, and this has been crucial for helping me feel the passage of time. March feels like it was yesterday, but if I frame it in terms of “how many video game nights has it been?”, I can at least feel some distance.

The most stress I encountered was probably the period between the 2020 election and the period where Joe Biden was announced the winner, with the second-most being the following period where it was unclear whether democracy would hold in the United States, and the following period was reading about the George Floyd protests and seeing the widespread police violence against protestors. I have a nervous habit of chewing my nails when I’m thinking or nervous, and this evolved into literally chewing open sores into my fingers. Thankfully these have mostly healed. At this point, I can handle lemons and limes again without fear. In 2020, I donated a lot of money to causes (Biden’s campaign, organizations like Black Girls Code that bolster education for underrepresented minorities in tech, and organizations that seek to selectively replace policing with policies targeted to specific problems), but I didn’t donate much time this year. I don’t know how to feel about this.

My girlfriend is a professional translator and précis writer. She is extremely concerned with the precise definitions of words. This means that I had the misfortune of learning the difference between the terms coronavirus (a class of viruses), novel coronavirus (a placeholder name before a significant coronavirus strain is named), SARS-CoV-2 (the official name of the virus causing the current pandemic), and COVID-19 (the human disease caused by SARS-CoV-2). Why misfortune? Because I watched people use them interchangeably and incorrectly all year, while also knowing that it wasn’t worth correcting them. This was my small 2020 cross to bear.

2021

My biggest focus for 2021 is getting Jaunty, Inc. on a sustainable course. I would like to end the year by paying myself enough of a salary to cover all of my monthly expenses, and also to be able to rent an office somewhere. $10k-15k in monthly revenue is the line where many people can start doing this. This would put me close to hiring my first employee, but that’s getting ahead of myself.

I’m hoping that I will receive the vaccine by the end of summer. I would like to travel to see my parents. And I definitely need to travel somewhere for a vacation. Getting the vaccine by the end of summer would be exciting, because that means that I’d get to start enjoying NYC again.

I used HEY for a week, but I’m going back to Gmail

I’ve been trying alternatives to Google services lately. No offense to Google. I just used their services uncritically for years. Now I want to evaluate them against their competitors. For example, I now use DuckDuckGo instead of Google.

Basecamp released HEY recently. It is a privacy-focused email client that aims to give power back to the user. This sounded like something that I might appreciate. Every Gmail account I’ve owned uses a similar combination of features. Priority inbox, some specific settings that must be checked, a bunch of filters, etc. It’s always the result of iteration and resignation. It never feels quite right. It’s easy for me to believe that an email client could provide me a “wow” experience by encoding my workflow into the UI, and providing an “I’ve never known it before, but I’ve always wanted that!” moment.

I got a launch invite and decided to try it for a week.

Let’s cut to the chase: HEY is a good email client, but it’s not a good fit for my relationship with email. I’m not going to pay for it. But this post isn’t a hit piece. Negativity is cheap and lazy. I’m going to explain the value that HEY provides. I will also explain why it wasn’t a good fit for me.

How I evaluated HEY

I forwarded my personal Gmail into my hey.com account for one week. I got ~120 emails from ~80 senders. I only sent a handful of emails. This matches my personal email load for a typical week.

I kept a running Google Doc with notes. I especially wanted to split my negative notes into a few piles: bugs, dislikes, and mismatches.

I want to focus on mismatches in this post. When did HEY make me feel uncertain or afraid? When was I fighting it?

I’m not going to mention bugs. Do you really want to hear about a problem with using keyboard shortcuts to scroll through email? They probably fixed it before I published this post.

I’m not going to tell you about nitpicky choices that I didn’t like. This post would become a monument to my own change aversion. “The information density is too low! I can only see 9 emails on my laptop!” Jake. Chill. You’ll get used to it.

Anyways, I used HEY on a variety of platforms. I used the iOS client on my iPhone X. On desktop, I accessed it through Firefox on my 15″ Macbook Pro and my Windows gaming machine.

A picture of me in a pumpkin mask.
Thanks to coronavirus, I had two modes this week: feeling unsafe outside and testing HEY inside. I wore my mask for both.

Privacy-first

I like HEY’s privacy stance. HEY explicitly blocks pixel trackers and loads images through a proxy. It will also “name and shame” companies that send emails with trackers by putting a special binoculars icon over the email.

An example showing a pixel tracker notification from Etsy
An example showing a pixel tracker notification

Some digital marketers don’t like this. Mailing list health is an important metric. If they can’t track open rates, then they can’t know how people are “progressing through the funnel” of reading their emails.

Fine by me. It’s hard to imagine receiving any benefit from telling a remote server, “psst, I opened your email.” I like that people can opt-out of ads with ad blockers. I also like that HEY focuses on opting-out of tracking pixels.

I didn’t care about the “name and shame” part of their pixel tracking. I’d be happy if they just had a counter saying “We stopped 531 tracking pixels this month.” I’m not interested in learning who sent an email with trackers. I just like that the filtering works.

The Screener

HEY requires you to “screen in” every email recipient. When someone sends you an email for the first time, HEY shows a button asking you to “screen them in.” You will receive all future emails from them if you say “yes.” You will never get their email if you say “no.”

Do you receive a lot of unsolicited email? Promotional email you never read? Recruiter spam? Then you should seriously consider using HEY. Imagine saying “no thank you” to a spammy recruiter and never thinking about their emails again. Imagine the promotional emails never grabbing your attention. Imagine opening your email every day and only seeing the emails you want to see. That seems to be HEY’s vision, and I like it.

I interacted with the Screener a lot. I received email from ~80 different senders this week. I screened five of them out.

I don’t receive much unsolicited email. I aggressively unsubscribe from promotional mailers. I turn off email notifications that I don’t want. I sometimes delete services if I get too much email as a result of being a member. As a sidebar, deleting my LinkedIn account was a huge email quality-of-life improvement. The constant parade of recruiters dropped to manageable levels. You should consider it.

I spent lots of time considering some of the Screener decisions. I used to have a Netlify project that I have since deleted. I don’t need to receive email from them now. Maybe I should say “no” to a promotional email that they sent me. But what if I want to use Netlify in the future? I liked Netlify. I might use it again. Would my “no” still apply? I would be missing email that I need to receive. What if I lose my job in the recession and Netlify contacted me about a job opportunity? Would it be screened out? I had this kind of debate repeatedly throughout the week. Who is a sender? Is it a single email address? Is it a company? Is it an individual who could be represented by multiple email addresses? What about catch-all addresses like noreply? When can I safely reject email? I only felt safe using the Screener in a few narrow cases. In cases like Netlify, I screened them in and unsubscribed from the mailing list.

I’d like to make two caveats to this section. First: it seems that Gmail does not forward spam to HEY. I don’t know how good HEY’s spam filtering is and I don’t know how important the Screener would be in relation to it. Second: I only used HEY for a week. The Screener was a constant presence in the beginning. It appeared less as the week went on. I imagine that it wouldn’t appear much next week.

The Imbox, the Feed, and Paper Trail

When you screen an email into HEY, you can choose one of three categorizations.

The primary location is the Imbox. This is the IMportant BOX. It’s an intentional spelling, and is designed as an inversion of an email inbox. The logic goes like this: Other people get to decide when stuff appears in your inbox. You need to intervene to stop it. On the other hand, something only appears in your IMbox when you declare it IMportant enough. This means that you have reclaimed power over the email that you receive.

This is also why HEY provides The Feed and Paper Trail. These represent common email types that you may not need to see right away. This is designed to further improve the Imbox experience by moving these emails out of sight until you want to see them.

The Feed is “The place for newsletters, marketing emails, or anything you want to casually browse.” I put a word-of-the-day email, some Google Alerts, and some newsletters into The Feed. Instead of acting like an email inbox, it is designed to be a content reader. You can periodically skim this content. But it’s not front-and-center in your Imbox.

Paper Trail is “The place for receipts, confirmations, and other transactional emails you receive.” I put automated notifications into here: online order confirmations, credit card purchase notifications, Twitch’s “this streamer is now online” notifications, etc.

After using the categorization for a week, it was clear that I struggled with both of them. I receive a daily newsletter with lengthy emails (Money Stuff by Matt Levine). It’s too big to read all at once during my workday. In practice, I sneak 5 minutes here, 10 minutes there. When it’s in The Feed, this means that it was not an email. Instead it’s a card that is slowly being pushed down by other things in The Feed. The later in the day I started reading it, the harder it becomes to complete it 5 minutes at a time. Maybe I’d move this specific newsletter out of The Feed. There’s not much left at this point. I’d have to keep polling to find when the two or three remaining things ended up in The Feed. Everything might as well be in the Imbox.

I also regretted putting many of my emails into Paper Trail. When I buy something, I want to see the purchase receipt Right Now. I also receive credit card alerts for every purchase I make. This helps me identify recurring purchases that I no longer need. When these are in my inbox, I can read and clear the notification immediately. When things are in Paper Trail, they don’t seem to have “Unread” markers. You need to scrutinize timestamps and dates to figure out what might be new. If my Amazon order ships, I want to say “Cool” and then delete the notification. I definitely want to see it.

I fought against this workflow all week. HEY does a good job of explaining its categorization system. But I struggled to live in it. I really just wanted everything to appear in the Imbox. This is the same reason that I stopped using the “Multiple Inbox” feature in Gmail: I’d rather stop unwanted emails at their source, instead of moving it into a separate low-frequency box.

To be clear, this is a good system that is a mismatch with my relationship with my emails. I don’t “casually browse” my newsletters, and I want to read all of my transaction receipts while my brain is still thinking about the purchase I just made.

Other advanced features

There are other advanced features that I didn’t use, or used lightly.

Search worked well. I looked for a few things. I found what I was looking for.

HEY has a pair of features called “Reply Later” and “Reply Focus Mode.” This allows you to put off sending replies to emails. Later, you can enter a focused mode that allows you to reply to these specific emails without any UI distractions. I forwarded myself a few emails to put into here when I was experimenting with HEY, but I didn’t end up using the mode with any real seriousness. I don’t receive a ton of email in my personal account, so I don’t run into this problem much.

You can “Set aside” an email if you need to reference it. I can imagine needing this at work. If someone sent me a lengthy meeting summary that I will convert into calendar invites and bug tickets, I can imagine using this feature. I can’t imagine ever using it in my personal account.

If I could change one thing about Hey

You might expect that I’d want to change something about its workflow. After all, the workflow didn’t work for me. But it’s someone else’s workflow. They enjoy it. I’m not going to mess with someone else’s workflow.

I would invert how the tutorial works. I experienced the tutorial as a three stage process:

  • A guided tutorial of UI elements.
  • A series of emails explaining the UI features.
  • A Screener help card that lasted until I categorized 15 emails.

I experienced this as a breadth-first iteration across the UI. It started broad, and then explained all of the deep features. “This is Hey! We have a Screener! And an IMbox! And Paper Trail! And a Feed! And Reply Later! Here’s the Hey menu that shows all of them!” 

This was stressful in practice. It felt like I was expected to memorize all of the definitions before I proceeded. But then I went back to my Imbox and I didn’t see anything that had been introduced. I realized that it’s all hidden behind a menu. HEY did tell me about this menu. But it told me quite a lot in a 5 minute span, so I didn’t remember.

I came back the next day. I didn’t see any of the other inbox types. Where did all of it go? Oh right! It’s all hidden behind a menu. On the plus side, HEY sends you some of the tutorials as emails. This gave me an easy-to-find reference. They definitely helped. I kept revisiting them over the first few days.

It didn’t need to feel this stressful. HEY’s home screen is an intuitive email inbox. I could read and write emails immediately. I could use the default email functionality without a tutorial. It felt like they wanted me to immediately be a power user, without ever being just a user. Starting out as a power user is a lot of work for my first half hour of using a new product.

I wish that Hey’s tutorial was more spread out and depth-first. I spent most of my week screening emails. I did that more than anything else. So I wish that it focused heavily on the Screener in the beginning, and then introduced the Feed and Paper Trail when I moved emails into it. Later, it could describe the more advanced features as emails enter your Imbox. I understand the pressure to differentiate yourself and prove that you’re worth $100 early in the user’s journey. But the education process didn’t feel good to experience.

The Verdict

HEY is a fast and easy-to-use email client. I think it’s going to have a lot of users and will be fairly successful. It gives me hope that there will be an email client that I would pay for someday.

There are a few situations where I would recommend HEY:

  • Someone reads the HEY features and says “oh hell yes” because this is how they view email.
  • Someone receives lots of unsolicited email that they don’t want to read.
  • Someone is really into multiple inboxes and wants to try a Gmail alternative.
  • Someone needs a structured workflow to manage an out-of-control email inbox. They lose emails under the pile of stuff they received.

After years of heavily curating my email inbox, I believe that I’ve prevented myself from benefiting from these workflows. I found myself pushing back against the multiple inboxes feature. I can’t imagine myself using the “Reply later” feature. All I’m left with is the Screener and the Imbox.

I’m only going to permanently switch away from Gmail once. I won’t be switching to the 2020 version of HEY. I hope that they continue to evolve the email client in a thoughtful way. I can imagine myself switching to a future iteration of HEY based on its privacy stance and its speed.