I had a bunch of stuff that I was planning to write for this week, but the news that the week brought made me reconsider what I was going to write about.
About companies and jobs and layoffs
This week was brutal for many folks from many companies, big and small. I haven’t ever been laid off, and I can’t imagine the feeling, especially for folks who rely on that income (or the benefits) to keep their lives in order. Even when the severance benefits are generous, layoffs involve a great deal of pain and frustration.
The number of “real” full-time jobs I’ve had can be counted on one hand, but every time I’ve ever considered changing companies, there’s an inertia that must be overcome to make the switch. You’re taking some investment in your career (your time, your energy, work ethic) and the comfort of day-to-day normality (i.e., avoiding the toil of setting up your 401k, direct deposit, enrolling in health insurance, getting your workflow in order, etc.) and making the active choice to leave that investment and comfort for something new.
It’s not uncommon to take time off, but “something new” usually always it means “the unknown,” which is really what makes that inertia so great. When we decide to take extended time off or accept a new job, we don’t know what’s in store for us. We know a bit about the people that we interviewed with, we know about the company, but we have no way to actually know about what it’s like day-to-day. All of us know that it’s impossible to get a good read on a company while interviewing, and certainly there are plenty of us who joined a team (or company) to find that it wasn’t what we expected. And certainly most of us know how to put on a welcoming face for conducting interviews, or answering hard questions about our roles in a way that HR would not frown down on.
Besides the uncertainty of the work, we spend a huge portion of our lives “at work” (for whatever you consider that to be). Many—if not most—of the people we interact with are coworkers. I find that many of the people that I consider my closest friends are folks that I first considered a coworker.
Leaving a job means that we are severing those relationships. Some folks we’ll keep up with, some folks you might keep up with occasionally and send a heartfelt reaction to on LinkedIn every dozen months or so—maybe you’ll see them on Instagram posting a major life event. And many other coworkers, though they’re well-liked, will simply disappear from your life. It’s a weird dissonance: you could stay in touch, but you probably won’t. But you’ll still miss them, like the characters of a TV show that got canceled.
What’s most reassuring about overcoming that inertia is that it forces you to confront the uncertainties and effort of leaving your role very explicitly. In the same way that a bird chipping its way out of its shell helps it to become strong enough to survive, overcoming the inertia of changing jobs helps you to become psychologically ready to change jobs.
Layoffs never off that mental and emotional stability because they remove the element of choice. You don’t have inertia to overcome, the decision to leave is made for you and you’re forced to immediately accept the consequences of leaving. Severance benefits are perhaps a reassuring cushion, but they don’t offer any fortitude to your personal wellness. In a way, it’s like being on the receiving end of a breakup for a relationship that (whether you like it or not) you have a significant reliance on.
As cringeworthy as some of the layoff letters read, it’s important to really internalize the “it’s not you, it’s me” part. Essentially 100% of the time, layoffs are the result of a leadership cock-up. You can’t make a layoff feel good, but you can be sure to recognize it for what it is: the fault of the captain of the ship, not the deck-hands. No IC caused this, it’s the collective actions of the company, and the collective actions of the company are literally the job of the executives.
What I saw this week after Stripe announced its layoffswas a lot of shock and pain. Some folks sent me some absolutely heartbreaking messages. Folks who weren’t laid off reeled from the upheaval—seeing good folks around you being let go is equally painful to experience. Some folks tweeted through it. Other folks went radio silent. Some took to LinkedIn to rally recruiters. Some breathed a sigh of relief. Almost everyone, though, suddenly saw the company that they looked to for stability and (some amount of) purpose stumble.
There’s really nobody (certainly not me) who can do much of anything about the situation, but I’ll say two things that I hope are worth reading for folks who have felt the effects of the layoffs:
First, in my parting notes I said that if there’s anything that has persisted as a great attribute of Stripe in my time at the company, it’s that the caliber of people is exceptionally high. The success or failure of Stripe has little to do with who they’ve made part of the team and much more to do with their ability to organize and lead those folks to collectively do the right things. Patrick admitted as much in his letter, but it’s worth saying explicitly: nothing about this past week has been a failure of ICs.
Second, your worth as an IC or a person is not dictated by the machinations of capitalists so distant from your work that they wouldn’t recognize the name of your team. The outstanding effort and outcomes that everyone at Stripe (and elsewhere) have produced in your tenure speaks for itself, and you don’t need an orange website or social network to validate that. It’s really easy to get caught up in the latest attention-grabbing headlines or snarky comments, but your lived experiences of delivering important value for real people and businesses should be at the forefront of your mind when reflecting on what you did.
If you have the privilege of being able to take some time to breathe, I’d encourage you to do so. There’s something refreshing in being able to disconnect and clear your mind before you plunge yourself back into the ritual and performance of job hunting.
If you’re not able to take some time off, please don’t be a stranger—to me or any of the other Stripes and ex-Stripes. You’ll find a lot of folks who are eager to support you however they can, be it networking or job referrals or just taking some time to sit on a call and truly hear you while you vent. If you want to reach me, you can always message me at
My original plan for this week was to write about something near and dear to me: career progression. A lot of folks asked about how to progress up the career ladder as a front-end engineer, citing difficulty making the responsibilities of that role line up with engineering ladder rubrics. I have a lot of thoughts about this, but frankly I’m not sure this is the right week to talk about career progression.
Instead, I want to talk about something else that a lot of folks asked me about in my last week or so before I left. This was the second-most frequent question that I got in the (many!) one-on-ones that I had: how do you voice dissent in an org without being branded as a troublemaker?
I’d made a bit of a name for myself at Stripe for calling out what I saw as “bad things” in a fairly public way. Truth be told, I could have definitely done better in the early days. You very much do spend social and political capital calling attention to things that you see as problems; the goal is not to eliminate the capital that you spend, but rather to minimize it. In return, if you do a good job, you’ll hopefully earn much of that back (or more) by growing respect among your peers and the leaders around you.
Tackling the right problem
The first thing you should be thinking about when you see a problem you want to flag is that you are indeed flagging the right problem. One of the folks who’d scheduled a 1:1 with me to talk about raising their concerns sent me a fairly lengthy doc that they had written. It outlined problems they saw, what they believed to be causes for those problems, and potential solutions.
This is ultimately not a bad thing! However, when I read the doc, I had questions that revealed something unfortunate: this person had identified the wrong problem.
To paraphrase, the problems they were calling out had to do with the engagement of a team that was a critical dependency for their own team. This person’s team wasn’t getting the attention and resources that it needed to be successful, which blocked forward progress. Their proposal for a solution included things like regularly scheduled meetings. On the surface, these things all make sense.
What I asked was this: is the team you’re blocked by well-resourced? Do they have enough time to dedicate to addressing your needs? The answer was “probably not.”
The real problem to address here is not a team-level problem, but a management problem: management had not seen that this team is an upstream dependency, and hadn’t given them the people they needed to serve all of the functions that they needed to serve. Asking the already-overburdened folks on this team to attend regularly-scheduled meetings isn’t going to get more work done, it’s going to have the opposite effect. The real solution is to convince leaders to reallocate resources.
The takeaway here is to look at the problems you’re raising and, from first principles, try to identify the why before you determine that this thing is really what you want to focus on. Maybe there’s a complex feedback loop! Maybe there are hidden agendas or perverse incentives at play! If you point the finger at the wrong thing, you’re setting yourself up to have your thoughts dismissed on premise—even if the frustrations you’re facing are correct and valid.
Saying it nicely-ish
The number one biggest issue that I see a lot of people making when they call out a problem is not that they have chosen the wrong problem to point out, it’s that they don’t know how to call it out in a way that doesn’t feel angry. I’ve had a few folks express frustrations to me which I think are important and valid, but when they tell me how they called it out (or want to), it was obvious that the vehicle for their criticisms was inappropriate.
Some quick thoughts:
Choose the right venue for delivering the criticism. A salty rant on Slack is hard to structure in a way that reads well and can be consumed at the pace it should be consumed at. Writing a doc and forwarding it to folks feels the best, and doesn’t risk getting lost or drowned in replies.
Don’t emphasize your frustration, emphasize why the things you’re frustrated at are frustrating. Take the time to choose which things are real problems and which are nit-picks. Don’t die on hills that aren’t worth dying on.
The people who have the power to make the decision to fix the problem probably want to help. Don’t let your frustration about a problem turn into criticism of past actions, because it’s easy for that to be taken personally. Point out why the status quo is problematic and what you’d rather see instead.
You can still word this strongly, but don’t let your strong wording be mistaken for a personal attack.
Never get upset with people, get upset with process or outcomes (or the factors that lead to those outcomes). Those people will often advocate for what you want—they want good things too! But they won’t do that if you point the finger at them instead of at the problem they’re adjacent to.
Don’t write when you’re angry. Take some time to gather your thoughts and only write when you’re confident you can say what you want to say without letting the heat come out through your fingertips.
Check your facts
Always take the time to go over what you’ve written (at least a little bit) and make sure that you’re not saying something that’s based on falsehoods. You might have heard wrong, the facts may have changed, or you might have misremembered. Nothing will sink your credibility quite like making assertions based on incorrect information.
I like to take a quick pass over what I write and just look for anything that reads as a statement of fact or an assumption. Then I search for it. If I can’t find information to back it up, it’s worth considering whether I should have written it in the first place.
If I’m writing something that I intend to be consumed by more than a small number of people, I’ll also run it by a small audience of folks that I know well to see if anything stands out to them as incorrect. We all miss things and make mistakes, and your coworkers are often glad to help. And, it just feels nice to be trusted to offer insight on something before it’s released to a broader audience.
A related aspect of this is making sure you’re sending your thoughts/criticism/proposal to the right audience. Some time ago, I wrote a doc with a coworker about how we could do company-wide migrations better after a series of company-wide migrations caused a great deal of toil for our teams. When I asked for feedback on it, the folks running the migrations were upset. Not because they disagreed with what we wrote, but because what we wanted was what they wanted the whole time. The reason the migrations had not gone great was because they were pushed to rush the migrations by leaders who didn’t understand the consequences of cutting those specific corners.
In hindsight, and a good lesson for readers, is that I should have talked with the folks running the migrations in the first place to understand what had gone wrong. I’d have saved myself a lot of time, and could have directed my feedback upwards rather than preaching to the choir.
Like a delicious, slow-cooked piece of meat, good writing shouldn’t be rushed. The best outcome for flagging something that you believe should be addressed is that you get messages/feedback/comments expressing strong agreement with your thoughts, especially from people outside of your immediate circle. That means writing in an approachable way.
“Approachable” is a challenging goal to achieve, though, because there’s no right way to write approachably. There’s a balance between writing plainly, being honest, and being passionate that you need to strike for folks to say “wow, this person cares and this strikes a chord with me.”
Read, re-read, and solicit private feedback from folks like your spouse or even kidson how they think your writing reads. Here are some of the things to be careful to avoid:
Don’t sound too business-y. Writing in an overly-professional tone makes your doc sound robotic and dry, and it makes your passion for the topic come off as passive-aggressive. Drop the prose and write how you’d speak.
This one can take practice. Don’t be afraid to write a draft (or part of one) that you intend to throw away.
Don’t get too fired up. If you write with too much spirit, it’s hard to take your writing seriously. Which is to say, don’t get too impassioned and start swearing or writing like you might write to a close friend.
Be honest and don’t dance around the problems. Folks don’t want to read between the lines to understand what you really want to get across. Be explicit and direct, don’t avoid actually saying what you want to get across.
This is something that I read once, but quickly searching for it now, I’m unable to find any reliable sources to back up the veracity of the statement.
Stripe, in particular, because of how close I am to so many other Stripes. I still ache at the turmoil that Lyft and Twitter and all of the other folks at all of the other companies face.
I recognize this is a trope at Stripe that’s eye-roll-worthy, especially in a public forum. I do stand by it, though, and despite the many flaws that Stripe has, I have yet to encounter a company who has more folks who are genuinely good people who are good at what they do.
In fact, my optimism for Stripe is based largely on that: I’d be far less bullish if I thought that Stripe had hired a bunch of inexperienced jawns. You can’t lead your way out of that problem. Said another way, the problems Stripe will need to overcome in the coming months and years are top-down problems, not bottom-up problems.
This is its own challenge, and I won’t get into how to do that in this section specifically.
Kids have a surprisingly good sense of what sounds good or not.
“In the same way that a bird chipping its way out of its shell helps it to become strong enough to survive 1, overcoming the inertia of changing jobs helps you to become psychologically ready to change jobs.” I love this analogy