I thought this was going to be a story about my time working at Block. And it is, for the most part.
At its core, though, this turned out to be a story about fear, and overcoming it, and discovering that the universe will always have your back if you stay true to your values.
I wrote this story for me, so I don’t forget. I hope maybe it will be useful for someone else, too.
Obligatory disclaimer: All opinions herein are my own and are not meant to represent those of any other individual or company.
Serendipity
I usually begin my career story by saying that I grew up at Red Hat. And what a magical place it was to grow up. Everything about who I am and how I show up today, professionally and personally, was molded by open source principles and practices, as well as by the people in the communities who give of themselves to help others grow.
I was at Red Hat for almost 12 years and had intended to stay until retirement. But, alas, macroeconomic headwinds, functionalization, reducing complexity, pick your phrase of choice resulting in reorganizations and role realignments and while they weren’t kicking me out, suddenly there wasn’t a great fit for me there anymore.
I had no idea what to do when it became clear it was time to move on. I was scared about everything. I was scared I wouldn’t be able to find a job aligned enough with my niche experience to be interesting, scared I wouldn’t be able to assimilate into another company after so much time at the same one, scared I wouldn’t be able to find “my people” in a new organization, scared I wouldn’t be able to navigate changing insurance carriers, you name it. I was even scared about having to use a different operating system (Linux FTW!).
A close friend saved me. They were setting up an engineering operations team at GitHub and knew the org could use my particular odd blend of skills, so they brought me in. I was paired with a manager who (bless him and his seemingly endless patience) helped me work through all of my anxiety and rediscover how smart and capable I actually am.
But the honeymoon didn’t last long. By the end of my first year, I was neck-deep in some of the most toxic sludge I’ve yet been exposed to at work, the kind that threatens to give you stomach ulcers. I will never forget the time I went to someone for advice and he asked me, “What’s more important to you, your job or your friendship?”, and I replied, “My ethics.” Then I spent my holiday break writing a blog post to try to reconnect to the parts of my job that I loved in a desperate attempt to hang on to my sanity (and to learn GitHub Pages, but that’s a tale for another time).
Once again, I had no idea what to do when it became clear it was time to move on. But that time, it was a cold LinkedIn message from a recruiter that saved me.
I thought these kinds of things only happened to people in movies. I’d had recruiters reach out before, sure, but usually to offer me junior technical writing roles (and I haven’t been a tech writer since 2012). But this job description had been written like someone had gone into a room and closed their eyes and imagined they needed me specifically, even down to my open source roots. The Block team acted apologetic whenever they mentioned they had split the operations responsibilities into a separate peer role, but I could hardly believe my luck, feeling like they’d cherry-picked all the fun responsibilities just for me.
Thanks to GitHub, I was no longer scared of the same things: I’d learned that I could find “my people”, usually hanging around the nearest Open Source Program Office; I could assimilate into a new company and culture just fine; and I could use a Mac, as annoying as it was to figure out all the shortcuts. However, while my experience there had allayed some fears, it had given me a new one, making me terrified of working anywhere near executives (much less becoming one myself). I wasn’t sure if climbing the upper rungs of the corporate ladder required working in ways that rubbed uncomfortably against my values, or if getting to the top of that ladder changed people, but either way, I’d been thinking my next best move would be to take as low a level IC role as I could get so I could hide in a dark cubicle and just work without the Game of Thrones drama for a while.
But then I took a chance and met dhanji, which was the first step on a journey that would restore my faith in an executive’s ability to lead with heart, and in my own ability to keep succeeding without losing mine.
Five companies in a trench coat
My first impression of dhanji was of his kindness. It wasn’t from something in particular that he said, but I could tell from the questions he asked and the way he spoke about Block that he cared deeply about what he was doing and the team he was building out. His motivation was less about title and acclaim (he actively shied away from using the CTO title and would just say he “works in engineering”), and more about being excited to meet the once-in-a-generation moment that AI represented. He also said the magic words “we want to make Block an open source company,” which sold me on the spot.
I soon learned that Block was a different kind of company than the ones I was used to. During my interviews, people kept referring to Block being “founder led”, in the context of, “well, you know, it’s a founder-led company” <wink wink, nudge nudge />. I’d just laugh and shrug it off because I had no idea what they were talking about. In practice, it turned out being founder-led meant that “we have to pivot every time jack takes a hot shower”, as one of my dearest colleagues once so eloquently stated. You eventually learned to run at full sprint in one direction while staying ready to pivot at any time to head a completely different direction without losing speed, and depending on your mindset and how the strategy du jour impacted you, that was either exhilarating or exhausting (maybe both at times).
I’d also never worked at a fintech company before, and when I tried to ask what the differences were there, folks would say, “we’re not a fintech; we’re a tech company with financial products”. What that meant in practice was there were certain areas of the business that had to deal with more regulatory compliance than others, but otherwise it seemed like a pretty standard tech company to me, just with its own unique flavor of cross-functional dependencies.
Something no one warned me about in interviews was how differently time worked at Block. Every day that passed contained the volume of stuff (tasks, announcements, changes, events) I would ordinarily expect to experience during the course of one week at any other company. Taking a week off meant coming back feeling like you’d become a month behind. There was certainly never an opportunity to be bored.
The time warp was probably due to the massive amounts of change Block was undergoing when I joined, which didn’t let up for most of the time I was there. When I was introduced to the company, it was still what I affectionately referred to as “five companies in a trench coat”, with each brand structured like its own independent company, for better (e.g., speed) and for worse (e.g., duplicate infrastructure). Square reorganized from a GM model to a functional one just a few minutes before one of my interviews, throwing my still-processing interviewer off a bit, and then the whole company functionalized a few months later. I often described the situation as walking into an engineering organization that had none of the foundational infrastructure you’d expect to find because that organization didn’t exist until a few days ago, and we had to start with the basics: communications channels, consistent level expectations, general operating principles, a shared mission, and, heck, just answering the basic question of “who are we?” when almost everyone came in with such strong attachment to their brand identity (and sometimes equally strong animosity toward folks from other brands).
All of this combined meant that my role existed in a kind of permanent state of becoming: there was no playbook and no precedent (in fact, when I’d said to dhanji during our interview that I didn’t think roles like this existed, he said, “They don’t!”). It was exactly the right kind of mess for me.
Leading with heart
dhanji and the original OCTO leads
Once the big rounds of reorgs settled and dhanji felt confident he had the right mix of leads, we all met as a team for the first time in New York. As part of an icebreaker activity, I was asked a question about my dream job or career goals, and I answered honestly that I couldn’t see beyond the role I had because it was everything I’d ever imagined whenever I’d dared to imagine a dream job. It was pretty cool to discover that everyone in the room felt the same. Like dhanji, they also impressed me with their kindness and intelligence and wit, and they all had really inspiring backgrounds and stories. One had grown up in Bosnia. One had worked for Partners in Health in the tiny country in Africa where I served in the Peace Corps. One had been a forensic investigator for the United Nations. I think all of us had lived on at least two different continents. It’s hard to describe what it’s like to be on a team of brilliant people who are all extremely passionate about their niche areas and locked in on a shared mission, and I’ll forever be grateful they welcomed me to be a part of it.
Something else I shared during that icebreaker activity was that my career has been shaped over the years by a handful of people who really saw me and believed in my potential enough to invest in my growth, sometimes believing in me more than I did myself. But I’m not sure anyone’s ever seen me the way dhanji did. He had a knack for handing me problems that required me to pull on every strange skill I’d accumulated over the years, like he’d taken one look at my weird professional toolkit and started building a to-do list. Every new challenge was somehow both adjacent to things I’d done before and entirely new. The role stretched and challenged me, but it rarely felt stressful because I felt so supported by both dhanji and my peers. To my occasional embarrassment, dhanji was not shy about his public vote of confidence, which nearly became an all-hands drinking game.
These public displays of confidence were a double-edged sword. On one hand, knowing I had dhanji’s explicit backing meant I could skip the exhausting work of convincing people my job had value and just, you know, do it. On the other hand, reporting directly to him had a negative effect I didn’t anticipate. Block’s levels weren’t public, which had its pros (like theoretically encouraging meritocracy while avoiding the HiPPO effect) and its cons (like not being able to celebrate promotions or hold anyone up as an example to aspire to). But reporting to dhanji made my level glaringly obvious, putting me firmly on the “them” side of the “us vs them” equation in most people’s minds, which was a genuinely strange place for me to find myself.
I’d built my career by being an active member of the community. Most people who worked at Red Hat while I was there know my name from my escapades on memo-list, the company-wide email distribution list, where I’d earned a reputation for speaking truth to power on one hand while helping everyone have empathy for decision-makers on the other. I’d managed to gain a similar reputation in my brief time at GitHub, though I’d certainly leaned more heavily on the “speaking truth to power” side. And suddenly there I was at Block, part of the “power” that people needed to speak truth to. It changed the ways I interacted with the org in some ways (always being mindful that my voice could potentially shut down others, even if I didn’t mean for it to; working through my team or others when I felt my voice wouldn’t be the most helpful). It turned out there was a lot to learn from the other side of the table.
I was invited to be part of core, the 100-person group that jack and his directs (known as innercore) used as a sounding board for early ideas. When I started, we met weekly (unless there was no agenda), and jack emailed us every week sharing some of his top-of-minds and asking for ours. As someone who likes to say “I don’t have to be right, but I need to feel heard,” I loved this structure and the invitation to safely share any concerns or observations as they happened in real time because it prevented any frustration or resentment from building up: I could escalate the concern and forget about it, trusting that it would get taken care of if it was important, and if not, at least I’d done my job in raising it. It also gave me an invaluable pulse on the company: hearing jack’s thoughts directly, getting dry runs of presentations before they went wide, and being part of the conversation at that level kept me connected to what was actually going on in ways that made me better at my job.
I also quickly learned that there’s Jack Dorsey (the man the myth the legend who dominates the major news cycles in 17 countries every time he Tweets “hi”), and then there’s jack (the wicked smart, sometimes kinda awkward guy running the company). His brain reminded me of a computer, taking in vast amounts of input and looking for patterns to action on. I learned a lot from observing him in the short time I was around, including the fact that I would never survive any level of fame with my sanity intact. Once, there was a thread that mentioned something about me on Blind, an app that functions like an anonymous company forum (which is as full of butterflies and rainbows as you’d expect an anonymous forum for disgruntled employees to be), and it felt awful, both because it generally feels awful to know people you work with are talking about you behind your back, and because it was frustrating to have to read it without being able to share the full context of whatever it was that was going on so I could correct misperceptions; hours later while doomscrolling, I found a picture of jack on the global front page of Reddit with hundreds of comments ragging on him for wearing an older t-shirt and clogs during a trip to Kenya, and I realized my brain is simply not built to withstand that level of scrutiny and exposure.
I’ve struggled with self-validation most of my life. Many years ago, an exec coach helped me unpack that the core story I internalized in childhood was “you could always do better”, which threw off my internal compass and resulted in me never knowing if I’ve done a good job unless someone else confirms it. The problem was that at Block, especially at the level I was at, nobody had time to help me manage my personal insecurities, so I was finally forced to grow up and get over myself. A few things helped with that process, starting with getting to know my peers better and coming to understand that every one of us (even dhanji, to some extent) had some degree of imposter syndrome. And it helped engaging with another exec coach, who taught me how to executive and was an email away if I ever needed confirmation I had the right approach to anything.
Me and Iveta
But the person who had the largest impact on my growth was Iveta. I’d never had an executive assistant before (or executive business partner, as they’re titled at Block) and had never liked anyone touching my calendar, but I was struggling as a team of one for my first several months and was desperate for help. My coach (as part of teaching me how to executive) advised me to give Iveta full access to everything from the jump so she could be effective, so that’s what I did: I let her in and showed her every raw, messy, imperfect piece of myself and how my brain worked. It helped that neither of us liked small talk (she’s Eastern European and I’m an awkward introvert), so we skipped right over the pretense. And I can’t express what a gift it was to stand there exposed and vulnerable and have her, a partner I trusted who had worked with so many others in positions similar to mine that she knew from experience what good and bad looked like, validate that I’m good at my job. Maybe I finally heard it because it came from someone I knew would never bullshit me, but for whatever reason, it stuck, and I was able to let go of many of the insecurities that have plagued me for decades. (Thank you, Iveta.)
Anyway, I’m leaving out a ton (traveling once a month, being reorged to a centralized EngOps team, building out my own team, working with cutting-edge AI tools, et al) because nobody wants to read a laundry list of everyone I met and everything that happened over the span of two years, but I’m proud of what we all were able to accomplish. I made mistakes, of course, and there’s plenty I’d do differently if I could do things over, but I poured everything I had into it, and I did the best I could with what I knew in each moment. I can live with that.
Everything, all at once
My final “holy shit how am I going to pull that off” assignment was in the lead-up to our all-company in-person event called Block by Block (BxB). I’d known the event was coming for almost a year, but the specific ask for me wasn’t clear until a few months before, when I was told I was responsible for planning and executing a three-hour block of content for the thousands of members of the engineering org in the Oakland Arena on the final morning.
The first thought that came into my mind was that everyone was going to be exhausted by the third day, so trying to cram more substantive content into their brains would be counterproductive. But if we didn’t make it meaningful, people would be angry we’d made them all gather just to waste their time.
At the time, we as an org were in the throes of the AI-related identity crisis facing software developers everywhere: If I’m no longer writing code, then what exactly am I doing here? And the overwhelming push for velocity at the cost of everything else was starting to suck the energy and excitement out of everyone. I stumbled upon a blog post by Annie Vella titled The Heart of Software Engineering Still Beats, which helped me reframe the situation and realize the most impactful thing I could do for the org was to help all of us reconnect to the parts of our craft that bring us joy, even if the expression of those things has shifted.
So I built the segment around that idea, theming it This is Block Engineering: Yesterday, Today, Tomorrow. If the goal was to help people reconnect to what still lit them up about their craft, one answer was right in front of us: the joy of coming together to solve hard problems with people who care as much as you do. The agenda was built to remind everyone of who we were, who we are, and who we wanted to be. With Iveta’s help and about a dozen other co-conspirators, we pulled together an agenda that wove together stories from Block Engineering’s past and present with a “battle of the bots” vibe coding competition, a lighthearted segment to get to know the engineering leadership team as humans, and video montages of engineers sharing their favorite memories and what they were still hopeful for.
We pulled it off without a hitch, even ending a few minutes early when I’d been sure we were going to run over. It was phenomenal. I’m extremely proud of it, but not for the reasons you might expect: it’s not because I got to show off any skills or because I got any credit, but because I got to build a platform for others to shine on. Hearing from the presenters afterward about the impact it had on them made every exhausting moment worth it.
Max (+ Goostave), ALR, jack, me
When it was over, I walked out to a tent where core was meeting for lunch, hoping to finally get a chance to speak with jack in person. And I did, although all my awkward self could come up with before someone swept him away into a different conversation was to ask if he’d enjoyed the morning, having spotted him in the audience.
And then began a series of conversations that made me feel like I wasn’t just closing a chapter that day, but the whole book.
The first was with an engineer I’d sought out early on, when I’d asked dhanji to point me toward the most opinionated engineers so I could learn where I could be most helpful. He had a legacy in the Android world, a long tenure at Block, and absolutely zero patience for inefficiency or bureaucracy. He also had the classic open source trait where if something were broken, he’d yell about it until someone fixed it, and if nobody fixed it, he’d do it himself (honestly, the way it should be: if you’re going to complain, be willing to put your money where your mouth is!). He’d done a segment with us during BxB with a tenured iOS engineer about Block Engineering’s yesterday. When he found me in the lunch tent, what he said stunned me so thoroughly I kind of blacked out, and I can’t for the life of me recall his exact words. What I remember is the feeling of them: “I finally get it now.” As in: I finally understand what you do and I can see the difference it makes. From someone I respected that much, it meant a lot, and it was hard not to cry.
Iveta found me next, coming to sit beside me at the table. She very gently told me that she was being reassigned to a different executive, primarily because our working hours didn’t overlap much and it was starting to take a toll. That did make me cry.
And finally, dhanji. I’d asked our admin team to please make sure I bumped into him so I could say hello in person, and they surprised me with time for a 1:1. He took Iveta’s place at the table and shared that he was stepping back from leading engineering. We had a warm conversation reminiscing on the previous year, then shared updates on our families and what video games we were playing, almost like we were both already transitioning away.
And then.
I’ve never felt a cultural shift happen as quickly and as viscerally as the one I experienced at Block after we all got home from that event. Someone made an unofficial hat to summarize the era, and I think that says something, because only people who genuinely care about a place would make something like that to process our collective grief.
“3 axes” represents the ever-changing strategy. I don’t remember what the axes were, but before that were the three vectors, and before that, a string of other things, all sent by email, all without change management. I think today it’s “intelligence”? It was hard to stay motivated and to feel like your efforts had any value when projects kept getting canceled and teammates reassigned.
“4.3 PRs” represents a metric that came to symbolize something I hadn’t expected to feel at Block: a loss of trust. People do their best work when they feel psychologically safe, and I watched that safety erode in real time as engineers who had once talked passionately about their craft started quietly calculating how their output would be perceived. I’m fundamentally opposed to performance frameworks that pit people against each other, and when I felt that dynamic take hold around me, the joy I’d been trying to help people reconnect to started draining out of the room.
And “4 sentences” represents the weekly email jack sent to core with his top-of-minds and asking for ours, which I’d loved as a way to stay connected to what leadership was thinking and to share concerns in real time. When he expanded it to the whole company, something got lost in translation. What had felt like an intimate pulse-check seemed, from where I was sitting, to generate more anxiety than clarity for many people, with folks agonizing over what to send or whether to send anything at all, rather than finding the reassurance it had offered me.
I was fortunate that my team’s work was largely insulated from the strategic whiplash, but I wasn’t insulated from everything. I’m a Type A anxious overachiever who’s pretty responsive to feedback, if I do say so myself, and in my entire career before Block, I’d never received a rating below “exceeds expectations”. But during the engineering-wide calibrations, my annual rating was lowered from “meets expectations” to “inconsistently meets”, triggering an offer for me to either “recommit” to the company, or accept an opt-out package.
That would have been soul-crushing to the version of me from years ago who struggled with self-validation. But the version of me that received this news could see the bigger picture and realize that choosing to stay and to try to “meet expectations” in that type of environment would require working in ways that don’t fully align with my values. (Plus, I want to work somewhere that wants me there!) So the choice, when it came down to it, wasn’t really a choice for me at all.
From here
I still have a hard time describing what it is that I do. I’ve settled on saying that I am a really great partner to a specific kind of engineering leader: one who is genuinely invested in the care and development of the human beings under their charge. Given the current prioritization of AI above all else in big tech these days, I didn’t have much hope that I’d be able to find another leader like dhanji. I figured maybe, if I took a sabbatical and waited about six months for these companies to suck the souls out of everyone to feed the AI overlords, they might come back around to the realization that inspired humans outperform fearful ones and have a need for people like me in their ranks again.
But for the first time in my career, I wasn’t scared. I knew the universe was on it.
On a Monday in February, I signed the paperwork to accept the opt-out package.
That Tuesday, I scanned the LinkedIn job board. I happened to see a role posted that sounded so much like me that I had to re-read it a few times to make sure I wasn’t missing something. It was supporting a VP of eng for a smaller org at a company known for prioritizing learning, and the job description had human-centered language like “ensure that operational rigor doesn’t come at the cost of trust, autonomy, and psychological safety”. I figured it couldn’t hurt to apply.
That Thursday, I got laid off along with about 40% of the rest of Block, which moved my last working day up and extended my garden leave.
By the end of the following week, I’d begun the interview process for the new role I’d found.
And I’ll be starting my new job the day after my garden leave from Block ends, a few weeks from the time of this writing.
I was asked once during a Q&A session at Block about my career and how I ended up where I was. I was honest in saying that a lot of it was serendipity. They followed up by asking how they could find or create that luck, and I didn’t have a good answer (I responded by saying we have to create it for each other, lifting each other up as we go). All I can say is I’m grateful for the luck I’ve had, and that the universe has always made sure there’s a net under me before I’ve hit the ground. And I’ve learned, finally, that staying true to what I believe in is exactly what keeps that net in place.
I’m genuinely looking forward to what the universe has in store for me next, especially because I can go into it unafraid.
This post is an exception to the Creative Commons license that covers other content on this site. All rights reserved © Allison Matlack. Please do not reproduce or republish any portion of this piece, including media, without explicit written permission from the author.