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the misfit manager

Oh, this page does not exist. You can head back to homepage.

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the misfit manager

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the misfit manager

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the misfit manager

about

about melissa

about melissa

chipper californian

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the misfit manager

a crappy year in review

To clarify, it was a phenomenal year, this is just a subpar review of it. Someone who has been writing for much longer would have a much better year in review but I waited until the last minute, didn’t start the year with intentional goals so I can’t “measure progress” and the things I’m really proud of are maybe anti-goals for some folks.

Career

I joined Calm with a very explicit intent to practice things I have not previously been good at. I love the term ego-tucking, introduced to me 5 years ago by a wise mentor. This year I got really good at aligning my views and opinions with those of people above me in the organizational hierarchy. I wanted to get promoted, and did so. I have also cemented my commitment to building my career in the mental health space.

Friends at work

I’ve given far more constructive feedback this year than I ever have. Some of the recipients genuinely appreciated me for it, and a number of them probably thought it unwarranted. I learned that it is really hard to communicate areas of improvement to someone whose approval I seek more than I value the output of the team (i.e. friend-first vs colleague-first). Unfortunately as a result, I’ve gone too far in the other direction. For fear of making it harder for myself to act in the interest of the company, I have been minimizing social situations and coming across as quite bitchy. I’ll seek to restore the right balance here.

Writing

I started writing in late 2021. I didn’t really enjoy a lot of the writing I did this year because I worry more and more about saying the wrong thing or in more cases, leaving out nuance for sake of brevity and hoping someone doesn’t spear me for being inconsiderate.

I’ve had two engineering leaders whom I respect tell me this year that my writing will be career-limiting; my vulnerable style of writing is a liability when people are trying to hire for their leadership roles. What I find funny is that I don’t see this as particularly vulnerable. The term implies some degree of susceptibility to harm, but all the thoughts I share are ones I don’t guard. In fact, that comment is perfect because it acknowledges that this is a conventionally different approach to leadership – one that I would like to keep building upon. I shall continue writing.Overall I had a wonderful 2022. I ran more miles than I biked (1450 vs 1360), jaunted around Italy with my best friend and most importantly achieved homeostasis in Deep Okayness. I’m setting very intentional goals for 2023, in hopes that in a year from now I can share a less crappy year in review.

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the misfit manager

a girl's girl in a man's world

My junior year of high school, the local all-girls school closed and 80 girls joined my co-ed school. In the disrupted equilibrium, my friend group was unwelcoming to this new class of girls. High school became a competition trying to get a starting spot on the lacrosse team or a prom date.

In college and early career, I found myself surrounded by men in the computer science classroom and the workplace. At first I didn’t mind being the only woman. I felt like one of the boys, watching football and skiing on the weekends. But over time, I realized they were elevating each other at work, but never me. Even though I won our fantasy football league and could beat them down the mountain, they never treated me like a professional peer.

Throughout my 20s I intentionally gravitated toward women – socializing, running, working. We spent hours and hours chatting on the trails, discussing workplace politics and potential business ideas. We gushed about our successful female peers and our favorite women in leadership. To celebrate my friend’s 30th birthday, seven of us rode our bikes 100 miles to Napa. With these women by my side, I made the biggest strides in my career.

In high school, without consciously knowing why, I was competitive with other women because life was a zero-sum game. But the stakes are different in the professional world. It is easy to regress into a scarcity mindset when we look at the lone woman on executive leadership teams, but C-suites don’t actually have a female seat cap. In a world where the odds are already stacked against us, not helping other women only perpetuates this reality. The only way to ensure a better outcome is to uplift women everywhere. The more successful women we have in positions of power, the sooner we can eradicate the stereotype that board seats are for men.

These days, I am the first to congratulate women when they beat me in a race or earn a promotion. For me, a successful career is one that results in more opportunity for women to be financially independent. If women support each other, if we have each other’s backs, we will take more professional risks and make bolder decisions. The boys are already doing it.

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the misfit manager

acclimitization

As someone who enjoys climbing both mountains and career ladders, I have come to respect the benefits of acclimatization.

An elevation of twelve thousand feet has forty percent the amount of oxygen as sea level. Several years ago, I learned this the hard way as my little San Francisco lungs gasped for air in a steep chute on the side of Mt. Shasta. I couldn’t believe how breathless I was just being up there, let alone continue my journey to the summit. My skis were tented on my back, borrowed crampons on my feet and a brand new ice axe in my hand. I somehow dragged my body to the summit, largely thanks to my partner’s encouragement, but it goes down in my books as the most painful experience of my life. (More painful than marathons and 50k’s, and that’s saying something.)

I wrote about my new role at the beginning of the year and how intimidating it felt. It wasn’t just one dimension that was different, but all of them – peers, responsibilities, manager. It very much felt like going from sea level to 14k ft overnight.

Two years ago, I was preparing for the Salkantay Trek in Peru, which involves crossing Salkantay Pass at 15k ft. I worried that it would be another excruciating experience – that my little lungs would once again leave me crippled on the side of a mountain. However, this time around I kept a pretty quick clop, never breathing particularly hard, and finished well ahead of my group. I was in a comparable state of fitness; the biggest difference between the Salkantay and Shasta experiences was the 3 day acclimatization period spent in Cusco at 11k ft, giving the body plenty of time to adapt.

As someone who enjoys climbing both mountains and career ladders, I have come to respect the benefits of acclimatization. While I’m not going to run out of oxygen at my job, treating new roles and changes in responsibility require appropriate adjustment time, especially when the delta from the origin is large. I’m much more likely to maintain high altitudes if I ascend responsibly.

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the misfit manager

advent of code

Advent of Code is a 25-day programming puzzle challenge. It’s exactly like an advent calendar, except instead of a piece of chocolate, you get an equally delectable coding puzzle. This year, in a fit of determination to prove something to myself (or maybe to the ICs [1]), I embarked on the journey.

It’s currently Day 13, but I could not get past Day 12. In fact, I almost didn’t make it past Day 7, and barely squeaked by Day 10 (part 2). I non-trivially adjusted my life to accommodate this challenge, mainly in the form of skipping morning runs since I stayed up too late coding. Here’s a couple takeaways.

Coding is enjoyable. [2]

It’s a nice change of pace directing all of my energy and focus into solving a singular problem. Too much of my job is spent bouncing from virtual problem to virtual problem, rarelly getting to a satisfying solution. This is the first extended period of coding since I became a manager, though I often daydream of it. I want to persist this practice; I’m setting a goal of coding 365 hours in 2024. While I could also consider switching my career back to full-time development, I’m certain that this company derives more value from my non-coding skills than from my coding ones.

Coding builds community.

Past companies I’ve worked at have had small pockets of interest in AoC but this is the most active contingent I’ve encountered. Even though I’m still pretty new to this company, it’s been fun joshing around with engineers I don’t work with. I’m really impressed by the enthusiasm and intellect of my coworkers, especially with the Engineering Director staking his claim in the top 5. I think the best software engineers (or any profession, for that matter) are the ones who derive some amount of genuine enjoyment from the activity.

Anyway, I’ve been on a beach vacation for the past several days. Something about cramming Day 10 into a red-eye layover and a bumpy flight to Nicragua really took it out of me. That sounds like a pretty good excuse for quitting now, doesn’t it?

[1] I think my plan backfired because I have actually proved the opposite.

[2] unless I don’t get the answer.

You can see my garbage code here. Days 1-3 were done in a very slow Swift playground, and then I borrowed (stole?) the launch config from a very good friend to start the rest.

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the misfit manager

be nice to your manager

I exercise extensive friendliness to my colleagues and friends. I never say no to a coworker who needs a favor and I’m the single millennial keeping USPS in business with snail mail birthday cards. It’s a notable part of my professional identity. In fact, my bio has been “chipper californian” ever since Internet bios have been around.

my twitter bio

my twitter bio

But recently, as I was sympathizing with a friend as she talked through the strife between her and her manager, I realized this behavior was missing from one crucial professional relationship - that with my managers, past and present.I’ve had eight software engineering managers, each one different from the next. However, after similar experiences with several of these managers, I discovered I had a proclivity to find fault with them much more often than I would my peers. One day, these grievances reached their climax. After a stressful top-down planning cycle and a disagreement over hiring left me feeling frustrated and ineffectual, I lashed out at my manager on Slack telling them that they had ruined my day. Oof. Needless to say, I shattered what was already a splintered relationship.

In the software engineering industry, it is too easy to feel entitled to our positions - that we are doing everyone around us a favor by choosing to work at our companies. Attrition is expensive, good talent is hard to come by and many of us believe that we are the carriers of exceptional quality. Because we hold this threat of leaving, we expect our managers to recognize and reward our accomplishments, to constantly shower us in accolades.

On top of that, cross-functional teams’ requests, company initiatives and hiring processes are simultaneously pulling a manager in fifteen different directions. And if they are doing their job well, we employees will be shielded from that chaos. Because this is happening unbeknownst to us, it can appear that our manager is full of free time and should be tending to our needs, many of which are out of their control or we never even communicated. And if not, then we place on them the burden of disappointment and subsequently label our poor manager, who cannot read minds, as insufficient. In essence, by setting unrealistic expectations, especially considering that we are not their singular focus, we dehumanize them by creating this image of unachievable perfection that is guaranteed to result in their failure.

After spending more time in management and consequently, a colossal amount of time and energy being a good manager to every single report, it was shocking to experience how little I got in return. I would spend hours crafting thoughtful career guidance and expend all of my emotional energy to deeply understand the unspoken needs of my reports, leaving me a shell of a human by 5pm every day. And still, someone would complain about a missing edge case in a design spec.Luckily for me, I have never had to manage myself. Having experienced this managerial drudgery, I cannot imagine a worse feeling than having one of my reports, whose career I nurture and life I care about, express such extreme discontent and ungratefulness as I did.Unfortunately for those around me, it took me having been both the thankless report and the tortured manager to understand how sacred this relationship is, and why it should be treated with even more care than that with your friendly peers. We are all doing the best we can, and making the experience positive for everyone will only help everyone in the end.

Now before each 1:1 with my manager, I consider:

  • How can I be an employee that managers want on their team?
  • How can I appreciate and learn from my manager’s strengths?
  • In what ways can I contribute to improving this professional relationship

To all of my managers past, I’m sorry for being a pain in the ass.

*Sometimes, and it is much more rare than you might think, if your manager truly is not a good fit, the best thing you can do for your career is to part ways.

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the misfit manager

betting on myself

During a recent Office Hours session for Elpha, someone asked about my recent take on imposter syndrome. My little soliloquy made it seem like the unwelcome feeling vanished overnight, but that’s far from the case. Upon further reflection, it was actually little to do with external factors like positive performance reviews, but rather a shift in my own mindset. When I joined Strava in 2017, I met a community of coworkers who strived, both in and out of the office. These brilliant people I worked with could also run sub-5 minute miles and some ran marathons…before work.

A smaller group of us new to Strava were by no means fast runners, but we were determined to participate in this buzz of energy. We established a weekly routine of meeting at 5:40am on Tuesdays in the Marin Headlands to get in a 2-hour, very hilly trail run before our 9am (in person!) meetings. These mornings were painful: feeling nauseous if we didn’t sleep well, enduring freezing temperatures in the winter, lungs and legs burning because we were literally running up a mountain. But we kept showing up week after week for each other, building grit together and proving to ourselves we could do it. In the office, this same group attacked work with the same determination that got us out of bed at 5am – leading large projects, presenting in front of the company and taking on more and more responsibility.

Prior to this, I used to fear trying my hardest or setting goals because I irrationally believed that failing would destroy me. I was really making my life even harder by adding self-doubt to already challenging situations. But with this support system, I started experimenting with this alien notion of trying even though it felt really uncomfortable.

I started saying yes to things that were way beyond my perceived limits. I never fathomed I would summit Mt. Shasta on skis (it took me 13.5 hours). Just two weeks later, I dragged myself through a 120mi ride through the Rockies, at one point sitting on the ground 80 miles in, desperately wanting to give up … but I got back up and finished it.

We faced plenty of failures together: bombing presentations, missing promotions, DNFing races; I even watched my friend throw up (twice) but still finish a gnarly trail race. Every time, the projected feeling of failure that was so scary and intolerable was actually a lot less painful with the safety net of our little community.

Over time, I started to believe in myself a little bit more every time. And that pesky little voice that used to constantly tell me I was a fraud, that I couldn’t code, that I couldn’t lead? It got overpowered with the effort to try, the encouraging confidence of women around me and the knowledge that few things in life are more painful than running a marathon.

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the misfit manager

embrace the crazy

I have become a much more boring person. No one laughs at my jokes anymore and I leave happy hour when the sun is still out. My professional peers are also less fun now, but I do not believe that they are actually uninteresting people; it appears that conformity simply increases as you go up the career ladder. This is understandable – managers are obligated to be inclusive common denominators and instructed to recite the company line. However, the degree to which it happens feels counterproductive to me.

I’ve seen the same situation happen over and over again. In the name of professionalism and office politics, a talented leader becomes so constrained and fearful of doing the wrong thing that he becomes incapable of thinking independently. Someone who once inspired creative ideas reduces his own role to shuttling information between his boss and his direct reports, rendering himself colorless.

But what if we had organizations that fostered and encouraged risk-taking? What if we capitalized on our people for their unique experiences and ways of thinking?

As a leader, the best thing I can do for my team is to jettison uniformity and trust each individual’s intelligence and judgment. We should lead by example and share our opinions that challenge the status quo. In an ideal world, we would embrace the crazy and celebrate the hot takes; on the other side of monotony lies fun and creativity.

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the misfit manager

farewell, imposter syndrome

When I started taking Computer Science classes in high school, I loved how everything was so logical and fit nicely into my uber-pragmatic way of thinking. But my dad was pretty adamant that girls don’t code and I stupidly believed him and chose not to pursue it in college. Luckily for me, my floormate was taking Intro to Computer Science first semester and I thought oh, she’s a girl and she’s coding! So I joined her the next semester. My mom gave me a copy of Sandberg’s Lean In to “help me”.

In college, I read a lot of articles describing a phenomenon that many women in this industry experience known as “imposter syndrome”, and these articles instructed me on what signs to look for and how I should feel in response. People would look at me with puzzled looks on their faces when I said I was a Computer Science major, so I felt puzzled as well. Whenever an exam was particularly challenging and I should have reacted by studying harder for the next one, I instead wondered if there was just something intrinsically about me, like the lack of a Y chromosome, that rendered me incapable. Becoming a full-time software engineer, I really started questioning my identity as a female software engineer. Did I hate the House Security team shooting Nerf guns all around me because it was truly annoying or because I was a girl? Could I not figure out Swift closures on my first day because functional programming was a brand new concept to me or because I was a girl? Did I crash half a million sessions of a very large tech company’s app due to a poorly bolded string because it’s an easy mistake to make or because I was a girl?

I tried to sound artificially more assertive in communication and completely overdid it. I sobbed through more than one performance review telling me I was too abrasive, not quite grasping why “leaning in” was having a negative impact on my career. Every single action I took, I hesitated for a split second to consider if I was representing the female gender in the right way. I even debated not going down the management track because it could signal that women weren’t technical enough to be staff engineers.

After a lot of painful feedback sessions with patient managers and self-reflection, I eventually stopped trying to stuff myself into the box of what these articles and books dictated for women in the industry. I became less helpless and miserable. Additionally, I actually listened to and accepted the positive feedback for things that I wasn’t explicitly trying to do, i.e. enthusiastically leading projects and asking tough questions. Imposter syndrome was kind of rudely bestowed upon me by society, but my normal self already fit in quite nicely.

I had a pleasant feeling today. I noticed that I haven’t felt in a while the crippling anxiety of barely escaping through each day without being unveiled as a fraud. Sure, I’m still constantly acknowledging my oversights and mistakes, but it no longer makes me existentially question my sense of self in the role. Ironically, I have to intentionally add more smiley faces after my Slack messages because my default is quite curt, and woman or not, no one wants to work with a curmudgeon. After enough successful launches and genuine conversations, I’m really confident in my abilities to turn ambiguity into clarity, have tough conversations and be deeply empathetic. There are enough systems in place that will correct us when we misstep, so we all deserve to be a little bit truer to ourselves.

If you need someone to crush a massive engineering deliverable or make engineers feel genuinely valued, I’m that person. But I will definitely not be scaling your Kubernetes cluster, or whatever it is that our staff engineers do.

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the misfit manager

i love my team 🥹

Last week, I was in a meeting with part of my engineering team. It was just like any other recent meeting (lively technical discussion interspersed with laughter), but it was a perfect representation of the brilliant, efficient and goofy team that has made this past year of work so enjoyable.

I put a ton of time and energy into shaping this team, as individuals and as a whole. Despite warnings about perpetuating stereotypes by becoming the “mom” of the team (an organizational role that women typically fill), I choose to intentionally foster team dynamics because of how positively it impacts team output. When we enjoy each other’s company and encourage each other to be better, we are happier and more collaborative.

People first.

As a remote-first company, we reside all over the world (Seattle to Florida to Croatia), with something like 6 different accents. We have vegans and non-vegans, parents and non-parents. With so much diversity, in-person time is extra crucial to establish common ground and build empathy. In May, we did a quick team gathering in San Francisco and in December, we all joined the company offsite in Palm Springs.

Spending time together allows us to connect as people and not just transactional colleagues. When we all genuinely like each other, we don’t have to spend time sugarcoating communication. It also means we support and cover for each other through family emergencies, natural disasters and severe illness, all of which we’ve endured together this year. The real proof is that we’ve all started referring to our partners, children and pets by their names, because they’ve become part of our team as well.

Maintain a quality bar.

This is the part of my job that I lose the most amount of sleep over. Even though we have fun together, we come to work every day to exchange labor for compensation. As an IC, I’ve been on teams where people would complain an underperforming peer, and the manager’s lack of enforcement would be a silent acceptance of the level of output that was tolerable. As a result, everyone would get just a little bit worse. Being judicious about performance management is crucial to your team health and output.

Additionally, whether it’s insolence or lack of motivation, some folks don’t think that contributing to a positive work environment is part of the job requirement. I only ever want people on my team who actually want to be there and are willing to contribute to an environment of positivity (i.e. be someone people want to work with). This creates a healthy culture of optionality for each team member, to know that you are surrounded by people who are also choosing to be here.

I am really lucky to work with every individual on this team. Even though I cannot come close to capturing the feeling of camaraderie, in Palm Springs, I witnessed two members of the team sharing a slice of cake, four of them debugging a heat lamp, and the whole team pitching into tracking Jeff Warren’s every move so our resident fanboy could meet him.

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the misfit manager

i’m lonely

Before you click away, don’t worry, it’s not contagious. In fact, you’re probably lonely too.

But I am not talking about the greater cosmic loneliness problem that is occurring as we dive deeper into online connections. I’m professionally lonely.

As a manager, I’m a contractually obligated secret keeper. People tell me things that are legally risky to share; as an extreme example, building a termination case. It would be seriously problematic if I still went around telling everyone every new piece of information I learned. (I say still because I used to do that early in my career, treating the workplace like a school playground.)

Nothing feels lonelier than being close to friends at work and knowing things that directly pertain to them but feigning ignorance. This thin veil of secrecy inhibits trust and creates distance.

So what will we do about poor lonely manager Melissa, an overly friendly creature who craves social connection everywhere she goes?

I refuse to believe that we have to bury those trust-filled intimate connections. Rather, we have to consciously carve out professional secrets and find the appropriate spaces to discuss those.

One of my favorite meetings is a biweekly gathering of frontline engineering managers whose problem sets look similar to mine. Here, since we share the same purview, we are free to air our grievances in a setting that is appropriate for discussing sensitive topics. It’s true that misery loves company.

And in my case, I’m supremely lucky to have a best friend who is also a software engineering manager. The ability to share our professional woes and wins alongside those of our personal lives is core to my ability to maintain conviction in this career path.