How to Say Goodbye

Every other Sunday for the past six years, at 7am PST, a calendar reminder goes off, and I hop on a call with my good friend Anyi, who lives in New York. We met back when I was living there myself, and we ended up job hunting together for a few months, before we both entered the next phase of our careers – she, remaining in New York, and I, moving to San Francisco.

Sometimes, we’re lucky enough to share a personality quirk with someone. When we decided to stay in touch by creating a recurring calendar event, I don’t think either of us knew it’d still be something we’d stick to six years later, but it turned out that we both were the type of person to commit to this sort of thing, and – barring the odd blip here and there – we would accumulate six years of shared conversations about everything, including work, the topic that first connected us.

When Anyi got the opportunity earlier in the year to teach a design class at NYU, and asked if I’d be willing to be a guest, I said yes in an instant. A couple of months later, after I had jumped through the internal hoops at my company to make this happen, I found myself at NYU facing a small group of college kids.

I went over some prepared slides, and talked about how we designed and developed product, but the discussion, while more energetic than most college classes, still felt sterile and corporate.

“Well, if you all don’t have any more questions, I have questions for you.”

I was winging it.

“As someone who’s old now,” I say, to (polite?) chuckles, “I’m just curious, what do you all want to… do?”

Audible gasps and uneasy laughter breaks out. My gamble had worked.

Of course, none of them knew. I’d be shocked if they did. I told them that it was an unfair question – I didn’t even know what I wanted to do when I was defending my dissertation.

That confession seemed to put them at ease, and opened the doors to a conversation that started with how to deal with uncertainty career-wise but quickly veered off course, into a deep discussion about life: How to deal with the fact that not everything is in our control, how to balance the fact that we could all live till we’re ninety, or die tomorrow; how and when to decide what hills to die on; what all of this means.

As we went through these topics and I gave them advice, I could see their eyes light up, and as someone who’s spent way too long in school doing a PhD, I knew they were here for it.

As it turned out, the timing was serendipitous; we had gone through a turbulent period at work, and I felt like I needed to hear the words coming out of my own mouth – that the principles we live our lives by would always transcend the relative minutia of work – even if it doesn’t always feel that way. I wouldn’t know it, but by the end of the next morning, I’d be right.

I’m not someone who usually dreams, but that night, I had the strangest one.

There I was, standing in line at food stall serving brunch items, finding myself holding a receipt for “strawberry waffles”. I was staring at the piece of paper in my hand, when the man behind the counter placed a dish on it, with the corresponding order chit. I looked at the piece of paper, and was just about to see if the order numbers matched, when a girl behind me reached over, grabbed the plate of strawberries and cut up hard boiled eggs (look, it’s a dream okay?), and walked away to a nearby table. I opened my mouth to ask what had happened, but closed it, assuming the plate must not have been for me.

After a few minutes, I made eye contact with the server, and was about ask what had happened to my order, but stopped as he pointed his chin at the girl eating the plate of strawberries and hard boiled eggs.

I turned to look at her. She returned my glance. I looked at the server. Then looked back at the girl. Time seemed to stop.

The girl stood up, walked over, and reached out with the plate of half eaten strawberries and hard boiled eggs, as if offering them back to me. The person behind the counter shrugged, as if the problem had just been solved, and walked away.

I asked, rhetorically, if she had eaten it, knowing full well what a ridiculous question that was, considering I had just witnessed her scarfing down the plate of food. But she just walked away, uninterested.

The dream sped up and turned into a montage: me making fuss, me throwing a tantrum, me calling the manager, and so on. All the while, I feel like I’m yelling into the void. Like this is a huge injustice. Like nobody cares about my damn half eaten strawberries and hard boiled eggs.

But time soon returned to its natural tempo, and as the manager brought me to whoever was really in charge, I discovered that this brunch place was owned by someone I knew in secondary school, who had become a mob boss (LOOK, it’s a dream okay?).

As I walk up, he says to me all gangster-like, “there are starving people out there, what necessitates bringing this to my attention?”

I stutter, suddenly aware of how much things have escalated, and I say it’s something really trivial, that he shouldn’t bother.

Then it’s night, and I have just woken up, and I am filled with overwhelming shame and grief. Because I realize I could have just let go of the issue.

As I drift off to sleep, I think to myself, sometimes it’s better to be happy than to be right.

When I awake, the remnants of the dream swirl around my thoughts like a mist, and as I lay in bed, I wonder if there’s a more subtle lesson here – that the people in my dream would have cared more about my plight if only I saw them as more than a vector for a plate of breakfast.

As I lay in bed, I thought about the journey I took these college kids and myself on. I thought about the things I said to them: that work, to me, is about collecting people to come to my funeral; that it’s important to compromise, but that the compromises we make become a part of us; that it’s important to think of the whole journey, and not just the moment in front of us.

I try to think of these things an hour later, when I get an email from HR, sent both to my work and personal email, and a calendar invite with my boss scheduled for half an hour later.

I can be dense sometimes, but I know what this means.

In the intervening thirty minutes, I try to write a farewell note, but it’s stuck in the ethereal form that all writing has to gestate in, before woodshedding makes the ideas concrete. It would take a few more hours for me to write a few hundred words.

I join the meeting, and am met by Daniel, our head of product, and a representative from HR. I think to myself, if this has to happen, let me remember handling this moment well.

“Is this going to be a rough meeting?”

“Yup,” Daniel says, solemnly.

“Let’s do it then”, I try to smile.

I know war analogies are a cliche, but as I’ve gotten older, people in power around me tend to fall into two neat categories: leaders who I would gladly follow onto the battlefield, and leaders who I would gladly throw onto the battlefield.

Daniel, thankfully, sits squarely in the former category. Being one of the first hires at the company and rising through the ranks over the course of more than a decade, he’s definitely earned his stripes. But most of all, for me, he embodies something I believe to my core: That the spectacle of eloquence and charisma will always come in second to actually having clear, human values. He cares, and it shows in his actions every day. And over time, that is more believable than any single piece of communication could ever be.

This is why I had told him a few months earlier, while we were going through some tough times as a group, that if he was ever ousted, I’d see myself out too.

He reads from a script, to make sure he gets things right. Says a lot of nice things. I am quite good at my job, after all. But then he surprises me, as he’s getting let go of as well.

These things are short, and at the end, I say two things. The first, to Daniel, is a reminder of my earlier promise, and like a wish made with a monkey’s paw, the fact that he’s leaving makes my own termination a formality. The second, to both of them, is that although this is not pleasant, I know everything will be okay, and that there are worse things going on in the world.

A few minutes later, the surprises continue. I find out that Carissa, my manager, is in my layoff cohort as well.

Carissa’s journey ran similar to Daniel’s. She’d also been at the company for over a decade, and earned every step of her career progression, perhaps more so than most: She’s a better person than I am for having the temperance to put up with some of the nonsense that’d been thrown her way over the last ten years.

In my first year at the company, we would meet weekly as peers, talking about work, but oftentimes drifting to video games and everything else under the sun. I’m ashamed to admit that when I was first told that I’d be reporting to her, I had doubts over how that dynamic would work out. In retrospect, I was just someone else she had to unfairly prove herself to. I’ve never seen someone care as much, and be as willing to work herself to the bone for others.

I had made the same commitment to her.

I’m not trying to be melodramatic. It’s just that as someone who grew up with the most strained relationship with authority, there have been scant few leaders who I’ve happily followed. I guess it’s easy to be loyal to your precious few masters.

A few hours later, after responding to as many emails and messages as I could, and after taking a few calls, I was at the airport, waiting for my flight back, when I get a call from J, one of our former executives.

Replying to his original farewell email, I described him as “an exec I want to be like when I grow up”. J, if you’re reading this, I’ll probably get in trouble if I say more but that’s pretty much the highest compliment I can offer. I also said to him, shortly before he left, that even though he’d never once ordered me to do anything during the time we worked together – only sending long, drawn out thoughts while keeping to his word that they were for me to “do as I pleased” – it felt like all my best ideas came from him. He’s just an inspiring person to be around.

And now, with the news having found its way outside, I found myself pacing the airport commiserating with him about the group of us – myself, bundled with my two favorite bosses, together with a handful others that J described as the “A-team”.

Selfishly, this made things so much easier to accept. I had joked with Daniel and Carissa that I now got to steal a bit of their valor: They were amongst the people that had built the company; I just got to enjoy a short time in it. If I had to leave outside of my own volition, I could not think of a better group of people to do it with.

As we continued to talk, it’s like I can feel the best of myself being drawn like a well, and even though J never says these words explicitly, a deep-seated, deeply-rooted core of an idea forms within me: that if we show up every day with ambition duly tempered with love and compassion, then we must never fear the consequences of who we are.

J’s time with us was short, but I tell him what I believe to be true: That while the impact on our users and customers can sometimes be hit or miss, the effect we have on our friends and colleagues is entirely within our control, and during his time with us he showed us a different, more inspiring way that we could be led, and that we are all better for it.

At the end of our conversation, it’s finally time for Group F to board, and I step onto the plane, without a job, but with that one thing you get when you don’t get what you want – experience. And what a group of people to share that experience with.