What we are looking for
Interviewer: In a New York Times article from 1998, you were quoted as saying, “What I’m looking for is poetry on the margins.” Have you found it?
Dave Isay: Absolutely. That must have been a comment regarding the documentary work, but what we’re finding now is poetry everywhere. Because we live in a society that is so money- and celebrity-obsessed, everybody who is not a celebrity or very rich is on the margins. It’s the rest of us who interest me.
- Interview with StoryCorps’ Dave Isay, 2011
First, poetry on the margins - what a wonderful phrase. What a wonderful thing to use as a compass for doing interesting work.
Second, he found what he was looking for. When he first made that comment about poetry in 1998, he hadn’t even founded StoryCorps yet. But by the time he was asked about it in 2011, not only had he founded StoryCorps, it had grown for about a decade and had become a defining piece of his life’s work. He found what he was looking for - “absolutely”.
How often do we find what we’re looking for?
How often do we realize it?
On understanding why it is the way it is
I found myself saying,
"You can look at what they have and critique it and come up with all these ideas of what they should have built instead, but how about finding out why they ended up with what they have?”
I think there is this gap in product understanding. You can always say something should have all these features or should work this way instead. But the thing is the way it is right now, because a certain set of decisions were made. The builders had certain goals in mind, made some choices, made some mistakes, and faced certain constraints. There are always constraints.
Things can always be improved, and very often should be. I’m not saying we should let people off the hook for building awesomeness. But I think we should extend that courtesy - that generosity of perspective - to the builders to understand why they have built what they built, instead of perhaps what they would have liked to build in an ideal world.
Because if you understand their goals, their constraints and mistakes, then it becomes much easier to solve problems and actually make things better - make things closer to how you would have done it.
The best thing you can do with a problem
"Perhaps the best thing you can do with a problem is describe it as accurately as you can, then chip away at it with as much insight, clarity, humility, and kindness as you can muster."
- Frank Chimero, Designing in the Borderlands
This I believe.
He is talking about design, but I believe that is the nature of problems in general and how they want to be solved.
On finding mentors
A friend was talking about wanting to get more guidance on how he can grow in his role. He wanted a mentor. Over a year ago, I found myself in the same position. Some people find mentors easily, but that has never been the case for me. But in the past year, I learned this:
1. Assume you will not find any mentors. Do everything you can to improve your performance on your own.
2. Make a list of questions. What are the things you’d need to know to advance your performance?
3. Find people to answer those questions.
You will get the advice you need from people. At that point, whether or not you get mentors, you will get mentorship.
On doubting what you know
'…Make decisions by embracing Pfeffer and Sutton’s definition of wisdom: act on the best information you have, “while doubting what you know.”’
- Adam Grant, The Most Valuable Business Degree Doesn’t Exist
A terrific description of how we hope to operate. We never have enough information, never have enough time to make sense of it all. You just have to act now. But be ready to be proven wrong, so that as you learn more, you can move swiftly to act differently later. We hope to meet uncertainty with both conviction and an open mind.
On working only on what you love
Over the years I’ve worked on digital products and services, I’ve been fortunate to learn many things, but one thing above all: work only on what you love. Make time for ideas you care about; fight hard (and diplomatically, of course) for things you believe in; follow the people who matter to you; make time for projects you want to see in the world; take risks for what matters; be happy with your work. Do that one thing, and everything else falls into place.
I read that and I think, yes, yes, all those things are true, but that is not one thing. That is a very long complicated list of things. Even if you went with the distilled version - “work only on what you love” - that is an over simplification of what it takes to have it be good. You need to do lots of things that you don’t love in order to have the privilege of working on things you do love.
Then I pause. And think, why am I complicating it. Why am I picking on it. If I believe these things to be true, then use them as they are. This is not a map, this is not a checklist. But it can be a compass.
Good meeting, bad meeting
The worst meetings are failures in kindness. They are not the ones where you don’t get your way or the ones with heated arguments or even the ones where you’re told that you are totally wrong. My worst meetings are my failures in kindness.
I start to feel it in the middle of the discussion when it starts to feel like things are slipping out of control. The other person starts to act out and let their emotions do the talking, or they retreat into an uncommunicative bubble.
By the end of the meeting, I will feel guilty. At first I won’t know why, then later after I turn it over many times in my head, I will realize it is because I said something to make the person feel small. Usually the comment was an oblique one. If a direct insult is hurtful, sometimes an unintended, implied one even more so.
Why do I let that happen. I’m still trying to understand the triggers. How can I be kinder. Why is this so hard. I don’t really know.
Let me tell you about the best meeting I’ve had lately.
I had to tell someone that his behavior, when interacting with another team, was out of line. Neither this person nor the person issuing the complaint has any reporting relationship to me. So who am I to go around correcting behavior like that anyway. But I believe it’s important to get these moments right. So I thought about it and went for it.
I approached the situation assuming he was willing to learn. What do you think of this situation. Here’s the problem I see with it. Then a little ask for empathy - this is probably what the other side was thinking when they said that, maybe, we don’t know, but possibly, consider it. How would you feel if the tables were turned and this reverse hypothetical situation happened.
The conversation ended with him thanking me for feedback. The next time a similar situation arose with the other team, he handled it perfectly.
One of my favorite stories about my father is how he once had to fire an employee. He did it in such a way that years later, when he met this former employee again, she shared that she had gone on to have a terrific career elsewhere, and she thanked him for setting her on that path.
To me, that is the gold standard. Management can be a noble endeavor because of moments like this. I feel like if you can take these moments, moments that should actually totally suck, and turn them into moments that make work more humanizing, moments that help human beings grow, then I think you can feel good that you have made the world a slightly better place. Small dent of kindness in a big universe.
[Details changed to protect identities.]
Walking the line on bondbreaking
I used to think I had a bottomless well of empathy for all unhappy scholars. But lately, when I receive these bondbreaking emails, I find that I have nothing to say.
When I started getting emails from unhappy scholars a couple of years ago, I was overflowing with eagerness to help. I wanted to share my experience and help these scholars make sense of what they were going through. Each time I received an email, even if I could not fix their financial constraints, I felt that I needed to go out of my way to help them shift their perspectives to see the possibilities and make the most of their situation. Most of all, I wanted them to know that they were not alone. Their frustrations were valid. They should expect their jobs to make them happy.
When I had dinner a few months ago with a friend who finally broke his bond, I was reminded that what I do is so small, but also huge for a handful of people. My friend told me how much it meant to him to know the story of someone who made it through, did the deed, and built a very happy life on the other side. Because, to him, in the middle of all the stress and the sacrifices made, there were times when he wondered if it was all worth it. He needed something to help him believe. The gratitude in his smile just made me feel like… like I was doing the most meaningful job in the world.
But along the way something changed. I became increasingly irritated by the emails.
It started small. Emails that just rubbed me slightly the wrong way. One person asked, “What does 10% compounded mean - is that costs multiplied by 10%?” It makes you wonder how they are selecting these scholars. A couple of people revealed without apology that they frankly just wanted to make a lot of money. I started to ask myself, do you really want to spend your time helping people like these?
Then I encountered someone who has known since college that he wanted to be a chef. He was not interested in the research career path ahead of him at his scholarship organization. Despite this, he not only finished his undergraduate degree but also completed a PhD, because he lacked the guts to get out earlier. Now he wants to break his bond. By this point, the bond is worth close to a million dollars. I felt like I should have had a lot more compassion for this scholar - how unhappy he must be! - but all I could think was, “You seriously have no idea how much a million dollars is.” As the grown ups used to say, money does not grow on trees.
I have become one of those grown ups. I know I have become one of them because these days when someone asks how to get the money, I think, “You think this stuff grows on trees?” As a young scholar, whether it’s $300K, $500K or a million dollars, all the numbers sound unimaginably large. I don’t think it’s something you can even appreciate when you receive your first paycheck. I think you have to get to the point where you or your peers are considering purchases of that magnitude - a house, a child’s education - that the enormity begins to sink in. We are talking sums that many, many people never see in their lifetimes. Kids, seriously. This stuff does not grow on trees.
Then I got an email from someone who was determined to break even without the money lined up. This is a first among all the emails I have ever received. This person sounded like he was willing to consider leaving his guarantors stuck with the bond. Your guarantors are the two people who agree to be financially responsible for your bond should you fail to serve or pay it. The idea that a scholar would be willing to leave his well-meaning, probably unsuspecting guarantors in a position where they could go bankrupt… I was disgusted by the whole thing.
To the general Singaporean public, bondbreakers have a reputation as selfish, irresponsible brats. In being very public about my story, I wanted to shed light on what it’s really like to be a bondbreaker. Most of us actually do want to contribute meaningfully to society. We want our skills and talents to be put to good use, and not wasted in some corner of bureaucracy due to incompetent human resource management. But when I received that last email, well, it is one of the most irresponsible things I have ever heard. I want no part in defending that.
But here is the thing. I am particularly incensed about that selfish brat case (let’s call it that for now) because I know there is a fine line that separates him from the 23-year-old version of me. Are our motives that different? I have vague memories of my parents trying to tell me, “Why do you have to be so unhappy about the bond, it’d be good if you served your country.” All I could think about at the time was the depth of my despair. I hated my job. It did not occur to me that my problems were, if I had cared to just lift my head a little, first world problems. Why should anyone, even one’s parents, fork over several hundred thousand dollars for someone to pursue their happiness.
At this juncture in my life, I see both sides and hold incredibly mixed feelings. On the one hand, I believe strongly that professional fulfillment is an important part of a well-lived life. You should invest the effort to have work that makes you happy and helps you grow. Your relationship to your job should not be hatred or even indifference. On the other hand, a happier job is not a right. The world does not exist so you can have a happier job. Certainly, no one else’s retirement fund should be emptied for it.
The 23-year-old version of me would have rolled her eyes, but now this is all I want to tell some of these scholars: you don’t get to have what you want at any cost. There are bigger problems in the world than your professional dissatisfaction.
To be fair, I also receive a lot of emails from very nice scholars. One unhappy scholar would not even ask her parents if they had enough money for the bond, because she knew they couldn’t afford her siblings’ education as well.
There is a wonderful NYTimes Modern Love column where the writer is talking to an inmate, Mike, who has served 16 years in prison and has 8 more to go. (It may seem a little dramatic to compare a scholarship bond to a prison sentence, but trust me, any unhappy scholar will find that the analogy resonates.)
“These young guys - they just got locked up and they’ve got five years to do and they hate it. I get that. When you’re 20, five years is a long time, so they act out. I used to be like that… But then I realized: Man, this is my life. Do I want to be that guy? Always mad? I’m not going to get married or have a family… There are some things I’m never going to do. And I can spend my life being mad about that, or I can try something else…”
"I decided to be the best prisoner I could be."
His wisdom is humbling.
I don’t believe for a moment that we should all suck it up and accept our fates as prisoners. My admiration for Mike is not that he gave into his fate, but that he saw what he couldn’t change and instead turned his attention to what he could. He decided to “try something else” within his constraints. Even within prison walls, one can be some kind of “best”.
I don’t know that you can accelerate maturity. Maybe you do need to “do time”. It is true that when you cross 30, a six year bond no longer seems to stretch out into eternity as it once did. When you live long enough to face your own share of disappointments, you learn to hold and hope with more open palms, instead of insisting with closed fists. You learn that resilience trumps stubbornness.
I would not have changed my decision in any way. The day I walked out free remains one of the happiest days of my life. And what an incredible ride it has been since. I have always known that I am beyond fortunate that I had that option. I have also always known that I wasn’t grasping the full magnitude of my good fortune. Now I know what I was missing: I cannot imagine what it must have taken for my parents to trust that my happiness was worth it. That magnanimity, too, is humbling.
[Some personal details were changed to protect identities.]
On hard conversations, softly posed
"A poet recently was looking at a poem I had written and said, 'This is a hard poem, softly written.' I really liked that description. I don’t know if all of my poems accomplish that, but I think that that’s often something that I am looking for.”
- Sarah Kay, on how her spoken word poetry has been described
Lately, I have been thinking about hard conversations, softly posed. Some of the toughest, most interesting parts of the job are about having to initiate confrontations. I don’t mean starting a fight. I mean broaching an uncomfortable subject.
This comes in two flavors. In one version, you are telling the person something that they don’t want to hear. The delivery of unpleasant news. You tell someone that they need to correct their behavior. You tell someone that an event that they were responsible for went badly. You turn someone down.
In another version, you are telling the person something that you are terrified of sharing. The reveal of the self. You tell someone that you actually completely disagree with their view of the world. You ask for something you need that the other person will probably say no to. You say, “I need help,” not this issue needs help, but I need help.
In most of these conversations, both flavors are present. Two sides of the same coin - are you concentrating on how they feel or how you feel?
What you want is to be heard. You don’t want to just talk. You want to hear and be heard. Which is difficult because you need to soften your point enough so that it is received, but not soften it so much that it loses its edge. But don’t mistake this for an exercise in euphemisms. This is an exercise in courage.
Because, you see, hard things are made softer by your willingness to be vulnerable, but it is vulnerability that gives soft things their backbone.
Resuming the blogging
So I have silent here for awhile. I actually haven’t stopped writing. I have actually been posting to a semi-private blog. I described it as “an experimental log where I look at work and say, this I believe.”
I wanted to learn how to write more directly about work without being worried every single time about, “What are my colleagues going to think of this?” Then I go into this self-editing spiral and my mouse never makes it to the publish button. Is not good.
So the private blog became a nice and safe little playground. After three months, I feel like I have found a little of my stride in how this could work. I’ve fallen into this pattern where I’m reading a post or an interview about someone else, and they’re talking about their work, which has nothing to do with my work. Their work is very rarely about tech startups, it is definitely never about product management. But these people are often entrepreneurs of some kind in their own fields - microfinance, creative non-fiction, treating autism, baking. (I just realized I have quoted two bakery owners recently - wow.)
So I read what they say about their work, and something catches my eye, and I think, that, I want more of that in my work. I am often stretching the limits of interpretation. I’m sure half of them would be appalled by how I have distorted what they said and rehashed it for my purposes. But hey, the interesting stuff happens at the adjacent possible, okay?
While staying anonymous in a tiny corner of the internet is nice and all, after awhile I realized that it is more fun writing for a larger audience. I like the audience I have here. And also, I really wish I could share some of those private posts. Of course, my next thought is, I can actually do that.
So the plan is to stop writing there, start writing here, and post some of that other blog’s material here over time. The next post is a post I had started for the private blog, but I have decided will be published straight to this one.
As Brené Brown reminds us, “Courage starts with showing up and letting ourselves be seen.”