Ailian Gan | >140

Launching the scholarship bondbreaking advising service

Tue, 29 May 2012 00:02:28 -0400

Months ago, I wrote about wanting to set up a simple service to advise anyone considering breaking their scholarship bond. I have thought a lot about it. I thought through many ideas for how to position it. Should I buy a new domain? Should I write a collection of articles first? Should I have testimonials from happy clients?

Basically, I ran into the problem that many of us face with projects: I failed to ship.

Last week, a total stranger emailed me for advice on her bond. This hasn’t happened in awhile. (Been getting a lot more startup related requests lately.) But I was reminded of what I had set out to do in the first place. Pay forward my good fortune at being able to break my own bond years ago. Put myself out there. Help people live more fulfilled lives. Help people as only I can.

She didn’t need me to build a fancy website. She didn’t need me to establish my credentials in some bio. She didn’t even need a form. All she did was find my posts on bondbreaking - hooray for the power of search - and email me. Hopefully she got something useful from my exchange with her. I am immensely grateful for her trust and for the chance to help her. (If you could spend 90 minutes of your time and have a stranger tell you that you are one of the most inspiring people she has come across in her life, you, too, would do the same.)

So I have decided to just ship. Here I am hanging out the shingle.

It’s here! Check it out:

So you are thinking of breaking your scholarship bond?

The way to take responsibility

Fri, 25 May 2012 01:53:41 -0400

Don’t demand authority.
Eagerly take responsibility.
Relentlessly give credit.

- Seth Godin, on The quickest way to get things done and make change

A few months ago, I reached the point in my job as Product Manager when I became the go-to person if anything related to the product broke. All the complaints came to me. I felt constantly under the gun for things beyond my control.

This was very hard to take. I was constantly caught off guard. To be clear, the product generally works tremendously well. But minor things always come up. I felt like a deer caught in headlights whenever someone raised an issue. Because I cared so much, I took every complaint personally. Not that I felt that I was being insulted per se, but I felt personal grief (as a colleague once said) over the product’s every minor failing. It was very difficult to bear.

At one point, I considered distancing myself and trying to learn to not care. If I cared less, it would be easier to swallow, easier to let things roll off my back. Easier to not feel my stomach clench up every time someone came by to tell me some aspect of the product wasn’t working.

I also got defensive. Totally natural response. Emotionally, in my head, the first reaction was to defend myself. But I didn’t even build this thing! I didn’t know this was going on. (Then I felt guilty - how could I not have known this was going on.) This is not even my customer. (But it is my product.) I can’t even fix any of it. Someone else has to go into the code and fix it. Why isn’t that person being blamed.

Then came the hardest part. I needed to take all of this frustration that was being thrown at me, and I had to swallow it and filter as much of it as possible (which will not be enough), and I had to turn around to the engineer and ask in cheerful spirits if he would please fix this bug, it’s important to our customer.

(In really difficult cases, I had to work through the engineer’s protests and persuade her that this was a good investment of her time.)

Good times.

It was only in the last couple of weeks that it dawned on me that my dad’s job as manager must be like that. All the time. This is the crux of management. You are responsible for everything, even though you don’t actually do anything. But if you want this role, you must take responsibility, regardless of whether or not you think it’s your fault. It is always going to be your fault. So take responsibility. Take it willingly, take it eagerly.

As for feeling like you have no control, that is not an acceptable response. The way to earn authority is to exercise it before it is bestowed upon you. Take responsibility first, act with authority, get things done. Eventually if you keep doing this and do it well, official authority will follow. But by that time, it won’t matter to you. You won’t need official authority to get things done.

And when the bug is finally fixed by the engineer, give away the credit. Give away all of it. That, too, is an act of authority. That, too, is part of the responsibility.

(How’s that for working in public.)

The highest craft

Thu, 10 May 2012 00:28:44 -0400

Over the weekend, I saw Jiro Dreams of Sushi, a very lovely film especially if you love sushi. It follows the story of an 85-year-old legendary sushi chef who runs a 10-seater restaurant near a Tokyo subway. Meals start at $300 (USD not yen). He has been awarded 3 Michelin stars. He has been making sushi for 75 years.

I was struck by Jiro’s commitment to this single specific craft. He has dedicated his entire life to perfecting this craft every single day. There is no room for being a generalist here. I think of how in schools, in career advising, we’re told we should acquire transferable skills, skills that are broadly applicable. So many of us are obsessed with keeping our options open.

Jiro’s story preaches the opposite. Be a specialist. It matter less what you choose and matters more that you chose it and continue to choose it day after day. Put in enough cycles of 10,000 hours and you get to reach the rarefied air that is the top of your craft. (By my rough estimates, Jiro has put in more than 20 times of 10,000 hours.)

Choose a craft you love and be an expert. Except that this is not about mere expertise. This is about artistry. Be an artist. Elevate your craft. Invent a new aesthetic.

And that’s where we get to this notion of the highest craft.

In Frank Chimero’s The Shape of Design, there is a story he tells where his favorite professor was reviewing his portfolio and pauses to say, “Needs more love.” Frank goes on to say:

At the time, I took it to mean that I should improve my craft, but I’ve come to realize that he was speaking of something more fundamental and vital. My work was flat, because it was missing the spark that comes from creating something you believe in for someone you care about. This is the source of the highest craft, because an affection for the audience produces the care necessary to make the work well.

Is it about caring for the audience really? Did Jiro do any of it because he wanted to please an audience? I disagree. I adore Frank’s phrasing - the highest craft - but I disagree.

I think the caring, the spark comes wanting to do the work right. Regardless of an audience. Above everything else.

Seth Godin writes of the wonderful Caine’s Arcade, the 9-year-old boy who made a cardboard arcade:

The first thing that made me smile was how willing Caine was to do his art regardless of how the world responded (it didn’t). Caine didn’t care. The goal wasn’t to be accepted, the goal was to do it right.

That kind of commitment, I believe, is the heart of the highest craft.

I think about what I do at work. I think about what I do outside of work. I have to accept that I am not wired to be a specialist the way Jiro is. (I know very few people who are.) I will always be more generalist than specialist. But whichever I am, my work, whatever I choose it to be at that moment, could use more love.

So I ask myself, when was the last time you were performing the highest craft? When will you do it again? Why don’t you do it every day?

Failing successfully

Tue, 08 May 2012 01:24:30 -0400

Since starting, I have gone through cycles of feeling like I’m doing well and feeling like I’m failing. From the outside, it probably looks like things are constantly challenging but generally improving. The stages are probably not noticeable at all, or at least nowhere near as pronounced as how I experience them. Internally, it’s helpful to identify where I am in the cycle to maintain perspective. If I’m at a low point, it’s useful to know I will probably not stay there forever. It’s also useful to know that a lot of the stages are defined by changes in my own expectations rather than external factors.

1. Doing well
The good part. I expect myself to be able to do certain things in my role at my level of experience. And I do them well. I am meeting my expectations. Things are under control. To quote Paul Graham, the spinal cord has the situation under control.

2. Failing
Then at some point, I receive external feedback. Why are you not doing X? Why did you not think through Y? Or something breaks and I wonder why didn’t I anticipate that, this is under my purview, I should have known better. I tell myself, feedback is good, don’t get defensive, listen to feedback, keep an open mind, listen! But critical feedback is never easy to stomach.

3. Feeling like I’m failing
So I feel like I’m failing, and it generally sucks. I start to identify all the other things that I should be doing that I’m not doing or not doing well enough. I actually feel like I’m failing at everything, even though I know it’s not true. I become the world’s worst boss of myself.

4. Being prepared to suck
At some point, I realize the self criticism is not helpful. It is also tiring. I realize what is perhaps the most important thing of all - the bar has been raised. I am not actually failing. I am merely failing relative to a much higher bar. I have earned the right to fail against a higher bar, and that’s a good thing. I start digesting the feedback. I accept that I am going to be underperforming relative to this higher bar for awhile. I become prepared to suck. I lean into that awful feeling instead of running away from it.

5. Learning
And this is where the learning can happen, if you choose to accept it. The criticisms, internal and external, are not personal attacks. They are instructions for change. They might not feel great, but if I commit to the work and keep chipping away at it, eventually…

6. Doing well
Eventually, I do well again. The good part returns.

Rinse. Repeat.

Finding the guts to work in public

Sun, 29 Apr 2012 16:54:36 -0400

Working in public. I first came across the idea in Tony Chu’s blog. He talks about opening up the learning process, the creation process by writing publicly about the journey as you go through it. Write vulnerably, gather feedback, expose yourself to interesting ideas.

He linked to a post over at Snarkmarket - the art of working in public. The post is about other (famous) people’s working in public. On BERG’s Matt Webb and The Atlantic’s Alexis Madrigal:

They both conjure a sense that the piece is almost being written as you read it. It feels like they’re just a [paragraph] or two ahead, and if you picked up the pace, you could catch them—overtake their blinking cursors. It feels slightly chaotic and totally thrilling. They both let you inside their heads.

You see, I’ve been trying to find the guts to work in public. I want to write about product management on this blog. But I am terrified.

I don’t know where to draw the boundaries. I feel like I cannot say too much about what goes into building our product because I don’t want to reveal trade secrets. I feel I shouldn’t write about my coworkers, even though I think extremely highly of them, because it doesn’t seem fair or polite to expose their learning experiences here. (I am also still getting used to the idea that some of you, dear coworkers, read this thing. Hello! I am flattered that you bother to read.)

I feel that I cannot write about when things go wrong. I feel I cannot write about when I’ve screwed up or have fallen below the mark. I cannot write about all the times I am totally making up my job as I go along. I cannot write about the moments when I face severe decision fatigue and struggle to stay objective and positive and helpful. Or the days when I do all that and I am still asked why I didn’t do better, and then I just want to hide under a rock. Except I can’t. Because someone else is pinging me with an issue.

But that is where it is all fascinating. Where I most need to take a magnifying glass to the problem and study and learn.

I want to reveal things to you and to myself, because I want to think more critically, more clearly, more originally. I want to ramble about things I still don’t understand, about the gaps in my knowledge, about the things I’m only vaguely aware that I should pay more attention to. So I can figure it out. I want a record of when I didn’t know.

I want to work in public because a lot of this work is utterly and endlessly interesting to me.

There you have it, the struggle. I’ve been trying to blog more to find the guts to work in public, but all you get are posts about everything else. Some of it is better than I expected, even as I go after volume over quality. But I am still trying to crack the heart of it.

I want to talk about product management.

The Snarkmarket post describes the sensation of reading weeknotes by CEO Matt Webb of the design firm BERG:

For the span of a few thousand words, you are riding shotgun as co-CEO of BERG.

There is often an extra office chair stationed right by my desk. I have taken to calling it “my office hours chair”. There is almost always someone - a PEM, an engineer - sitting in that chair asking me a question, a problem, a thing I need to make a decision on, a thing I need to commandeer resources for so I can say yes to, a thing I need to find a reasonable way to say no to.

If I could figure out how to work in public, this blog would put you, dear reader, in that chair. Imagine that blog.

How to work in public and reveal nothing. That is the question. That is the art.

Meanwhile, I’m going to cross industry boundaries and go read some weeknotes over at BERG.

Habits (or how I got myself to go running)

Sun, 22 Apr 2012 15:11:00 -0400

In most areas of life, I am relatively disciplined. But when it comes to exercising regularly, I have failed time and again.

A few months ago, I made a new friend. She is a triathlete. She was so enthusiastic, so effusive about getting me to exercise, I couldn’t say no. She broke it down into a simple routine. Run 3 times a week, 30 min each time, pick a route you like. She wakes up early anyway (4am?) so she said she’d even text me in the mornings to encourage me. External accountability. Great. This is supposed to help, right?

So I went running. Twice. Maybe three times. Not per week, but in total. And I did not feel better. I felt more tired and irritable, probably because the routine was cutting into my sleeping hours, so I stopped. I felt bad about it - failed yet again - but the running clearly made me feel worse than any guilt from not running. I decided I just wasn’t cut out for this.

But 3 weeks ago something changed. I started getting up before 7am to go running. I ran 3 times the first week. It rained the second week, so I ran once. I thought my momentary success was short lived, but on the third week, this week, I ran 3 times again. How about that. I would hardly call this a habit, but it is also more running than I’ve done in the past year. I feel pretty good that I will run again next week and the next.

This feels different. This feels like the beginnings of a habit.

So what changed?

Charles DuHigg has done some interesting work on habit formation. Essentially, a habit is defined by a loop that has three phases:

1) the cue - the trigger that causes the habit to occur in the first place
2) the routine - the behavior itself
3) the reward - something pleasurable, which is the brain’s way of saving the habit and encoding it for future use

The key is finding the right reward. I’ve had other people tell me that the endorphin rush will be reward enough to keep me going. Uh, no. Totally didn’t work for me.

Apparently, the best way to get yourself to develop an exercise habit is to give yourself a treat right after. I know someone who would treat herself to a piece of chocolate. I have considered this, but I’d rather eat chocolate at other times of day. I have also considered enticing myself with an elaborate breakfast. But that’s too much effort. I have also once bought myself nice exercise pants to entice myself to go running. I have worn those pants a fair amount. I just wear them for other occasions like doing errands on Sunday.

Like I said, repeated failure. Or as Mr DuHigg is more likely to point out, I have not found the right reward. This is the hard part.

Three weeks ago, I accidentally discovered a reward that works for me. I was making another attempt to go running. The day before I came across a bunch of blog posts linking to talks I wanted to listen to. This was Albert Wenger’s talk to the Entrepreneurial Design class over at the SVA IXD program. So that morning, I remember the talks and played them on my run.

The interesting thing is that I really enjoyed it. I already listen to podcasts on my drive to work, but there are always more I’d like to listen. For instance, all the Stanford eCorner podcasts.

I figured out a few other reward attributes that were important to me. I needed to be sufficiently engaged, so I wouldn’t think about how much pain I was in or how much longer I had to run. Music doesn’t work for me for that reason. Music is distracting but not engaging for me. Something with a story or with content I cared about (startupy, techie stuff ) was perfect. I needed to find series of podcasts, so that I wouldn’t have to find a new podcast every single day. I needed the talks to be longer than 30 minutes, so I would run for at least 30 minutes.

The research says that eventually my brain should be able to find intrinsic reward in the exercise, and I won’t have to trick it with a reward. The research is unclear on how long it will take me to get there. Based on my track record, let’s just say I am glad that the internet has a large supply of good podcasts.

Next up, how do I get myself to blog more regularly…

P.S. This is not my running route, but one positive side effect of running is being able to take in gorgeous 7-mile hikes.

Ducklings vs. rainfall on water

Fri, 20 Apr 2012 00:04:21 -0400

A friend explained to me that at her school, the students were described as “ducklings” - calm above water but paddling hard beneath the surface to keep up. The same can probably be said of people who work in startups in the Bay Area. People appear chill, and they sort of actually are, except when you discover how hard core they are about their work.

I prefer the opposite analogy.

(What is the opposite of a duck? I have no idea. But bear with me.)

There is this print I bought from 20x200 by Chikara Umihara titled Rainfall, Upstate New York. There is nothing eye catching about it. Heavy rainfall on a lake. What caught my imagination was Umihara’s interpretation of the image.

Here, in this work, a downpour violently hit the water; there weren’t ripples and nothing is reflected on the surface. But after I printed this image, I realized that this is my first image that perfectly reflected my subconscious mental state—disturbed, but calm.

I think of what it’s like on my craziest days. The ones where people keep asking for 5 minutes of your time, and your attention is pulled in a hundred directions. The ones where someone is agitated, occasionally blaming you or someone on your team for something you had limited control over. A confrontation. Or the ones where you know you’ve fallen below the mark because you couldn’t quite get your act together and it’s all too much.

Disturbed, but calm.

There are many things that I cannot change about my environment. The “violent downpour” is an intrinsic part of the role, and indeed often the source of the intensity, the fun.

But what I would like to be more of is the “calm”. To be like that body of water. Agitation absorbing. Unshakeable beneath the surface.

I have a long road to get there.

Ari Wallach's synthesized problem solving

Tue, 17 Apr 2012 12:04:40 -0400

“All Synthesis is, is myself and my partner running the back end. It’s like cloud innovation; we’re really trying to build a next-generation consultancy, drawing on a different kind of expert network…

“We’ll hire a stay-at-home mom who doesn’t want to return to a position at McKinsey, but will give us 15 brilliant hours a week in between everything else she’s doing in her life. We can bring in an urban-graffiti practitioner or someone who builds amazing shelters at Burning Man and used to build DARPA-contract structures and get them to reframe what they do so it’s relevant to a client’s issues. We don’t have a one-size-fits-all process like other consulting firms have.”

- Ari Wallach, Founder of Synthesis, as interviewed by Fast Company as a Real Life Problem Solver

I love this. I have minimal interest in politics, but I am totally inspired by what Ari Wallach has done with his career. Here is someone who has figured out how to do what he is.

He started out with a degree in political philosophy, and since then has done everything from working for the Democratic National Committee, to doing new-media projects, to consulting for nonprofits, to leading the “Great Schlep” campaign for Obama. It’s random, it’s all over the map, and together, synthesized, it makes perfect sense. Now he gets to be his own boss and work with clients ranging from the US State Department to the Ford Foundation to CNN.

Above all that, in that quote, we see that he is contributing both original solutions in his work for clients, as well an original business model that solves the modern day work/life/talent balance dilemma. I am drawn to people who ~~cannot figure out~~ take time to figure out how to do what no one else can do. And this, this is awesome.

Not urgent but important moments

Sun, 15 Apr 2012 12:23:56 -0400

If you work in a startup, you will understand that it is very, very hard to get out of operating in the urgent bucket and into the not urgent but important bucket. The bigger important things are easier to identify (you should build X). The smaller important things, those are hard to catch and sometimes seem frivolous, but they add up. They matter.

From the not urgent but important bucket this week:

Spent 45 minutes shopping online on behalf of the company for a gift for a well-loved coworker who is a brand new dad. Smack in the middle of a day when I should have hurried up and finished work so I could leave for an event which I missed. What can I say, I really like picking out nice gifts when I care enormously about the recipient’s happiness.

Two long chats with someone I rarely have long conversations with about recent company culture. It is a privilege to work with people who care so much about building a company that’s a great place to work.

Invested many hours this week trying to find new contractors to outsource some work. Who knew trying to get other people to do work would be so much work! I want to get better at this. I’d like to outsource more of my life.

Blogging. I have been trying to hit publish more often without worrying so much. I’m intrigued by this 750words thing. I would sign up except that 750 words per day (3 pages!) is too daunting. But really, I am under all kinds of fascinating, if sometimes crushing, pressure lately. It makes me think a lot about how I could do just a little bit better in every single moment.

What actually matters in goal setting

Thu, 12 Apr 2012 11:54:34 -0400

The engineers on my product team asked why I didn’t defend their interests in our quarterly goal setting meeting. This is presumably part of my job as Product Manager. (This is funny to me, since it’s the only time they have ever accused me of not defending them. Whether they like it or not, I have far more frequently erred on the other side.)

The senior leadership exec was doing his job of raising our goals. All the numbers were being adjusted upward. By “adjusted” I mean ratcheted way up. We have been here long enough to know he does this every time. This time, as with all previous times, a couple of the engineers tried to convince him that these goals were impossible.

I would agree, except for this:

Two quarters ago, the leadership set a revenue goal that I thought was a major stretch. To give you a sense of magnitude, I think most people would agree that any goal that requires more than a 100% increase is intimidating. But we blew through that target. In fact, we blew through it with a month left to go in the quarter.

Last quarter, encouraged by our success, we set what we all believed was a genuinely bold goal ourselves, only to see the leadership raise it far beyond (what I considered) reasonable reach. The number was so ridiculous that it made me nervous to think about it seriously, so I turned it into a bit of a joke. When we made major decisions or shifts in the way we operated, I would say, “Oh yeah, we need to hit that $X revenue goal.” In the end, we missed the ridiculous goal but came surprisingly close to it. We are likely to pass it fairly soon, if we haven’t done so already. The joke, oddly enough, became inspiring because it was a Big Hairy Audacious Goal.

With this track record, we’ve pretty much lost all credibility for our claims that certain goals are impossible. We have done “the impossible”. A slightly bizarre, mostly good problem to have.

So this time I didn’t step in to argue down the numbers.

First, we have consistently lost this argument over numbers with the leadership. We can persuade but cannot control what number they want. Similarly, they have limited control over whether we reach that goal. They cannot force us to reach it, if it really is beyond reach. Ultimately, we build what we build.

Second, the number doesn’t really matter. I mean, it does matter in terms of training our motivations. A very high goal trains us to raise our ambitions. On the flip side, if we set a more humble goal, it’s not like we’re going to reach it mid-quarter and go take a vacation for the rest of that quarter. We don’t operate that way.

Third, we were in broad agreement with the direction of the goals. These were priorities we had selected. We believed they were the most important goals for our product at this stage. So regardless of what the numbers were, the work wasn’t going to change very much. Our team was going to put its best foot forward in the direction of the goals.

I have no idea if we’ll reach these goals this time. I never know. But I’ve learned that that’s part of the point. If you can see a clear path to your goal, you’ve set the goal too low.

Stories that are too big too tell

Wed, 11 Apr 2012 11:42:48 -0400

Do you ever have this problem where something means too much to you, and when you try to communicate it to others it always falls short? Usually, it’s not because they don’t get it. Usually, it’s because it is too intensely personal and you are scared of sharing it. You would feel too vulnerable.

There is this story that I have been telling over and over in the past few months to any good friend patient enough to listen. The story isn’t even mine. It’s about someone else’s life, a collection of anecdotes, that made a deep impression on me.

The stories carry some kind of transformative power. When I tell the story, I can feel my tone change. I’m telling a story that is someone else’s act of greatness, but it is a story that is thundering through me.

The stories are not personal. The stories aren’t mine. They are something I aspire to. And I want so much to share them. But the retelling feels intensely personal because I am profoundly moved by these stories and they have made me live differently.

The problem with tactics

Thu, 05 Apr 2012 11:58:18 -0400

When I am under greater stress or feel like I’m floundering, I resort to looking at those around me and trying to learn tactics. Why does X get ahead, despite X’s [insert some undesirable trait]. I try to copy. I try to emulate the tactics. The whole problem is that these moves are just that - tactics. They work in the short term, they work in surface relationships, but they don’t add up to trust. They don’t add up to character.

For instance, learning how to manage difficult clients. I have observed how some people do it and the things they get away with. The things they say, the kind of posturing that works. I think, wow, they got what they wanted! And I make a note to employ their tactics next time.

But then I think of how the same tactic has been used on me. In those cases, it temporarily diffused the situation, but I felt… managed. To put it more bluntly, I felt manipulated. It didn’t increase my respect for the person.

If these tactics don’t work on me, why should I use them on other people. These tactics twist you into agreeing with words, but in your heart, you feel anything but agreeable. This is not going to work.

What is needed is an emotional shift. Of greater empathy, I would argue. If we could listen better, if we could get closer to what really motivates people to act the way they do, if we weren’t afraid of facing people’s feelings as they are, we wouldn’t need tactics. We would be more direct and kinder. We’d get closer to saying what we actually mean. We would both feel understood.

All that takes a lot of courage.

Do what you are

Sun, 25 Mar 2012 21:10:51 -0400

“He believes in a theory. He believes in a position. And then he tries to manifest it…”
- Jerry Colonna on Mixergy, on Seth Godin starting Yoyodyne and Squidoo, two companies that reflect who Seth is

My negotiations professor at Wharton, Adam Grant, is writing a book called “Give and Take”. The book is about:

- Givers - people who prefer to contribute more than they receive
- Takers - people who want to get more than they give
- Matchers - people who try keep the giving and receiving in balance

From the synopsis:

Giving is professionally dangerous, but it can also be professionally powerful. Over the past decade, my research has uncovered a paradox. Givers are not only over-represented at the bottom of the success spectrum. They also dominate the top of the success spectrum.

If you have ever met Adam Grant, you will know that he sits firmly in the givers camp. Giving, selflessly giving, is intrinsic to Adam Grant’s personality. The fact that he is doing research on a topic that is so wholly him is wonderful.

We spend a lot of time thinking about where we want to go. What’s next, what’s next. Too often, that is dictated by what other people tell us we should want. Sometimes there is an actual person telling us what we should want. Sometimes it’s just a sense that this is what people are supposed to want. Or we want the emotional outcome (social approval, financial security, etc.) so we end up choosing a path that other people tell us will lead to the outcome. Career decisions end up being a matter of picking from a menu of options.

But sometimes, some people forge their own paths. They look at what is available on the menu and combine things, or choose something in between, or create entirely new flavors. They pour themselves, their being into their work.

They do what they are. It is a rare gift - to themselves and to the world.

I don’t know what the process is for this exactly, but I want to do more of what I am.

Giving credit where it's due

Thu, 08 Mar 2012 00:34:05 -0500

The salesguys had gotten free tshirts and jerseys from a client. Really nice brand, nice swag. It’s been a ton of work to get this launch out. The salesguys H and S were giving out shirts to the people who worked on this.

I told the salesguys, make sure you give one to A!

A is the engineer who has been working incredibly hard on one crucial part of this. There were many pep talks involved, many frustrated discussions about why we were doing this. She is not one to fight for the limelight, but this one took an incredible amount of mental and emotional effort. All that success that people were predicting and making bets on? None of that would happen if not for A’s work.

Later that day, salesguy H came over with a jersey. He told A to put it on. She put it on not realizing what we were trying to do. I said, how do you like the logo? She looked down and noticed. It was great. She kept the jersey on for the rest of the day. Every time someone commented on it, she beamed.

That evening when A had left, I saw H on his way out. Why aren’t you wearing one of those shirts, I asked.

H goes, I gave mine away.

And there I was feeling pleased with myself for being the kind of PM who makes sure that the engineers on my team feel good about their work and get the credit they deserve.

H’s gesture has made me feel better about working here than anything else in a long time. I feel great about many parts of the job, but that - that was grand.

An afternoon in Brooklyn

Sun, 04 Mar 2012 18:36:26 -0500

The Brooklyn Bridge

The Manhattan Bridge

One Girl Cookies

One Girl Cookies (I love their lighting)

Dumbo Arts Center

Things that cannot be taught

Thu, 16 Feb 2012 08:54:00 -0500

…that I wish could be:

1. How to make yourself happy

People I know who are best at making themselves happy were also acutely miserable at some point.

People I know who are bad at this have only known a numb unhappiness and a lot of inertia.

Being able to make yourself happy is different from being lucky.

2. Professional judgment

In roles that require managing people and processes, the difference between the average performer and the very best is professional judgment.

3. Self awareness

It is the pre-req for the ability to self correct, which is important for growth beyond the limits of your natural talent.

Or can they be taught?

Or perhaps they can’t be taught but they can be learned?

Discuss.

For giving to feel like receiving #generosityday

Mon, 13 Feb 2012 21:32:23 -0500

I didn’t always get generosity. Sasha Dichter once ran a Generosity Experiment. For 30 days, he said yes to every request for help, for money, for anything from friends, people on the street, anyone. I loved the idea. I also thought it mildly crazy. I wanted to feel what he felt, but couldn’t get comfortable with it. Giving is supposed to feel good theoretically. But in reality, sometimes I feel bad after giving. For instance, I often struggle with what is the right amount to donate to charity. Once I finally pick a number, I feel worse. I feel like I haven’t given enough, but I also start wondering if that’s really the best way to help. Is that really the best use of my money.

Giving didn’t make me feel better. It made me feel conflicted.

In recent months, something changed, something clicked. I experienced acts of unexpected generosity that have led me to this: the giving must feel like receiving.

Generosity feels good to the giver only when we have the right intent. In too many instances, we have mixed intents. We want to be patted on the back. We worry about feeling good about being good. We wonder about the return on our generosity. I realized that mixed intents are what made me feel bad. For giving to feel right, we need to have the right intent. That comes about when the giving feels like we are receiving.

If you’ve never had the opportunity to attend a Wednesday meditation session, it is quite a profound experience. The Mehta family plays host. They open their house to friends, strangers, anyone who comes by every week. They invest the time to build this community, to create this meditation space. Then they provide a satisfying dinner to every single guest. The fact that they do this entirely free of charge is already an amazing act of generosity. You feel wowed by how they’ve created this feeling of abundance. You feel gratitude to be able to be part of the evening.

As if all that is not enough, we come to the part that really gets to me. Every week Nipun Mehta will basically say, we thank you for the opportunity to host this gathering.

What?? It sounds like it could be some ridiculously corny line, except that these hosts mean it fully. They are the ones who have given so much every Wednesday evening, we are the receivers, and here they are saying thank you. To have to listen to a “thank you” of that magnitude after having received so much generosity is… it is almost too much. But you see, for this family, giving feels exactly like receiving.

I have no idea how you get there. All I could think was, these people have seriously figured something out. I want that. That is the kind of generosity I seek in myself every time I give.

In that spirit, I have made my Generosity Day pledge. Sasha Dichter & co. are rebooting Valentine’s Day as Generosity Day. If you’re intrigued, I encourage you to sign up too. I think it’s the best thing that’s ever happened to Valentine’s Day.

Connecting online to offline

Fri, 10 Feb 2012 00:59:02 -0500

For these two weeks back home, I’ve scheduled lots of meals (when one is in Singapore, one eats) to catch up with friends. These are typically with Singaporean friends I’ve known since my school days. This is the first time that most of these meals are with people whom I’ve gotten to know in the past year. A couple of you I’ve only met once in person. One of you I have never met in person. We have only had a very long Skype call.

I suppose our circles have evolved. I have taken more introductions since b school and since joining the startup community. The more introductions you take, the more you want to do, the more you receive. A virtuous cycle.

I have been fortunate enough to meet most of you through very good email introductions. The first degree friends who did the introductions knew why we should get to know each other. There is context, there is some kind of essential common ground. There is something valuable that could be exchanged. That something valuable is most often each person’s perspective (on startups, on bondbreaking, on whatever). Not all introductions are created equal. With weaker introductions, that something exchanged is information. With very good introductions, that something exchanged is friendship. In the best cases, a kindred spiritness.

In all these instances, our offline interactions have been enhanced, sustained by our online presences. I think about the friend I am meeting for dinner. We have only met once in person for maybe 10 minutes in a group setting, had one long Skype conversation. But through all our other mutual reading of blogs and tweeting and email exchanges, I feel I know him well enough that I would be glad to use my social capital to recommend him to anyone. (And I also feel close enough to demand that he bring an autographed copy of his new book to dinner!)

I would go so far as to argue that there are meaningful parts of online interactions that cannot be replicated offline. When you read someone’s blog for instance, you get to hear a version of what they sound like to themselves and how they want to be heard by the world.

Emails, long pensive personal emails, achieve a similar effect. I once had a friend call me and he said he wanted to pick up the phone and call because he was tired of how emails felt so impersonal. I thought to myself, no, that’s just because you don’t understand how good emails work. I love a great 2-hour catch up phone call, but don’t dismiss email. A good, thoughtful email gets closer to how that person wants you to know them when they are presenting themselves, edited and uninterrupted. There is communication and then there is communication.

I’m not about to suggest that online interactions are better than offline. Of course not. I do think it’s simplistic to insist that all offline interactions are “better”. I don’t know what “better” means. You can’t build the same connection across different media. But that’s the whole point. A smiley face :) is a poor substitute for how it feels to have someone beam at you in person. But there are tones of a lighthearted Twitter exchange between friends that cannot be replicated in an offline conversation. You cannot speak a URL.

The point, to me, is always the connection.

The internet doesn’t change what we as human beings need to feel connected to each other. It’s just another tool, another medium. Our psychological and emotional needs for connectedness are the same as what they have been for thousands of years. The internet, if you get how to use it, is connection enhancing. The very opposite of isolating.

People who want to connect will find a way to do so meaningfully in any medium. On this trip, I am glad these online interactions can go offline. And I’m sure we’ll pick them back up online. Seamless. It’s wonderful.

Of business trips and a three-year-old

Wed, 01 Feb 2012 20:14:00 -0500

Another day, another business trip. This place is growing on me.

It’s funny but there are things mentioned in the meeting that refer back to things that happened months ago. I remember what happened and I also remember how I felt back then, how lost, how mildly terrified that I was going to screw up a big deal. Except that of course, I had no idea how big a deal. And I had no idea that this particular working relationship would turn around and become a partnership. We’ve come a really long way.

Getting to see people change is an amazing thing. Getting to see companies change equally so.

I squeezed in an extra meeting that afternoon. I got to catch up with a b school friend over ice cream. He brought his two daughters along. Kate is 5 and Jane is 3. At one point, I have a moment alone with little Jane and she decides to pretend to be Kate.

I ask Jane, “Okay, if you’re Kate, what would Kate say? Say something that Kate would say.”

Jane thinks for a long time. Then she bursts out, “‘No, Jane!!’ That’s what Kate would say.”

:)))

When we leave, I hug my friend. I get in my car. Then Jane decides she wants a hug too. So her dad carries her over. My new three-year-old friend hugs me and kisses me on the cheek.

May all your business trips be so full of blessings.

Growth requires friction

Tue, 24 Jan 2012 02:17:18 -0500

In the first couple months of my job, the two most common phrases I used to describe my experience were “thrown in the deep end” and “drinking from the fire hose”. I felt slightly overwhelmed on most days, totally overwhelmed on a few days, and it was great.

Fast forward half a year later, I work less hours (somewhat). I generally no longer feel lost. I am less stressed. Which is great… except that in order to be in flow, you need to be sufficiently challenged. Growth requires friction.

In the next 6 months, my biggest challenge will be to force my learning curve to be steep enough so that I stay in flow. I could optimize around the edges - be faster to respond to clients, know the product better, tweak processes. But that is pretty much cruising to me. Not very interesting. The point, the proper use of my effort, is to be performing at an entirely different level in 6 months.

Need to go think about how to do that.

I wrote the part above around the new year. A turn of events in the last couple of weeks has basically offered me my challenge. I’ve had to shift from thinking about what I can contribute as an individual, to what we need to contribute as a team.

And lately, I find, the less you think about yourself and the more you think about everyone else, the better things seem to work out.

(Perhaps one could also say, the less you think of yourself and the more you think of everyone else, the better things seem to work out.)

I am definitely back to feeling the learning curve. And feeling grateful for that.