Time to honesty

You get back, energized from the conversation over a great meal, only to find a glob of food stuck between your teeth. When you’re finished being mortified, the questions set in: did they notice? why didn’t anyone say something?

It might be tempting to question the character of the people involved, or the quality of those relationships. After all, a good person would discreetly call your attention to your teeth, so you could take action and avoid embarrassment. Instead, were they laughing inside the whole time? Or thinking of telling you but finding it too awkward?

Take a step back and invert those questions. Did you give people the impression that you’d be embarrassed? Or that you’d overreact to someone calling it out? Perhaps they didn’t feel it was their place to tell you.

Whether a morsel in your teeth, a crippling character flaw, or a terrible business decision, in every facet of your life peoples’ willingness to point out your mistakes is crucial to your success.

At what point does someone cross the arms-length boundary of formality and feel comfortable revealing the hard truth?

I call this your time to honesty, or TTH. How long this takes is partly a function of social norms, but mostly a function of how approachable, laid back, and open to feedback you seem.

It turns out, having a dangerously long TTH is common among executives and middle managers. As you rise in formal rank, be it in your business or your social circle, you begin to seem “other” and distant. People become wary of offending you or overstepping the bounds of their ranks, particularly to comment on your limitations or mistakes.

This has an isolating “death spiral” effect — the more important you become, the more you become reliant on your longstanding friends to be real with you. And as you rely on these confidants more, you perceive new acquaintances to have their guards up, and they perceive the same from you.

It’s hard to imagine that you’re complicit in your own blindness to faults; after all, it’s being imposed by others restraining their feedback. You might indulge in rationalizing your own behavior and shifting blame.

But ultimately, the fault is your own. As you get older, more important, and more set in your ways, you need to proactively counter this effect every day by leaning in and making yourself easier to approach with bad news.

The lean-in is a subtle habit worth practicing in every conversation. Sometimes it’s making a joke about yourself to demonstrate that you don’t take yourself too seriously. Or showing a chink in your armor, allowing others to see you as sometimes weaker than you’d like them to know; for example by acknowledging a difficulty, lack of skill, or missing knowledge. Anything to show that as your own world’s emperor, you don’t mind being told the new clothes are missing altogether.

Counterintuitive, perhaps. It’s the exact opposite of the impression management we’ve learned to maintain for every public action. But others will only admit your imperfections when they can see that you already know yourself to be imperfect.

Pride may cometh before the fall, but that’s a spurious relationship. It’s really perceived pride that leads to fault-blindness. The only way to limit that perception is to systematically test it and break it down through actions.

So the next time you feel a seed stuck in your teeth, don’t be so quick to pick it out. Count your TTH, and check your posture. You might need to lean in a bit.

Conversational risk

It was freezing out today. Which was pretty unusual, because it’s been really hot out lately in the middle of December. We thought it might be global warming before but now it’s so cold. But at least it’s not raining.

Sound mundane? I hope so. But it’s very real. So many conversations walk a well-trodden path: the exchange of biographic details, the search for points of commonality, exhaustion of those points, the discussion of mutual acquaintances, further exhaustion, and the soft fizzle-out on an inane topic like the weather.

Now, think fast – pick a first meeting that left a lasting impression.  What was different?

You dug deeper. You jumped around and landed on a topic that you both actually care about. You weren’t too politically correct, and didn’t act like everything you said was being recorded. By the time you walked away, you felt like you learned something new, ended up closer to each other, and laid the foundation for a continuing friendship.

Backtrack. What led you into that memorable conversation?

One of you let your guard down, made yourself vulnerable. Asked a question that might have been offensive or gotten you laughed at. Offered up a personal detail that was a little ‘unsafe’. Someone took a conversational risk.

I bet every one of your closest friendships has started with just that kind of uncertain moment. One of you volunteered to take the dive. And then magic happened.

You found the joke funny, or connected with a shared childhood experience. Or maybe you had the same opinions on those highly personal no-no topics. Politics, sex, drugs, religion, the military, your boss, relationships, education, race. It was polarizing and you ended up on the same pole, or you had a heated debate but liked each others’ style.

I’ve found some of the best conversations evolve around important decision points in our lives. Pick a tough one: leaving a job, ending a relationship, choosing a school, starting a company. Always ask ‘why.’  When you dig into how someone makes decisions, and the lessons they carry from past mistakes, you learn what really makes them tick.

But don’t get me wrong, it’s always a jump. Like hopping on the top of a seesaw and hoping this person you don’t know will get on too before you hit the ground. I’ve hit the ground a lot, but I keep jumping.

Why? I think real new friends are worth the risks. You put your social capital on the line, and nine times out of ten, you’ll fail miserably. You have to get comfortable knowing that most aren’t going to like you or agree with you. You remind yourself that the nine don’t last, but the one does. I’d take that bet any day.

So next time you find yourself with someone new, remember that you’re starting at a point on a terrain like this, but you can’t see the peaks and valleys.  All you can do is jump. The possibility of an abyss is worth it, because the upside is a summit that you’ll both carry with you forever.

If we just met, don’t be off-put by my pointed questions and deviations from comfortable topics. I’m betting we’ll find a mountain worth climbing.

Checking it once

I replaced my light bulb tonight. That may not seem like much of an accomplishment, but it’s a victory against myself.

Let me explain: in my bathroom, there’s a commercial grade fluorescent light bulb that’s been dead since before my September move-in. My roommates had cleverly installed another small lamp on the counter to avoid having to replace the fluorescent.

“Fix the bulb” has been on my to-do list for almost three months. But the list grew around it, and I took care of other tasks first. I always felt productive, checking off items every day but also adding more. So I rationalized that I simply didn’t have time for the bulb, or that it wasn’t a priority.

The truth is, I skipped over the bulb every time because I predicted it would be difficult. Getting up on the counter, being covered in dust, trying to figure out it’s type, finding a replacement in Manhattan (it’s at least four years old). Everything felt like an ordeal.

This blog is another great example. It’s been two months since I wrote my last post, and my average before that was 15 days. “Write a post” was always on my list. And the blog even had its own sub-list: the 81 drafts I’ve jotted down to remember my ideas. Every time I went to start, I felt overwhelmed. Which post was worth writing first?

So I thought it appropriate to restart my blog with a post about lists.

I’m majorly guilty here, as a self-diagnosed chronic listmaker.  Writing a list of to-dos is a relief on my memory. I forget things constantly, so if they’re on paper, at least in theory they’re more likely to get done.

We all know how that story ends, though. The very act of putting tasks in a list makes it harder to get any of them done. Let’s explore why.

Fake productivity = problem avoidance

How many of us can honestly say we attack the hardest items first? I don’t think I ever have. There’s always a task or two that you can finish in five minutes and feel accomplished. “Small wins” is a decent theory – it should be a motivator, right?

In practice, not so much. These small tasks amount to only a convenient way of tricking ourselves. We feel like we got something done, so it’s easy to reward ourselves with a little unproductive relaxation.

But you feel guilty about actually relaxing, so what happens instead? You read. Pick the feed of your choice. News, RSS, Twitter, Wikipedia, whatever. Somehow consuming information is the greatest mental trick of all, and leads to hours of rabbit trails on the Internet. You’re sitting in front of a computer and reading, which implies that it’s productive, you rationalize. It’s not purely fun. So in that sense, it’s doubly a waste of time.

I usually call this “mental masturbation”. To carry out the metaphor, reading leaves you feeling satisfied, accomplished, and tired. But also bearing no fruit — you get nothing done.

You look at the list again. There they are, the sinister tasks you’ve been avoiding. You can still get to them tomorrow though.

Maximizing and lists

The next sun arrives, and you revisit the list with fresh energy. What task should you start with, now that you’re ready to attack the hard ones?

Turns out, that’s a hard question to answer, and often we get stuck. We maximize between the tasks, trying to decide which is the most important to get done right now. We try to categorize tasks, prioritize them, and spend time planning out just how we’ll hit all the deadlines.

Planning is one of those investments that sounds logical but actually hurts. Planning ahead of our deadlines feels productive – and we can see how much extra time we have. But that makes us feel too comfortable. In project management, there’s a notion of “slack collapse” — we tend to let all the extra time pass before starting at all.

The lesson: paradoxically, we have to train ourselves not to invest so much in planning. Pick the hardest task you can think of, and just start doing it.

Getting started, really

But there’s a good reason you were avoiding that hardest task. You probably don’t know where to start.

We have a natural aversion to two things: unknowns, and asking for help. A hard task presents both. You’ve probably played out in your mind how hard it’ll be to figure it out on your own, all the troublesome steps you’ll go through, the parts you’re unsure of, mistakes you’ll make, who you’ll have to ask, and what they’ll think of you.

Most of this is over-forecasting. We’re not sure, so we guess that everything will go wrong. It’s the same mentality that makes us never try to attack our greatest goals in life. They’re hard. We won’t see benefits for a while. And we could fail.

The solution, of course, is to take one small step toward the task. Remind yourself that getting started is the most important thing you can do, even you do something wrong. It’ll be easier to pick up the task again once you’ve made a little progress.

Whatever you do, never start listing out all the steps you need to take, or breaking the task down into pieces. You’re not a factory. That conventional wisdom gets us nowhere – it’s just making another list!

So what now?

If you’ve read this far, this is pretty meta, but you might actually be engaging in fake productivity right now. Especially if this is the second time you’ve read this sentence.

My experience with procrastination taught me to re-think my personal productivity. Get started, with some small (possibly wrong) step on the hardest task you can think of. Save the easy tasks for later. And stop listing. No matter how much it feels better to list, if you can’t remember the task, it probably isn’t worth doing.

Your will is a muscle. We exercise by forcing ourselves to attack hard problems and tasks we don’t enjoy. If you don’t exercise your will, it’ll atrophy over time, and you’ll be fake productive for the rest of your life. Now is the time. Get up and do that really hard task you’ve been carrying over from list to list for the last week.

I just finished mine. Wasn’t so bad, after all.


June 25, 2009, and October 5, 2011.  What those two dates have in common is that I’ll remember exactly where I was, forever.  2009 was Michael Jackson.

And 2011 brought Steve.

[youtube http://www.youtube.com/watch?v=TahH7B_aUZc]

The song playing in the background couldn’t have been more appropriate: Speed of Sound, by Coldplay.

I was absolutely frozen in place by the lyric “if you never try, then you’ll never know“.

Steve was a brilliant man, but I had a more mixed relationship with him. I was a late adopter to the Apple craze, and resisted probably longer than anyone else.

Almost exactly a year ago, I bought my first Apple product — an iPhone 4, on August 8, 2010. Prior to that, I had never owned another Apple product, nor used any of its software, including iTunes.  I found it too unbending to my desires.

In Steve’s world, functions were stripped of excess to their core. In my world, having choice meant better fit, and choice meant more functions. So I resisted.

But as I reflect today on how deeply my iPhone has embedded itself in my life over the last year, I better understand how Steve’s vision has inspired and improved lives of millions.

Simply put, Steve stood for perfection.  He wouldn’t release something that hadn’t reached it. My iPhone experience was so dramatically better than any phone I had previously owned that I now have trouble imagining what life was like before it.

Now, as we all collectively ponder Steve’s legacy, I find more understanding of his management style. He was a notoriously difficult leader, with an extremely strong sense of vision, and an unwillingness to settle for anything less than what he imagined possible.

This makes more sense in context of his passing away.  Steve had no time for imperfection.  He lived every moment as part of his legacy.  He lived as a man would when he knew he was running out of time.

We often pay lip service to living like it’s your last day, and think up bucket lists for ourselves in terms of things we might like to experience before we die. But how often do we internalize them?

Steve’s bucket list contained entire markets and categories of things we interact with.  And he lived with the fire of someone who knows he’s almost out of time. Yet he did that for years, instead of months.

So he checked off most items in his bucket list, and changed the world over and over again.

Tonight I can only echo the thanks that many others have given to Steve for inspiring us all. “Change we can believe in” matters most when the change actually happens. And change he did.

Stacking business cards

I started a new job a few weeks ago, and my employer unwittingly gave me a bunch of future collectibles and items worthy of a museum. Let’s quickly recap the process:

  • Filled out a bunch of government and insurance forms by hand
  • Got a box full of crisp new business cards
  • Given a plastic corporate credit card
  • Had my picture taken and got issued a prox card for the building
  • Was mailed an insurance card
  • Set up direct deposit by stapling a paper check to a paper application

Sitting at my desk for an hour on my first day filling out forms, it struck me how absurd this will all sound in ten years’ time.


Quickly, let’s review the several ways these old processes are going to die:

  • Near Field Communication – no need to exchange information by holding anything other than a phone.  I don’t suspect that I’ll be using many of these 300 business cards.
  • Virtual wallets – plastic cards won’t be around for too much longer.
  • Electronic distribution – already exists, but hasn’t made its way into older systems like insurance credentials yet. So they’re still sent via snail mail. But the USPS itself won’t be around for much longer in its current form.
  • Persistent, linked virtual and real-life identity – at some point, governments will issue us all credentials that we can use for jobs, security, applying for credit cards, and so on.  No more bringing your passport to the office to fill out your I-9.
  • Remote access control – my credentials to enter the building will reside on my phone, and can be tracked and granted/revoked remotely.  See the Yale NFC door lock.

That said, these changes won’t see substantial adoption for annoyingly long.  Michael Arrington wrote about business cards dying three years ago. And probably a hundred companies have started to attempt to manage the problem.  Yet still the paper cards persist and I got a new pack in 2011.

It’s a great reminder that, while things happen lightning-fast in tech world, the “normal” world still inches along. And summarily rejects the majority of our attempts to uproot systems that have existed happily for decades.

Humbling and frustrating at the same time, but it makes me so excited to write a retrospective on this in October 2021.  It’s on my calendar already.

Say their names

José comes all the way from Costa Rica every year, leaving his family behind for six months.  Peter moved here from Ireland fifteen years ago and thinks Americans can’t drink.  Aubrey lives in the Bronx and remembers every Yankees stat you could think up. Mae just started a new job and doesn’t know many people in the city yet.

What do these people have in common? You’d probably never have noticed them.

As I go about my day, I’m overwhelmed by the thought of people who made it possible. I’m not talking about parents, who made all of my days possible.  These people play a more subtle role, making life just a bit easier in this particular day.

Some are distant.  I type this post on a keyboard that twenty people handled between its assembly and my use.  I may never know who they are, because it’s abstracted away from me. Logitech didn’t make my keyboard; twenty nameless people did.  But I have only Logitech to thank for these keystrokes.  I know nothing of these individuals and what they sacrificed for me.

Yet some of these people are much more accessible.  José woke up at 5 AM, mopped the lobby floor, and opened the door for me on my way to work.  Peter cleaned all the front windows, even though his back isn’t great.  Aubrey stays up until 3 AM each night, alone, keeping our office building safe.  And Mae took out our trash, got on her hands and knees, and scrubbed around eight toilets — even in the hard to reach places.

A couple weeks ago, I realized I had passed by all of these people, and many more.  I smiled, but didn’t know who they were.

Could you imagine if your life’s work was completely taken for granted?

So I asked.  I gathered up the courage (why does it take courage?) and said hello, introduced myself, and asked their names.  They were all taken aback in different ways. This is outside of social norms, for whatever reason, and some didn’t know how to respond. Mae was hesitant because she thought she had done something wrong.

It didn’t take me long.  I spent maybe five minutes learning a bit of their life stories, and exchanging some of mine.

That half hour of conversation has added more fulfillment to my days than all the office chats I’ve had in three weeks.  I know some more people, they know me, and for thirty seconds passing by I can remind them how meaningful their personal sacrifices are to me.

All it takes is a handshake, a smile, and a name.

So, here’s a challenge to you and to myself: be mindful of what it took to make your life easier. And get to know one person you see every day but don’t know anything about.

Then do it a few more times.  Soon enough, you’ll have a little family to greet every day. And I’m willing to bet that they smile bigger than your coworkers.

Labor therapy

June to August 2011 marked my last ever commitment-free summer.  I spent the majority of the time in Cali and Seattle, picking up web programming and devising a startup.  Soon I found myself spending 80% of my waking hours at my computer. Though I flew west bearing four books, I had finished only two by late July. Between code, e-mail, chat, Twitter, blogs, and distractions, there was seldom time to think – let alone disconnect.

My salvation came in the form of a kitchen table, purchased at IKEA for my friends’ new place. It was almost perfect for their dining room, but the wrong color: a faux-antiqued chestnut stain.  I offered to re-stain it a more modern ebony.

The last time I had undertaken such a project was over six years ago, staining a small bench at my house.  So when the painstaking process of sanding every surface of the table and matching chairs — over 40 pieces and 130 surfaces — took a whole week, I found myself frustrated and anxious to finish every day.  Nightfall was my enemy.

Yet the time I spent outside on that deck, sanding from sunrise to sunset, was actually quite calming.  There was fresh air, an absence of electronic distraction, and time to think. Sawdust is so sublimely hostile to our gadgets and devices that they dare not enter the land of the workbench.

Calculating it out, the week and a half I spent sanding and painting was the longest contiguous time I had not been in front of a computer, for about as long as I can remember.

While my hands were at work, it freed my creativity. Ideas, which would normally linger on the tip of my mind’s tongue, were consummated into full mental soliloquies. Every day I spent on the table, I came back inside with ten ideas to note down.

Working on a project with my hands was about the closest I’ve gotten to a vacation in years.

Many digital natives like me pass time at the office as so-called “knowledge workers.”  Our tools are our minds.  So on most days, we try to satisfy our inner thirst for kinesthesia by running on treadmills and playing Wii sports. But with music blaring and a TV on, the sense of solitude is missing.  As is the feeling of creation when you make something from nothing.

So let this be a reminder that a vacation to get away isn’t always the answer. Pick a project, build it, fix it, cook it, paint it.  All it took for me was some wood and thirty bucks at a hardware store.

P.S. here’s the actual finished table, in case you were wondering:

Baby gaga

Staring at a blank canvas is both daunting and inspiring at the same time. I imagine this is how many parents feel when looking at their babies just after birth. Perfectly innocent, malleable, and dependent on your every move.

So I’m puzzled when I see so many parents paint without giving thought to the works they’re creating.

Here’s an early example. Babies acquire language from the sounds they hear and context they perceive. No matter which of the various theories you believe, the way adults speak helps kids learn pronunciation, syntax, and vocabulary.

Why, then, do parents babble back to their babies? Goo goo, ga ga, fawning sounds and exaggerated tones. These hinder, rather than help child development. We learn best when our abilities are stretched constantly, and when we can test many hypotheses rapidly. Babies do this experimentation when babbling, but rely on us to actually spend time interpreting and correcting them (as detailed here).

The babble-back mindset carries on into later stages of growth in a more subtle way. Parents and teachers dumb down their ideas and words, presuming kids won’t be able to understand. And when kids ask questions, it’s much easier to blow them off with a quick answer than to go into detail on a topic, only provoking more questions.

As adults, it’s our responsibility to raise children who love learning, grow constantly, and are never deprived of their potential. Yet we do just that, every time we try to fit kids into our image of what a child should be — innocent and incapable.

Sometimes, this image of our kids can even have long-term psychological effects. When we assign them levels in school, we implicitly assume they can only achieve within their appointed level, breaking that confidence that leads to expanding beyond current abilities.

Worse still, these presumptions can lead to unintentionally destructive value messages. Lisa Bloom noted last week that when adults meet young girls, they default to commenting on how pretty the girls are, outfits, hair, makeup, and the like. She reminds us that, if we always jump to beauty, girls learn that’s the most important thing for them to focus on.

So let this be a reminder: to talk to babies like normal people, to empower kids to reach out and explore beyond their capabilities, to answer their questions, and to be intentional about the values we imply with our choices of words. Just because the canvas is a child doesn’t mean we should finger paint.

Conversation, hold the coffee

I’ve taken a lot of meetings this year, and aside from meals, they always seem to follow the same format. We meet for coffee, or drinks, or dessert, at a nearby shop, and spend about an hour, at a cost of somewhere from $5-15.

And that would be totally fine, except that I don’t actually drink coffee, and rarely want any of the other assortment of snack and drink options. I’m neither hungry nor thirsty for anything but a good conversation.

It bewilders me that so many people who don’t actually want a cup of coffee would meet at a coffee shop, buy one or more, and drink them. Every time they have a meeting!

I’ve tried to understand this behavior, and I’m sure there are some rational explanations. Maybe it’s:

  • Space that’s neutral and not ‘owned’ by either party
  • Convenient location somewhere in between both people
  • Ability to leave whenever you want by just finishing the drink
  • Setting that’s not too intimate and not too formal
  • Public area in case you’re afraid of the person (?)

But actually, in most cases, I think it’s out of habit or social norm. Meeting for coffee or drinks is the standard good excuse to spend a significant amount of time in front of someone. We need these to avoid feeling awkward, and to ensure we can quickly justify the meeting without committing too much.

It seems those needs are a bit foolish, and end up exacting a rent on the meetings we have with others. Talking is free, but coffee is $5. Why put ourselves through this social dance if neither party actually likes the beat?

This extends to other social meetings as well, including time spent out with close friends. Often the need is to feel like you’re justified in spending a night out together, by having something socially acceptable to talk about. “We were out at a lounge” is a great way to avoid anyone noticing that what you actually wanted was time together.

Our quality time ends up being much stronger when there are no distractions, anyway. So let’s take a walk or go to a park. I promise, we’ll both remember more of the conversation.

So, if you happen to be meeting me and suggest coffee or a bar, I might decline and forward you this post. Please don’t be offended, but I don’t really want to pay someone’s Starbucks dividend. I just want to spend some time talking to you.

Jobs: a roundup

Yesterday the east coast had an earthquake, but today the entire world was shaken by the news that Steve Jobs stepped down as CEO of Apple. He’s going to continue as chairman, but retiring from daily operations.

He leaves at a time when Apple is truly at its height. He’s disrupted some of the biggest industries in the world: phones, PCs, music, and publishing. Apple’s products have dominant marketshare in markets they almost entirely mainstreamed – smartphones, tablets, ultra-thin computers. And they’re on the verge of launching major product upgrades in the coming months, and maybe even more.

An investment in Apple in 2006 would have 4x return to the beginning of this year, and Steve leaves at a time when Apple became the most valuable company in the world by market cap (exceeding ExxonMobil).

So, here’s another roundup of the best articles about Steve I’ve found around the web today:


NY Times: Jobs Steps Down at Apple, Saying He Can’t Meet Duties

WSJ: Jobs Quits as Apple CEO


AdAge: The 10 Best Ads to Come out of Steve Jobs’ Reign at Apple

GigaOM: Steve Jobs in Magazine Covers throughtout the years

WSJ: Steve Jobs’ best quotes

Wired: Money Quotes, Steve Jobs Style


Robert Scoble: A Front Row Seat to Steve Jobs’ Career

Vic Gundotra: Icon Ambulance

Marc Hedlund: You’re The Ones

James Altucher: 10 Unusual Things I Didn’t Know About Steve Jobs

Dharmesh Shah: 16 Brilliant Insights from Steve Jobs 1997 Keynote

Omar Malik: Steve Jobs and the sound of silence

Josh Bernoff: Steve changed the world five times

Walt Mossberg: The end of an era

Steve himself

And of course, the famous Stanford commencement speech: Text and Video

These paint a picture of Steve in the aspects that I most admire. Yes, he has incredible vision and obsessive dedication to quality. But he is also very humble, and a thinker, and an inspiring leader.

What most amazes me today is how Steve’s managed to even touch my own life. A sworn anti-fanboy from my first contact with a bright green iMac in fifth grade and its one-button mouse. Even I am using an iPhone today, begrudgingly love it, and will be buying the next one. Bravo, Steve.

This post is mostly for posterity, and to remind myself at some point in the future to Think Different.