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.


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: