Thoughts & Observations

Actionable Empathy

I didn’t really understand how important dedicated bike lanes were until I tried riding a bike in a part of the city that doesn’t have them.

I didn’t understand how crappy the software was that some of my staff had to use every day until I sat down and spent a few hours trying to use it myself.

It wasn’t that I hadn’t been empathetic about these situations in the past. I always thought bike lanes were a good idea. And I certainly listened to my team when they complained about their software.

But I didn’t really, truly understand deep down in my gut until I actually became the biker and the software user.

Before, I simply had empathy.

After, I had actionable empathy – empathy that would move me to do something, to fix something, or to at least be prepared to shout my support instead of keeping it quietly to myself.



Thoughts & Observations

An Infinite Supply

Yesterday, I was thinking about being ready for opportunity, which subsequently got me thinking about what happens when an opportunity disappears – when you lose a job, when a relationship ends, or when what was supposed to be your big break ends up barely qualifying as a small crack.

Our tendency is to flip out a bit. To get angry. Or sad. Or both.

And our tendency is to assume that we’ll never get an opportunity like that again.

But if we’re really being rational about it, that doesn’t make any sense.

Whatever opportunity we are a lamenting the loss of probably came our way unexpectedly. We didn’t board the airplane expecting to find love or sit down at the coffee shop expecting to find a job. But we did.

The supply of unexpected opportunities is actually infinite. No, they won’t be the same. They will lead your life in different directions. They will teach you something different. But they will be there. 

And the interesting thing about unexpected opportunities is that the more you open your heart and mind to them, the more they show up.

Some of the things that have happened to me over the past few months have seemed a little magical to some people. But the only magic, perhaps, is in my shift in mindset. While I do seek opportunities and work hard to make things happen, I don’t pursue things with desperate aggression or with a unilateral vision on one and only path. Instead, I make sure that I’m open to whatever people and opportunities show up.

Approaching the world that way has helped me appreciate and enjoy what I have in the moment, understand the lessons from it when it goes, and be ready for the next thing when it comes. 

Thoughts & Observations

What’s the Prize?

We often go through life behaving like we’re trying to win a prize. 

But I was thinking the other day…what, exactly, is the prize? 

We’re competitive, constantly comparing ourselves to other people, trying to have more Facebook friends, get more Twitter followers, sell more books, get more press, win more awards, or earn more money. 

And there was a point when those prizes held some level of value for me. They are easy, visible validators of our existence. 

But I realized the other day that except for the almost impossible to curb occasional twinge of natural human jealously over someone’s massive Twitter following, I have lost all of my desire to win for the sake of those prizes.

It isn’t the prizes that matter, it’s the work that matters. And not just any work, but work that is transformed into meaningful art – art that gives the world a prize instead of the other way around.

Thoughts & Observations

When Input Exceeds Output

In the past two and half weeks, I have spent most of my  time putting New York City’s public transportation system to work, transporting me from meeting to meeting throughout the city while I try to absorb as much as can of the New York tech scene.  My days have often started with breakfast meetings and not ended until after midnight, when the networking drinks were done. 

This time has been all about input: listening in meetings, reading emails, scanning my Twitter stream, reading blogs. 

This is not all a bad thing. I needed to rapidly gather information so that I could get a running start in my new role at NY Tech Meetup, and I’ve gained some great insights that will provide amazing guidance going forward. 

But I was listening to an interview with Sherry Turkle, author of Alone Together: Why We Expect More from Technology and Less from Each Other, the other day, and it hit me how much of an issue we have with input vs. output.

Turkle talked about how most of our days are built around trying to keep up with input from every direction. We in fact spend so much time trying to deal with input that we have no time to think or be creative, or actually create any output. (and no, email doesn’t count as real output)

It’s kind of like calories in calories out. If you gorge yourself on too much food, you get so full that you are hardly capable of doing anything – you just want to sit around, hold your belly and groan. A diet consisting of too much information input creates the same kind of paralysis. 

With calories, we balance the calories in by exercising and making sure that we burn some of them off. We need to do the same thing with information input.

If we turned off the flood of input for chunks of time during the day, we might actually get something real done.

Thoughts & Observations

Finding Autonomy

I’ve been feeling pretty content lately. Something that I talked a little about here and here.

And because this feeling of overall contentment is somewhat new to me, I’ve been wondering where it’s coming from.

Superficially, I could say that it’s situational: New York is pretty awesome.

But I think it’s something deeper than that. I think a big piece of my contentment has to do with my level of autonomy.

I have more autonomy now then I have ever had at any other point in my life.

From what brand of toilet paper I buy to choosing to eat a cupcake for dinner to what meetings I take and what projects I work on to where I work on any given day, it’s all up to me. I am the architect of my life.

It makes total sense that this is influencing my level of contentment. Autonomy is one of the key factors in motivation and engagement. And I think one of the key factors influencing how content we feel.

When oppressive bosses and governments create environments void of autonomy, it should be no surprise that people eventually find some way to rebel.

Thoughts & Observations

The False Advertising of Happiness

A friend of mine once told me that he wasn’t striving to be happy, he was striving to be content.

And I think I have to agree with his approach. Striving to be happy all of the time puts a lot of pressure on us, and then we tend to focus on all of the moments when we’re not happy. And the truth is, we can’t exist in a constant state of joy and delight every minute of every day.

But I think we can strive to reach the point of being content. The point where we’re not always wishing we had someone else’s life or someone else’s stuff or someone else’s lawn.

This doesn’t mean settling and it doesn’t mean not pushing to make things better. But it means reaching a place where there is a consistent undercurrent of contentment flowing, no matter what your day is throwing at you.

Somehow, over the past few weeks I have found that place of peaceful contentment. It seems strange in a way, because on the usual list of what is supposed to make us content, I’m missing a few things: my sublet runs out on March 9 and I have no permanent place to stay after that, I have no consistent paycheck, I’m not in a relationship, I don’t own a house or a car, and I never seem to have enough time to get all of my work done.

That’s not an equation that most people would think adds up to being content. But I feel more content now then I did when I had all of those things.

Not only do I think I had been striving for the wrong thing, but I had bought into the false advertising of what I needed in order to get there.

Maybe that’s ok when when you’re caving into buying a ShamWow! for the low, low price of $9.95. But when it comes to my life, the false advertising is no longer going to have such an easy time winning me as a customer.

Thoughts & Observations

The Only Path Was That One

There are things I’ve done wrong. Bad decisions that I’ve made. Things that I would do differently if I had an opportunity to go back and do them again.

In the end though, I’ve come to realize that the only way I’ve ended up where I am now is by going through everything that I went through in the exact way that it happened. Had one variable been different, my life would look different.

And the truth is, I don’t want my life to look different. Despite the bumps and bruises, the ups and downs, and the fleeting moments of freak out about surviving on my own, I feel content.

The only path was the one I took and that makes it pretty difficult to have any regrets.

Thoughts & Observations

How Seth Godin Plays Pictionary

Seth Godin is really good at Pictionary. In fact, from what he says, he rarely loses (a fact also just confirmed by his son Alex).

This is how he does it:

Before the person drawing can even get their pen down to the paper, Seth starts shouting out words. He continues to shout out whatever words come to mind even when the only thing that has made it onto the paper so far is a single straight line. As the drawing takes shape, he continues with the barrage of words until he inevitably guesses correctly and wins once again.

Most people don’t play Pictionary that way. Most people hesitate because they are afraid of saying something stupid. They think, and pause, and edit. They don’t want to be judged. They’re worried they will say something crazy and everyone will laugh at them.

We all hesitate for that reason more than we think.

Try writing the words “I am afraid people will laugh at me” down on a piece of paper.

It looks a little ridiculous. Because, really, as a thing preventing us from moving forward, it kind of is.



Thoughts & Observations

Stress and Creativity

Two weeks ago, I went to an interesting Meetup: ClubTED was created because Erika, the organizer, often found herself watching videos of TED talks and then felt the intense desire to discuss them, but had no one around to discuss them with.

A group of about 10 of us gathered in the loft office space of Loosecubes to watch and discuss Elizabeth Gilbert‘s talk on creativity.

One of the key areas of debate that rose to the surface after watching the video was the idea of whether stress and pressure kills creativity. One person in the group had the perspective that the best creativity can only come in a completely stress-free state.

And I can see where that thought comes from. Being in a world that is driven by deadlines and staying ahead of the competition can create an almost paralyzing level of stress. We reach information paralysis with increasing frequency – not only can we absorb no further information, but we can’t do anything with the information we have. Our minds become overstuffed filing cabinets, the kinds packed so tightly that you can barely see what they contain anymore, never mind fitting anything else in.

I would agree that creativity can be a little bit difficult to spark if you have a boss standing over your shoulder demanding that you be creative on the spot – like creativity is some kind of on-demand performance in a circus side show. Quick side note: This is one of the main reasons why I don’t believe in company-mandated creative time (i.e. the 9 to 5 work day).

I think the “creativity can only exist in a stress-free state” perspective may also stem from the timing of when many of us get creative ideas: it seems to be when we are doing something unrelated to the problem we are trying to solve, and something that is often very relaxing, like taking a shower or going for a walk. But the reason that we have creative ideas in those moments isn’t because they are stress-free, it is because we have placed ourselves (and the problem we are trying to solve) in the fresh context of a different situation.

I don’t think that creativity only comes in a tension-free state. In fact, I think it is the existence of some tension that pushes creativity forward. Without some amount pressure, you enter a state of stasis and complacency. In that state, the motivation to think, to change, to move, can become almost non-existent over time.

Creativity tends to rise when there is a tension between the two forces of serenity and stress.

Thoughts & Observations


Disappointment only exists in the context of our expectations.

If we expected nothing, then we would never have anything to be disappointed about.

If you were expecting a big bonus, but didn’t get one, you might get upset. This is not because of the absence of the big bonus itself, it is only because your expectation wasn’t met. If you hadn’t been expecting a bonus in the first place, there would be nothing to be upset about.

This is important to keep in mind, because often times we sink in pools of disappointment not because what is actually happening to us it bad, but because it is failing to live up to what we wanted.

I had visions that when I didn’t have a standard 9 to 5 job any more, I would finally find time in the day to do everything I wanted: exercise, read lots of books and other people’s blogs, tackle more of my Regret Me Not lists, meditate, spend lots of time connecting with friends and a whole host of other things on top of the actual work I’m doing right now to pay the bills.

I’ve been feeling disappointed that I haven’t been able to fit as many things in as I wanted to and am hard on myself for not somehow being able to conjure up magical powers that enable me to function without sleep or cram 40 hours of work into a 24-hour period.

But when I stopped to think about it, the only reason I’m feeling disappointed is because my expectations for what was possible were so big. It’s not a bad thing to set your expectations high – it means that you stretch and really push yourself to try and meet the bar you’ve set.

In the end though, if you spend too much time focusing on how your expectations aren’t being met, you miss all of the amazing things that are happening. Especially the things you never knew to expect in the first place.