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.

Thoughts & Observations

When You Don’t Know How

There are a lot of things that I postponed doing in life because I didn’t know how. One of the biggest was going out on my own and starting my own business. I thought all of the people who had opened their own businesses or who had launched their own websites had some magic understanding or ability that I didn’t.

I was having a conversation with my 17 year-old co-conspirator in crazy projects, Emily-Anne, the other night and we were talking about the issue of not knowing how. We pondered whether we could create something that answered the question of “how” for potential entrepreneurs (especially kids) so that they wouldn’t stall like I did.

As we talked, there was something that wasn’t quite feeling right about our plans. Emily-Anne made the observation that there really wasn’t a way to define how, at least not in the recipe-like way that people are often craving. Yes, we could tell someone how to build a website or get their company on Facebook, but we couldn’t tell them how to BE Facebook.

When Facebook was being built, Mark Zuckerburg wasn’t even sure what he was building. He had some of the basic skills, but he certainly didn’t have a road map for how.

In fact, when it comes to launching new companies, not having a recipe is what actually creates the magic. It’s what ends up making them stand out.

I’ve been seeing a few mainstream shoe companies mimicking Tom’s Shoes, even upping the ante by giving away two pairs of shoes for every pair you buy. But there is no magic in that. It’s the same old recipe.

Saying you don’t know how is convenient way to avoid doing something.

There are lots of people who came before you who didn’t know how either, but they moved forward anyway.

You will create the how yourself, but only if you start moving.

Thoughts & Observations

A Framework for Choosing

One thing New York is not short on is choices.

Having a plethora of choices is one of the main reasons why I wanted to move here: an abundance of choices means an abundance of possibilities.

But the main problem with having so many choices is that you eventually have to pick something. I could walk out of my apartment and eat breakfast at any one of dozen places within a couple of blocks, but I can’t eat breakfast at every place at once. There are three events I want to attend tomorrow night, all happening at the same time, but the laws of physics (and public transportation in New York) prevent me from being able to get to all three in one night.

The science of how we decide tells us that the more choices we are presented, the more stressed out we get, and I will admit that one of the only things that has been stressing me out just a little bit over the past two weeks is trying to decide what to do with my time.

I was thinking yesterday about a very successful friend who has his life goals clearly outlined from where he wants to be at the end of this year to where he wants to be five years from now. He was pushing me the last time we met up to make much faster choices about what I was going to be working on over the next few months and he wanted an answer on the spot, but I found coming back to him with anything concrete incredibly difficult.

There are lots of reasons for my hesitation: I just had the disruptive experiences of stepping away from a long-term job, long-term relationship, and long-term home almost concurrently. I had also been totally caught up in the insulated world of Girl Scouts and now feel like I’m a little kid, discovering the world for the first time.

But this morning I had a big realization: it is very easy for my friend to make fast choices because he already knows with extreme clarity what his goals are. When faced with the choice between meeting with one person or another, or spending time blogging or building a network on Twitter, he can make a decision in a split second because every day he is in the habit of testing his choices against how they align with his goals.

When you don’t have clarity around where you see yourself or what you want for your life in the future, it becomes infinitely more difficult to make choices.


Thoughts & Observations

But I Put So Much Time In Already

The doctor who hated doing surgery but stuck with being a surgeon anyway, just because he had “put so much time in already.”

The writer who, three-quarters of the way through writing a novel, realized it wasn’t what she wanted to write, but finished it and turned it in anyway because she had “put so much time in already.”

The couple who has been together for 10 years and are both miserable, but decide to enlist in another 10 years of misery just because they “had put so much time in already.”

When we’re young, we’re taught the value of sticking with what we start until it’s done. And that’s a good thing because otherwise we would all be eating half-cooked meals in half-built houses that we drive to and from in half-built cars.

But I think focusing on the value of sticking with things concurrently diminishes the value of quitting. We eventually get to the point where our subconscious is constantly buzzing in our ear, telling us that quitting anything is bad.

We also tend to feel that the more time we’ve put into something, the more value there is to sticking with it. If you’ve trained for years to be surgeon, then you better damn well continue to be a surgeon. It’s as if sticking with it will somehow give it value that up until that point had been completely missing.

But zero multiplied by any number equals zero.

If I have put five hours or five days or even five years into something and it is making me miserable, not adding value to my life, not my best work, has little prospect of getting better, has little long-term benefit, or was just simply the wrong path to take in the first place, then putting in another five hours, days or years continuing down the same path is not likely to make it any better.

We avoid quitting because as much as sticking with something can make us miserable, quitting and having to start over can be downright painful. It can be gut-wrenching and vomit inducing. But I think I’d rather deal with the momentary unpleasantness of barfing then deal with feeling queasy and uneasy over the long haul, knowing I was still walking down the wrong path.

*Seth Godin has a few interesting things to say on this subject – check out The Dip

Thoughts & Observations

Bend Your Knees

When we were kids, there were two pieces of advice that my dad would impart with enough frequency to illicit eye-rolling and groans: “mind over matter” and “bend your knees.”

When he was teaching us to ice skate: “bend your knees!”

When he was showing us how to play tennis: “bend your knees!”

When we were negotiating how to balance on a moving sailboat as it cut through the water: “bend your knees!”

I was totally unappreciative of the wisdom of his advice at the time. He understood the physics of how our bodies work and realized that lowering your center of gravity in almost any situation gives you more control.

As I was navigating up an icy sidewalk in high-heeled boots the other day, I wondered how I was going to stay upright, when I remembered his advice. “Bend your knees,” I said to myself, and it worked. I glided along that sidewalk like I was back on the ice rink in New Hampshire.

As I’ve been riding the train throughout the NYC over the past week, muttering “bend your knees” to myself has kept me from doing a nose dive into my neighbors as the train jerked around the track.

But I’ve come to believe that “bend your knees” means something more than that. When you’re bending your knees, you’re not only lowering your center of gravity, but you’re also setting yourself up to be able to be agile. When the train moves suddenly, you can adjust yourself quickly and avoid completely falling over.

If you’re too stiff, too uptight, too afraid, you’re more likely to get knocked down and the fall will be harder and hurt even more.

When you’re scared and facing a lot of unknowns, inside of stealing yourself against what’s to come, bend your knees.

Thoughts & Observations

Will It Be Good Enough?

There is no shortage of ideas.

There is no shortage of dreams.

But there is a shortage of people actually willing to turn their ideas and dreams into something.

If you’re waiting to start something or launch something or create something because you aren’t sure it will be good enough, join the club. Almost everyone you know has been secretly (or very vocally) dreaming for years about writing a book or starting a company. The majority of the time, people stay in that state forever.

Everyone has ideas. So stop worrying about whether yours is good enough.

Just realize that if you actually do something with your idea, you’re already ahead of 99% of the people out there.

*Inspired by a little kick in the pants by Seth Godin