Thoughts & Observations

Anxiety & The Art of Picking

You’re standing in the lot at the car dealer getting ready to buy a car. Do you pick this one or that one?

You’re scanning Yelp looking for a place to grab dinner. Do you pick this place or that place?

Not earth-shattering decisions, but still opportunities to get something wrong.

And we don’t like to get things wrong. We don’t like to have the finger pointed at us when someone says “who decided to buy this lemon of a car?” or “who picked this awful place for dinner?”

And the anxiety around picking escalates as the depth and breadth of impact goes up.

Have I picked the right way to phrase this email I’m about to send to 30,000 people?

Have I picked the right presenters to put up on the stage in front of a discerning audience who will write about and talk about what they see?

And if I pick wrong, am I out? Are they going to stop trusting me to pick?

We fear picking because we fear being wrong and because it seems a bit out of our control.

And yet we all know people who seem to be very good at picking, like that friend who always seems to pick amazing restaurants or perfect gifts. Or the radio producer who always seems to find just the right story to feature.

But those people aren’t good at picking because they were born with a special gift.

It’s because they have a knack for paying attention – for noticing things – and for practicing picking.

When you pick something, you have the opportunity to learn from your choice, to notice what happens.

Did that presenter that I put on stage get laughs or no reaction at all? Did that email I just sent out resonate with someone and get positive feedback, or did no one respond?

Once you get in the habit of picking, you have the opportunity to recognize patterns that help you make better choices in the future.

What are the signs, for instance, that someone will make a great presenter or a bad one? I’ve noticed that the presenters who pitch themselves the hardest to get on stage are usually the ones that fall flat (maybe because they’ve gotten used to the hard sell required to sell their product because their product doesn’t sell itself?) It might not be an absolutely certain measure, but in my experience of picking month after month, it is almost always right.

If you want to pick a great gift for a friend, the easiest way is to notice things. Not only noticing how they might react to other gifts, but noticing when they say “ooohhh, I love that!” as you’re window shopping together or when they make mention of how they desperately need placemats.

Noticing consistently makes it immeasurably easier to pick well.

And as much as picking is a practiced art, even people who pick things for a living get it wrong every once in a while. There are TED talks that are duds. The ones that make it to are the best selections, fully edited to take out the technical missteps or the moment when the presenter forgot what slide she was on.

Even when you have gotten quite good at picking, there will still be anxiety.

If there was no anxiety, there would be no risk, and it is the presence of that risk that indicates that we are in the space of possibility to create something magical.

Thoughts & Observations

No Time to Think

We no longer leave ourselves any time to think.

No open space in our days.

No white walls or blank sheets of paper.

No time when we aren’t reacting to what just happened and aren’t worrying about what will happen next.

As the amount of time that I spend responding to emails and Facebook messages and Tweets has gone up, I sense very deeply that the amount of creative thought that bubbles up during my day has gone down.

When we leave no blank space, we leave no time to notice things, no time for our synapses to connect, no time to connect the dots and synthesize bits and pieces from here and there. When we can’t do those things, we leave ourselves no opportunity to create and to make art.

We often leave no time to think for the same reason that we leave no time for exercise or any other type of self-care. We don’t do it because it can feel selfish and indulgent. We have work to do. We have people counting on us. We have people waiting for a reply to that email they sent 15 minutes ago. What are we doing relaxing in a yoga class or taking a 30 minute walk? The world needs us, so no, no, we can’t take any time for anything other than actively doing something directly in service of what the world needs right now.

But is that really what the world needs? Does the world really need us to be master emailers who get back in record time? Does the world need us to forgo our personal health and squash all of our creativity just so that we can fit in one more meeting?

We are in an amazing age where we have every technological and connection tool necessary to contribute something unique and interesting to the world. And yet those same tools – when allowed to rule every waking moment of our days – threaten to ensure that we could make it through life without much to show for it but a pile of sent emails and a clean inbox.

I think we want something different. And we can get there, if we just allow ourselves some time to think.


I’ve been thinking about all of this for a while. Staring a bit longingly sometimes at photos of rural Ireland or country roads upstate – thinking about space and time to let the mind wander. And then I stumbled across this post Scott Belsky published a couple of years ago that got me thinking even more – check it out for some of his insight and ideas on how to get some of that thinking time back.


Thoughts & Observations

Just Ask

There are many people in the world who are more famous, more accomplished, and more powerful than I am at any given moment. 

And I’ve realized that there have been times when I’ve let that stop me. It has stopped me from asking them to join us at a dinner party at our place or join me for coffee. It has sometimes made me hesitate in asking them to speak at something I’m organizing or attend an event. 

But I re-learned an important lesson recently when I reached out to a well-known author and thought leader to ask her to speak at a conference I’m organizing. As I was typing my email, the voice in the back of my head kept saying “Who are you to be asking her? She’s famous. She’s not going to want to participate. This won’t be important to her.”

I hit send anyway. And waited. 

And then something unexpected happened. She wrote me back. And it was not a rejection.

Instead she said this: “So great to hear from you! I had actually be meaning to reach out to you. I love what you’re doing.” 


The exact opposite response of what I expected. 

And all I needed to do was ask. 

Lesson (re)learned.