What Keeps You up at Night?


I'm a night owl.

Often people will hear back from me in the wee hours because I get creative at around 4pm and then stay in flow for hours after that. By the time I realize I'm cold from the heating going to low for the night, it's way past bed time.

When I get into flow, I shut everything else down and experience deep concentration, from which I draw creativity and a sense of well being.

I was thinking about that experience at lunch, as I was listening again to this TED Talk by Mihaly Czikszentmihalyi, the man with the most challenging name for me to pronounce (he'd probably say the same for mine).

One consideration from his extensive work is the question — how do you feel when something goes well? It's where you get to play in the spot between arousal and control.

Creativity is enhanced when I suspend System 2#, or the deliberate, analytical and consciously effortful mode of reasoning colored with judgement, long enough not to talk myself out of exploring possibilities with System 1, which proposes through intuition.

There is more to that than a simply dualistic explanation. It will need to do for now so we can regain a sense of order and proceed with the question I posit in the post.

What keeps leaders up at night?

A short couple of years back, we had a series of live conversations with CEOs where we asked specifically that question looking to peel back the business layers and get to the philosophy of what drives leaders.

For example, we learned with Pernille Lopez, who was at the time President of IKEA North America how she was living and working with the policies she helped champion when she was head of HR for IKEA.

By the way, there is a reason why we say "growth curve" — it behaves more like a cycle.

We posed the question to Glen Senk, then President of Anthropologie (now CEO, Urban Outfitters), and talked about the company's retail strategy based upon their employment and merchandising philosophy.

The issues that kept these leaders up at night were all about people — employees, customers, partners take the lion share.

By the time you get to those positions, you are skilled in one domain (at least), which means you were self-driven and in control while getting there. Staying there is a completely new ballgame.

It starts with learning to manage yourself differently. It's the same for entrepreneurs, by the way.

When change happens

At around the same time, David Pottruck, who at the time had just been fired as CEO of Charles Schwab, shared with attendees of the Wharton Leadership Forum that when he went to sleep he slept like a baby — he woke up every two hours crying.

Here's how it went down — after a sudden executive session of the board, Schwab met with Pottruck (emphasis mine):

The words that followed ended a 20-year corporate career in less than 20 seconds. "I'm sorry," Pottruck remembers Schwab saying, "but the board has met and decided that they have lost confidence in the direction of the company and in your leadership. We've decided to make a change and have me come back to the office." Effective immediately, Pottruck was to step down, and Schwab would become CEO again.


In a heartbeat, David Pottruck's life — and identity — was forever changed.

In Good Business, a book Czikszentmihalyi authored after the widely-read Flow, he reports that the definition of success offered by good business leaders includes both helping others succeed and meeting challenges/being challenged.

Lack of environmental feedback is part of it. CEOs live a business reality where everyone they work with reports into them, and the people they report into they don't work with. When the two are in tension with each other, everything possible must be done to regain a sense of order.

This tension is now the new normal due to the escalated complexity of modern organizations still structured for 20th Century business and reluctantly dipping toes in the collaborative nature of 21st Century reality.

Regardless of how change happens and to whom it does, we're all called to respond. We all mourn the death of something we held ourselves to — we're connected to that identity for better or worse. We feel like a failure when we fail.

Successful people learn to let go of the past as quickly as they can by asking a different question — what contributes to a life worth living? How can I do that now?

What keeps you up at night?

Chaos and uncertainty can be very uncomfortable feelings. They make us cling to the worn path of answers that worked before.

Going back to Czikszentmihalyi's TED Talk, beyond apathy, a challenge becomes daunting when we experience worry and anxiety and feel a loss of control over how we're going to tackle it.

When our reference points are taken away, we experience helplessness, the imaginary friend that keeps us away from flow.

Ironically, it is by freezing in place and thinking the worst, or constantly looking back at what we had (or thought we had) that we gain the least clues to begin to change how we think about what we're doing now.

And we're at a loss in using creativity to make the situation better than it was before, or make a better promise altogether.

It's late at night, and the movie is all happening in our head. The brain doesn't know if it's real or imagined#. That's also the good news, and there is a whole field of research on creative visualization to back it up.

So there you are, it's night time and there's a lot on your mind and in your brain (we'll leave the relationship between those two to science/another day) — what keeps you up? It feels real to you, or you wouldn't be up thinking about it.

Can you shift the focus to a different question that very moment? Who would you be if your identity weren't so closely vested in what was or what you think it might be?

Maybe not. Maybe the best antidote that very moment is a head fake — taking a small step in a different direction, the field of possibility. It's waiting for you.


Two tactics I use to get there that give me just enough sensory feedback to get unstuck:

  1. a very small task that engages the creative side of my brain. For example, designing a couple of slides in a presentation deck for which I already did the conceptual heavy lifting 
  2. catching up on my reading or inspiration videos I saved for later in a special folder. For example, a TED Talk, re-reading a good story, or poetry. 

This is how I reconnect with the feeling of doing and purpose.

What keeps you up at night and how do you get yourself to go from obsessing about it to contributing the solution (or preparing the ground for a more fertile moment)?


Leave a Reply

Your email address will not be published. Required fields are marked *