I like to listen to podcasts when I walk my dogs.

These are my dogs.

Aren’t they just the cutest? 😍

I especially like to listen to Lenny’s Podcast. On one such walk, I listened to Lenny interview Sam Schillace. Sam is the Deputy CTO and Corporate VP at Microsoft (he’s also self-employed at “Not interested in consulting” 😆).

At the time, it was a challenging time at work where a lot of things I thought we’d figured out weren’t working anymore. As a result, a lot of new ideas were thrown around, and things I’d worked on personally were in question.

It was a real crossroads: I could get defensive and push back, or I could reframe my thinking and be open to new ideas and approaches. Truth be told, I was struggling.

In swooped Sam’s thoughts on pessimism vs. optimism, and they were exactly what I needed both personally and also to effectively lead my teams through a hard transition.

I just personally feel like [ being pessimistic ] I’ve missed out on more than I’ve protected myself from. If I sum up both sides of that equation over my career, I wish I had been more open-minded and more optimistic, and more willing to try things, and more focused on possibilities rather than problems…And actually, the best posture in that world is to be creative and curious and open and optimistic and try things…

Being pessimistic is safe and comfortable. And by pessimistic I mean that you’ve gotten to a point where you’re not really trying to push the limits anymore. You’re not open to new ideas because you think they aren’t good or they aren’t your ideas or that they’re a waste of time and won’t work. Things are already fine the way they are, why do something different? Fill in the blank. You know the mindset, and I guarantee we’ve all been there at some point in our career.

But if you want to innovate (or even just dig out of a hole), you have to break out of that mindset and find yourself in the land of possibility and wonder again. You have to be open to trying some shit and asking dumb questions and just seeing if it works.

To quote Lenny’s paraphrase of Sam’s ethos:

“Get to the edge of something and fuck around. That’s the strategy.”

A lot of designers actually like to fuck around at the edge of something. But they don’t do it very often. Why?

Maybe it’s the twenty items in the backlog. Or the stakeholder telling them what to build rather than defining the problem. Possibly the scathing critique from other designers or PMs or engineers or execs (or all of the above) of a design that took a real risk. You name it. In this job, it’s easy to get pessimistic, and pessimists love company. Together, they can commiserate and infect an organization. Then nothing gets done. At least not of consequence. You might ship a lot of shit, but it’s not moving the needle.

A lot of people can make a living hoping around from job to job where pessimism is welcomed by other pessimists…for a time. But you won’t build anything great.

You can’t both be simultaneously pessimistic and innovative. The very nature of innovation requires hope that the future can be better. And, well, that takes optimism.

Now, I’m not saying “Be gullible or Pollyanic. Say yes to anything that comes your way. Don’t be critical.” That would be stupid.

I am saying be open. Have a default mode that says, What’s interesting here? Where could this idea lead us? What am I not understanding yet? Why am I resistant to this idea? How can we do that? If not this, then what?

Not, We can’t do that. Not hiding behind process. Not saying, Sure! but really thinking no way. Not closed minded and closed off.

How can you build anything of worth that way?

I guess what I’m trying to say is, with everything you’ve got, get to a default mode that says, Let’s fuck around and find out. Only then will you have a shot at building something great at the edge.