The Goldilocks zone between productivity and creativity

How overproductivity can stagnate your business, and what to do about it

Happy Friday, dear entrepreneurs, and welcome to Second Mountain Startup. I’m so glad you’re here.

Let’s start with a foundational belief of mine: entrepreneurs are artists, and the best work looks closer to art than ladder climbing. Not all leaders are artists (hired guns, lucky sperm, etc), but all entrepreneurs are artists.

Recognizing my own artistry, really leaning into what that meant for my business-building-process, opened up a new, much more fulfilling way of life for me.

Let’s dive in.

Entrepreneurs are artists that produce at scale

Beethoven used all twelve musical notes to compose his symphony number nine. Twelve tools, uniquely combined into 136,000 sounds (closer to 70,000 distinct sounds due to the prevalence of tied notes).

For years in running a startup, I thought I could get by with only two notes: On, and off. On, as in running full tilt toward the next objective, and off, as in recharging (either sleeping or in front of the TV) so I can do it again.

Saying nothing about the myriad costs to my relational, social, mental and spiritual health, this binary way of living that I was so convinced was the secret to my success actually stagnated innovation within my business.

I’ve since learned that there’s a spectrum. On the one side is productivity, and on the other, creativity.

As tilted as I was toward the productivity side of the spectrum, I checked a lot of boxes while slowly but surely our innovation stagnated. What had once been a font of creative output, slowly, by degrees, became an optimized machine driving ever more efficiently to where the puck used to be.

If this sounds like your average slow, legacy company, let me just say it’s remarkable how quickly nimble startups can turn into those if they’re not careful to nurture at least a little of the creative recklessness that they started with.

Legislating creativity vs the role of the leader

As a leader it’s up to you to model the behavior you want your team to exhibit. This means, yes, to increase the innovation at your company you may have to work in a slightly less regimented way yourself. Schedule less meetings. Intentionally give yourself some time to be creative. To do less, better.

Recall that this is where Google’s 20% time comes from. The structure that birthed Gmail and so many other excellent products. And it’s not just tech companies — 3M’s 15% time actually predates Google’s 20% time, and was responsible for many scientifically developed manufacturing products still in use today. Google, 3M, Atlassian, and a metric ton of small businesses around the globe, when faced with a lack of innovation, structure unstructured time for their employees to putz around and try shit. And it works.

This type of legislated fun goes a long way, but if the leader of the organization doesn’t participate, if she drives herself to the end of the productivity spectrum while telling her team to be creative, the senior leadership will pick up on that disconnect and err toward productive as well (as that’s what the boss actually values, they can see), regardless of what she says. Then, so will the people reporting to them, and on and on down the chain until it takes a countercultural effort by an employee to actually take advantage of their 20% time. Thus does a good cultural idea go down the tubes, with the leader often wondering why the heck people don’t just listen.

This dynamic (the leader’s behavior talking louder than any program she creates) is at the core of all culture work, not just innovation. While legislating creativity through unstructured fun-time is possible, it’s not practical unless you as the leader do the same with your own time.

Of course this ebbs and flows, and there’s absolutely a time for extreme output in growing a company. But as a leader it’s important to monitor how you’re navigating the spectrum between creativity and productivity, and recognize the impact that has on your team, to ensure you don’t limit your success by getting stuck too far to one side for too long.

So… Fun... Shit. How do we do that again?

This may be remedial for some, but I can speak from experience in saying it’s not for all. It’s easy to optimize yourself so far toward productivity, toward doing the right thing, that you forget how to have fun (as in, play. As in, no goal, no winner, just, play. Like your kids do. Yes, that’s ok for adults, too).

So do we just deliberately not do work things for some arbitrary amount time and hope for the best? Or might it be possible to optimize for creativity?

The question seems sort of nonsensical for obvious reasons, but in my experience there are effective frameworks for creativity. In other words, there are more productive ways to be creative.

If you’re one of the lucky founders who knows exactly how to have fun, then please do it right now. Further, please talk about it on social media to at least the same degree as your productivity porn, to help normalize fun-having in the founder set. It’s needed.

On the other hand, if you’re convinced of the importance of a little fun in the name of innovation but wondering where to start, I have an exercise for you. The Imaginary Lives exercise (modified from The Artist’s Way, by Julia Cameron) not only played a role in helping me rediscover the ten musical notes I had been missing — catalyzing a depth and breadth of creativity that is directly responsible for this newsletter, my coaching practice and many other projects — but it also made life more fun.

Imaginary Lives:

If you had five other lives to lead, what would you do in each of them?

I would be an astronaut, an author, a professional basketball player, a hippie, and a physicist. You might be a cowhand, a psychic, a scuba diver, a cop, a writer of children’s books, a belly dancer, a painter, a performance artist, a history teacher, a healer, a coach, a scientist, a doctor, a Peace Corps worker, a psychologist, a fisherman, a minister, an auto mechanic, a carpenter, a sculptor, a lawyer, a painter, a computer hacker, a soap-opera star, a country singer, a rock-and-roll drummer.

Whatever occurs to you, jot it down. Do not overthink this exercise. The point of these lives is to have fun in them—more fun than you might be having in this one.

Look over your list and select one. Then do it this week. For instance, if you put down country singer, can you pick a guitar? If you dream of being a cowhand, what about some horseback riding?

Next week, do the next one. And so on.

The secret to this exercise is in realizing that you only have one life. You probably don’t want to sacrifice your current life en toto to go off and become a cowboy, but you won’t get another chance to experience the thrill of landing a lasso unless you take steps to make it happen now. Today. In this life.

Not only does this work wonders for juicing your creative capacity (which as a leader impacts more than just you) it is a great launchpad to a more nuanced, complex, and complete way of life.


Lesson Learned: Share your runway with your team

I remember the first time I raised money, and was introduced to the stressful concept of Runway.

Runway, as in the amount of money you have as measured in time until it runs out. As in the amount of time left before everyone who works for you loses their job, and you walk away from your dreams in shame.

That kind of runway.

It’s a pretty loaded concept for entrepreneurs, loaded with fear of failure and of being vulnerable, so for a long time I didn’t share it with my team.

My logic was:

  • The company will succeed or fail based on these people’s performance, and I need them operating at top capacity

  • Knowing that we’re going to run out of cash in 60 days stresses me out, so it will probably stress them out and keep them from their top capacity

  • Therefore, to make the company succeed, keep employees operating at top capacity by avoiding sharing specifics around runway

The logic seemed sound, but that’s not how it turned out.

I remember being in a strategy meeting, when our head of Engineering blew up at me. He couldn’t figure out why the heck I would be making such shortsighted decisions when it was clear as day to him that there was a long term opportunity that would be sacrificed. I wanted to say “we only have 60 days of runway, so I frankly don’t care about the long term if we can’t hit our short term numbers.” But instead I remember coming up with some dumb reason that I only kind of believed so that I could “protect him” from the truth.

He, and others from our team, left shortly thereafter. Understandably. There were other reasons for their departure which I’ll write about some other time, but my lack of transparency around this critical issue, and the accompanying manipulative tapdancing it forced me into, were a key driver.

There can be good reasons to not share certain things with members of your team. Selective sharing is definitely not the same as lying. That said, its implications can be pretty similar.

This true story is also a parable about the cost of information silos and transparency. It relates to more than just runway.


How Zuckerberg’s tie helped Facebook overcome a growth plateau

As a leader, it’s important to recognize the importance you have as a figurehead. As a living symbol of the company you lead, for better or worse. And as such, your actions carry outsized importance.

Yes, this means that it doesn’t matter what values you write on your wall if you don’t live them personally, and that your 20% time will underachieve unless you also take it. But it also means that you can help your team accomplish great things through symbolic gestures as simple as wearing a tie.

An early employee at Facebook, Dan Rose told a super interesting story of how a specific symbol helped the team do something no other social network had ever done. I won’t spoil the story, but here’s the link:

As a leader, your actions speak too loudly for anyone to hear your words.

Far from only a cautionary statement, this is an invitation to play with symbols in your leadership. A tie, a shaved head, a slogan, when used skillfully, all go further than you think.


Mark Cuban is good people

I’m not a fan of the Dallas Mavericks, but I am a huge fan of owner Mark Cuban for so many reasons.

If you’re running low on reasons to love Cuban, I present the following without comment:


Grand Rapids welcomes a new $25mm fund dedicated to economic inclusion

I was excited to hear the news that the New Community Transformation Fund LP has closed their first $7m, and is close to closing another $17m to bring the total up to $25mm to invest into companies owned by minorities in our community.

In a move to support economic inclusion, The Right Place Inc. initiated formation of the New Community Transformation Fund to invest in second-stage businesses owned by people of color. That’s been an area where venture capital historically has flowed the least in the U.S.

“We are not doing well in a very, very big area of our community ... our communities of color have not participated in the success of West Michigan in the past 15, 20 years,” (CEO Birgit) Klohs said. “Money is always an issue for an entrepreneur, and it’s a much bigger issue for an entrepreneur of color.”

This is what progress looks like. More than protests, deliberate efforts by real people to change things. Kudos to The Right Place, Consumer’s Energy, BofA, Mercantile Bank, Spectrum Health Ventures and more for taking concrete steps to walk the walk.

Like any milestone, it’s worth celebrating this traction thoroughly. And then it’s time to get back to work.


DIVE DEEPER

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