"The only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars. . ."

Jack Kerouac attended Columbia on a football scholarship. This was an ironically "All-American" start for a young man who later became a central figure in the notorious Beat Generation which defied formal academics, renounced materialism, and loathed society-anointed "values".

His life doesn't fit the profile of someone we'd typically look to for leadership advice: Jack Kerouac never became a billionaire. He didn't start a tech company or become a Fortune 500 CEO. The only "unicorns" Jack knew of were from his psychedelic encounters while driving across the country with Neal Cassady (if you haven't read On the Road, highly recommend).

But despite his lack of business credentials, Jack was a true visionary who's eccentric lifestyle yields three powerful traits for those aspiring to grow in their leadership career:

  1. Authentic: embrace your "true original" inner spirit
  2. Simple: value the elegance of simplicity over complexity
  3. Spontaneous: harness the creativity—and fun—of life's serendipity

In short, be an ASS*. 

*I couldn't write a blog post about Kerouac and leadership in good conscience without somehow incorporating his special brand of counter-cultural irreverence. So there you have it: be an ASS. I hope Kerouac would approve.

Let's expound on these traits a bit.

AUTHENTIC. What does it mean to be authentic? Why is that important to good leadership? In short, authenticity is the absence of inner bullshit. It is comfort in candor. It is the ability to embrace your "true original" inner spirit while knowing—sometimes in a self-deprecating way—both your strengths and weaknesses. Authenticity isn't just important to good leadership, it is critical. Your peers can sense posturing, conflict and optics a mile away. Being authentic is the antidote to all perceived bullshit. The best article I've ever read on this topic is Tim Urban's Why you should stop caring what other people thinkTim elucidates the idea of your Authentic Voice in a uniquely powerful way to help us all become more true to our inner authenticity.

This is step 1.

SIMPLE. Today's business world has an insatiable appetite for complexity. At times, it can make your head spin. To address this challenge, our team recently spent a full-day offsite ruminating on the idea of "exceptional simplicity" to figure our how we can do the simple parts of our job (Customer Success) exceptionally well. One CSM offered up the idea of In-N-Out burger as a tangible example of "exceptional simplicity" in practice: simple menu, consistent, tasty. Does your leadership style or business workflow resemble the menu of In-N-Out or McDonald's?

If your leadership style or business focus resembles the myriad of options on the right, it might be a good time to get back to beat basics. A the saying goes, if you have more than three priorities, you don't have priorities.

SPONTANEOUS. The Beat Generation was know to prize spontaneity, particularly as a catalyst for creativity. For today's leaders, spontaneity can be an incredibly effective trait to harness the creativity—and fun—of life's serendipity.

Why in spontaneity important? Because business is inherently NON-spontaneous. The nature of business is often planful, deliberate, and predictable. Adding a dash of spontaneity to your leadership approach can help you break through the rote monotony of the work day to unleash your team's creativity and passion.

“Whee. Sal, we gotta go and never stop going till we get there.” “Where we going, man?” “I don’t know but we gotta go.”  - Dean Moriarty speaking to Sal Paradise, i.e. Neal Cassady to Jack Kerouac; from On the Road (1951)

This isn't to suggest being spontaneous in, say, a sales forecasting meaning. . .

VP Sales: What is your expected new bookings growth in Q3 2016?

You: I don't know, could be anything! We're being spontaneous is our approach this quarter. We'll see what happens and update everyone when the impulse strikes.

{awkward silence}

{VP Sales' face gets redder, twitchy}

VP Sales: You're fired.

To be sure, process and predictability exist for very good reasons in business. By embracing spontaneity, however, you can amplify your special brand of leadership and set yourself apart.

How you can be spontaneous as a leader:

  • Instead of taking your next meeting in a conference room, ask the other person if they'd be open to going for a walk
  • Surprise your team with an unplanned team lunch outside the office
  • Share positive feedback on the fly
  • Instead of your typical team meeting, take your team to a nearby park and draw stuff on construction paper
  • Hire Speechless to deliver their (amazing) improv session with your team

Okay, let's recap:

Leadership learnings from Jack Kerouac. In short, be an ASS!

  1. Authentic: embrace your "true original" inner spirit
  2. Simple: value the elegance of simplicity over complexity
  3. Spontaneous: harness the creativity—and fun—of life's serendipity

Let's make Jack Kerouac proud. Let's go Further.