When I worked at Bloomberg a decade ago most of my colleagues were lifelong investment bankers. Many had been groomed for this job their whole life. Their greatest ambition was a bigger bonus, a bigger job title, a fancier vacation. Many would stop at nothing to accumulate these things.

And then there was Jane.

Jane was a brilliant tech analyst who wore jeans if she didn’t have client meetings. I always thought that if Debbie Harry (pictured above) had worked on Wall Street rather than as a punk singer she would have looked like Jane. She took her team out for a long, boozy lunch every Friday, and cared deeply about them. She encouraged them to challenge her. In a culture that was cutthroat and Darwinian, Jane was compassionate, bold, and humble. She was also brilliant. Her investment ideas consistently outperformed. She and her cluster of analysts sat behind me and my cluster of analysts. And I badly wanted to be on their team.

One day we received a memo dictating that we needed to be in the office by 7:30am and stay until 6:30pm. After three warnings we’d be fired.

Jane called our intimidating group CEO when she read it. “Hi D****, it’s Jane. I got your memo about taking attendance. Thanks for sending it. I’ve thought about it, and you should just fire me right now.”

D**** said the rule didn’t apply to her and her team.

“That’s not the point“ Jane said calmly. “I’m too old to be treated like a high school student who got caught cutting class. We’re either delivering growth or we’re not.” 

So Jane left. She wound up working for a huge hedge fund and making tons of money. She brought most of her team with her. I miss Jane.

Jane was a Business Punk.

A Business Punk contains two qualities that rarely exist in one person: vision and chutzpah.

Vision - they clearly see how things should be different and better than it is.

Chutzpah - they are undeterred by the threats that drive every other visionary to abandon their dreams, hate their job, and collect their paycheck. If they have to choose between impact or prestige they choose impact every time. Come what may.

Below, I unpack how people arrive at that magic combination of vision and chutzpah that makes a Business Punk.

“Free within Ourselves”

“We build our temples for tomorrow, as strong as we know how, and we stand on the mountaintop, free within ourselves.” This quote from Langston Hughes pretty much nails it. A Business Punk is what you become after you reject someone else’s definition of success and define success for yourself. At some point, usually between the age of 35 and 55 (probably correlated with a degree of economic stability, savings, and boredom), you care more about honoring your own version of winning than complying with someone else’s. That transition is how we do the best work of our lives as the truest version of ourselves. 

The Urgency of Now

Business Punks feel a sense of urgency to detach from stagnation and embrace change. The ‘maybe someday” excuses that lead us to defer our biggest dreams are drowned out by a fiercely urgent “right now.” This often means they walk away from stability, security, and prestige that most people value above all else. 

The Power of No

After I left Bloomberg I lost the ability to lie about myself. I couldn’t pretend to admire McKinsey, or care about golf, or Coldplay, or the new Escalade, or to engage in some pissing match about who bought Apple stock when it was $30/ share. I loved punk music. I built great products that were contrarian and swam against the tide. I had a deep understanding of corporate obstructionism and how to innovate in the face of it. I loved working with people who had the courage to speak truth to power. I had no problem getting fired for building something incredible that broke the rules.  And, under no circumstances, would I ever wear a suit to work ever again. So don’t ask me. I’d rather be rejected for being me, than be accepted being someone else. When you become a Business Punk, everything that isn’t a “Hell Yes!” is a “No”.

Punk is love - not war

There are certain moments in every company's life when the status quo creates a crisis of such epic proportions that the only person who can rescue the situation is a complete outlier who in the normal course of business is often ostracized and isolated. What you learn as a Business Punk is that you are uniquely qualified to add tremendous value in those situations. But Punk is an act of love - not war. It took me a while to have compassion for the institutions and people that sustain a broken status quo. But I met too many C-Suite leaders who are as frustrated by obstructionism and politics as I ever was. Business Punks are uniquely capable of understanding the true problem they need to solve, and offering an alternative path forward. That is an act of love - albeit tough love - not an act of war.

You’ll never walk alone

One of the reasons I launched Punks & Pinstripes is because Business Punks have a unique sense that they are alone, isolated, and defective. The differences that make them detach from their previous life, feel like defects when the urgency to escape first emerges. Until they meet everyone else who is a Business Punk. Then they find solidarity and sense of community that is an incredible source of power and joy. There is a giant undercurrent of emboldened and empowered Punks who make progress possible. 

One more thing…

Next Wednesday, November 6th, we’re hosting a Punk Salon with a brilliant business Punk, Bree Groff, whose forthcoming book “That Was Fun” is a brilliant manifesto on how to unf**ck corporate culture. There are only a few spots left. It’s free for members of Punks & Pinstripes, and $60 for everyone else. RSVP here.