Friday Sabbatical: On gender norms in leadership, Inner conversations, and more than one definition of success

Whatever you’re doing this Friday, wherever you’re going or whatever box you’re checking, I invite you to take a moment, just now, and stop doing it at all.

I’m excited to share with you my favorite tools/ideas/resources about leadership and entrepreneurship from this week.

1. How Women Manage the Gendered Norms of leadership

This analysis from the Harvard Business Review about the five paradoxes that women are asked to hold in order to be successful as leaders was fascinating. While, as a man, I’m able to simply be assertive and demanding, if a woman does the same they’re viewed as a bitch. They need to also be caring and participative. I can assure you that I went through probably my first seven years of leadership without caring or participating, and was roundly applauded the entire time.

However, what I find doubly interesting about these paradoxes is that the best male leaders in the world are increasingly people who can hold both ends simultaneously as well. My growth as a leader over the past few years, for example, was all about growing in the more “feminine” part of my personhood to balance out my natural (and socially reinforced) masculinity. So men and women leaders are increasingly embodying the best of both the masculine and feminine, and while men have had a huge head start I wonder if this isn’t a sign of the tide turning.

The longstanding “bro” culture of leadership is on its way out, that much is certain. And the victorious leaders, be they men or women, will be those who can both drive results in a pinch, as well as develop deep and lasting, human relationships with coworkers. Society is catching up to that norm, I imagine providing tailwinds to women taking their rightful place in the C-Suite.

2. How to have the best week ever

I’m on a lifelong quest for the perfect day. I’ve had more than my share. I really appreciated Ryan Holiday’s look into how the Stoics architected their perfect week. Perfect days/weeks don’t happen by accident (often enough for me), so it’s useful to put your thumb on the scale where you can.

My favorites:

  • Clarify Your Principles
    • “You’ve wandered all over and finally realized that you never found what you were after: how to live. Not in syllogisms, not in money, or fame, or self-indulgence. Nowhere. Then where is it to be found? In doing what human nature requires. How? Through first principles. Which should govern your intentions and your actions.” —Marcus Aurelius, Meditations, 8.1
  • Review
    • “I will keep constant watch over myself and—most usefully—will put each day up for review. For this is what makes us evil—that none of us looks back upon our own lives. We reflect upon only that which we are about to do. And yet our plans for the future descend from the past.” —Seneca, Moral Letters, 83.2

3. Founder of Pinch and angel investor, Maia Bittner recently tweeted:

The criteria she outlines is, reductively, what you’d think (or at least was not surprising in the least to me having raised from both coasts). East coast investors are practical, looking at deal terms, revenues, and actual traction right now, while West coast investors are looking at long term trajectory of humanity and how the company might play a role in that someday. Practical & near term vs strategic and long term. There’s a lot more nuance in the thread if you’re interested in pitching to either coast.

What I thought was so interesting about this take is the very real juxtaposition of the two types of investors back to back, and how instructive that is for people looking to lead others. Whether fundraising, selling or leading teammates, this thread articulates that the person you’re talking to has a preexisting conversation going on in their head to which you naturally have no access, and just how important that conversation is. Your ability to lead someone has much less to do with how well you pitch, and frankly much less to do with you at all, but much more to do with how well you understand their inner-conversation, and can help them see your company/tool/initiative as the solution.

Seek first to understand has very real, business applications.

4. Reflecting on my failure to build a billion-dollar company

Sahil Lavingia, founder of GumRoad and one of the first (if not the first) to launch a Rolling Fund (which it seems may drastically alter the VC landscape and which you should know about if you’re a VC or are raising money), wrote an amazing, vulnerable and viral piece about trying and failing to build a billion-dollar company, and building an amazing eight-figure company in the process.

Startup culture has conditioned us to think that it’s Unicorn or bust. Lavingia bought into that earlier in his career, as did I. It’s natural, given that VCs run the industry (he who has the gold, and all that), for entrepreneurs to default to a VC’s definition of success.

But a VC’s definition of success, although it feels normal early on in the journey, is one of many thousand possible definitions of success. I learned that the hard way. You get to pick your own definition of success, if you step into your right to do so, and I loved how Lavingia showed how a win can look much more like a Zebra.

And more than that, how sufficient creativity can change the rules. Bravo, Sahil.

5. My new favorite productivity tool, and the tool I’ve been most excited about for a long while, is Roam Research. Think of it like your very own, personal Wikipedia. I take notes like I would in Evernote, but by cross-linking terms Roam brings up other relevant notes where I’ve used that term in the past. So I link the term [[Conscious Business]] and underneath the note I’m typing in I have the synopsis of Fred Kofman’s book, Conscious Business, that I typed after reading it last year just waiting to provide additional context.

It creates happy accidents between present-you and past-you, and leads to some pretty cool insights that would otherwise never have happened.

That’s all for this week. Thank you for reading! And please, forward this to your fellow Conscious Leaders. Together we’ll create a movement.


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