In Part 1 of this post, I delved into my worry that practicing mindfulness — which deliberately works to maintain calm and distance — would suffocate my high-revving inner motor, the ambitious, restless part of me I always believed to be the beating heart of my entrepreneurial life. But then I realized mindful equanimity didn’t squelch that motor, it fine tuned it, allowing me to be focused on what matters. On the guided-meditation app, 10% Happier, pioneering teacher Joseph Goldstein puts it this way:
“The simplest, most profound meditation instruction is to be aware, and don’t cling. Not clinging doesn’t mean to be apathetic. It doesn’t mean we shouldn’t be undiscerning. It means we’re not identified with what’s arising. We’re not clinging or attached to our experience. We’re open to it, we’re feeling it, we’re being with it, without grasping, without clinging, and in that openness we see more clearly the proper course of action.”
I’m passionate as ever, as nuts as ever, too. And I always will be. But now, once in a while, step by tiny step, I herd my mental cats a little. I’m learning to be better at not clinging to impulses. One fleeting, semi-successful meditation at a time. Meaning I mostly fail. My cartoon network brain distracts me and pow, back on the rollercoaster. But that’s not failing. Not in the long run. You just sigh and smile a little… and begin again.
This positively impacts my life as an entrepreneur and angel investor. A close colleague and I recently had the opportunity to day one invest in an exciting “hot” startup. We were in love with the concept and team and though big league investors were already in place for the deal, we convinced the founders to let us in. They loved our passion.
We were exhilarated. Then the company showed us the terms the big investors had agreed to. And we were flummoxed. The terms were wildly aggressive. We couldn’t negotiate — the big investors had happily committed and the company wouldn’t make another deal. Duh! Why would they?
Ugh. Agony! Our passions were so high. We were enamored of the opportunity.
But our dispassionate minds suggested some less emotional due diligence. And that spoke clearly: The present high would wear off quickly and we’d still be left with the super aggressive terms plus the reality that such investments likely gestate for many, many years…
Meaning, it wasn’t a good fit for us. No disrespect to the company, it was maximizing opportunity, as it should. But we were trying to be smart, small-time investors, taking on huge risks, of course, but trying to avoid (what for us would be) crazy and unnecessary ones. We had capital to make a few bets, but not enough to make too many.
Hearts beating, mouths dry, sanity checking ourselves eight million times, we passed.
We assumed we’d have to wait years to find out if we were right, but it was a crypto deal in what rapidly became an insanely volatile market, and our detached view was validated in just a few months.
We didn’t gloat. We didn’t even tell anyone. But we did take a mindful moment, just between us, to note: It was a healthy, organic mix of passion and dispassion that worked so well.
Which made me think back to my days as a startup entrepreneur. Would such an approach have made me a better founder and CEO?
The part of being a work leader I always liked least was managing other people. The bureaucratic HR stuff, of course, but worse, the messy, nuanced interpersonal relationship aspect of management, both in any given moment, and over time. My attitude was, yes, I know we’re all sensitive human beings, but for the sake of our success, and changing the world, during work hours can’t we all just be efficient, unflappable and unemotional? I don’t think I was harsh or cold. Just impatient with what I perceived to be the non-essential.
But what’s obvious to me now is, a little mindfulness would have gone a long way. The “non-essential” is actually the most critical: Being able to have calm perspective on the human, emotional side of working with others. Of being with others. Of just being. Creating trusting and lasting relationships. Helping me deal with my own emotions, and as importantly, those of others interacting with me.
Alex, I hear you and I love you. But I think you’re wrong. And next time we meet, you’ll hear how, well, passionate I feel about that.