“Hunting for Heartbreak”

Happy 2020.

I spend a substantial amount of time on email (despite resolutions otherwise) or Linkedin reaching out to folks that I find inspiring or interesting.

I’ve had this habit for a long time, borne of a feeling that reaching out to the right person, and catching them at the right serendipitous moment, might lead to some unknowable opportunity, or a kernel of wisdom based on their own success / experience that would provide immediate clarity and a path forward.

I’ve had varying degrees of success cold-reaching out to people. A small portion respond, gracious and appreciative of my interest, but unsure what to do with me and my humble inquiries. However, a large portion of my emails sit dormant in the inbox of busy people inundated with similar emails from equally passionate people.

My rate of success has improved ever-so-slightly since beginning at Harvard Business School (HBS) in August, although I’ve mostly self-selected HBS or MBA alumni as subjects of my reach-out, counting on feelings of obligation / service towards their alma mater/degree, or empathy towards me as a younger version of themselves: chasing opportunity, ambition, and the unknown.

This routine was thrown completely on its head in late 2018, when I opened my inbox to see an email from Shawn Askinosie, author of the memoir-cum-business book Meaningful Work (pretty darn great title) and purveyor of ethically-sourced, service-minded, and transparently-operated Askinosie Chocolate.

The week prior, I had written a capsule review of Meaningful Work on this site, and Shawn reached out to thank me for reading and sharing my thoughts on the book. I seized the opportunity to strike a correspondence with Shawn, asking questions about direct trade (I was exploring the coffee business at the time while in Brazil), and general advice about life and work.

Several months later, I shared with Shawn the news of my admission to Harvard Business School. Given the privilege of being accepted to one of the world’s top business schools, and the time and space to think about the next stage of my professional life, I asked Shawn: how should I think about prioritizing and balancing what’s important to me with what the world needs, and how I’ll feel fulfillment, or at least contentment with the path I’m on.

Shawn’s response was as follows:

“remember that some misery is part of the life we lead. I know you’ve seen my TEDx, but I talk about that very thing. Misery and heartbreak. You want a life in which you go hunting for heartbreak. Ouch.

I’ve now sat on Shawn’s email for several months. At some innate level, I deeply understood what Shawn was getting at, but found it too abstract and intangible for me at that stage, time, and place.

Early in the experience, HBS students are inundated with the messaging that anything is possible, that simply by being accepted and sitting amongst your 900-person cohort that you’ve gained entree to a society of high-achievers, and that HBS is the place to unleash your ambition onto the world. Even the early curriculum spans the worlds of sport, medicine, industry, and science, inviting students to opine and insert their opinions on these diverse pursuits, as if any and all are possible simply by virtue of membership.

Sitting one semester into my experience, with the physical and mental distance of a long winter break and the need to begin taking action towards an eventual post-MBA career, Shawn’s advice has returned.

But rather than returning as words, it’s surprisingly manifested itself physically – the feeling of heartbreak. At the risk of sounding dramatic, as I’ve begun “putting myself out there” – reaching out, applying for opportunities, and asking for work in pursuit of next steps in my career and stage of my life, I’ve felt deep pangs of disappointment mixed with uncertainty and unknown. While I don’t know if this is ‘heartbreak’ exactly, it certainly feels as if it comes from the same place.

Rather than running from this feeling, I’ve taken Shawn’s words to heart – that a life spent chasing heartbreak (and feeling it often) is an indicator that I’m on the right path. As much as the heartbreak and related emotions are difficult, I recognize that this means that I’ve bypassed insecurity and leaned into my self-confidence in the pursuit of heartbreak. Deep down, I feel as if I’m going for it.

One of the key insights that I’ve felt in my first semester at Harvard Business School was in a leadership and organizational behavior class. The professor/researcher explained that individuals with an achievement-orientation tend to externalize their day-to-day success as a series of ups-and-downs – feeling especially low in moments of disappointment or discontent, and very high in (momentary) success and goal-reaching. The conclusion of the academic study was that this psychology should be avoided, and changed to a more even-keeled mindset, a constant feeling of “6/7” in lieu of alternating “1/2″ and “9/10” on a scale from 1 to 10.

By all means, the last few months have been plenty of “1/2” days, with a few “9/10″s sprinkled in. How to achieve this contentment and ongoing growth mindset, while chasing heartbreak, is the next stage of my journey, what I hope to work towards in my coming semester, and beyond.

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