The Gift of Permanence

It was widely reported last week that Diane Hessan was leaving Startup Institute to pursue an opportunity leading up to November that she, “just cannot turn down.”

This is worthy of press coverage for a few reasons: Diane is arguably one of Boston’s most talented executives, most recently leading C-space from startup to successful acquisition by Omnicom; Startup Institute is a key asset to the startup ecosystem, developing and feeding new talent into companies of all sizes; Diane sits on boards, advises, mentors, and cheerleads people to greatness. Why else is this press worthy? Well, of course, we’re talking about politics in an election year.

As many of us have witnessed first hand, transitions like these are hardly black and white. External press covers the rationale for the transition, perspectives of shareholders and contemplates the impact to the company. Internally, those are important too, but the real story often lies in the emotions associated with a respected a coworker’s departure: loss, grief, mourning — and ultimately acceptance.


At the time of departure, more often than not, there’s a subconscious desire to share something that is deep and personal about working together: the impact of a skill gained, critical feedback that changed a career, a never-to-be-forgotten personal interaction that forced attitude reflection.

The outlets to express these feelings are minimal — and fleeting. Maybe a brief conversation in the hall, a long hug or a speech at a goodbye lunch. Maybe the tame office-humor “hasta la vista”card, passed from desk to desk and scribbled with platitudes. The hard part here is that like anything, time ultimately erases the majority of the reflection and the power of its meaning. We spend so much time focusing on the future, we forget most of the past.

In today’s social age — with the social scroll and mere seconds to send a snapchat — permanence has become a practical impossibility.

We created Mylestoned to help people find that outlet for permanence. In a case like this, coworkers having a place to lend their voice, in a space they know won’t dissipate into the social ether, becomes a powerful mechanism for reflection. And together, it becomes a collaboration that may somehow acknowledge the importance and impact of the departure.

A memory contributed to Diane Hessan’s Mylestone

Most importantly, for Diane it is a gift. A rare observation of love that is there for the world to see — permanently — in a form that can’t be missed or dismissed.