Sometimes the bold goals we set out to achieve actually happen, and sometimes something even more amazing happens - something better than we can imagine.

Usually that happens because of the people we meet along the way, the conversations we have, the unexpected connections we make that open up new doors - in a word, Serendipity. I had always wondered about what amazing, powerful and sustained conversations led to the High Line Park in New York City becoming a reality.

Have you walked the High Line? Literally millions of people a year walk some of its 1.45 mile length, enjoying expansive views of the city and hundreds of local plantings, as well as amazing art installations. But it was slated for demolition and considered an eyesore and a relic, as long ago as the 1980s.

Built in 1933, it was at the time a revolutionary elevated train line that was colloquially called the Lifeline of New York City since it was regularly bringing millions of tons of meat, dairy and produce by rail, directly into the warehouses and factories of lower manhattan for preparation and distribution. The rail line wasn't just a lifeline because of the food it brought, it also moved the rail lines safely above the city's growing traffic - in the 1910s, hundreds of people were killed by the ground-level trains that ran in the middle of the bustling 10th avenue!

By the 1960s the line was growing obsolete due to the rise of trucking, and by the 1980s, it was a hulking relic of the past.

In 1999, Robbie Hammond, my guest for this conversation, co-founded the Friends of the High Line along with Joshua David. The two met at a local community board meeting where the High Line's future was being discussed. Rudy Guliani, NYC's mayor at the time, had signed an executive order for its demolition - many property owners wanted it gone so they could take back the land occupied by the tracks and build bigger buildings - a dream of greater square footage and increased rent rolls.

Currently Robbie is the President & Chief Strategy Officer for Therme Group US, where he is leading an initiative to bring large scale bathing facilities to the United States. He also currently serves on the boards for Little Island, Sauna Aid, Grounded Solutions Network, and the San Antonio Museum of Art.

When I was a little kid in NYC in the 80s, I looked up at the hulking tracks and thought "what the hell is that doing in the middle of the city?!" Many adults thought the same thing.

Robbie and Josh looked at the tracks and thought "we should really do something cool with that instead of tearing it down."

In 2009 the first section of the high line opened to the public. In 2019 and 2023 new sections were completed.

Against all odds, "two neighborhood nobodies" (as one writer described them!) created a coalition, learned to raise money and garner the favorable attention of local politicians, and persisted and succeeded. The park is maintained, operated, and programmed by Friends of the High Line in partnership with the NYC Department of Parks & Recreation and is run on donations.

There are many amazing angles to the story of the Highline:

Maybe you DON'T need a coherent or complete Vision or Mission?!

Robbie makes it clear that they didn't even have a clear vision or strategic plan for some time…just the idea that the elevated line was worth saving and doing something with…they discovered what they wanted to create along the way. He actually credits the vagueness of the mission with creating a "big tent" that attracted more people to the organization.

From a conventional dream to something better than anyone could imagine

One surprising insight is that the property owners had a rather conventional dream - tear the elevated tracks down so they could build bigger. Turning the High Line into a park seemed like a low-value, impossible pipedream - sex workers and drug users congregated under the overpasses, after all! But the High Line's millions of visitors have transformed the value of the area far beyond the addition of a few extra square feet.

The High Line as a symbol for dreamers of impossible dreams

One of Robbie's greatest points of pride is that the High Line now stands as a symbol to many "crazy dreamers" who find inspiration in the story of outsiders persisting and accomplishing more than they ever dreamed possible. The High Line is now a global inspiration for cities to transform unused industrial zones into dynamic public spaces. But Robbie loves the personal stories of folks who come up to him at talks, who are working on all sorts of projects and who find inspiration in Robbie and Josh's "keep going against all odds" story.

The importance of Talking to People

Robbie talks about how he was always willing to pick up the phone and talk to anyone - the fearlessness of someone raised in sales. But the Friends of the High Line were also willing to host conversations with community groups and listen to them, and learn from them and communicate with them about why they were listening to their ideas and why, in some cases, they weren't going to. Open lines of consistent communication made the High Line possible.

The Alchemy of the Co-Founder Relationship

In this conversation, Robbie is bracingly reflective and shines a sometimes harsh light on himself. Here at the 15th anniversary of the opening of the Highline and the 25th anniversary of the start of the project, the founding of the Friends of the High Line, Robbie looks back and is refreshingly honest about his own challenges and shortcomings, as well as missed opportunities along the way to do things differently.

What was truly surprising to me in this conversation is that Robbie was so open about his challenges as a co-founder, and is so open-eyed about how essential this most intimate of relationships can be…and how much he and Josh were willing to invest (in time, energy and resources) in that relationship to keep it intact, functional and flourishing.

The Energy and Anxiety of Creation

Robbie suggests that it is common for creative people (which includes entrepreneurs, and anyone that starts anything) to have a drive to accomplish their dream - that is what keeps them going… but that there is often "an undercurrent of anxiety". Meditation helped Robbie reclaim a higher level of happiness as the High Line approached realization, but it took him years to undo the deep grooves anxiety etched in his psyche. It's a worthwhile lesson for anyone listening out there who's creating something, start taking care of yourself sooner rather than later.

You can follow Robbie on Instagram at thehighlineguy and stay in the loop on Therme's projects at https://www.thermegroup.com/.

Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders.

Links

https://www.thermegroup.com/

https://www.instagram.com/thehighlineguy

Therme post (2021)

Robbie's Book: The Highline:The Inside Story

https://www.thehighline.org/history/

Early documents from the highline: Reclaiming The High Line: A Project Of The Design Trust For Public Space With Friends Of The High Line (2002)

Talks:

Rail Yards Talks 2011

"High Line: The Inside Story of New York City's Park in the Sky" - Richard Hammond

https://www.ted.com/talks/robert_hammond_building_a_park_in_the_sky

Are You A Lover Girl Or A Hater B*tch? with Tefi Pessoa | 1

Lemme Say This

Memorable Moments from Cannes and Pop Culture Chatter

The AI-powered Podcast Player