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  • Pat Libby

A Tale of Two Cities: What Boston and San Diego Taught me about being a Nonprofit Leader

I love Boston with a passion.

I was born, raised, and lived most of my life in and around the city. Because of that, Boston was a city of firsts for me – first kiss, first job, first husband, first time as a nonprofit CEO, first consulting practice, and first stint as a professor.

Working in Boston is radically different than working in San Diego for a variety of reasons. This is what I learned working for and with nonprofits in the Hub:

  • Collaboration is key

No matter how large or sophisticated your organization, partnering with others is central to success. This is because no single nonprofit has the expertise to fully understand how to address the seemingly intractable problems that nonprofits attempt to tackle. Working collaboratively is essential to developing pathways for long-lasting impact. In Boston, many organizations meet regularly to hash out ideas for how to move collective agendas. Depending on the constellation of personalities, it can be an exercise in aggravation and brilliance at the same time (see “tell it like it is” below).

  • Think big

Bostonians are audacious. We imagine outcomes on a grand scale and then work backward to figure out how the hell to make it happen. And we usually do. It’s a culture of “if you build it, they will come.” This big-picture thinking permeates the city and the institutions that surround it, including the nonprofits. As a case in point, Boston spent years tearing down a major highway that ran through the city, put it underground, and built a gorgeous park in its place. The “big dig” is the epitome of Boston thinking big.

  • Tell it like it is

For better or worse (and admittedly, it’s not always for the better), Bostonian are blunt. When you meet with people to discuss ideas, they’ll tell you exactly what they think without any ifs, ands or buts. That means that if someone thinks an idea is ill-conceived, they’ll tell you in no uncertain terms to your face. Bostonians are also fond of four-letter words. You’ll never leave a meeting feeling confused about the outcome or the action that needs to be taken next.

All of the above makes for a dynamic environment where things more forward quickly, where egos show themselves, and where workaholism is as common as Red Sox, Celtics, Bruins, and Patriots fan gear (which is to say, nearly everybody is caught up in it).

Having lived in San Diego now for more than two decades, I’ve learned a lot as well. Here are the lessons I’ve absorbed from nonprofits in this left coast city:

  • Take some time to chill

In Boston, many nonprofit folks live to work. In San Diego, they also work to live. That means that on Friday afternoons around 2:30 or 3:00, it’s hard to find a San Diegan slaving away at their desk. That’s a good thing. People need to step away from the constant grind of this important work in order to take a deep breath and get a better perspective on things.

  • Being nice matters

I’ve rarely heard anyone in San Diego raise their voice during a meeting, let alone use a four-letter word (unless it happened to slip from my own lips). Similarly, San Diegans tend not to jump into the business at hand before spending a little time sharing small talk with one another. That chit chat is a nice way of signaling that you actually have an interest in the people with whom you’re meeting. On the flip side, sometimes people are so nice and careful with one another, they don’t reveal what they actual think. This hinders true and effective collaboration.

  • Listening is a sign of respect

There are a lot of smart people in Boston who have (or think they have) a lot of smart ideas. That leads to people competing with one another for attention and talking over each other at meetings. I don’t see those outsized egos within San Diego’s nonprofit sector. I see people who are good at listening fully before they respond with their own thoughts and ideas. At the same time, more frank talk at meetings would produce more momentum and achieve better results.

The gift of working in these two cities has been experiencing these lessons first hand. It’s led me to see how they can be melded together to produce the best of both worlds and a better nonprofit sector.

I love my adopted home town – what could be better than yoga in the Japanese Friendship Garden?! – but I’ll always be a Boston sports fan.



Pat Libby is a change management consultant working principally with nonprofit corporations. She is author of The Empowered Citizens Guide: 10 Steps to Passing a Law that Matters to You, Oxford University Press, The Lobbying Strategy Handbook, second edition, Oxford University Press, and Cases in Nonprofit Management, SAGE. She has served as an academic, senior executive, board member, and consultant to innumerable nonprofit organizations and foundations for more than three decades.

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