Courageous? Brave? HA! (non profit leadership)

This post isn’t specifically about fundraising, but for anyone in a leadership position, I think you might relate.

Have you ever thought of yourself as fearless? I certainly never did…until fairly recently. I want to share my journey, and offer some encouragement in the form of five big ideas, for entrepreneurs, nonprofit leaders, or anyone who wants to affect meaningful change in their lives.

Back in 1987, just a couple of years out of college, I packed up and moved from my native New Jersey to start a new life in Boston.

I knew that suburban living was definitely not for me. The same went for New York City (at that time anyway). And to be truly honest with you, I was also propelled by the dream of finding the world’s greatest romance with a friend who settled in Boston post-graduation.

(The romance was not to be, but a life-long friendship endures.)

Some years after, one of my Jersey friends shared with me how much he admired my courage for making that move. I was a bit dismissive of his observation, as I never considered myself a courageous person. And I never thought of my move to Boston as being the least bit brave. It just just a thing that I did.

As the years went on, other major life moves would follow.

Seventeen years after arriving in Boston, tired of the dreary New England winters, my now ex-partner and I decamped for South Florida, not knowing not a soul.

Six years ago, with 25 years’ experience as a nonprofit executive under my belt, I quit my job and started GKollaborative, my own consulting business.

Then a client — a woman I hold in extremely high esteem — convinced me to put the business on hold and come work with her for a couple of years — in New York City (talk about coming full circle).

Time to gather boxes and hire the movers, once again. The stakes were higher this time though, because this move required my husband to leave his kids behind in Miami with their mother. (I’m still in awe of his willingness to do that for me.)

Non Profit Leadership

And earlier this year, with my work in New York accomplished, I rebooted the business and we moved once again, back to Miami.

(Never again will I move, I swear.)

Discovering fearlessness.

Some people would consider these moves as brave. I still have a hard time with that notion because inside, I’m still a scared little boy.

When I step outside of myself and reflect on these moves in my life, I understand, however unbelievable it seems to me, that maybe, I might just be a bit fearless.

You see, a few years ago I discovered a considerable body of work being done on the concept of fearlessness by the Case Foundation. Started by Jean and Steve Case (he of AOL fame), the foundation “invests in people and ideas that can change the world, with the ultimate goal of making giving back a part of everyday life.”

As the Case Foundation turned 15 a few years back, they reflected on their own evolution and realized that they were most successful when they were fearless — when they explored and experimented — and the least successful when fear or caution became a driver of decision-making.

Previously, when I heard the word “fearless,” I thought of some comic book hero. That sure as hell isn’t me. I have no super powers or the ability to be repeatedly pummeled and then get back up and return the favor to my opponent.

Some simple, yet massively big ideas.

But the Case Foundation’s five-point definition of fearlessness helps me find a narrative thread for my life and work:

1. Make big bets and make history — setting audacious, not incremental, goals (when I’m working on big-picture planning with teams, I like to use Jim Collins and Jerry Porras’ concept of BHAGs — big, hairy, audacious goals).

2. Experiment early and often — not being afraid to go first. But I don’t think this has to be limited to being first. Individuals and organizations should be willing to experiment with ideas that are new to them, if not to the rest of the world.

3. Make failure matter — failure teaches, and we should learn from it. Fortunately, I’ve never experienced catastrophic failure. I also learned from a wise woman years ago that what can be viewed as failure, ain’t necessarily so.

4. Reach beyond your bubble — working with the known is usually more comfortable than reaching out to the unfamiliar. But going beyond the known, be it your skills, past experience, or those with whom you collaborate, is what leads to growth, stimulation, and innovation.

5. Let urgency conquer fear — don’t overthink and overanalyze. Just do. Many of us want to study a thing before taking action. But we can’t anticipate every outcome. Yes, I think it’s important to be thoughtful and planful, but sometimes, we just have to act.

When I think about what I’ve done in my 54 years, I realize that I’ve been following these principles all along, albeit unconsciously for most of that time.

I’ve made big bets by moving to Boston, to Miami, to New York, and back to Miami. Each move has opened wondrous doors to new experiences and people. I find it hard to imagine having the same the richness of life (and I’m not talking about money) had I not left “home.”

I made a big bet by leaving behind the stability of a paycheck and health insurance in favor of starting my own business.

Mentors and business partners throughout the years have given me the latitude and encouragement to experiment and fail, if necessary. I’ve been forced, if you will, to reach well beyond my bubble.

One mentor, the long-time dean of a dental school in Boston hired me, at just 28 years old, to create a development and alumni relations department for his school. Mind you, I had no experience in fundraising. What the hell did this schlepper from Jersey know?

My client in New York stunned me by asking me to become the COO of our school. I told her she was nuts. Once again, I knew nothing about IT, human resources, security, facilities management and the other aspects of my new portfolio. But she nonetheless prevailed.

Today, as I reboot my business, I’m bursting out of my bubble again by expanding the scope of my work into nonprofit and corporate branding through a partnership with two brilliant brand strategists.

Let me tell you, these leaps have all been accompanied by copious doses of fear, but I’ve been determined that the urgency of each situation would allow me to move forward.

Why am I writing about all this?

Whether you’re considering a change in your life, starting a new company or social venture, leading a nonprofit, or otherwise striving for progress, I encourage you to explore the Case Foundation’s work in this area. I keep a post card with their definition of fearlessness posted next to my computer. It’s the first thing I hung in my office after returning to Miami six months ago.

When I’m nervous, scared, uncertain, confused, all it takes is that reminder to set me on the right path. I think you’ll be inspired as well.
Amusing post script: My client-turned-dear-friend from New York recently called me on her very first day on a new job as a college president. I quickly informed her, “No, I’m not moving back to New York.” But I’ll gladly fly in regularly to consult.

Find your inspiration to be fearless at the Case Foundation Be Fearless Hub. Quotes and other citations in this essay are from “To Be Fearless,” The Case Foundation, 2012.

If you want to learn more about how I work with nonprofit organizations and businesses that want do well by doing good, visit my company’s website, or that of my affiliate partner, MOK2. I can be reached at

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