The distance from Alcatraz to San Francisco is roughly 1.2 miles. About a 15-minute ferry ride. That lonely, iconic island in the middle of the Bay is not very far from the city at all, but when I stood on the small beach just below Ghirardelli Square and looked out, when my toes curled in protest in the icy water and I struggled to yank the zipper of my wetsuit all the way up, it looked immeasurably far.

I swam it in 45 minutes.

On November 1, 2015, I swam from Alcatraz to San Francisco to raise money for That Man May See, the support foundation of UCSF’s Ophthalmology Department. I raised over $6,000.

I trained hard for that swim. I like to swim but I’m not a swimmer. I love the ocean but had never swum in icy cold water before, and I’d never worn a wetsuit. The water was murky, the currents were wild and the weather was unpredictable. And also, there were sharks.

I trained hard, overcame fears I didn’t know I had and learned a great deal. I learned how to swim in a tight and uncomfortable wetsuit. I learned how to breathe without turning my head, so that I could gauge my distance from the shore. I learned how to swim in an ebb and flow tide and I learned that, no matter in which direction I thought I was going, I would always come in from the left.

And after more than a decade of fundraising for nonprofit organizations, I learned three important lessons about how to raise money:

1. Take a risk. Do something crazy, creative, outlandish. Something you never dreamed of doing. Like swimming Alcatraz. Building a state-of-the-art facility or implementing a fantastic new program. You might not make it, it’s true. There may be a shark in the Bay or your goggles might break, but you’ll never know until you try. People out there in the world are excited by crazy, creative, outlandish. They want to get involved, to help and be a part of it. And chances are you’ll swim successfully to shore, and pull yourself up on the beach with the blood roaring elatedly in your ears and your heart pounding in your chest.

2. Aim high. Set yourself a goal that seems a little unattainable but not impossible. This is more for your donors than yourself, as people are more likely to give if there is still perceived room to give. For this swim, I subtly increased my fundraising goal three times, moving from $1,800 (which I already thought was too optimistic) to $5,000. Each time I neared the goal, I noticed a plateau in the giving. So I raised it a little higher, eventually bringing in $6,000, which is more than I’ve ever raised single-handedly. I was one of the top three fundraisers in this Swim For Sight.

3. Hold yourself accountable. I ran my campaign on social media and from my first day of training at a pool in the Oakland hills, I shamelessly posted my intentions and progress on Facebook, Instagram and Twitter, with photos. That is how I owned my progress, and stayed accountable to myself: I named it, in public. Not only did it keep me engaged and driven, but friends and followers online and in real life were motivated to give and to support me in so many wonderful ways. 

Nothing about this swim was easy. I struggled through the waves, I swallowed dirty, brackish water, I thought I’d never make it. At night, I fell asleep before my kids and dreamed uncomfortably about sharks and sea lions. It consumed me, overwhelmed me, exhilarated me.

Mostly, it proved that I can do something difficult, something out of my comfort zone, and something amazingly worth it.

Nicki Gilbert, an alum of the Wexner Heritage Program (East Bay 10), is a writer and country music lover who lives in the East Bay with her husband, four kids and dachshund. She is a regular columnist for J., the Jewish news weekly of Northern California, and her essays have been published on NYT Motherlode, The Huffington Post, Kveller and elsewhere. She can be reached at or on Twitter at @nixgilbertca.