Interview with Sasha Dichter, Founder of Generosity Day

New Dream's Edna Rienzi spoke with Sasha Dichter, founder of Generosity Day, about his proposed alternative to Valentine's Day commercialism and his own experiences with generosity. Sasha is Chief Innovation Officer with the Acumen Fund and also has a personal blog.

Generosity is…

Opening your heart, being courageous, creating connection, living a life of service.
 
What is something you know now about generosity that you didn't know before your generosity experiment?
 
A lot. Honestly I’d never given any proper thought to generosity before my generosity experiment and I never thought of it being particularly important. That is, I always admired generous action but I never understood how foundational generosity could be in our relationships, how it is the foundation of all philanthropy and social change work, how all the major religious traditions have generosity as a core foundational pillar, etc.
 
I find that we walk through the world deciding what to notice. So before I had kids, I never really noticed kids. And once I became a father I saw strollers everywhere! It’s been the same with generosity. Once I started paying attention to generosity, I started seeing it everywhere.
 
Did your generosity experiment change your behavior in any lasting ways?
 
It did, but it really was the first steps down the path. I’d love to say that I’m radically altered, but I think change takes time. I’m naturally a highly analytical person, and I think that mindset can create separation. I see people who don’t have to overcome this like I do and I really admire them. That said, like everything in life it is a practice, and by creating a different intention and by creating space for a new orientation, I have seen changes big and small. I’m keeping at it.
 
In your blog, you wrote that you believed that Generosity Day struck a chord with people because everyone is hungering for more connection and more meaning. What do you think makes connection and meaning more difficult to attain in today’s society?
 
At least in the West right now, we’re all so hyper-connected, hyper-busy. We’re running around with our heads buried in our devices and our inboxes overflowing. So on one hand we’re more in touch than ever, but it also feels to me like we've created so much separation. It’s so easy to tune out the world around us these days, and in some sense I feel like in doing so we’re denying our basic humanity.   
 
How do you respond to critics who say that it is irrational to give just because someone asks? Some, for example, would argue that it’s a more effective use of your money to donate to a homeless shelter than to give to someone begging on the street.
 
Of course it’s irrational to give just because someone asks! I don’t think giving starts with rationality, I think it starts with expressing a purpose, acknowledging abundance, and confronting the terrifying notion that you (the giver) and the person who receives your gift are not so different from one another.
 
What I think confused some people about my generosity experiment was that they might have understood me to be saying that everyone should give to everyone always. I don’t believe that. But I also believe that if you never pick up your head when someone asks for help, if you never actually see the person right in front of you with their hand out…well then you’ve lost a tiny piece of your humanity.
 
I see a lot of parallels between my generosity experiment and my yoga practice (which was pretty regular up until last year when my third child was born!) So much of yoga is about teaching yourself, through repetition, to unlearn patters of thought and reaction that you’ve taught yourself over decades. So while it’s not actually important to be able to contort your body into some strange position and not panic, it’s really important to learn how to be in stressful situations and stay grounded. The yoga poses are practice for real life. Similarly, I wanted to create a new pattern, to cut directly against the grain of saying “No” every time someone asked for a handout—just to see what a habit of “yes” would feel like and how it might change me. So far I’ve been happy with the results.
 
Are there any requests for help that you would refuse even on Generosity Day?  
 
Sure—ones that seemed ugly or self-serving or intentionally against the spirit of the day.
 
Does romance fit into your vision of Generosity Day or does that get lost in the “reboot”?  (One of my daughters, by the way, accused me of being the Valentine Grinch when I explained Generosity Day to her!)
 
My wife and I still celebrate Valentine’s Day—in fact, if anything, I’ve been more comfortable with Valentine’s Day than she has over the years! I finally understood what she was saying when we had one of our most romantic dinners early on a Saturday afternoon right before she drove me to JFK airport for a trip to Kenya. I’m a real romantic, but I do agree with my wife that saying, “OK, tonight we’re going to have a special memorable evening!!” can raise the stakes too much, and that the most romantic moments are often the unexpected ones.
 
What do you hope Generosity Day accomplishes this year? And in the next 10 years?
 
I’ve had this dream that we could actually shift Valentine’s Day and create broader traditions of love and giving on this day. There’s no reason that can’t happen—I think it would be a relief to people (well, maybe not to Hallmark and Godiva, but to lots of folks).
 
This year, we’re really focusing on people engaging in generous action—in addition to spreading the word. Because the day won’t really stick with you if you don’t behave differently.
 
I promise, if you engage in just one act of radical generosity this February 14th, you’ll remember it for years to come!