Our Summer Laddership Circles, are in full swing, and it's beautiful to watch it unfold. Our Week 3 Monday call yesterday was filled with gems. 

Across airwaves from Chile to New England, California to India, the collective wisdom that emerges in these calls continues to humble us:

As Saejung put it in a post-call note to the group:

“I am deeply humbled and inspired by everything you all shared tonight. I honestly feel like a toddler learning to think and express myself in midst of you. It is truly exciting to actually feel the growth and transformations taking place within me.”

We all felt that as well, as in just 90 short minutes, topics ranged from nuances of gift vs. free, focusing on process vs. results, inner vs. outer designs—and a resonance in having more questions than answers.

In our check-ins alone, questions of the nuances of designing for generosity, and the power of operating with integrity and humility emerged. Saejung noted how just operating out of integrity has unexpected ripple effects—as she found herself in a minor car accident while making a house call, left an apologetic note with her contact information, and later found out that the owner of the car was her client’s friend, who later texted her saying, “I’ve never encountered such an honest person. Thank you so much. It was only a scratch.”

Along the lines of car trouble, Zilong encountered a flat tire on his way home from a 10-day workshop. As the driver called AAA, a couple others befriended a mechanic down the street who jumped in to help fix the flat and refused to accept any payment for it. He noted how designs can create a culture or habit that “wires us to call AAA to send help in from afar, or to just go to the shop or house down the road and ask for help from a neighbor.”

Bonnie noticed a shift in her view of service a privilege rather than burden, and how simple things become when we let go of the need to have all the answers, which she comes across in her role as a minster. Similarly, Arathi-- calling in from a Compassion Summit in LA-- noted the power of humility. At a Global Compassion Summit to honor the Dalai Lama’s 80th birthday, she noted how when the Dalai Lama was presented with a species of caterpillar named after him, he lightly made a joke about how he was afraid of caterpillars as a child and never thought one would be named after him.

Sachi opened her check-in with, “All my plans of being mindful this week got bulldozed by insecurity and fear.” She reflected on the challenges of running her business with integrity in a cut-throat competitive environment, and felt grateful for a space that kept her grounded in these values.

Among their thoughtful shares, Pranidhi, Grant, and Fernando asked, “Am I designing enough for generosity?” Pranidhi questioned if she should have a ‘free’ option for her yoga studio’s tiered pricing plan. Grant was inspired by a small, full-of-heart mom and pop shop, and wondered what it would look like if he offered them his pay-it-forward rewards program for free. Fernando noted how a period of patience is asking him to question, “What’s the real purpose that I’m doing this for? How can I bring the element of generosity into my shoe business? Should I just give shoes for free?”

As we dived deeper in the conversation, Pranidhi noted how design elements don’t only have to be about money: “I like this vocabulary of small evolutions, because it takes the pressure off… there are other things we can do that are outside the financial sector.”

Saejung brought up how designs can bring out the ‘contribution mentality’, and noted the example of a criminal law attorney who inspired her. Thirty years ago, he sat down with his wife and budgeted their finances to cover their family’s needs. Instead of going with the market rate of $500/hr today, he still maintains $100/hr rate, though he is highly experienced and respected. “I have no desire to change my fee structure because the market changed. I made an agreement with my wife, and we’re comfortable. Our kids are in college and we’re not in debt,” he’d explained to her.

Min was reminded of her father-in-law, who was a doctor and treated one patient at a time. Over the years, this process actually racked up a lot of debt. But the entire community felt the ripples of his integrity of practice and intention in his work. After 20 years, the government changed and forgave all his debt. This left her wondering, “Do I have the courage to just let go of outcomes?”

Bonnie brought up the edge of how sometimes not charging money for services make it easy for people to flake or take it for granted. She remembered how in an online meditation program she offered, the people who didn’t pay for it didn’t end up opening the emails.

Various folks wondered—when does generosity get taken advantage of? And when does it not? What are those elements that influence how people respond?

Fernando noted how it’s now actually a business trend to use social enterprise as a marketing strategy—that by ‘looking’ like they are helping or giving a large donation, they will become a more popular business. He remarked, “I want to help them on a human level, not just give money. I want to be honest, not just go with the trends.”

This reminded me of another story of Dr. V. When he was just starting Aravind, it was financially difficult, and they were pawning family jewelry to make ends meet. One day during that period, he was treating two patients. After the treatment, Dr.V sat and talked with them for awhile. After some time, one of the patients said, “It’s been a delight, but we really have to get going now. Can you give us the bill?” To which Dr. V chuckled and replied, “Your bill is to bring me 10 more people from your village to treat.” Even though they were financially strained, his focus was on his deeper intention to serve humanity, with full faith that if you “do the work, the money will follow.”

Birju remarked how it’s easy to pedestalize an inspiring figure like Dr. V, or on the flipside, to compare ourselves with someone like that and think, “If he can do it, I can too.” Yet there’s value in knowing where we are, and from there, to explore where and how to take the next step, rather than taking 10 steps too far before we are ready. Min honestly reflected on how she and her startup have experienced taking "10 steps too far"-- one day she and her team would wear their ‘Mother Teresa hat’ and then that afternoon they’d be talking with a bank, wearing their ‘Richard Branson hat’. After some time, they realized it wasn’t working, and decided that rather than try to go all in on their ideals before they are ready, they could collectively design creative constraints into their organization, and take steps in that direction.

As the conversation unfolded, we all began to feel more at peace with not having all the answers. And though fear comes up in the process of deciding to live, work, and operate in a way that leads with generosity, something propels us to keep doing it anyway. To keep experimenting and holding space in ways that honor our interconnections, and deepen our transformation. With conversations like these, how could we not? :)