We recently connected with Ryan Greer and have shared our conversation below.
Ryan, appreciate you joining us today. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.
Some of the most important vocational inflection points in my life have involved a great deal of risk. A few of those risks have paid off tremendously and allowed me to gain unique experiences doing incredible things, while others fizzled away into dead ends. When I was 19, with two years of college under my belt, I was feeling directionless and unenthusiastic about my prospects for the near future. I had already changed my major three times and, while still a good student, just couldn’t see myself in any of the roles my professors and fellow students were talking about. I decided, yet again, to try something new, and decided to drop out of school and move to Jordan in the Middle East. I had no money, not much of a plan, and the calmer and wiser voices in my life were urging me to exercise caution. But, crucially, the voices I listened to did not try to stop me. They knew I wasn’t happy, knew I was looking for something else, and encouraged me to follow my heart. I spent a year doing volunteer work, studying Arabic, making friends and listening to stories from people I might otherwise never have encountered in my suburban life in the US. That one “foolish” decision redirected my path and gave me focus. I eventually returned home, finished school, and went on to earn a Masters Degree in International Development with a special focus on Disaster Relief & Mitigation.
Many years later I took another risk by leaving my job as the National Director for a non-profit in Bolivia to start over as an intern in a brand new organization. Why would someone make such a drastic career change in, as many people would say, the wrong direction? For me, I still had questions that needed answers, questions about my own ability to work in the high-stress environments of a post-disaster setting. I was comfortable in my work but needed to risk the uncertainty with changing jobs, moving countries, and starting over in the hope of following my passion. That risk again paid off, as I was able to pick up new skills and deploy to countries around the world as part of an emergency response team in the wake of catastrophic natural disasters.
Not all big risks turn out how we might expect, however. After more than 15 years pursuing dreams of a career in disaster relief, I reached my goal and realized the work demands on my personal life were more than I was willing to pay. I had risked a great deal in a variety of contexts to achieve certain milestones and, upon reaching that particular summit, decided it was not for me. The beautiful thing about taking risks, however, is that you do not ever have to ask yourself, “what if?”. I was able to pivot my career and utilize the skills I had already acquired to start a new career in homeless services, where I remain to this day. I am deeply grateful for the nontraditional route my career has taken me that has allowed me to participate in incredibly challenging yet meaningful work, without ever having to doubt what might have happened had I been willing to take more risks.
One of the most important lessons I have learned from all of this work, and that I try to share with others, is that risks shouldn’t be avoided just because they might be hard. Trying something new, and failing at it, is more rewarding than never having tried at all.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
I currently serve as the Senior Director of Programs for a non-profit called Friends In Deed, based in Pasadena, CA. We run a bad weather shelter during the winter, a food pantry, a rental assistance program, a women’s drop-in center, and outreach services to people experiencing homelessness. I have never considered myself to be an entrepreneur, or even an innovator. I am someone who is much more comfortable in roles that support others with their ideas. Nevertheless, I have come to learn that this space is, in itself, a place in need of innovation. We are well and truly living in a post-Covid environment. I do not know a single person who does not struggle with feelings of isolation, with political polarization and disillusionment, with feelings of nihilism in the face of large forces outside our control (climate change anyone?). I grew up as a missionary kid, living in four different countries and changing schools 13 times in 12 years before graduating high school. I am more comfortable than most with change, but I am also very keenly aware of the importance of perspective, of making our own meaning in life, and choosing the stories that we want to live by. I began my career as a humanitarian aid worker, witnessing tremendous suffering and deprivation as a result of extreme weather or human conflict (or, most often, a combination of the two). Now as my career has shifted more locally, and I am working and providing services in the same city in which I live, I feel it more keenly than ever the importance of finding new ways to bring meaning and value to what has traditionally been seen by many as the 40 hour grind. We all need to find meaning in the work that we do, whatever that work is, but this generation is much more aware that work does not equal identity, that earning more money does not equal taking care of yourself, that just because certain goals and priorities were handed down to us does not mean we have to make them our own.
There is space in there for innovation, for new ways of viewing our vocation, and I’m happy to live in that space.
What’s a lesson you had to unlearn and what’s the backstory?
I think it’s safe to say many people reading this are raised with the notion that life should always be leading towards the next big thing. Make sure to get good grades so you can get into a good college. Do well in university so you can get a good job. Work hard so you can make more money. Network with the people who can help you achieve your goals, and on and on. This is a functional enough worldview for many, but is one that I had to unlearn if I ever wanted to feel a sense of peace in an otherwise anxiety-inducing culture of over-indulgence and self-centeredness. Early on in my career I always felt immensely distressed if I wasn’t selected for the next big opportunity, if I didn’t get the job or wasn’t able to advance to the next position or otherwise move in that linear path towards “success”. That pressure kept me hungry for new opportunities but, in many ways, it also kept me quite unhappy. I think, as a society, we need to encourage each other to pursue new experiences just for the sake of curiosity, not because it will further our careers or leverage us to do more. I’ve worked as a painter’s apprentice, as a waiter in a retirement home, as a disaster response specialist, as a chess instructor, as an environmental conservationist, as a rental assistance expert, as a hospital groundskeeper, and as a whistleblower investigator. Some people might chide me and say, if I’d only focused, I could be the CEO of a major company by now, but I’d much rather have the multitude of stories and experiences from these diverse roles than anything a traditional career path might have offered.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?
I love this question because I love books. As Anne Tyler said, “I read so I can live more than one life in more than one place.”
Philosophically I’ve always appreciated the work of Alan Watts in bringing core concepts from eastern philosophies like Buddhism into the conversation for many of us living in the Americas. I also recommend the book, This is Water, that was originally a commencement speech from David Foster Wallace for those looking for a better way to think about thinking. She’s practically a household name at this point, but I’m also a big fan of Brené Brown, her book Dare to Lead has important things to say about bringing your authentic self into the workplace and embracing vulnerability as a tool for growing teams and encouraging open communication. I also appreciated Jonathan Haidt’s book, The Righteous Mind, for it’s ability to help me understand how to better relate to and empathize with those who think differently. I also read a lot of science fiction and love the works of Octavia Butler, Ursula Le Guin, and Liu Cixin. We need to make more space for imagination and a little magic in our lives if we ever hope to make the world a better place.
Contact Info:
- Instagram: @friendsindeedpas
- Facebook: https://www.facebook.com/FriendsInDeedPas

