We’re often in (or feel we’re in) uncharted waters - a place where making things up as we go is a necessity. Feeling lost in those places can be anxiety-inducing. We feel incompetent. We feel shameful. We can end up feeling that everyone has figured it out but me. But how true is that, really? And perhaps the better question--how can owning my own anxiety in these areas help me step more fully into my authentic self and even increase my capacity for happiness? We are honored to welcome one of our key teachers at Reboot, Sharon Salzberg, to the podcast. In this conversation, Sharon and Jerry discuss Sharon’s own entrepreneurial path, a new definition of success (and failure), authenticity, loving kindness and the question: Does anyone really know what they are doing?

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My name is Mara Zepeda, I am the co-founder and CEO of Switchboard, which is a startup
based in Portland, Oregon.
Investment comes from the Latin which means ‘to dress in a particular clothing or uniform’ and I
think what’s interesting about that is, so often we think about investments coming from investors
or mentors, and really the definition of investment is that somebody is taking a chance on you
and they are envisioning what your future would look like in some future costume that they are
certain that you can wear with authority and return the process. CEOs need to be able to buy the
story that they are telling which is that that uniform and that costume is one that will fit and one
that they can deliver on, and no amount of posturing or smoke-and-mirror, song-and-dance is
ultimately going to convince the CEO. It really comes down to doing the type of self-exploration
that you do at Reboot to convince yourself that you are the leader that you can be. And so,
Reboot is the top example that I can think of for CEOs, if they want to make an investment in
themselves and in their role as leaders.
To hear from others about their Reboot experience, and to learn more about investing in your
leadership, go to reboot.io/praise.
Welcome to the Reboot podcast. Before we start today’s episode, I wanted to take a moment and
introduce you to our new sponsor, JustWorks. JustWorks is awesome. They help businesses take
care of their benefits, payroll, HR; they do it all so seamlessly, easily, automatically and we
know they are awesome because we use them. The Reboot podcast really is more than just Jerry
and guests; it takes a whole team to put it together and JustWorks makes it easy to support that
team.
Charles Gammill: Hi, I am Charles Gammill; I am a freelance podcast producer and audio
engineer, and I am an assistant producer to Dan on the Reboot podcast.
Dan Putt: So Charles, do you want to talk a little bit about how we came to make this ad?
Charles Gammill: Yeah, so we were talking about all the different angles we could take; it
struck me how much more difficult it’s been to record this than it’s ever been to use JustWorks
and it reminded me when Ali was taking care of getting everything set up for how to pay me. So
she sent me this link to JustWorks and like two or three minutes later, I was done. I was like, “Is
that all there is to it?” And so, it seems like I had a meeting with Ali a few days later and I put on
the agenda specifically to ask her, “Did I do JustWorks right?” because it seemed too simple. All
I had to do was fill in my – you know, how I wanted to get paid and it was done.
Dan Putt: And I’m not joking when I say setting up JustWorks to set up our payroll, our
benefits, our insurance actually took less time than it took for Charles to describe it. And we use
JustWorks; we are so grateful for their support of this podcast and to learn more about how they
could work for you, go to Reboot.io/justworks.

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“Life is to be felt, not just figured out.” – Thomas Hardy
“We have no idea what we are doing. We’ll never figure this out.” I bemoaned to my coach,
Jerry. This was many, many years ago, long before I was recording podcast introductions. I was
Jerry’s client and I had just spent a very, very long Memorial Day weekend with my three co-
founders. We had been cooped up in a dark apartment, frantically trying to perfect our make-or-
break pitch. The pitch was still a disaster, we were exhausted in arguing, and I felt shame. “Why
can’t we do it if the company Z can?” Jerry smiled, “Ah, company Z; their team was in here last
week, you know what they said to me? “We have no idea what we are doing.” You my friend,
you are now seeing how the sausage is made. Welcome to being an entrepreneur.”
As entrepreneurs and leaders, or dare I say as human beings, we are often in or feel we are in
uncharted waters, a place where making things up as we go is a necessity. Feeling lost in those
places can be anxiety-inducing. We feel incompetent, we feel shameful. What can make things
even worse is that we often only hear and see the finished products, the sausages if you will, of
others. We can end up feeling that everyone else has figured it out but me. But how true is that
really? Or perhaps the better question, how can owning my own anxiety in these areas help me
step more fully into my authentic self and even increase my capacity for happiness?
We are honored to welcome one of our key teachers at Reboot, Sharon Salzberg to the podcast.
In this conversation, Sharon and Jerry discuss Sharon’s own entrepreneurial path, a new
definition of success and failure, authenticity, loving kindness and the question, “Does anyone
really know what they are doing?” As always, show notes, quotes, links and more on our website
at reboot.io/podcast. Enjoy.
Jerry Colonna: I’ve had friends, I’ve had clients, I’ve had past clients; I’m going to be honest,
this is the one I am most excited about. So, I love you everybody else, but Sharon
Salzberg is my teacher, and I feel honored to be in dialogue and conversation with
you today. So, thank you for joining us today, thank you.
Sharon Salzberg: Well, thank you so much. I feel honored to be here.
Jerry: Well, you know, when we were thinking about potential guests for the podcast, I
often thought about asking you and you and I have had dialogue over the years
and talked about some of the things that I do here at Reboot, and some of the
things I do as a coach, and we kind of laugh and I am going to put words in your
mouth; I think you hear the similarities between the work that you might do with
a student and the work that I might do as a coach, not to put me at the same level
as any other teachers, but the notion of we are all working with the same
materials. I think it was Jack Kornfield who wrote “One Dharma” –
Sharon: Joseph actually –
Jerry: Joseph Goldstein, right.

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Sharon: Yeah.
Jerry: You know me, like everybody I confuse between then.
Sharon: That’s true, everybody does. That’s right.
Jerry: And there really is only one dharma; right? It’s just kind of the truth. So with that,
I thought it would be really kind of fun to explore with you, someone who has
taught me so much, both directly and indirectly through your works, through your
incredible writing, some of the issues that I encounter fairly frequently as a coach,
some of the things that really in so many ways, bring people to their knees and
they don’t necessarily understand the relationships that are there. The first thing
that I was hoping to explore was the whole notion of working with uncertainty,
and the reason for that is that you know, you could argue that all of life is
uncertain because it is; right? And you could argue that all of work is uncertain
because work is an aspect of life, so it is. But there’s something particularly
challenging around life in a startup, in which you are inventing new products and
services, you are inventing, often times, a new way of delivering those products
and services, you are inventing out of whole cloth an institution, and for many,
many people, it’s the first time they have ever led people. And so in that classic
teaching way, it’s such a teachable moment because it just brings up such lack of
awareness about what’s going to unfold. Does this resonate with you at all?
Sharon: It does in a funny way; I’m listening to you right now and just started thinking
about the Insight Meditation Society and whether that qualifies as a startup.
Jerry: Absolutely does.
Sharon: I met joseph Goldstein at NGM and then we met Jack Kornfield in Boulder,
Colorado, the first summer of Naropa’s opening 1974, and we were wandering
around teaching retreats when we get an invitation and at the end of that retreat,
we never knew if we have another retreat till the next invitation came. And then
someone suggested we start a retreat center of our own and we went with it. And
the people who really knew how to do it, meaning they could be on a board of
directors [Unclear 0:09:49] and so on [Unclear 0:09:51] so we came back to the
east coast to look for property and ended up buying this property in Baran,
Massachusetts so that was 39 years ago.
Jerry: Wow.
Sharon: I was 23 years old, and we didn’t have maybe a new product or service because it
was pretty ancient service except that it was in a completely new form and
nobody had ever done what we were doing. It was the first center begun by
westerners, run by westerners, that wasn’t referring back to a particular Asian
teacher or monastery and everything was new, everything was up for grabs.
Should we have Buddha images or no Buddha images? The practice is not about

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becoming a Buddhist, why should we have Buddha images? But then we also
didn’t make this stuff up, and everything – there was total uncertainty about how
it would be received. We were creating a market actually which did not really
exist. There were very small pockets of people who put in a lot of effort to find
this stuff, you know, it wasn’t that easy and suddenly, we were saying, here it is,
in your language, in a way that you can understand, with imagery that wasn’t only
about chariots and you know –
Jerry: Yeah.
Sharon: – that’s about here and now, for you, and that was taking into account other social
forces like feminism and it was all brand new and really scary at the same time.
But now looking back, I think wow, what a time.
Jerry: Yeah, well, as someone who has been a part and parcel of the startup community
for 20-22 years, yes, that’s a startup. The fact that it was a non-profit, the fact that
it was not necessarily driving a particular technology doesn’t mean anything. It
was entrepreneurial in its endeavor, and the re-invention, I mean, every idea that
we generate is derivative and as a former investor, one of the things I used to say
as an investor was, “What is the analogue analogue? What is the non-digital,
previous incarnation of this?” And there were previous incarnations, no pun
intended, of creating retreat centers but you were inventing a new way to make
that accessible and you and Jack and Joseph in particular, but I know that there
was a group of people around you in effect – for our listeners who don’t really
know this, really brought these ancient teachings in a modern world. Now, there
was Trungpa Rinpoche who was bringing Tibetan teachings, there was Suzuki
Roshi who was bringing Zen traditions, and there were some incredibly powerful
and important teachers, all bringing these different teachings to light. But you
happy band of crazy wanderers, ex-hippies all, right?
Sharon: That’s right.
Jerry: – were trying to – from – as you are student and heir in some ways, looked at this
and said, “You seem to be trying to bring these teachings into a new container to
make them accessible in a different language and a different culture.” Is that
right?
Sharon: That’s completely right and that’s why it’s interesting that you know, I feel so
grateful that we have one another and that we really had a community ‘cause one
of us knew what we were doing and it was a tremendous balance; we had a vision
and we also had a building, you know, all of a sudden where they had a roof and
people kept saying things like, “What if the roof starts to leak?” You know, their
real life concerns here that this is the country where everyone needs to buy health
insurance and we have a staff, we have to take care of them. We can’t just say you
are on your own, and we had a vision and trying to find balance between all of

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that and I’m just endlessly grateful we had one another and that we could bounce
all those concerns off one another.
Jerry: You know, I was really struck by and you saw me run over to write it down; you
said, “None of us knew what we were doing.”
Sharon: Mm-hmm.
Jerry: Sharon, I can’t tell you, the number of laughs that I get, when I speak in front of
entrepreneurs and I say, “Who here is brave enough to admit that they haven’t a
clue as to what they are doing?” Because that feeling which is a kind of utter
incompetence on making this up, that feeling is so prevalent that even when I
name it, people look – like their eyes dart left and right to say, “Oh my God, other
people have this feeling too?”
Sharon: Yeah, isn’t that amazing?
Jerry: So to add to the understanding of it, I think what they may be experiencing, which
I suspect the three of you didn’t necessarily experience but I don’t know, is that
they couple that with a sense of shame because they live in an environment where
the implicit expectation is that they are supposed to know what they are doing,
when the truth is, everyone is making it up, every single day. And so in addition
to feeling incompetent and overwhelmed, they feel ashamed.
Sharon: Mm-hmm, that’s a pity. I don’t know that that we were totally free of that. I
wouldn’t have called it shame, I have to think about it. I wasn’t you know,
ashamed at not knowing what I was doing because I really didn’t know what I
was doing but I think the balance was so hard to strike that – we did have a
product, so to speak that had a lineage, you know, and so we couldn’t really water
it down, and then there was that big uncertainty was, this is a bridge too far, you
know, like, have I blown it? Have I really let go of the – have I lost the essence?
Have I really taken this in a bad direction and so there’s a lot of fear and we
weren’t always in total accord with certain tradition-bearers, and we really felt we
had to find our way. And so that was also very emotionally laden process to kind
of say, – I mean, we did make plenty of mistakes too and say, “Okay, we got to
take another look at this; we’ve got to look for another angle” or “I hear what you
are saying and I am really going to listen and in the end, I am going to have to feel
what’s the right way”, or we’re going to have to feel what’s the right direction. So
there was a lot of emotional layers but I didn’t feel bad about not knowing what I
was doing because nobody really knew what they were doing.
Jerry: Right, you weren’t necessarily constantly comparing yourself and my partners
and I often refer to it as “the middle school atmosphere” that a lot of the listeners
deal with. So, imagine if you will, growing up in and shadow of an uber, and so
layering all of this fear, layering all of this wish to do justice to the idea, to the
vision, the fear of disappointing that vision, plus the sense of incompetence and

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the fear around how do I actually handle everything that just feels like it’s in
constant jeopardy all the time while simultaneously watching what feels like,
everybody else succeeding, and me making no progress; and that’s the life of a
modern entrepreneur.
Sharon: Yeah, it’s tough.
Jerry: It’s tough. It’s really tough. You know, I often think of the teachings and when I
think of those situations and I don’t know if you are comfortable with this but I
am going to ready some of your words back to you.
Sharon: Yeah, sure.
Jerry: So this is from ‘Lovingkindness: The Revolutionary Art of Happiness’, one of our
favorite books.
Sharon: Thank you.
Jerry: And it’s two separate quotes, two separate sections but each dealing with the same
things. “The basis of the Buddhist psychological teaching is that our efforts to
control what is inherently uncontrollable cannot yield the security, safety and
happiness we seek. By engaging in a delusive quest for happiness, we only bring
suffering upon ourselves. In our frantic search for something to quench our thirst,
we overlook the water all around us and drive ourselves into exile from our own
lives.” So beautiful.
Sharon: Thank you.
Jerry: So, am I crazy or does that really apply here to what we are talking –
Sharon: No, I think it does; I was going to ask you, do you think it works to redefine
success?
Jerry: Oh yes. Say more though, tell me more, what occurred to you.
Sharon: I’ve done a few programs now with my friend, George Mumford, who is currently
the meditation coach of the New York Knicks and his programs have all been in
New York and Knicks apparently had a ghastly season, you know, so previously
who was the meditation coach for the L.A. Lakers and before that for the Chicago
Bulls, he has some championships behind him but every time we do this thing in
New York, you know, we are just talking about practice mindfulness and how he
applies it and how I apply it and somebody always asks about the Knicks and you
know, how badly they are doing. And he said, “I redefined success. I think
success is doing better than you did before, you know, that’s how I’m defining
success with them and that’s our aim.” And you know, he also had a very
interesting thing, which maybe fits in as well where he said, “The move from

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being solely fixated on individual excellence –” because of course, these are
superstars, “– to considering yourself a part of a team is actually the essential
move so that you see the interdependence of everyone on the team instead of
feeling, it’s all up to you; your glory, your failure.” And so people say, “Well,
how do you get these people, you know, these amazing superstars to think that
way?” And he said, “That’s how you win. That’s how you actually have to do it.”
So there were really those two things; can we define success differently? I mean,
not in a goofy sort of way, but you know, in a real way.
Jerry: I think a question was really pressing because that is an essential element of what
I try to teach, and what I do is, I take it back – one of the first things I do and I’m
from Brooklyn so I’ll curse, I’ll say things like, “I don’t give a fuck what happens
to your company. I actually care if you survive.”
Sharon: That’s right.
Jerry: Because – and the words I tend to use are ‘greater resiliency’, greater capacity to
withstand the vagaries of every day. And you know, I know that there is a
neurotic attribute to my wish; it’s neurotic in the sense that it’s based in my own
suffering and having been 38 and coming to the edge of a deep, deep, deep
depression where I was suicidal, and realizing that I needed to back away and
really alter and redefine success and failure. And by redefining the success, as not
necessarily as a greater and greater shareholder value, but a greater and greater
emotional experience so that work becomes a means for full self-actualization, so
that work becomes a means by which we become more human, not less. All of a
sudden, what we are seeking, the suffering we are seeking to alleviate is that
“dukha” is that internal suffering, that existential question. So you know, from
where I sit, I do think that the redefinition of success and the corollary to that is
the redefinition of failure.
Sharon: Mm-hmm.
Jerry: So failure is not necessarily, you know, running out of money. Now, there’s an
interesting by-product when you do this, which is that I think you start to create
organizations where the inherent humanity and creativity of people starts to
become unleashed and just like George maybe experiencing on the court, what
ends up happening is, individual superstars start to act like a team and the
interdependence, so their experience of being together is better and it’s not a
direct correlation, but they do start to perform better by traditional metrics.
Sharon: Right. Yeah, it’s funny you remind me of – I just told someone the story of the
Dalai Lama where I was at Emory University some years ago, and he was on a
panel with Richard Gere and Alice Walker and the first question – the panel was
sponsored by the art department so the first question was basically “Does great
creativity have to come out of great suffering, great torment?” And Alice Walker
said, in her early career she felt that, he mentor was Langston Hughes, he felt that

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and she picked that up but she said that now as she’s getting older and she’s
getting happier, she thinks her work is better. And then Richard Gere said, when
he was an angry young man, he could only play angry young man, and then as we
got older and happier, his range actually expanded; and the Dalai Lama did not
understand the question. It was like so foreign, and he was like – he couldn’t get it
because he comes from a totally different perspective, and finally said – I mean,
he didn’t say schlep, but he basically said, “People are schlepping me to see these
things, to say, wasn’t it beautiful, wasn’t it wonderful, isn’t it interesting and he
said, in Tibet, something was considered beautiful and wonderful and creative
depending on what happened to the creator in the process. It’s not the product that
you assess like, wow, that’s a great work of art; what you say is, wow, that person
became so much kinder, or that person learned so much, you know, maybe spent
20 years on one object, carving it, creating it, but you really are the work. It’s you,
not it.”
Jerry: So success becomes defined by who I am –
Sharon: That’s right.
Jerry: – moment to moment to moment in that process.
Sharon: Yeah.
Jerry: Oh that’s beautiful. You know, one thought occurred to me as you were relating
that question, I also used to hold that view and I adore writing, and I would often
tap into the dark places within me to write, and I think that what I have come to
understand is that the issue isn’t about whether or not it’s the dark stuff or the
light stuff, it’s as much as it’s the real stuff –
Sharon: Yeah, that’s right.
Jerry: – and it’s this notion of being authentically who you are in that moment. So if you
are sad, you are sad and if you are joyful, you are joyful. It’s not pretending to be
or trying to be, forcing your way to be something other than who you are. In some
ways, it’s a radical approach to leadership as well because a corollary question to
that that often arises is, “Well Steve Jobs was an ass and he really drove people
crazy, so should I be like him?”
Sharon: Mm-hmm.
Jerry: And my answer tends to be, “You’re not Steve Jobs so the question is moot”
because all you’re going to do is engender distrust and violence in the
organization, by you pretending to be someone who you are not in the moment.
Sharon: Right, that’s right.

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Jerry: I’ll bring up another quote and this time it comes from ‘Real Happiness at Work’
one of your more recent books. You wrote, “Authenticity is inextricably linked to
happiness on the job and off. It rests on a sense of belonging, not just in the way
we normally use the word belonging as being part of a team effort at work or
being accepted into a particular group, but also feeling centered, feeling at home
in our body, in our own sense of values, in our own dignity.” Tell me more about
authenticity and what you meant by that.
Sharon: I think it really means a sense of wholeness, you know, it’s not as people confuse
authenticity with impulsiveness, you know, like I’m going to lay into you because
that’s what I feel. I’m not going to consider skill or anything in that regard, and I
think don’t that’s sort of mean. So I think it means being able to express
vulnerability, if that’s what’s actually happening, being able to express
uncertainty and maybe the balance of uncertainty with vision or aspiration so that
you can say, I don’t know exactly how we’re going to get there, but this is where I
want to get and it’s a beautiful, frank, open expression. It’s not like blame on
others when there’s some responsibility to be had oneself and so I think it’s
presenting, it’s so rare workplace, where one is whole person and it’s one of the
biggest areas of compartmentalization. People can’t find themselves at work; their
values, their ethics, their hopes, their dreams, they’re all shut down for like 8-14
hours a day and then you go home. So it’s the possibility of really being present,
even if you don’t know the answer to something, it’s expressing that like, here’s a
dilemma.
Jerry: Yeah, it reminds me of a story; a client once said to me that they’ve been planning
to raise a bunch of money from an investor and they were expecting what’s called
a term sheet, which is the first stage in the process and they didn’t get the term
sheet. And so he called me up in a panic and he said, “What should I tell the
staff?” and I said, “Well, how about the truth?”
Sharon: Yeah.
Jerry: He said, “Well, they might all leave.” I said, “Would you rather have them stay
for a lie?” And the truth is, that is what we do; we create these conditions where
we try to protect people from feelings, we protect people from the authentic
experience, we push away what’s actually happening and we can flip out too
much. We can go into panic because in some ways, panic is an over-reaction, an
unreal reaction to the situation. It’s over-reacting.
Sharon: Yeah, well, it’s like saying there’s no possibility change, we’ve now seen the end
of the story and this is it, it’s bad.
Jerry: That’s right. And to me, they are two sides of the same experience; nothing is
wrong and everything is wrong.
Sharon: Mm-hmm.

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Jerry: Whereas, it’s just what is and let’s use some skillful means to discern what is and
what is not; what is my projection and all my fears from my childhood or my fear
of disappointing my teachers or the people who taught me, versus, the reality of
what’s actually happening in that workplace. When you were talking about the
experience of authenticity and the compartmentalization at work, it reminded me
too of a statistic that I read recently: something like 70% of Americans are
massively dissatisfied in their work.
Sharon: That’s a big number.
Jerry: That’s a big number and we spend so much of our lives in relationship to our
careers and to our jobs and to our aspirational work, whereas if we created spaces
I think through our own leadership regardless of our title, and through our own
presence, we might create space for the whole person and kinda lower that
dissatisfaction number.
Sharon: Oh definitely it’s like the radial redefining of success, right, like I was authentic
today, that’s a good day or you know, I mean, there are certain metrics that are
real of course, you would have to stay in business or even thrive but beyond that,
so much of it is a fabrication, like if I go to a book store and there are 20 people
there instead of the 50 I had dreamed of, do I only look at the empty chairs or do I
actually talk to 20 people who are there and have an authentic and real and often
beautiful relationship in that moment with those people? I mean, I had a book
launch, I guess it was ‘Real Happiness at Work’, and the blizzard at Brooklyn,
you know, I go, “Great, what if they cancel?” But they didn’t cancel so I had to
get from Manhattan to Brooklyn and I thought, “No, I will be there on zero.” I
thought, “If there’s zero people there, maybe I can go home.” But there were
people there and I think they must have all walked, you know, the people who
lived in the neighborhood. But what am amazing thing is people came out in a
blizzard and we can have an incredible time together or I can really look at empty
chairs and think, “Damn you, I should have canceled it, it’s all their fault.”
Jerry: And one of the reasons I love you, I love you generally but one of the reasons I
love you as a teacher is that even in these little moments, you reveal, “Oh right,
Sharon struggles with this too.”
Sharon: Yeah.
Jerry: You know, “Am I going to put a book out, are they going to accept it?”
Sharon: Yeah.
Jerry: And what’s going to happen here and what’s going to happen here. So how does
someone with a 40-year practice –

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Sharon: A little more, 44.
Jerry: – 44-year practice, how do you hold your relationship to your own sense of self as
it relates to that, your sense of self-worth or your sense of – you know, the fears
associated with it? You may not carry the same fears as some of the folks that I
work with but fears are fears. How do you work with those?
Sharon: Well, I think obviously there’s an enormous difference, you know, with 44 years
of practice, I see things so much more quickly, I have a almost like a relationship
of rueful amusement, [Unclear 0:35:35] you again, because I know, you know, I
don’t want to spend like the next 18 months thinking about that blizzard, you
know, and the publisher and the book store and it’s like there lies misery. And I
feel capable of so much happiness at this point, which I never started with at all
and not that it wasn’t there, but I feel like my capacity as a person and I believe
it’s everyone’s capacity, and I just don’t want to spend all that endless time – plus
it’s the irony of how much everything changes. There’s this quality in Buddhist
teaching called sympathetic joy, as you know, which is the joy and happiness of
others; like instead of feeling so jealous or envious, really feeling joy for them. So
I was once giving a talk at the Insight Meditation Society about sympathetic joy
and I used this example of the opposite and I said, it’s like you know, you’re in
New York City and it’s Sunday morning, and you go buy the New York Times
and you open it up to the book review section. And you open it up to the best-
seller list, and you see your friend’s book has gotten on the New York Times
bestsellers list, and you think, “Ugh, that’s too bad. It should have been my book;
and not only that, it would have been my book, except somehow they stole it. It’s
like the New York Times was heading right to my house and they like, hijacked
them and they totally don’t deserve it, I deserve it.” So by the greatest of ironies, I
had three different friends sitting in that room doing the retreat, each of them had
a book on the New York Times bestseller list and they each came up to me after
the talk and said, “Is that how you felt when you saw it?” And I said, “No, those
words just came out of my mouth.”
Jerry: Yeah.
Sharon: So like five years later or eight years later or something like that, I had a book on
the New York Times best-seller list, ‘Real Happiness’, which I still don’t know
how that happened. I felt like it was a total fluke, you know and –
Jerry: Well, it happens to be a great book –
Sharon: Thank you.
Jerry: – but that’s beside the point.
Sharon: But it was like what? And you know, and then I could be on the other side of it,
which was very interesting and you didn’t tell me, like when I was giving that

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talk, that I would ever see that turnaround, never. I never would have thought that.
But now, I’m old enough, you know, I’ve seen that as you see that again and
again and again, and it’s constantly changing and there’s not only uncertainty and
fear in that but it is endless possibility and movement. The ways we define
ourselves like “I am the kind of writer who would never get a book on the New
York Times best-seller list” like how do you know that? “I can only go so far” or
you know, “my possibilities, my sense of potential is really compromised and it’s
kind of blunted at this point.” But how do we know that? It’s only a construct that
we are laying on ourselves and even better is when that’s combined with a radical
redefinition of success. You know, like, maybe I’d never get a book on the New
York Times best-seller list, I’m happy for every single friend who does. I am
really, really happy.
Jerry: It was so beautiful Sharon and I am really struck by this phrase and the notion of
recognizing my capacity to be happy, and really working with that and then
expanding it out from that. So I’m going to ask a leading question because I think
I know the answer to this, having been your student now for a while, what’s the
relationship between cultivating the capability of happiness and loving kindness?
Sharon: I think it’s a great correlation between loving kindness for yourself.
Jerry: Same one? And some of the listeners might not really understand the term
“Lovingkindness” so if you can give a brief –
Sharon: Sure, well lovingkindness is the common translation of a word in Buddhist
teaching which has to do with a real care – the literal translation of the word is
friendship; so it’s like becoming a friend to yourself primarily, and then based on
that foundation, opening to a recognition of connection with others, ultimately all
others. So it doesn’t mean you like somebody or you are going to give him all
your money or take him home with you, but this is deep sense that our lives have
something to do with one another, that we live in an inter-dependant universe and
so we don’t feel so alone and cut off. And interestingly enough, it doesn’t begin
with self-abnegation or self-condemnation and utter deference to others; it begins
with lovingkindness for oneself because it’s almost like you are – you used the
word ‘resilience’ we need a reservoir of resilience within us. We need some sense
of resource within us or we can’t really care about others ultimately in a sustained
way and so I think that one of the phrases that’s used in lovingkindness
meditation is “May I be happy?” and it’s the gift-giving, it’s not meant to sound
like pleading or imploring, but it’s giving ourselves the gift like “May I be
happy?” And people hear themselves saying it like, “May I be happy? No way. I
don’t deserve that” or “That’s wrong, I shouldn’t be happy. I should be miserable
or I should be, at best, medium. I shouldn’t be really happy.” I have a friend who
was once quite clinically depressed and was taking anti-depressants, and she was
very embarrassed about that, which I am a big proponent of anyway, but she said
to me, “I want you to know, I’m not taking enough to be really happy. I’m just
taking enough to feel a little bit better.” I said, “Why don’t you take it to be really

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happy?” But that’s how we are. Like, “I don’t deserve to be really happy, I don’t
need to be really bad maybe, I feel a little bit better but really happy, no way.”
And so the more lovingkindness we have for ourselves, the more we understand
it’s like “Yes, may I be really happy? I am capable of that, I deserve that, and it’s
not to the detriment of others. That’s what actually allows me to care about and
try to be good to others, just because I have that going inside.”
Jerry: Well, I would add, in my brief experience in doing that form of meditation, a form
that you teach in that way, my own capacity for happiness for myself has not only
improved but my experience of actually being able to wish those friends of mine
who had bestsellers on the New York Times best-seller list, their happiness, and
genuinely feel it.
Sharon: Yeah.
Jerry: Not some patina of “Oh, this is the right thing to do, Namaste, I’m going to be a
good person.” But really be in that place of that being a spontaneous expression
and then noticing afterwards that I didn’t have that other spontaneous expression
that I used to have, which was jealousy, or envy, or a sense of diminishment in
my own self.
Sharon: Okay.
Jerry: Just noticing the difference there; that doesn’t mean I don’t struggle with it, I still
struggle with it.
Sharon: Yeah, of course. I mean, we are human beings, you know? It’s the nature of it, I
think.
Jerry: Yeah. I think, you know, it’s in that process, that tension of going back and forth
and that’s one of the things that I always appreciate about our relationship is that
we can go to those places and go back and forth and share those experiences with
a kind of – and you used the phrase before, a kind of rueful bemusement, “There I
go again” and –
Sharon: Yeah.
Jerry: – not self-flagellation, condemnation, “There I go again, what’s wrong with me?”
Sharon: That’s right.
Jerry: It’s beautiful. So listen Sharon, I thank you so much for this. This conversation, I
know folks are going to respond well to, and I encourage everybody out there to
read your work, take classes, reach out, go on retreats, check out Insight
Meditation Society; the work that you do, the work that you have done for 44

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years has been so powerful and so helpful for everybody and thank you so much
for taking the time to speak with us today.
Sharon: Oh thank you, really, it’s great to see you.
Jerry: Good to see you.
So that’s it for our conversation today. You know, a lot was covered in this episode from links,
to books, to quotes, to images. So we went ahead and compiled all that, and put it on our site at
reboot.io/podcast. If you’d like to be a guest on the show, you can find out about that on our site
as well. I’m really grateful that you took the time to listen. If you enjoyed the show and you want
to get all the latest episodes as we release them, head over to iTunes and subscribe and while
you’re there, it would be great if you could leave us a review letting us know how the show
affected you. So, thank you again for listening, and I really look forward to future conversations
together.
[Singing]
“How long till my soul gets it right?
Did any human being ever reach that kind of light?
I call on the resting soul of Galileo,
King of night-vision, King of insight.”
[End of audio 0:46:21]
[End of transcript]