What It’s Like To Live Your Purpose

And so that was the first time that it would like really hit me like a ton of bricks of, oh, there's this thing that I'm called to do for whatever reason that I cannot explain, but if I don't honor it, I know that it— life is not as full.

Welcome back to The Art of Accomplishment, where we explore living the life you want with enjoyment and ease. Today's episode is a special one. Joe sits down with Jerry Colonna and Steve Schlofman, who are both VCs who have become coaches. Jerry is the CEO and co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. Steve is the founder of Downshift and a professional transition coach based in New York. He guides executives and founders through intentional transitions and recovery from burnout. The three of them are going to talk about what it's like to live your purpose and the journeys that each of them have taken in following theirs. I hope you enjoy it and that you get a lot out of it.

Well, I just have to say, it's, it's an honor to be with the two of you as older brothers. I'm the younger brother here. And so, you know, it's hard not to start by going into where we are in the world today. There's a lot of uncertainty. A lot of people are scared. So maybe starting with you, Joe, you know, what are you seeing in the leaders that you're working with? You know, how are they holding this uncertainty in this new world that we find ourselves?

It seems like there's two ways in which it's being held. The first one is that they're holding it with a lot of fear. And so typically what that does is that creates binary thinking. So they, it's good and bad, black or white, right and wrong. When people are in the fear without feeling the fear. And the other thing that's happening is there's a lot of false end thinking that goes on. So if this happens, then doom, or if this happens, then the company will collapse, et cetera, et cetera. And the propensity to fall into that fear is based more in different parts of the market. The other group of folks that I work with see this as a massive opportunity at these moments of transition that we are inevitably going to go through as a society, as people, as a business, that it allows you to redefine institutions, allows you to have a lot of growth just the same way a marriage would or a divorce would. And those folks, they're deeply feeling into their fear, allowing that to move through them, and then looking for the opportunity. The way they find the opportunity isn't 10-year thinking or 5-year thinking, which you can do when there's some idea of stability, but they're finding the opportunity in a more like a 3-month-out period, a 6-month-out period.

Going back to that black and white thinking.

Yeah.

You know, how do you help someone through that and be able to process that fear and uncertainty in their system?

Yeah. So most of what happens is people's natural response is, how do I get out of the fear? And so if you want to, the best way is to get into the fear. And so typically you can feel that fear at any moment if you allow yourself to. And if you fully allow the emotion and the expression of that fear in your system, then you'll get to a feeling of greater capacity. It's interesting, our minds tell us Oh, if we allow ourselves to be sad, we'll be sad forever. But when we allow ourselves to be sad, we actually get happier. If we allow ourselves to move that anger, we actually get to clarity and determination. So for me, it's helping them through it. It's helping them feel it.

Jerry.

Hi.

Hey.

So what are you seeing from your vantage point?

I have learned that the way for me to work through whatever suffering I'm going through is through compassion, to be with. I was talking to a friend last week who's sort of in an adjacent space. He's a, he's got a big CEO advisory service, and he said something to me, which I think it's really brilliant. He said, I'm telling people you can't not say something. And it doesn't mean you have to take a stand per se. You have to take a stand for humanity. You have to acknowledge that this is a challenging time. Mm-hmm. And what I would turn around and offer is the normalization of grief.

Mm-hmm.

I'm sure you'd agree that part of what makes this being human so difficult is the belief that whatever experience we're having is something we're not supposed to be having.

Yeah, totally.

Right. And that includes grief. I had a client whose dog passed away, and the dog predated not only their children, but their marriage. And his wife had grown very, very attached to the dog. And he asked me if I would speak to his wife. And so I got on the phone and through her tears, she said, I feel like an idiot for grieving.

The story that I weave typically to help people in grief is every time we allow our hearts to break, it increases our capacity to love. Another story is that if you are actually in a transformational process, grief is necessary. There has to be a time where you grieve the fact that for X amount many years you've been doing something in a way that's been causing you pain and it's hurt. And without that moment of grief, the transition is really hard, the transformation is really difficult. And what I notice is that typically all that's required is just staying there with them in it. And if they go to the left or the right, stay there in the grief in yourself. And, and they'll usually look forward to joining you eventually once they realize, oh, it's safe because you're there with me. And On a nervous system level, however, that was a real trick for me to learn. You know, I was made fun of when I cried as a kid. So same here. My parents would take pictures of me, and when I was like 24 years old, I was going through the photo album and there was a picture of me crying where they had made fun of me. They called it a pity party or whatever it was. So I took that picture and I put it on my desk and say, that's why I haven't cried in 14 years, obviously. So I'm going to learn how to cry. But my nervous system was so scared of the attack that I just literally would not do it. So I lived in LA at the time, so I would drive to the middle of the wilderness and I'd hike a couple of miles down this trail that nobody went on. Then I'd hike off trail and I would sit in this, like, this little place and I'd pretend to cry because I was so embarrassed and so shame-filled of crying. And I did that for months before actually real tears showed up. And then when it came, I literally cried for like 4 or 5 days straight. The well opened up.

Yeah.

What I do notice is grieving in groups is fucking a shit ton better than grieving solo. It just opens up a door that takes a long time to walk through if you're doing it on your own. And the cool story I have on business around that is that a person I was working with in one of the Alphabet companies, they had a Day of the Dead celebration, and this was a place where they were innovating. So there's lots of great ideas and products that had died, like your friend. And they would have this day of mourning, and they'd put an altar with all their things, and they would all come in and grieve as a community.

That's beautiful.

It was awesome. And I found out that this one was doing— I'm like, okay, I'll work with you. I want to learn what you're doing. So the nervous system part can be really tricky sometimes for folks.

Yeah, I noticed for me, it took me, I mean, many years to be able to actually touch into it. And feel it and express it. There are those protective tendencies that we develop over a long period of time where it doesn't feel safe.

Yeah.

And that happens with all the emotions, whether it's fear, joy, elation, sadness, anger. Anger, I think, is the one that hits so many people. Not feeling their anger, that's like a huge thing.

And what I've noticed is that on the other side of anger is what?

Clarity, determination.

And also for me, sadness and grief.

Often, yeah.

And then on the other side of that, it's like, oh, that feels so good. Jerry.

Steve.

How do we learn to trust again?

A story I often share: a woman has lost her baby, and she comes to the Buddha for relief. And the Buddha gives her an assignment to go to every house in the village and to take from that house a mustard seed.

Mm-hmm.

From any house that has not experienced grief or loss. And of course, she comes back empty-handed. And what I find so powerful about that story is not the minimization of grief that one could read into that, but in fact, the universality of the experience. The fact that not a single household could produce the mustard seed. And the reason that I think that that is an important response to the question about trust is that to understand that all that we have been sharing happens to all people all the time.

Mm-hmm. Every day.

Every day.

Every minute.

In fact, you could make the argument that it is an essential part of what defines us as human beings.

Mm-hmm.

And so we can use this process of having our hearts broken to actually understand that we are human. And from that place, to imagine trust being built not from a brittle place of Can I trust you or you being trustworthy? But can I trust this thing called being human? Because you might do something that hurts me.

Inevitably.

Inevitably. Because that's the other side of love, right?

Yeah. It's finding solace or comfort in the shared experience of humanity.

That's right. That's right.

The thing that struck me in the question was that if somebody's grieved and said, now I'm— had to find trust, I'd be like, you need to grieve some more.

Yeah.

Because what I notice is that when the grief moves all the way through, there's nothing to be scared of. So when I see people having a hard time trusting after a breakup or a marriage or a bad business partnership or something like that, it typically means that they haven't grieved the whole thing.

Mm-hmm.

How do you think about it when we have these patterns?

Yeah.

How do we begin to welcome what's unfolding within us?

Yeah, I do think it's an order of operations thing.

Yeah.

I think it is recognition of the pattern, feeling the emotional component that's hooking that pattern in place and repeating it. So I deeply welcome those emotional experiences and I get back to state of balance, then the call becomes very, very obvious. But I remember the first time it happened to me, like, where it was just so clear. I was running one of my first long-term workshops, and I interviewed everybody who came in. And there was a CEO and came up to the office, and we were talking, and my kids were in the yard, and he left, and the kids were like, do not hire that guy. I was like, it's not for hiring, it's for letting him in. Don't let him into the thing. Both my kids, and they were young, and my wife had met him and was like, don't let him in. And I got phone calls from other folks, don't let him in. And I sure as hell did not want to let him in. Like, but whoa, it was just so clear that this is what I needed to do. Like, it was just so clear in my system it was going to be uncomfortable. So I did, and it was an 18-month course and I'm so grateful he was in that course. He was such a lightning rod that allowed everybody to see themselves so clearly. And my learnings through it were amazing. And so that was the first time that it really hit me like a ton of bricks of, oh, there's this thing that I'm called to do for whatever reason that I cannot explain. But if I don't honor it, I know that it life is not as full. But underneath that, like almost all of us, just an absolute sweetheart of a human being who really wanted freedom from his own personality that he had constructed.

Yeah, I love the distinction between welcoming and acceptance. Yeah, because acceptance for me was so hard to get. You know, I would sit there with some of my teachers and they'd be like, can you accept yourself for being scared?

And I'm like, I don't know.

This idea of welcoming, which is a very different energy.

Yeah.

Yeah.

I don't know if you remember this passage in my book Reboot where I talk about a life on the roller coaster and I'm describing clients who come and they're in that seat of all of a sudden they get bad news from their co-founder has a cancer or the client is rejecting the or their funding has dried up or whatever, and they're up and they're down, they're up and down. And I think the thing that I think means the most to me about this duality of freedom and acceptance, the point of riding the roller coaster is not to get better at riding roller coasters.

Mm-hmm.

It's to learn to not board the roller coaster in the first place.

Mm.

And so if I were to say, what does freedom and acceptance mean to me?

Me.

It means being able to enjoy the roller coaster from the ground, to not attach my sense of self-worth or my sense of safety, my own essence, to some sort of outcome. And that feels like freedom. Mm-hmm.

Where I want to go is, for those listening, that are currently on the roller coaster.

Yeah.

What's that shift to go from on it to on the ground?

When I think about the roller coaster ride and it's like success and failure and, you know, things coming true that you want and the attachment that we feel to things, when I think about that as it relates to my own being, it feels really good to be able to sort of look at that and go, I don't really care. I really don't care. Now, that said, I am not free of that Velcro. It still gets stuck. And it gets stuck for me. You know, I'm the old fart in the room, right? My kids are 34, 32, and 28. And so where I go is, will they have the life that I want them to have? And will their children have the life. When I see people that I love struggling, you have a kid who goes to college and they're having a rough experience, oh my God, my heart breaks. That's where I'm still riding the roller coaster. And I don't know that I'll ever be free of that one. And I don't know that I want to be free of that one. You know, my daughter got married in September, and I said at the wedding, like, this father of the bride thing, it's fucking real. It's like a real feeling, right? But when she came up to me and she said, Daddy— and I always say she melts my heart when she calls me Daddy— Daddy, Thank you for giving me the most beautiful day of my life.

Mm.

That's it. I'm done. I'm just— stick a fork in me. Like, I'm just done. Because in my mind, she's still the same age as your daughter. Mm-hmm. You know? Right? I relish having my heart broken for those reasons.

Yeah.

In that though, what I'm hearing is as you move into this new season of life as an elder, as a parent, hopefully one day a grandparent—

from your lips to God's ears—

there's something really beautiful in that where there's this recognition of that's what matters.

It's like, what a gift impermanence is. Yeah. Because it breaks your heart. One minute you're shopping for sneakers for a 6-year-old, and the next minute you're walking them down the aisle. I mean, holy crap. Isn't life beautiful and heartbreaking?

All I want to do now is tell stories about my daughters.

This is the Father's Day issue.

This is the Father's Day issue.

I'd say over the last 5 to 10 years, it seems like there's been a huge interest in whether you want to call it coaching, healing, spaceholding, specifically from where I sit in Silicon Valley, founders, executives. You know, some might have been burnt out, others in transition, or some, you know, really hearing a deeper call to service, to supporting other humans. And like, overall, I think it's a really beautiful trend. And it's the shift from a very, in many ways, transactional sort of existence to one that's more relational, more service-oriented. And what do you hope those that are starting to hear the call, that they understand and embody before answering it?

What I notice is that there's a lot of things in that call. Often. One of them is a bit of a narcissism. My daughter has a phrase, she calls people gentle narcissists. And so there's like a gentle narcissism in that call typically. And sometimes it's an important part of the call because you're doing it to have that part of you eroded away. But I find a lot of people want to do it because it allows them to stay in this idea of the person who knows. Instead of the person who's ignorant, the person who's looked at for an answer, the person who's needed, the person who's still valid or validated, or some version of that. And then the other one is the person who helps. I don't think you go through being a coach without having some of that.

Mm-hmm.

And the more you can see that clearly and deal with the issues underneath that stuff,, I think the better you are for yourself and for everybody that you're serving. And, you know, it was 25 years of deep internal practice that I went through before I even began to think that I was equipped. I don't think it has to be that long. And I have my own issues with it and didn't want to be an authority figure and a whole bunch of other things. But I would hope is that somebody would actually do quite a bit of their own work and that they're actually looking around and they're like, if I have an organization, it's healthy and functional. If I have a marriage, it's healthy and functional. If I have kids, it's healthy and functional. Now I'm ready to go and coach rather than, you know, I can't hold a relationship, my kids hate me, and my business is super dysfunctional, but I'm going to go coach because I had an ayahuasca experience. So generally something to that effect.

Yeah.

And I say that all and it feels like it could come with some judgment and it doesn't. It comes more with grief because I've just seen the damage that can be done if you aren't perpetually looking at yourself and using this path as a reflection. And in our organization, we've had people who've been working with us for 7 years before we would let them facilitate a week-long program, to see that their level of clarity to us is like an incredibly important part of it. And I realize that that's not going to be the case. Surely isn't the case with therapy or a whole bunch of things, but at the very least, it's just to continually look at yourself, continually look at the parts of yourself you don't want to see. That would be my hope.

Jerry?

I'd agree with virtually everything Joe has said. I would say that I think it's okay if you've done the work, if you've had those struggles in your life.

Oh, yeah.

I don't think you have to be perfect. Yeah. And I don't think you meant it that way, but the only thing I would build upon, I see this both as an opportunity and a little bit of a fear that I have. And that is, there is a belief that I've gone through coach training or I have gone through my experience and I'm done. As we all have experienced, being in conversation, being in partnership with a client, will trigger you. And that's a good thing if you know what you're doing, if you know how to respond to it. There's a reason why therapists by law must have a supervisor. And I would argue that coaches should have that as well. Absolutely. And even at 61, I'm still growing up, man. I am still a wreck. And that's a good thing. So that's the— that's what I would add to it.

I want to even put a bigger point on that. If you think that you have had an awakening experience, if you think that you're fully enlightened, you are not fucking done.

How does someone step into service from a place of integrity?

If you want to be of service, you can do that in every single aspect of your life. So you don't need to coach to be of service. If you want the moniker over the being of service, I would say that that's a pretty good sign that something's wobbly. If you're doing this to make money, I would also say there's something that's wobbly. And what I notice in most of the people who are training with us over a long period of time for coaching, what happens is there's a lot of coaching that happens just naturally in their life. People just start lining up and then Once there's enough people happen, they're never going through this process of, can I find somebody to coach? Can I fill my roster? It just happens very naturally. Then all of a sudden their roster is filled.

For me, there was a moment of clarity after I had been a VC, I don't know, 15 years or so. I was serving on too many boards because I was addicted to that. And being of service in a different way.

Being of service. Being needed.

Yeah, exactly. And this young guy came into my office because he was networking with the XVC, right? Networking his way to a job. And he was a lawyer. And I asked him a question. I said, well, you seem miserable. Why did you become a lawyer in the first place? And he started to cry. And he started to tell me about his father and pleasing his father. And I realized that that was something that I'd kind of grown up doing. It was at that moment that I realized that there was something about the alchemy of who I was and how I was that was repeating itself in a pattern. This is coaching before— Yeah. Right? And I called a woman who had been my coach when I was at JPMorgan, Chris McConnell. And I said, Chris, I think I want to be a coach. And she said, well, it's about damn time. I've been waiting for this phone call. So I had been in psychoanalysis since I was 30 years old. I continue to be in psychoanalysis. I remember originally going, I'll coach on Wednesdays. Yeah, yeah, yeah, yeah. That didn't work for long.

What I want to say to the people who are potentially wanting this is like, if you think you have a choice, don't fucking do it.

Well, it's hard to start the practice.

Yeah, yeah.

Hard. I have a funny story to tell, bringing it back to you, Jerry. 2016, I come to Boulder. I'm part of the VC boot camp that Reboot was holding. And I come home from it. I'm at, like, the height of my VC career. And I say to my wife, I think I want to be a coach. And she said, oh, you can do that later in life when you retire. You need to get more experience under your belt. And then sure enough, like 2 years later, I quit my job as a VC and then eventually followed this path. But there was this deep inkling that wouldn't leave me alone.

Yeah, right.

In those 2 years before I quit, I was talking to friends that had been through different programs and reading. And so it was that thing that I just couldn't refuse.

Exactly.

It's not Vocation, whatever vocation calls you, is not the alternate to the original plan. Meaning I tried to do this startup and it failed, so now I'm going to help other CEOs. Now, that impulse I honor.

Mm-hmm.

Yeah. Okay. Go be a peer mentor. Go work at Techstars or Y Combinator. Go, go help in that way. But if you're not answering the vocational aspect of it, that calling from the divine, what's happening is you're trying to help from an empty vessel. You know, you were talking before about the people were sort of leaning in to try to help. And I get it. The conscious place it comes from is well-intentioned, but it's the unconscious place. It might be the codependent structure. That's the problem. So if you're considering it, don't do this lightly. You'll do damage.

You'll do damage. We'll see if I can make a point crystal clear. I'll ask everybody in the room, the three of us. If somebody said, you know what, I'll give you $100 million right now to buy your coaching practice. The only thing is you can never coach again for the rest of your life. No fucking chance.

No chance.

So unless that's true for you, no chance.

Yeah.

So for those that are listening that are relatively early in their journeys and those that, you know, are trying to get somewhere with a client wanting the depth or to to really drive to outcomes. What do you say to them?

Well, let's pull apart what you said. There's the drive to outcome, which I'm always suspicious of.

Yep.

Because coaching as a term is so vague and unspecific. It can be lumped together with performance coaching and sales coaching and presentation coaching, there's a place and a time for that, and it's usually short-lived and it's not transformational. Outcome-driven coaching, it can have a shadow side, which is the fix-it mentality, which goes back even further to the I'm going to be the smart person in the room.

The savior.

Which goes back to I actually feel like shit about myself. So let me utilize this situation to feel better about myself.

I know probably both of us know some famous coaches and people who've worked with a lot of folks and whatnot. And one of the things that I notice is that whatever foible they have can be seen in, like, everything. Like, if there's this very deep moralistic side to them where there's this very strong right and wrong, you'll see that that trap is in most of the people who work with them. But I've never thought of a goal that's better than the life that actually shows up. Never. I've never had that experience.

Yeah, that's true for me as well. You know, Jerry says, do the work. And I can't help but go back to a saying that I've heard you talk about, which is, fools crow. The job of a medicine man is to be a hollow bone.

Yes.

And, you know, I'm really curious about, like, what is that hollowing out process?

My personal edge right now is exactly in this location. So there's a long time where I thought humility was thinking less of myself, not making myself big. And then humility turned into making space to have things move through me, like in Fool's Crow. So the idea of my job is just to be a clean vessel for something greater than me to move through. And then I was reading recently, I think it's in the Jewish tradition where they talk about humility as taking your God-given place in the world. That's like the translation for humility. And there's a personal thing to that. And so maybe a couple of years back, it's not me, it's the teachers before me. It's not me, it's that which moves through me. There was a very non-personal form of humility. And now there's this recognition of, oh no, it's me. I've done this work and this shit wouldn't be happening without me. And really, this is not me at all. It's holding both of those two things. And so the reason I say that is because part of the hollowing out process was first realizing, oh, I'm putting myself above people in my work. Okay, that's got to go. And then there was this form of, oh, this isn't me. And I was really scared to go back to making it personal because then I was going to put myself above. I had the whole thing. And then there was, oh, wait, no, there's actually something very personal about this. There's something very human about this. And by denying that, I'm actually denying my power and I become more dangerous to actually own the personal nature of it and to say, oh, wow, I actually, I do have a tremendous amount of power. I actually have a tremendous amount of influence. So what I notice is that the hollowing out process is also always going on. It's the evolution doesn't end. It's just this perpetual process of letting go of one epiphany and finding, oh, that epiphany has its own rut, and then just continuing to learn.

Yeah, that's beautiful. When I was listening to you, I was getting the metaphor of, like, we talk about, like, peeling back the onion. And what I'm hearing you say is sort of like this acknowledgment of, yeah, like there is this hollow vessel that life is flowing through, and yet there is this like creative force, this power that is coming from within me.

Yes.

Yeah.

And it's how do I hold both?

You know, when you were referencing Judaism, I started thinking about the parable of the talents from the Bible. And if you remember from that, the father gives his children talents, which is money. And one of the sons buries their talent in the backyard, in the garden, to protect it, whereas the other goes out and squanders it making investments and comes back with tenfold talent. And the parable of the talent is you're not You're not supposed to bury your talent. You're supposed to step into that. In my life, my father said to me— I was 21, and I had gotten a job offer to be the speechwriter for the CEO at NCR. I was a journalist at the time, and it was a kind of big deal. My father's reaction was very telling. He said to me, be careful. The higher up the pole the monkey climbs, the more his ass shows. And I remember saying to myself, that is the stupidest fucking advice I'd ever gotten. But it took me years later to understand that what he was trying to do was protect me from having my ass exposed. And he also tells you that he would bury his talent in the garden. Yeah. And I have I have, for the most part, chosen to try to spend my talents and invest my talents. And whatever good either I have done in the world or has happened to me stems from that choice.

So as the space gets more and more busy with these new practitioners coming in, like, what's your hope for them?

I think that the impulse comes from a good place, and I hope that they cultivate that. You know, in my Buddhist lineage, we talk about bodhisattvas and the bodhisattva vow, which is basically to work to the alleviation of suffering for all beings until all beings are free of suffering, and then I can get on with nirvana. Um, I hope that they approach it as We're all in this together. And yeah, do your work because— and I know you guys have experienced as well— when you are with someone shoulder to shoulder and then there's that satori, that moment of just awakening. Oh my God.

So good.

That's the Lord's work. You know, that's what I wish for them.

The quote that came to mind was this, I think it's from an Amazon tribe, and I think I read it in Lynne Twist's book, but it's, uh, if you're here to help me, no thank you. If you're here to work together for our mutual freedom, let's get to work. That would be my hope.

So that's, that's the source of that mutual freedom. Yeah, that's, that's really beautiful. Where do you see the potential for this to go, this next wave of coaching?

Yeah, well, I think before we were recording, Joe was talking about the cyclical nature of these times that we're in, and if we're fortunate, then we could raise a whole generation of folks who are dedicated to that smuggling consciousness, to putting their shoulder to the wheel of making things a little bit better, a little bit more humane. That's the opportunity. So that's where my hope goes. Mm-hmm.

Yeah, where my hope goes is that the institutions of the last generation of folks was very much about fairness, maybe some equality, but there was very much like a, how do we give everybody an equal opportunity? Not an equal reality, but maybe an equal opportunity. And my hope would be that the next generation of institutions is how do we, every institution we have, create healing moments and growth. Every once in a while you get to a wedding that feels healing. Oh, wow, that's healing. Get really lucky. Sometimes you go to a funeral and it's a healing funeral. It's not just, uh, people getting drunk and avoiding their emotions. And I think there's an opportunity for that to be the case in business, and it makes business more productive, and in boardrooms, and it makes boardrooms more effective, and in every one of our institutions. So my hope would be that if there's enough people who are holding that reality field of everything that we do can be a path of development, and then I think that we have a really great society. So that'd be my hope.

Wow. All right, thank you, Joe. Thank you, Jerry. Thank you, Steve. And thank you for pulling back the curtain on your journeys and responding to the call of purpose. As always, everybody, this show is hosted by myself, Brett Kistler, and Joe Hudson. Munyi Kelly is our producer, and this episode was edited by Reasonable Volume. Tune in next time.