Jerry Colonna

Founder coach and CEO of Reboot

THIS CHAT HAPPENED ON September 30, 2015

Discussion

Jerry Colonna@jerrycolonna · ceo, reboot.io
Hi...I'm Jerry. I tend to spend a lot of time thinking about the intersection between "who we are" and "what we do." I work with folks who find that intersection terrifying, challenging, exciting and, ultimately, gratifying. I became a coach, partially to save others from the kind of crazy life I found myself living and partially because I love meaningful and real conversation. Sometimes I say smart things. Sometimes I say stupid things. On the whole, I try for more of the former and less of the latter. Oh, and I'm the CEO of Reboot.io where we offer a twice-monthly podcast, coaching services, bootcamps, facilitated peer support groups and other stuff all designed to make folks feel less alone. We've already begun sharing.
Zack Shapiro@zackshapiro · Core Team at Nano
@jerrycolonna What's the best way to shake all of the "shoulds?" For example, "I should be further along in my career." Or "I should making money/starting a company/etc. like {insert person or acquaintance here}" They're loud and super-distracting. Is having a mission in your work the best way to drown those out? Or maybe practicing bringing the focus back to the present moment? Thanks for doing the AMA!
Jerry Colonna@jerrycolonna · ceo, reboot.io
@zackshapiro You're welcome. I wish I could type faster. :) Or should I say, "I SHOULD be able to type faster. What's wrong with me? I'm such a loser. Folks here are going to have this terrible time with this AMA and then they'll see I'm a fraud, probably stop listening to my podcasts, and then I'll have no clients. And then I'll be broke and wandering the streets, a laughing stock..." Oh wait. I think I know what you mean by "loud and distracting." ;) So this is counter-intuitive...don't try to drown them out. Think of them as the voices of people (or a person) trying to keep you safe. Trying to keep you safe, warm, and happy. As Dan Putt will attest, I recommend then blowing that person or those people kisses. Thank them for trying to keep you safe, warm, and happy. And then let them know that "You've got it." You don't need to be told what you "should" be doing any more. You're an adult.
Zack Shapiro@zackshapiro · Core Team at Nano
@jerrycolonna Thanks Jerry!
Ryan Hoover@rrhoover · Founder, Product Hunt
Hi, Jerry! This interview with you and @Jason on TWiST is one of the best discussions on the emotional challenges and depression those starting a company face:
Non-founders face the same struggles but the biggest difference is that founders can't really leave, which emphasizes the importance of choosing to build something you're passionate to pursue for a ~decade. What advice do you have for those wanting to start a company, especially when the emotional stress many founders face is entirely foreign to them?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@rrhoover Thanks Ryan. Getting @jason to tear up was a highlight of my career, if not my life. Wrt to the advice, the most important thing is to share...get over the fear of looking like an idiot or a failure and share. Talk to others. We're all kinda crazy. So what?
jason@jason · ceo, writer, event host & angel
@jerrycolonna @rrhoover perhaps my personal favorite episode... we went there.
Andreas Mitschke@andmitsch · I own a computer
@rrhoover thanks for that video... thank you so much!
Jerry Colonna@jerrycolonna · ceo, reboot.io
Me too @jason. ;) @rrhoover
Positivity Dan@positivitydan · n/a
@jerrycolonna How do you think about helping people "open up" about their feelings? How do you frame the benefits of these types of conversations?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@positivitydan The issue isn't really about how "open" people are as much as it is about authentic people are. Being authentic is scary but in the end easier. First, others respond well to it. And second, more important, faking it, as I'm found of saying, is fucking exhausting.
What kinds of things do you think that founders / entrepreneurs need to 'unlearn' in order to truly live and work authentically?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@tanmcg Most important is to stop thinking that there's one right way to be, or to lead. There's only one choice: Your way. So learn from those you admire. Emulate aspects of their style. But find your own genuine heart of leadership and take your seat.
@jerrycolonna Do you find that many more from the startup space are moving towards Buddhism, mindfulness or contemplative practices? Why do you think this is? What are the pros/cons you are seeing from this for both the organizations, the employers and employees.
Jerry Colonna@jerrycolonna · ceo, reboot.io
@tanmcg I think there are a lot of folks who are fed up with the systems as they are...the "playbook" if you will that we've all been handed and which all feels inadequate. The wider interest in showing differently is not only showing up in startups but in the broader work world. (I'll be speaking, btw, at the Mindful Leadership Summit in Washington, DC on November 7. Many of the folks who are trying to bring these practices into the corporate world will be there...many of my teachers.) I think the interest stems mainly from the dissatisfaction of the way things are. There's this underlying (and essentially correct) view that there has to be a better way. Our current ways induce too much existential violence, too much suffering. WRT to pros and cons...the only con I see is that people may prey to what some teachers have defined as "spiritual materialism"--supplanting an interest in and dedication to career advancement with a similar obsession in mindfulness or Buddhism.
Erik Torenberg@eriktorenberg · Former Product Hunt
Jerry! Welcome :) What's surprised you most since launching the podcast?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@eriktorenberg Two things...How open people would be in sharing what's really in their hearts and the universal support for such openness. I guess a third thing...how great a partner Dan Putt is (and how sexy his voice is). ;) https://www.reboot.io/podcast?=ph
Who would you say have been the trailblazers in this space for personal inquiry? Who set the stage for the work that you do currently?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@tanmcg Oh my...so many folks. The two that pop into my mind first are Ani Pema Chodron, the Buddhist nun, and my dear friend and mentor Parker Palmer. I remember being blown away by Parker's open and authentic description of his struggles with depression (in Let Your Life Speak). Reading that section changed the way I viewed my own feelings...it enabled me to see myself as merely human, albeit one who was in pain, and not as someone who was inherently broken.
Legendum Ltd@legendum_ltd · Kevin, MD, Legendum Ltd
@jerrycolonna how do I find a productive balance between work and family whereby family don't grind me down with wants/needs, so I can commit energy/effort to ventures?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@legendum_ltd Ah yes...the work-life balance is...so my famous blog post is called "Work-Life Balance is Bullshit." http://www.themonsterinyourhead.... Basically the goal should be a well-integrated life where the inner and the outer play together and reflect a coherence. Parker Palmer's concept of a life "Divided No More" also comes to mind. The issue is learning create coherence and resonance in all that you do. So that when you work, work; when you play, play; and when you're making love, don't answer email.
Mat Ellis@matellis
Why do people cry when they talk to you? By this I mean, what's REALLY going on when this emotion pours out?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@matellis Hey there...I think it's a function of people feeling that they are being listened to, really heard. Often times it's the first time that someone has taken a genuine and heartfelt interest in what they have to say. Moreover, I think that behind so much of what we do is, what one of my teachers called The Genuine Heart of Sadness (http://tzal.org/dharma-chogyam-t...). We all walk around with these deep wounds. We are socialized to gloss them over. Then when we encounter someone who is curious, judgmental and caring, we break open. There's an old saying that God places the words of the Torah "on" our hearts so that when the heart breaks open, the words can tumble in. I like that.
Nathan Bashaw@nbashaw · Head of Product at Gimlet Media
How do you help founders deal with the weight of all the uncertainty that's on them? Speaking from experience, it can get mighty tiring :)
Jerry Colonna@jerrycolonna · ceo, reboot.io
@nbashaw Your notion of the weight of leadership reminds me of my favorite quote from Shakespeare. Henry V has assumed the throne and is immediately challenged by France. He raises and army and invades and, the night before the battle he says, while walking alone amongst his soldiers: "Upon the king! “Let’s lay everything upon the king: our lives, our souls, our debts, our anxious wives, our children, and our sins.” I must bear responsibility for all of it. What a painful condition responsibility is. It goes along with being born to greatness, but it makes you get badmouthed by every fool who only has his own suffering to care about. What infinite peace do king’s give up that private men enjoy? " He's scared and hates the responsibility. It weighs on him. And uncertainty is a big part of the challenge. All things are uncertain. All the time. Learning to be with that is so important. Hugh MacLeod and I talk about this in this episode: https://www.reboot.io/episode/24...
Positivity Dan@positivitydan · n/a
@jerrycolonna some people have been "faking it" for so much of their lives without even realizing it (because of other's expectations, societal pressures, etc). How do you help those people realize the authenticity within themselves?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@positivitydan Great question. I found in my own life that exhaustion and suffering, my depression, was so overwhelming that I no longer had the energy to fake it. It was so scary and so liberating. That said, be careful of YOUR wish to help someone else realize anything. Each of us are responsible for our own craziness. So I'll turn it around. How do YOU show up in YOUR life? Are you being real? If each of us did that, it'd help others who might be timid about showing up themselves.
Emily Hodgins@ems_hodge · Community and Marketing, Product Hunt
Can you expand on what the intersection between 'who we are' and 'what we do' is? Are we defined by what we do in terms of career? What is your thinking on this?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@ems_hodge I think there's a potential for pain and suffering when "who we are" comes into conflict with "what we do." By understanding with deep radical self-awareness (and lovingkindness) who I really am (including all of the shitty stuff I'd rather hide and toss into the shadow), I get to create coherence in the work I do (and the way in which I do that work). I think there's an existential violence (closely related to the Buddhist concept of dukkha) that occurs when who we are doesn't map well to what we do.
Jacqueline von Tesmar@jacqvon · Community at Product Hunt ⚡️
Hey Jerry! What have been the biggest moments in your life that have helped shape you as a person, and helped craft your approach to coaching others ?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@jacqvon So many it'd be hard to list here. But I'd say things like walking away from my career as a VC. Crying my way through When Things Fall Apart and Let Your Life Speak. A vision quest I did in 2008. Meeting and falling in love with my partners at Reboot. I will say that the common denominator is that they usually involved me crying in some way.
Sarah Jane Coffey@savvysarahjane · Reboot.io
@jerrycolonna What does it mean to practice radical self-inquiry?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@savvysarahjane It means stripping away the masks that we all carry, that we're socialized to wear, so that our real self shows up. It means doing so with love and compassion FOR YOURSELF but with honesty and bravery. It means inquiring deeply into your own motivations. As my therapist would often say to me (with nothing but love in her voice): "What are your REALLY up to?"
Emily Hodgins@ems_hodge · Community and Marketing, Product Hunt
@jerrycolonna have you seen a rise in the amount of people searching for (or needing) help from coaches with your expertise? If so, why do you think that is?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@ems_hodge I have. I THINK, but I'm not really sure, it's a function of people becoming more and more open about the things they are struggling with. And THAT is really powerful and really helpful. There is a little part of me that worries that it's a fad, that's kinda cool to say, "Hey, I've got a coach..." But really I think it's an opening in the armor that tends to surround us. And, as my partner Khalid Halim likes to say, we'll "smuggle in consciousness" through that opening.
Ben Tossell@bentossell · newCo
@jerrycolonna how did you know you wanted to become a coach? Was there one moment, or a gradual succession of things that led you there?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@bentossell There was. It was a moment when a young man came to see me for advice about leaving his job as a lawyer. He wanted to network his way into a startup. And I got curious and asked him why he became a lawyer in the first place (since it was evident he hated it). He started to cry as he told me about pleasing his father. That's when I thought that the work I had done on myself might be helpful for someone else.
Positivity Dan@positivitydan · n/a
@jerrycolonna how can one get better at having the deep heartfelt conversations you mentioned above? How do you think one could best go about developing this skill? Thanks for doing this Ama!
Jerry Colonna@jerrycolonna · ceo, reboot.io
@positivitydan I like to say that God gave you two ears and one mouth for a reason. That's the ration between listening and speaking you should us. The key to deep, connective conversation is listening.
Joel Longtine@jlongtine · Software Engineer, RxREVU
One thing that comes up for me a lot as an engineer in the startup world is how to bring meditation, developmental psychology, organizational psych, etc. into the workplace in a way that isn't threatening or has people's "bullshit" detectors go off. Any thoughts on bringing _this_ depth of awareness and capacity to the every day intensity of the startup world?
Jerry Colonna@jerrycolonna · ceo, reboot.io
@jlongtine Start with yourself. Be open and a little skeptical of your desire to bring this depth of awareness to other people. Don't get me wrong. I'm a huge fan of this work. But I bristle when someone suggests I "should" open myself to something. If you lead (regardless of your power within the organization) from a place of genuine radical self-inquiry, if you lead from a place that is the consequence of being mindful, it will help alleviate suffering (yours as well as others). THEN, someone might say, hey there, that Joel guy, he seems alright. I wonder why that's so.
Joel Longtine@jlongtine · Software Engineer, RxREVU
@jerrycolonna @jlongtine Thanks, Jerry. That helps and feels really good. It occurs to me as seduction. Show a potentially better way, that answers more and more questions... and people get to see that. Also, it means that I don't have to suffer worrying about bringing it. Simply be it myself. No push, no striving, no grasping, either within or without. Also, saw you here in Boulder and Buddhist Geeks a couple years ago and really enjoyed your talk. Keep up the good work!
Sergey Nazarov@sergeynazarov · SmartContract CEO
Hi Jerry, thanks for doing this AMA. Would you say that Stoicism in the sense of "knowing thyself" and "wishing that things happen as they do" is a productive outlook for a technology company founder to have? I am also really interested to hear of any books you can recommend that reconcile buddhist ideas with the hard working self-sacrificial tendencies that seem expected of us when building a technology company. Thanks, Sergey
Jerry Colonna@jerrycolonna · ceo, reboot.io
@sergeynazarov I've read a bit from Marcus Aurelius but I wouldn't say I fully grasp Stoicism. But from what I've read, it feels deeply true and connected to Buddhism...especially Zen Buddhism. With regard to books on Buddhism, I would start with my teacher Sharon Salzberg, especially her books, LovingKindness or Real Happiness. Some of Pema Chodron's early works--Comfortable with Uncertainty and When Things Fall Apart--are very helpful. But I would also delve deeper, in that radical self-inquiry way, into the proposition of the sacrifices you believe you need to make. Maybe you do need to make them. Maybe you don't. Maybe making them is a way to protect yourself from the fear that what you are doing isn't good enough to quiet the demon that tells you you are unlovable. As I wrote earlier...Right Intention...and admitting what you're deepest intention is, is a super "mindful" way of understanding the challenges you're faced with. The key question to ask when you're trying to reconcile opposing thoughts is: which of these "opposing" ideas are actually true?
Sergey Nazarov@sergeynazarov · SmartContract CEO
@jerrycolonna thank you for the thoughtful response, I am astounded by how insightful it is. Can you please share where you have written about finding one's deepest intention or what you recommend reading for that specifically. Also, what book initially influenced you in this direction of thinking when you were feeling down. Do you think extended periods of solitude are helpful? I know there are retreats where you are purposefully left alone to practice vipassana meditation and I am seriously considering attending one of those whenever some time opens up.