Hugh MacLeod has tapped into his own heart and his own woundedness so that he can speak to the hearts of people and organizations to inspire, to question, to laugh and to grow. Hugh joins Jerry in this episode of The Reboot Podcast to discuss how how he got his start, what motivates leaders, and how to work (and lead) from the heart. (Hint: often the "how" lies in identifying our own wounds).

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“By the time we are 50, most of us have our shit together. And I am yet wondering what it does.”
“Amen, brother.”
Welcome to the Reboot podcast.
“If you can touch your shadow–within form–and do something out of your ordinary pattern, a
great deal of energy will flow from it.” – Owning Your Own Shadow, by Robert A. Johnson.
Why do you do what you do? Pay the bills? I’m sure that’s part of it or maybe it’s all of it, but
what else? Why or why isn’t your work meaningful to you? I know the answer for me. Sadly, the
story starts with the death of my mom from breast cancer; she was 53 and I was 24, and it broke
my heart. I had always been interested in making money, I always had a knack for it, starting
from a lawn-mowing business, successfully trading internet stocks during the nineties hay day
while at high school, and selling computers and PDAs to top eBay sellers all over the world
while in college. I knew I always wanted to build a business and I knew I always wanted to make
money, but that’s as far as I really got; and then my mom got sick, my world flipped, I was
broken. I went to New York for a fresh start and in my mind a bigger entrepreneurial endeavor,
one that would help to fill the void and instead, I met a coach who helped me become the man
and entrepreneur I am today. And here I shudder, thinking of that lost, 24-year-old, the one
looking to run from the pain of a loss, to fill the void with success and status, the guy who
thought all he needed were a few productivity tips and hacks and pointers and a map to the
riches; the guy who believed that work was about productivity, about grinding away and if you
ever want to be successful, you better be tough, you better be closed. Jerry showed me that not
only is the best work usually the result of being open, being vulnerable, but work itself can be the
way to achieve our foolish selves. If perhaps selfish, but it’s true, you’re hearing this podcast
because I simply can’t imagine that 24-year-old version of myself, not having an opportunity to
do this type of work, have these heart-centered conversations or even be exposed to them. You
hear these podcasts because in effect, I am trying to save myself. So, thank you for that. And so I
am excited to welcome some who is tapped into his own heart, his own woundedness, so that he
can speak to the hearts of others and help them uncover why they do what they do. Someone
who creates powerful, moving and inspirational art, Hugh McLeod from Gapingvoid, he joins
here in this episode and discusses how he got his start, what motivates leaders, and how to work
and lead from the heart.
As always, you can check out our show notes and see some special cartoons from Hugh at our
website reboot.io/podcast.
**
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If you are ready to grow your business and not your busy work, head over to reboot.io/justworks.
You’ll find out more about how we use JustWorks and how it could work for you. That’s
reboot.io/justworks.
**
Jerry Colonna: Hey Hugh, how are you? It’s been a long, long time and I am really, really happy
to connect with you. How’re you doing?
Hugh McLeod: Hi Jerry, I’m doing good, well, I’m in Miami, business is pretty good, no major
crises yet, so –
Jerry: And you are married and a dad?
Hugh: Yeah, I met my wife, actually I suppose, rather late in life, I met her about four or
five years ago, we got married about three years ago, and then Fiona was born in
December, and so I am a new father and probably far too old to be one, but that’s
okay. And actually one thing that I wasn’t prepared for was just how wonderful it
is. I mean, I was hoping to like it but wasn’t expecting to like it this much, my
goodness. We’re blessed with a very healthy, happy baby, which is like amazing
because there’s no guarantees in these things.
Jerry: Yeah, I mean, I think that the thing that people just are utterly surprised by is the
emotional impact of parenthood, positively or negatively.
Hugh: Oh yeah.
Jerry: It’s a mind-fuck for sure, and you know, what I often say, and this is a quote I’ve
stolen from somebody and I can’t remember who, but “Being a parent is like
wearing your heart outside your body.”
Hugh: Oh.
Jerry: You’re just like constantly exposed and by the way, you are welcome to take that
and turn it into a cartoon.
Hugh: Yeah, that’s – oh, I mean, that’s like – as opposed to your “heart on your sleeve”
which is kind of like more of a vanity of youth, I suppose?
Jerry: That’s right; the heart outside your body is exposed and vulnerable and utterly
unprotected.
Hugh: Yeah, and fragile.
Jerry: And fragile.

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Hugh: I mean, when you have this big awakening, when you are bout 14, when you
realize, and it’s very traumatic when you realize your parents are just as screwed
up as everybody else, but when you realize your kids are just as screwed up as
everybody else, you know – to quote my little Sunday school, we are all sinners,
including my child. I just wonder, which one is more traumatic, realizing your
parents are more screwed up as you or realizing your child is as screwed up as
you, which is more painful?
Jerry: Yeah, well the way the way I resolve that, and as you know, I’ve got three kids,
we’ve got three kids and the way I’ve resolved that is to understand that everyone
is wounded, including my children, and that the real task in life is to turn those
wounds into something sacred. And it’s actually our wish to make the temper
impermanent that is a major source of our suffering.
Hugh: Right, and I mean, when I was 18, I had a beautiful summer and I was like in the
eighties, and everything was perfect about my life. I had friends, I had girls, I had
a job, I had money, you know, I had clothes which I paid for with my own money.
I kind of resolved a major conflict of my parents, and kind of, achieved my spurs,
I guess, of my manhood, my first real whatever assertations of manhood I
suppose, and then the whole thing ended suddenly and it was over that summer.
Jerry: How did it end?
Hugh: I had to change country, leave Scotland and go to Texas, which was very alien
and also school was never my thing, and I resented having go to school. “Oh, you
have to go to school so you could get a job.” “Well, why?” You know what I
mean? “Why do I have to go to school now and listen to these losers and hang out
with these frat boys and you know, be bored?” ‘Cause what was interesting to me,
work was interesting to me at that time, and I wanted to continue working, but
you know, my parents’ marriage was dissolving and you know, my dad’s business
was dissolving and everything was bloody dissolving, and so I felt like my parents
couldn’t get their act together. So, hello – and as I got older, I go, sometimes you
know, shit happens and parents lose control of the rudder, and it could happen to
any of us just as easily. So, it’s not like – but I was – I don’t know, but at the same
time, you know, I’d go back to Edinburgh, I grew up in Edinburgh, and I just
liked to kind of, all these summers going back, I wanted to recapture it and I never
could and it always broke my heart somehow.
Jerry: Yeah.
Hugh: And I was always [Unclear 0:09:32] and had so many great memories and I lived
in a lot of different places; so my memories are very distinct if that makes any
sense. I lived in Scotland, growing up – even before my 23rd birthday, I lived in
Texas, I lived in Scotland, I lived in Massachusetts, I lived in Africa, you know,
by the time I was 23, I was in Chicago, you know, so I have all these very distinct
phases in my life, and so I have a lot to look back on that’s something I’m quite

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grateful for, but it’s – I spent too much time looking back, being grateful for these
things wishing – I’m not saying I’m not living in the moment, but I spent too
much time missing the past sometimes; so I think that’s my greatest flaw, I think.
Jerry: Yeah, I think that very poignantly, as you often do, Hugh, speak to some very
powerful issues and I just wanted to acknowledge –
Hugh: Thank you.
Jerry: – and recognize some of the things that you said which are – there you were,
going along with everything fine and then shit happens.
Hugh: Yeah.
Jerry: And then as I said a few weeks ago in a podcast, shit happens because shit
happens; not because of any reason, it’s just, shit happens.
Hugh: Yeah.
Jerry: And then shit happens, you find yourself covered in it, and trying to make sense
of it, and the natural human impulse is to hold on to some idealized moment in the
past and try to get back to that moment as much as possible, as quickly as
possible.
Hugh: Rewind the tape, I guess.
Jerry: Yeah, rewind the tape and freeze the tape; stop it in place.
Hugh: Yeah, in the perfect moment, yeah.
Jerry: And one of the things that Pema teaches in ‘Comfortable with Uncertainty’ is,
even though there is a quality of denial of death in that, there is in effect, a denial
of life in that because life does not consist of frozen moments, life consists of
moments that are continually flowing apart.
Hugh: You know, it’s funny that, because it reminds me – and I’ve been in a situation
too, but less extreme I think, I had a lot of friends who were creators and writers
and stuff like that, and all over the years, and this one friend of mine, who is a
writer, a novelist, he finally got the dream gig – he got a couple of screenplays,
you know, commissions, and he had this Italian wife from Sicily. So he ended up
like in a beautiful cottage in Sicily, looking over a magical view of the sea, with
all the room to write in –
Jerry: Beautiful.
Hugh: Yeah, but the guy was like quasisuicidal within six months –

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Jerry: Right.
Hugh: – because he had the ideal situation and it always killed him.
Jerry: Yeah, that’s right and for me, I was living in a place where the inner and the outer
were not in sync, and as a result, I was in enormous pain.
Hugh: And especially when you are likely to put it on paper, I mean, life looks pretty
funny on paper, it’s easy to walk away from.
Jerry: Yes.
Hugh: And whatever is perfect – I mean, I saw the movie a long time ago, The Stepford
Wives, where they strive – there’s a – what is his name, there’s a really good
Buddhist teacher called [Unclear 0:12:49] he’s an American –
Jerry: Yes.
Hugh: – and he’s quite goofy, I quite like him, and he goes, you know, “Why do the
Stepford wives pop pills and drink martinis at lunch time? ‘Cause they realized
that what they had was empty. But everything is empty.” That’s what he said, he
goes, “Everything is empty, there’s no inherent quality in a thing that is going to
make you happy.”
Jerry: Right.
Hugh: But people think that certain objects have mystical powers; Ferraris, and religious
symbols, and they have this magic like abracadabra-ness about them, and that’s
another source of unhappiness I suppose when we think that things have innate –
well we associate innate mystical qualities to objects.
Jerry: That’s right.
Hugh: Yeah.
Jerry: So Hugh, I am dying to ask you something; there is a black poignancy about your
work.
Hugh: Yeah, to be fair [Unclear 0:13:56] probably brown, actually.
Jerry: Yeah.
Hugh: I mean, there is a – I mean, it’s the only animation, when people cry [Unclear
0:14:05] the only time he ever cried out was [Unclear 0:14:08] around Christmas
where he –

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Jerry: Oh God, yes.
Hugh: – he chose the only real tree in the shop, and he got laughed at.
Jerry: Yes.
Hugh: That’s the human condition right there.
Jerry: That is the human condition right there; you just said it so well.
Hugh: Yeah.
Jerry: In fact, that goes back to the cartoon – the other cartoon that I wanted to talk to
you about, you know, you tweeted at me a couple of weeks ago, after listening to
one of the podcasts, you said, and this is a cartoon, “There is a higher truth to all
of this. Admitting it will get you laughed at.”
Hugh: Exactly, yeah. And I think it embarrasses us; we are all by the time we are fifty,
most of us have our shit together and I am yet wondering what it does.
Jerry: Amen, brother.
Hugh: And it’s like, I’m waiting for my first person to have his shit together in place,
and you know what, we’ll build a shrine to him.
Jerry: That’s right. I mean, we were talking again before the recording started and I said
to you, “Hey, don’t worry, about coming across as some sort of guru, just be you”
–
Hugh: Yeah.
Jerry: – and you laughed and you said, “Well, you too, Jerry” and you are right because
none of us have our shit together.
Hugh: Right.
Jerry: That would mean we are not actually being human.
Hugh: Yeah, well, there is a kind of – like I might be blowing my own trumpet here,
there’s one thing I like about my cartoons, besides, I don’t think I am smarter than
anybody else; I mean, they don’t all do this but some of them do this, and I called
them [Unclear 0:15:49] where you see it and you go, “Yeah, cartoon, whatever”
you read it, whatever and then like a week later, you’re like, “Holy fuck.”
Jerry: Yes.

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Hugh: Those are my favorite cartoons where people remember them the way – they
don’t get them at first but then they get them, they go, “Holy shit.” I like them
when that happens, they tell me about that because –
Jerry: Yes, well, it’s like the cartoon you once wrote on my behalf, when I asked you to
do a cartoon, when I was first starting off as a coach, and you flipped the card
over and it’s just a guy screaming out, “Now what?”
Hugh: Yeah.
Jerry: And in that piffy little “Now what?” for me, synthesized so much about what that
coaching client experienced when they walked in to say, “Damn it, I need a
coach” which is “Now what’s happening to my life? Now what do I have to deal
with? Now what?”
Hugh: Yeah, because I mean, I know one or two of your clients, I know one of them
became very, very successful recently; I mean, he was successful, but he just sold
his company to a major media outlet, and I won’t say who. A lovely guy, a lovely,
lovely, lovely fellow, and this is what I narrowed kind of on: being successful is
really complex.
Jerry: You said it.
Hugh: It’s like – I was reading, like a guy – I’ve met him once, he’s a lovely fellow,
came up a lovely fellow anyways, called Kevin Rose, who was the founder of
Digg and now he’s with Google Ventures and he’s a terribly successful fellow,
and he was saying – he was talking to Tim Ferriss on a blog post or something,
and he said something about his life is basically back to back meetings. And I
went, “Oh man, I’d hate that.” So why do I envy somebody who has something I
would hate? You know what I mean?
Jerry: I do.
Hugh: Yeah, as long as you are on the [Unclear 0:17:46] you get to be Kevin Rose.
Jerry: That’s right.
Hugh: And I don’t mean – I mean, he may like it, you know what I mean?
Jerry: That’s right.
Hugh: I mean, he may enjoy what he does, and that I’m sure he does, I don’t think I’ve
learnt all this time, it’s really hard to be successful doing something you hate, but
the thing is, I know I hate that.

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Jerry: Well, and what I often encourage is to really explore why do you love it; because
sometimes we confuse love with meeting some sort of a neurotic-emotional need.
I loved being a VC but the truth is, there were so many aspects of being a VC that
I loathe, and what I loved was being connected to entrepreneurs, what I loved was
being a witness to the creation of some incredible ideas. And now, I get to have
that, without necessarily having the parts of the job that I didn’t like. You once
even said, you said, “You skimmed the cream off the top and you created the job
that you wanted” and that’s right.
Hugh: Yeah, well, there’s a fellow I know, who is a CEO of a company and he was
perfectly – he was CFO, he was a great CFO, and then he got promoted to CEO
and basically drove the company to the ground, which is very sad. I mean,
spectacularly drove it to the ground just like – and a person close to us both said,
“Well, his trouble was, he liked being THE CEO but he didn’t like being A CEO.”
Jerry: Yes.
Hugh: He liked being the big man, but you know, the thing about I like to have A job in
advertising, I didn’t like MY job in advertising, you know what I mean? Does that
kind of –
Jerry: Yeah, well, what did having a job in advertising do for you?
Hugh: Well, actually I liked parts of it, I liked the – it was my first job out of college, I
liked the access to the adult world –
Jerry: So did it make you feel like an adult?
Hugh: Yeah, I liked that.
Jerry: Right.
Hugh: I liked having access to – like I worked for a world-class company, I liked
knowing what it felt like and get an insight to that. Again, I like being [Unclear
0:19:59] by smart people, that was good, you know, I think that a lot of my ideas,
sorry just a humble brag, a lot of my ideas were like frankly ahead of their time
and the world wasn’t ready for it. And so it was sort of like being “Oh you are
ahead of your time, no, you’re a freak.”
Jerry: You got laughed at.
Hugh: And no matter how hard I worked, I couldn’t get ahead in it, and I just felt like –
and it might have been me, it might have been them, it might have been the wrong
agency, and maybe I should have gone somewhere else but you know, I was so
enamored with my grandmother being able to name [Unclear 0:20:42] my

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company as opposed to my [Unclear 0:20:44], that I kinda stuck with the part
longer than I should have.
Jerry: So, let’s fast-forward and here you are now with Gaping Void –
Hugh: Yeah.
Jerry: – and Gaping Void has evolved so far from a blog in which you could put
cartoons and ramble on –
Hugh: Yeah.
Jerry: – into something that’s – I mean, I see you guys dropping these grenades into
corporate America, into businesses, and kind of cutting through bullshit and
naming it, and making people laugh and smile and really think at the same time;
am I identifying the company correctly that way?
Hugh: Yeah, partially; yeah, it has evolved a lot, and you know, I give Jason equal credit
for that, I mean, –
Jerry: Jason as in Jason Korman?
Hugh: Yeah, my business partner and he is the CEO, and he is a – he’s evolved as much
as I have, probably more actually –
Jerry: Well, he had more work to do – just kidding. So, are you now creating these
visual representation of ideas, these thought grenades if you will, for the people
stuck in the cubicles?
Hugh: Well, not just – yeah, I think so, yeah, I mean, I think the thing about engagement
is – the biggest myth about engagement is it actually happens. I think people are
very – a lot of people, if you are a leader, so a team of people who are
sleepwalking through their jobs are way less valuable to you than a team of
people who click their heels on their way to work. And actually, what’s the
difference? The people who are sleepwalking to work, is their physical reality,
their object to reality that horrible? No.
Jerry: What is the difference?
Hugh: Spiritual lull?
Jerry: Maybe. Or maybe it’s the leader finding a way to click their heels on the way to
work.
Hugh: Yeah, or – yeah, I mean, are the leaders engaged? I mean, the leaders, are they
doing it for themselves, are they doing it for some – are leaders actually doing it

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‘cause they love this stuff or are they doing it because they want to be the biggest
car in the parking lot? I mean, I think I’ve only been interested in what motivates
people and I think you have to be a cartoonist. I think you really to be interested
in what motivates people.
Jerry: And I think you just said something really powerful. You just gave articulation to
something I often say, which is, “Lead from your heart, goddamn it.”
Hugh: Goddamn it, and people – great leaders do, I mean you can say Steve Jobs
[Unclear 0:23:32] but at least –
Jerry: He led from his heart.
Hugh: Yeah, even if he didn’t [Unclear 0:23:42] he still led from it.
Jerry: That’s right.
Hugh: And I mean, there’s two interesting things about business; you know, how does
shit get done and why do people do it, or I suppose – why do people – so you
were making billion dollars selling books online Mister Bezos, why would
anybody want to do that?
Jerry: Right.
Hugh: Is it for the money? Is it for the – are you an internet geek, are you a book file, do
you love books or just books [Unclear 0:24:08] what it means to them, I mean,
what do you love? What do you care about? And there’s no right answer, it’s just
kind of why are you doing it? Why does anybody do anything? Why do people
like to be more like Jeff Bezos, and less to be a plumber or – why do people
choose their vocation or their work? To me, that’s one of the most interesting
subjects there are.
Jerry: So, take me to it; why did you choose your vocation and your work?
Hugh: Cartooning, I guess?
Jerry: Yeah.
Hugh: Gosh, I think when I was younger, it was something I was good at, you know,
finally it was something I was good at for a change, ‘cause I sucked at everything
else, [Unclear 0:24:57] mattered less to me. I think the great thing about – I think
you know, we live in moments of fog and blizzard I suppose, we are all trying to
like fog, whatever clutter or whatever, and I think we are both older now, and I
think we both realize that what is the most sweetest thing we can have in our
lives? Moments of clarity – time to think and moments of clarity; those are like –
I’m not saying those are the only favorite things, but those two things are my top

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ten lists; time to think and moments of clarity, and I think a great cartoon gives
you these amazing moments of clarity; and to make a cartoon, you need time to
think. So –
Jerry: Well, and I would argue, one other thing you need which is the ability to access
your own heart so that you can see into the hearts of other people.
Hugh: Yeah.
Jerry: And I think one of the things that I have always admired is about your ability –
Hugh: And that empathy thing –
Jerry: That’s right.
Hugh: The need – and actually I think empathy is, [Unclear 0:26:11] I always felt like
feeling sorry for other kids when they are having a bad day or they are being
bullied and crying, I always felt like showing sympathy was like a sign of
weakness and it scared me that I was – like somebody who was being picked on
or something if I stick up for them or I was being picked on, you know, I wasn’t
picked on that much really. But yeah, I always felt like showing sympathy – it’s
not that I never showed sympathy, I did, but I always felt like slightly – I always
wanted to recommend myself for showing weakness, but now it’s like it’s one of
the great things you can do.
Jerry: Yeah. One of the things I want to thank you for is your ability to really look into
the hearts of others by – with humor, exposing your own vulnerabilities and
insecurities, and in doing so, I actually – you know, you are part of the tribe of
people, myself included, I’d like to think, trying to make the world a little bit
easier for a crazy bunch of entrepreneurs and you’re doing it, my friend.
Hugh: Yeah, well, thank you, I mean, it’s beyond words; it’s way harder than it looks,
and it’s a lot less glamorous than it looks and you know what, it’s not always
worth it. I’m sorry.
Jerry: Well, with that, I think we’re going to need to wrap, but I can’t thank you enough
for this. This is such a delightful conversation.
Hugh: Well, you are always fun to talk to ‘cause we read a lot of the same books.
Jerry: We do, and I love the fact that we both were connected to [Unclear 0:27:42] that
way. So, thank you so much my friend, for coming –
Hugh: You’re very welcome.

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Jerry: And we will make sure that we get a chance to see each other, whether it’s New
York or Miami or Boulder.
**
One of the most important things we have the opportunity to do for clients at Reboot is to hold
containers in their safe space for them to connect honestly and openly with a community of their
peers. Many CEOs come to us, suffering fear, anxiety and isolation; really this underlying belief
that they are the only one who feels this way. Through our bootcamps and now our peer groups,
CEOs and startup leaders are able to connect and share with others facing the same daily
challenges, the same feelings; they know they are not alone. CEO and co-founder of
Codecademy, Zack Sims recently shared his experience of connecting with others in this way:
“So I think one of the biggest things that I took away from the bootcamp which is the general
thinking around transparency and authenticity in a company, and we read a lot of that all the time
in books and media outlets and whatnot, but I think going to bootcamp actually helped me
realize a room full of people who talked a lot about, always wondering if they had to have all the
answers, and learning to use their teams as the way of answering their questions instead of
feeling that because CEOs or because they were leaders, they needed to have all the answers all
the time. So, it gave me a new perspective on how best to get a group of people to come together
by providing them with a container they needed to be successful, and answer questions on how
to run a company.”
You can learn more about joining a community like this through our bootcamps and our peer
groups at reboot.io.
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 0:31:11]
[End of transcript]