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May 27, 2025 59 mins

In this episode, Debbie Millman explores how we can use failure as fertilizer and learn to bloom again. Debbie's book and this conversation is about more than just gardening tips or tools, it's about what happens when we let ourselves be bad at something, especially later in life. Debbie opens up about learning to grow and why failure might be the richest soil we have. Whether you've ever felt stuck, afraid to try, or unsure if it's too late to start.

Key Takeaways:

  • Personal growth and development through gardening
  • Lessons learned from failure and embracing new experiences
  • The metaphor of gardening as a reflection of personal growth
  • The impact of the COVID-19 pandemic on personal endeavors
  • The importance of understanding circumstances that affect growth
  • The balance between effort and environmental conditions in achieving success
  • The significance of being a beginner and confronting fears later in life
  • The role of external support and accountability in personal challenges
  • The interplay between creativity, self-worth, and professional obligations
  • The connection between nature, personal experiences, and emotional well-being

If you enjoyed this conversation with Debbie Millman, check out these other episodes:

Fluke or Fate? Embracing Uncertainty to Live a Fuller Life with Brian Klaas

How to Find Zest in Life with Dr. John Kaag

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
You don't control nature, not in the slightest. Nature is
much bigger and stronger and more capable, and that is
a very liberating realization. You can do your best, you
can try your best, you can try to provide the
best possible conditions, and you have to just leave it
at the door.

Speaker 2 (00:27):
Welcome to the one you feed. Throughout time, great thinkers
have recognized the importance of the thoughts we have. Quotes
like garbage in, garbage out, or you are what you think,
ring true. And yet for many of us, our thoughts
don't strengthen or empower us. We tend toward negativity, self pity, jealousy,

(00:47):
or fear. We see what we don't have instead of
what we do. We think things that hold us back
and dampen our spirit. But it's not just about thinking.
Our actions matter. It takes conscious, consistent and creative effort
to make a life worth living. This podcast is about
how other people keep themselves moving in the right direction,

(01:07):
how they feed their good wolf.

Speaker 3 (01:12):
It's not every day that someone you think you know,
someone urbane, accomplished, cerebral shows up with mud on their
boots and tears in their eyes from.

Speaker 4 (01:22):
Doing a pull up.

Speaker 3 (01:23):
Debbie Milman, longtime host of Design Matters and acclaimed designer,
returns to the show with a quiet.

Speaker 4 (01:30):
Surprise, a book about gardening.

Speaker 3 (01:33):
But the Garden isn't about tips or tools. It's about
what happens when we let ourselves be bad at something,
especially later in life. In this conversation, Debbie opens up
about learning to grow and why failure might be the
richest soil we have. Whether you've ever felt stuck, afraid
to try, or unsure, if it's too late to start,

(01:56):
this episode is for you. I'm Eric Zimmer and this
is the one you feed.

Speaker 4 (02:02):
Hi Debbie, Welcome to the show.

Speaker 1 (02:03):
Hi Eric, Thank you for having me.

Speaker 3 (02:05):
I am excited to have you back on. We are
going to be discussing your latest book, which is surprising
to me, about gardening, and we'll talk about that in
a second, but before we do, we'll start in the
way that we always do with the parable. In the parable,
there's a grandparent who's talking with a grandchild and they say,
in life, there are two wolves inside of us that

(02:26):
are always at battle. One is a good wolf, which
represents things like kindness and bravery and love, and the
other's a bad wolf, which represents things like greed and
hatred and fear, And the grandchild stops think about it
for a second. They look up at their grandparent and
they say, well, which one wins? And the grandparent says,
the one you feed. So I'd like to start off

(02:48):
by asking you what that parable means to you in
your life and in the work that you do well.

Speaker 1 (02:54):
As a designer, I think that we're constantly in a
mode of me making very deliberate decisions about our work,
solving problems, making choices about which direction to take, and
I think that extends to every aspect of one's life.

(03:14):
I think that we don't just design things. We design
our choices and we design our paths. So the parable
really dovetails quite seamlessly into I think, what it means
to be a designer.

Speaker 3 (03:33):
I've had you on the show before, and you very
kindly had me on your show a number of years ago,
and that day is carved into my memory as one
of my favorite memories. Tell me why I was in
New York City and you interviewed me. No, you're a
big part of it. You're a big part of why
I came to New York City. So I came to
New York City and you interviewed me, and I believe

(03:56):
I might have also appeared on Jonathan Field's show. But
it was a whole day where I did things related
to this podcast in its work, and at the time
I was still working a full time job in the
software business. But it awakened this thing in me that
was like, maybe someday this could be what I do,
and now it is. But anyway, I just think back

(04:18):
to that day. I remember coming to your studio and
everything about it was wonderful. So I want to thank
you for that day because I have a terrible memory,
but that day really stands out to me. That day
also introduced me to you in person, at which time
I thought, and this is similar to what you say
in the book The Garden about what your wife Roxanne

(04:39):
thought about you, which was I was like, she is
such a New Yorker, sophisticated and design oriented and all
of these like New York type things. So I when
I saw you had a book about a garden, had
a little bit of a double take. I was like,
I hang on a second, Like I've got you as
this very urbane, sophisticated person, not that gardeners aren't sophisticated,

(05:04):
but it just sort of surprised me. So when I
was reading your book and you mentioned that your wife Roxanne,
had the same reaction when you talked about gardening, it
sort of tied all these memories together for me. So
talk to me about why a gardening book now, Well.

Speaker 1 (05:21):
It wasn't something that I was seeking. But first, let
me just say thank you, thank you for having me
on the show again, thank you for caring about my work,
and thank you for sharing that memory because it's really
wonderful and I'm so glad that we have this connection
me too. As far as why a gardening book, now,

(05:42):
it's primarily because I was asked to write.

Speaker 4 (05:45):
One that'll do it.

Speaker 1 (05:49):
I was not in any way seeking about gardening, how
to garden, anything about gardening. Honestly, I've always, as an adult,
try to cultivate some sort of greenery around me in
the various apartments that I've lived in over the four
decades i've been in Manhattan. But writing a book on

(06:10):
gardening was not in my wheelhouse. Was it on my
bucket list. I had these various somewhat dubious attempts and
results in the previous spaces that I tried to cultivate
as some outdoor space slash gardening and as I mentioned,
various apartments since the nineties, but it wasn't really until

(06:33):
I came to Los Angeles during COVID that no pun
intended that my efforts blossomed. Roxanne had gotten this house
that I'm sitting in right now two weeks before we
started dating, and I had been living in Manhattan for
all of my adult life, and so when we first

(06:54):
met and started dating, we were long distance commuting to
each other. And she has a beautiful house. The backyard
when she first moved in was a very typical sort
of suburban backyard, beautiful, beautiful tree, a lot of grass, boxwoods, boxwoods.
And because I had always tried to cultivate some outdoor

(07:17):
space in the various places that I've been living, when
I first got here, I asked her if she would
mind if I judged it up a little bit, you know,
with some potted plants and various herbs and things like that.
There was a beautiful garden center a couple of blocks away,
so it was super easy, very convenient, and so that's
what I started doing. And it was very rudimentary because

(07:39):
it was during COVID. Let me backtrack. Then, when COVID
hit the world, we decided that I would come to
California because I had a lot more time, we had sky,
we had a car. It made more sense for us
to be somewhere where we could get out a little bit.

(08:01):
And so that's what I did at the time. You know,
we had no idea that the world was going to
shut down for as long as it did. I remember
the then president at the time saying, Oh, we'll be
all back together for Easter. And that was in March,
and so Roxay was like, oh, pack for two weeks
and I'm sure everything will come back to normal after that.

(08:22):
Well we all know what happened after that. And so
I need a lot more I need a lot more underwear.
And so we were here. I had a lot more time.
I was working on a book at the time, but
also had a lot of other time to do things,
and decided to expand my efforts in the garden as

(08:43):
a way of trying to feel closer to the world.
And I was having some luck because of the weather,
and so I started with the herbs, and then I
went to lettuces, and then I got more ambitious and
started to plant tomatoes and cucumbers and things that I

(09:03):
really loved, and I was documenting that on Instagram, and
I was making these little ten panel stories about what
I was doing, but it was also very much about
what was happening through the eyes of somebody that was
also as the rest of the world was living through COVID,

(09:24):
and how gardening made me feel more hopeful and a
bit more optimistic, and seeing how we could grow and evolve.
And the TED folks, who I have good relationship with
through my podcast and through speaking there and so forth,
reached out when the TED conference went completely online that

(09:45):
year and asked if I could create some interstitials between
the online talks to break up the talking, and I
made some stories about gardening masks mad if I would
make some visual essays that I would narry and that
would be shown throughout the conference, and so I made

(10:07):
one about gardening. Fast forward to twenty twenty one, and
for my sixtieth birthday, I had decided to take an
expedition to Antarctica for two reasons, one to see Antarctica
and then also to try and witness the total eclipse
of the Sun that was happening over Antarctica at the
end of twenty twenty one, and it was a magnificent

(10:30):
expedition and it was everything I hoped it would be,
except for the eclipse, which I didn't see because of
cloud cover. And so I wrote all about that and
also put it up on my Instagram and somebody from
a wonderful art director and editor saw it on Instagram
and she worked at a farm magazine and reached out

(10:52):
and asked if I'd be interested in doing a piece
for the magazine, which I did. Fast forward another year
as things happen, and I get an email unsolicited from
an editor at Timber Press, which is part of one
of the big five Hashet, and she asked me if
I'd be interested in doing a book on gardening, having

(11:14):
seen all of these visual stories that I had done,
and I thought she was pranking me, like I'm like
a New Yorker, I write, not a gardener. If you're
interested in my talking about my journey to try to
be a gardener and the myriad failures along the way,
and what I've learned and how I've grown and evolved

(11:36):
and so forth, then I'm all in. But if you're
expecting me to be the next Martha Stewart. You have
the wrong girl. And so she wrote back and said
that sounds great. A quest to become better at gardening
through the lens of visual storytelling would be welcome, and
so that's what I did.

Speaker 3 (11:53):
Yeah, And to say that it's a book about gardening
is to sort of describe it and also sort of
not right, because there's no real gardening advice in there
unless you take, like, move to California, because it's easier
than New York to grow things as advice which you
don't even directly give. And like you, it's a beautifully

(12:14):
designed book that, with very few words and not a
whole lot of pictures, really conveys some beautiful things. And
I think it's a lot like your design work in
your podcast, which on the surface, it's sort of about
the surface, right, and yet there's a deep reservoir right

(12:36):
underneath it of lots of depth and wisdom. And you
kind of start off early on by saying that seeds
are tiny and densely packed with their entire.

Speaker 4 (12:49):
Existence, what does it mean to exist?

Speaker 3 (12:52):
And you also sort of talk about how the universe
itself sort of came out of this seed idea, and
I think that's a off a place to sort of
start with, this idea of something coming from not quite
nothing but almost nothing. Yeah, talk to me about how

(13:12):
that as an overall idea has been important to you
throughout your life.

Speaker 1 (13:18):
Well. As I was beginning to become more adept at
gardening and was not just planting container plants and things
that I bought already born, so to speak, from nursery,
I was also planting seeds. And to think that any plant,

(13:45):
any vegetable, any tree, starts from this sort of tiny
compact enclosure that then opens to create an entire universe
of sorts is endlessly fascinating to me. And I'm somewhat obsessed,

(14:06):
endlessly fascinated at another right words here about how we
all got here? And I think about it all the time, Eric,
I think about it all the time, And in some
ways it's sort of depressing because I'm never going to know.
We're so far away as a species from understanding the
mysteries of how we got here and why we're here

(14:28):
and how it all started. And you know, how did
the helium and the hydrogen get here in the first place?
You know, where's the carbon come? From I had so
many questions that I have, and I'm on this quest
of trying to understand my purpose here and what my
contribution can be and how I could potentially, if at all,

(14:51):
make a difference, and so it all ties together the
universe and if we did get here from this big bang,
this tiny, tiny, densely packed point then expanded to create
what we are in such vastness that it's inconceivable. It's

(15:12):
incomprehensible for us to even be able to envision, yep,
what we're part of, and to think that, you know,
trees have this grand underlying root system that communicates, and
it's all so beautiful and so abstract and so mysterious,

(15:36):
and it all feels so mystical and magical in so
many ways that for me it became the ultimate way
of trying to express the questions that I have and
the tiny little answers that I attempt to tell myself.

Speaker 3 (15:56):
One of the things that I really thought about a
lot as I was read the book is that you
describe your early attempts at just buying plants and putting
them outside and them dying and failing, And there's two narratives.
I think that we sometimes tend to separate about what

(16:18):
doing anything successfully looks like. And one narrative is you
just have to keep trying, you know, failure is just
a chance to move on. If you just keep trying,
you'll succeed. And there's truth in that, absolutely, right. I mean,
you've talked about it a lot. There's a lot of
truth in it. And then at the same time, there's

(16:40):
another element that sometimes the story is well, yeah, except
it's all about circumstance. And what I think is interesting
about the gardening example is that you actually need to
bring those two together. You can't grow anything anywhere. You
could keep trying and it's not going to grow, right,

(17:01):
So it's not all about just keep trying effort. And
yet at the same time, it is about iteration, it's
about learning, and it's about saying, Okay, if I want
this thing to grow, whatever it is, whether it's this plant,
whether it's my career, whether it's my relationship, that there
are circumstances conditions that are more conducive to things growing.

(17:28):
And I think that's one of the big challenges that
a lot of people wrestle with. It's one of the
I think the core tension is like, do I just
keep going in this direction or have I learned something
that tells me, yes, keep going, but go in that direction.
And I feel like your book somehow to me, just
brought that whole question into really clear focus. And I

(17:51):
don't know what my question is. Now that's my reflection.
I'll let you go where you like with it.

Speaker 1 (18:00):
Well, I write about how as I've gotten older, it's
a lot more difficult for me, or it had been
more difficult for me to attend things that I'm not
good at. And it's a bit narcissistic in a way,
in a lot of ways to think that if you

(18:24):
try anything you're going to be good at it. Why
should you be if you haven't been taught, if you
haven't practiced, if you haven't extended yourself into a realm
that is further than what you're currently aware of. And
so asking for help has never been particularly easy for me.
Asking for favors has not been particularly easy, And so

(18:47):
the idea of trying to learn something new out of
a school environment where that's sort of the accepted norm.
And it's been a long time since I was in
a desk as opposed to behind a podium teaching. It
took a while for me to realize that in order

(19:09):
to no pun intended he or grow, that I had
to ask for some guidance and that watching HGTV wasn't
going to be enough, and so I really needed more
deeper learning about the conditions that I was in. And
this is a good metaphor for life, I think, and

(19:29):
how to how to grow from there, how to get
better at what I was attempting to do. And this
experience actually helped me find the courage to begin to
do other things that I've said for as long as
I can remember, that I really wanted to do, but
for some reason had this obstacle path in front of

(19:52):
me that felt too daunting to attempt. And it's opened
up that obstacle a little bit to make more attempts
at doing things that I never really felt like I
had the ability to do, and that's been liberating in
a lot of ways.

Speaker 3 (20:12):
Can you share what any of these new attempts have been, Well,
you don't have to if you don't want to, but no, I'm.

Speaker 1 (20:18):
Fine with it. I'm on day four hundred and eighty
one of learning French on due lingo.

Speaker 4 (20:22):
Nice.

Speaker 1 (20:24):
You know it comes a time where you're like, I
can't keep saying, oh, I wish I knew how to
speak another language. I mean, you either do it and
you don't do it. I just was tired of hearing
myself wishing for this magical ability and thinking that somehow
I'd learn it in my sleep. And so I've done
this now for a year and a half and I'm

(20:45):
not very good, and I'm not a great learner, but
I know a lot of words. That's been also revelatory.
And then the other is getting into shape. And so
I've been working with a trainer for two years and
so you know, got a little bit of message, all right.

(21:11):
And so those two things are things that I never
really envisioned that I'd be able to begin to do
in the way that I'm doing it now with consistency.

Speaker 3 (21:22):
I think that ability to do something and not be
good at it and still do it is so sort
of fundamental, and for some reason for me, I think
that it's an ability that has gotten better in me
as I've gotten older, where I think when I was young,
I thought that how good I was at various individual

(21:43):
things with some reflection on how good I was overall,
And now I've realized, like, whether I can roller skate
or not says nothing at all about who I am
as a person or my value. So if I go
out and make a complete fool myself skating, which I
assure you is what happens. I mean the last time

(22:04):
I went roller skating, they now have designed these things.
They look like walkers on wheels, and I'm out there
tottering around with one of them, which was I mean,
my younger self would never have got like, no way.
My older self is like, well, this is kind of
mildly humiliating, but I'm just going to keep doing it.

(22:25):
But I think that maybe it's certain things like I
decided early on I was going to be a musician,
and I'm not musically talented.

Speaker 4 (22:32):
Really, no, I'm not.

Speaker 1 (22:34):
I'm surprised.

Speaker 4 (22:35):
Yeah, I don't know why I am. I am deeply
not natural at it, but I love it deeply. But
I've just stuck with.

Speaker 3 (22:42):
It for I don't know, thirty five years now, and
I'm I'm okay, you know, Like my friend Chris is
a natural, Like I'll spend three months figuring out and
learning how to play something that he will then turn
around and play in like an hour of time, which
is mildly like eating, yeah, infuriating, and I'm like, you
know what, that just doesn't matter, Yeah, because I'm doing

(23:05):
this thing because I love doing it. And I think
that with your gardening is such a great example of
you just embracing learning how to do something because you
simply wanted to do it, same way with French or
with getting in shape.

Speaker 1 (23:20):
Gating in shape has been the hardest one for me,
even harder than French, I think because I'm much more
comfortable doing anything cerebral, and I'm also more comfortable learning
anything on my own in that I can go at
my own pace. I don't have to worry about judgment
for lots and lots of reasons that we've talked about
on your podcast before. I for all of my life

(23:45):
have been very cut off from the physicality of living
and always approach things from a much more cerebral point
of view, where I can think through things and not
necessarily engage physically through things as much. And so I
was forced to start working with my trainer when I

(24:07):
had surgery and needed to do PT and that's how
I started my relationship with my trainer. He's also a
physical therapist. He's a PhD in physical therapy, and I
was very compliant with what I needed to do. The
one physical activity that I did engage in on the
daily was walking. I'm a native New Yorker and was

(24:30):
always walking through the city and always walking wherever I
could go because I enjoy it so much, and I
didn't want to give that up because that was at
the time my only physical activity besides pacing. And so
I started to feel better about myself physically and then

(24:53):
decided that I should continue working with him in weight
training and so forth. And so that's what I've done,
and I've even started running. People I tell they're like,
did aliens take over your body? And I'm like, yes,
they did a long time ago. Now I'm shooing them away.

(25:14):
Right right when I first started with him, because of
all the trauma, if I couldn't do something eric, I
would start crying involuntarily. Like it wasn't like, oh boohoo,
poor me. This was involuntary projectile tears because I was

(25:34):
facing so much of my own I don't even know
what the word is, bad wolf. And so the first
time I did a pull up, actually cried, but it
was not because of my trauma. It was because of

(25:54):
my joy that I could actually do something like that,
and again it was involuntar and that's been one of
the most surprising things in my life. Actually, I have
to say, to be able to be conscious in that way,
or even allow my subconscious to bubble up in the

(26:16):
way that it has, has done a lot to help me.

Speaker 3 (26:42):
It's hard to separate natural affinity from avoidance responses sometimes, right,
So I think I do have a natural affinity towards
the brain. I think that's part of who I am,
and I think I was very disembodied for a lot
of my life. And so, yeah, physicality is something that

(27:03):
I've sort of learned, and I also paradoxically have figured
out that it is, for me the most important mental
emotional health tool I have. If you forced me to
only have one the rest of my life, which I'm
glad I don't because I need like twenty seven of them,
But if you force me to have one, I would
probably say it's exercise, really, because there's something about what

(27:27):
it does for me, the way it connects me up inside,
the way it releases anxiety, the way that it increases energy.
It's just it is for me, maybe my most important one. Again,
I'm glad I don't have to choose, but it's been
a really important one for me. And the thing about
exercise that I always find fascinating, and listeners have heard

(27:49):
me talk about this a lot, but I do find
it really interesting is how if something we come to
see as so valuable for me every time I've ever
done it, when I'm done, I'm like, I'm glad I
did that, like literally every time. Why does it remain hard?
You'd think basic reward learning would have me running to

(28:11):
the treadmill every day, but I don't. And I think
it's just because it's it's such a significant output of
energy that as organisms, we are designed to evaluate that
amount of output very closely.

Speaker 4 (28:26):
You just don't.

Speaker 3 (28:26):
You know, you just don't go running around for no
good reason as an organism trying to survive. But I
still remain kind of fascinated by that dynamic of how.

Speaker 4 (28:37):
I've faced it.

Speaker 3 (28:37):
Today, I was like, I know, I really the best
thing for me to do would be to get on
the peloton and ride.

Speaker 4 (28:43):
That's really hard.

Speaker 3 (28:44):
So what I've learned to do is I just went like, well, okay,
you're preparing for Debbie instead of sitting in front of
a screen reading, put in your headphones and just at
least go walk outside in the sun while you prepare,
you know.

Speaker 4 (28:56):
So those little sort of hacks.

Speaker 1 (28:57):
Yeah help. That's why I have to keep working with
the trainer Eric, because I'm too weak and lazy to
do it on my own, you know. David Foster Wallace
talks about what a real leader is in Considered Lobster,
his collection of essays, and he talks about how a
real leader is somebody who helps people who are weak

(29:21):
and lazy to do things that they would not consider
doing on their own. I'm paraphrasing, yep. But weak and
lazy we're in that. I'm not paraphrasing those words. And
that's what my trainer does for me. He helps me
get over my weakness and my laziness to do better
things that I can do on my own. And if
I don't have an appointment with him, I don't do it.

(29:43):
And I'm hoping that I can get to a point
where I can. The one area where I think I
might is actually with running now, and I don't know
that I'll ever be a runner. Maybe I'll be able
to do a five k one day. But I experienced

(30:05):
that runners high one time once and that was like wow,
I never felt something like that before. But I totally
hear you. It's not like I'm going rod time to run.
I mean, I haven't run since the last time I
had a training session, and I've been on a book tour,

(30:26):
so you can only imagine what that's been like. And
I do find it's super interesting this whole idea that
you just brought up, because I don't have any issue
starting to make a drawing. I have no issue engaging
in anything I really love on my own. I don't
need a trainer to draw. I don't need a trainer
to read. I don't need a train to ride, I

(30:48):
need an editor, but I don't need anybody to motivate me.
So I do find that I have to think about
that a lot. That's a really really interesting observation that
I need to mull. And if you do find this
to that, please let me know.

Speaker 3 (31:02):
Well, for me, the solution has been accepting that like
that that's normal, right, that it's just okay that like
making myself do something very physical is always going to
take a certain degree of coercion. Right, I told you
before the call. I just got done writing this book.
I turned it into the publisher about a month ago,
and a bunch of the book is about how we
actually change. And one of the things that I'd picked

(31:27):
up three years of doing the show, but also really
got driven home as I did a lot more research.

Speaker 4 (31:31):
For this book is that if you gathered all.

Speaker 3 (31:36):
The behavior change scientists together in the world and you
put them in a room, right, I think the thing
they would all agree on is that relying on our
own internal engine, what we would commonly call willpower, is
generally a bad idea for anything that is, for whatever

(31:58):
reason for.

Speaker 4 (31:59):
Us, difficult to do.

Speaker 3 (32:00):
Why is that because our environments matter so much, and
willpower is a very finicky thing because it's tied somewhat
to mood. Right, Because if we think about motivation or
willpower in the sense that most of us know it,
it has to do with how much we feel like
doing something. And if you've got a mood system like mine,

(32:25):
it is just up and it's down and it's up.
There are some people who are a whole lot probably like
you know, steadier up at like eighty percent. I feel
good eighty percent of the time and for them might
be a little bit different. But for people whose mood
system is as variable as most people, you can't rely
on just that. So it becomes all about what are
the strategies that you, as an individual need to figure

(32:51):
out that will get you across the start line for
whatever that thing is. So there may be people listening
to this or like, I don't have a problem going running,
get up and I just go running, But when I
think about sitting down to do something creative, oh my god,
it's like a total block comes up. Okay, and I
would say they're not lazy. You're not lazy. It's difference

(33:11):
in what we find easy to do. So for you,
you need to set up a structure, and a trainer
is a very wise structure. That's why fitness classes exist
because people are like, oh, if I sign up to
go to the class, I'm more likely to go, and
if I actually go, then I'm aren't likely.

Speaker 4 (33:27):
To work hard.

Speaker 3 (33:28):
It's just it's wisdom to know like, oh, I need support,
I need help, I need these structures, whereas for somebody different,
they might need to sign up for an art class
to do it because they just won't do it because
for them, the friction is high related to previous failure
or doubts that they're good at it, and so for
all of us, I think that change. To me, I

(33:50):
always think of just as like a puzzle, like what
are the puzzle pieces that I need to put together
that make this thing work? And for you, with exercise,
you finally got the puzzle piece is lined up, and
they'll probably get unlined again at some point and you'll
need to go, oh, let me think, Okay, what pieces
do I need to put in here?

Speaker 1 (34:09):
I think it also has a lot to do with
who's teaching you. Yes, And I think that part of
what has made me feel capable or emotionally available to
do this is my trainer. You know, he's so lovely,
he's so patient. He really I was very clear with
him when I started. I'm like, look, I have all

(34:32):
these issues and so I hope that you can be
respectful of them. And I have a lot of limitations
and blah blah blah blah blah. Yeah, and he was like, Okay,
he's been super respectful always, but he's also unwilling to

(34:55):
let my own limitations, my own self perceived limitations yep,
impact my actual abilities.

Speaker 3 (35:04):
Yep.

Speaker 1 (35:04):
And I'm not talking about abilities to do any physical activity.
I'm talking about my mental life.

Speaker 3 (35:09):
Your mental Before we dive back into the conversation, let
me ask you something. What's one thing that has been
holding you back lately? You know that it's there, You've
tried to push past it, but somehow it keeps getting
in the way. You're not alone in this, and I've
identified six major saboteurs of self control, things like autopilot behavior,

(35:31):
self doubt, emotional escapism that quietly derail our best intentions.
But here's the good news. You can outsmart them. And
I've put together a free guide to help you spot
these hidden obstacles and give you simple, actionable strategies that
you can use to regain control. Download the free guide
now at oneufeed dot net slash ebook and take the

(35:55):
first step towards getting back on track. My partner, Jinny,
who you met when I came to New York. She's
similar to you in physical things. When we met, you know,
I guess it's been almost eleven years ago.

Speaker 4 (36:08):
At this point.

Speaker 3 (36:08):
Probably she just hated everything that had to do with
exercise and movement. It was something she was like I
know I need to do it and I hate it,
you know, And she could find periods where she made
herself do it, and over time she has learned, I think,
just to appreciate it more. But I remember we took
I was like, I really want to learn to play tennis,
Like why don't we go take tennis lessons together? And

(36:31):
the first two tennis lessons, similar to you, ended in
tears with her. There was just something about a ball
flying at her that just brought up like being scared
as a child and like I hate this, yeah, you know,
and just the inability to know what to do, and
just so I think some of that stuff is really
real for us. And again I think that people face

(36:52):
this in different ways. I mean, I know people all
the time were like, I really wish I could learn
to play guitar, and I'm like, well, of course you can,
you know, but you have to be really really uncomfortable
for a while in doing it right, because you're going
to be terrible at it for a little while. I mean,
everybody's terrible at guitar to start, just because you can't
make those shapes with your fingers. Your fingers just aren't
strong enough. But any learning to do anything, and so

(37:14):
I think when we look at that and we're like, Okay,
there's this thing that I want to do and I'm
having a really hard time doing it, to me, is
just about okay, what you know, what's the strategy that
we can come up with? And you sort of snuck
in the back door of it by having to have
a trainer for your back that also then managed to
shepherd you through another door, right, yeah, which is amazing.

Speaker 1 (37:34):
I love how you're helping me better understand myself on
this podcast. It's fantastic.

Speaker 3 (37:44):
So, speaking of podcasts, when I was getting into and
preparing for this interview, something happened that as I was
doing it, I was like, that is amazing, and it
is this you have been doing your podcast. You're at
the point I am now I've been doing this podcast
a decade. So when I started this podcast, you had

(38:07):
already been doing it for a decade before that. And
everybody's always to me like, well, you're one of the
early founders. I'm like, no, not exactly, but holy mackerel,
twenty years does that fill.

Speaker 4 (38:18):
You with pride?

Speaker 3 (38:19):
How do you feel when you think about twenty years
of having these conversations.

Speaker 1 (38:23):
It makes me very humbled about the nature of time
because that went by flash. Yeah, And I remember my
first podcast. I was interviewing John Fulbrook, who was then
the art director at Simon and Schuster, and I was
super nervous. I had my notes in front of me,

(38:44):
but I also had because he's a book designer, a
book jacket designer, I had covers of his books all
pasted over my office wall so that I could easily
refer to something. I chose John not only because he's
a fantastic designer and a good friend, but because he's

(39:07):
extremely gregarious, and I felt like if I choked, which
was a really good possibility, he could carry on. Thankfully.
I think I've grown in the twenty years, but it's surreal, Eric,
It's surreal, and it's also surreal to see how both

(39:29):
I and the show have evolved and what it means
to again, coming back to this pun that I don't
really intend but to really grow as anything. I didn't
grow up thinking well, I want to be a podcaster
when I grow up. There was no such thing, and
that this very unusual path that my life took based

(39:54):
on a cold call from an internet radio network. Please
edit that out, Like what if I hadn't picked up
that call?

Speaker 3 (40:03):
Isn't that fascinating? I interviewed a guy recently. His name
is Brian I think you say it class, and he
wrote a book called Fluke and it is a on
many levels.

Speaker 1 (40:13):
Do you know the book or I'm going to read
it at great title?

Speaker 3 (40:17):
Yeah, it's all about how life is like you just described, like, yeah,
you don't answer that phone, your whole life is different,
you know. He talks about how the city of Kyoto
was originally on the slate to be bombed by the US,
and it turned out that the war director of the
US had gone to Kyoto about twenty years before on

(40:37):
a vacation and loved it. So he said, no, let's
not do that one. Like it's crazy, Like that is
life when you look at it. There's just all these
things that I could have just decided not to do X,
and my whole life would look different. And his point
is ultimately that if you embrace that how we actually

(41:01):
control and how little actually happens, like you know, for
a reason, that it can be freeing and liberating. It's
also deeply disconcerting on on some level too.

Speaker 1 (41:13):
I think, yeah, I mean, it takes both the good
and the bad things and puts them in a completely
different you see them through a different lens, and I
think that's also something to honor.

Speaker 4 (41:25):
Yep.

Speaker 3 (41:27):
It goes a little bit back to what we were
talking about earlier with gardening, right, like there's both what
you do which matters. What you do matters, and there's
all the elements that you can't control about growing anything.
You can be more strategic, like you cannot plant roses

(41:48):
like you once tried to do in a fully shady patio.
That's plant a fern there. Right, there's strategy and ultimately,
though you control what you can, but there's a certain
element of it that is just out of your control.
You can't make something grow.

Speaker 1 (42:03):
That's for sure. You don't control nature, not in the
slightest Nature is much bigger and stronger and more capable,
and that is a very liberating realization. You can do
your best, you can try your best, you can try
to provide the best possible conditions, and you have to

(42:23):
just leave it at the door.

Speaker 3 (42:48):
Another point of intersection with you and I a little
bit is that your wife Roxanne, and I both did
a project with a company called rebuind dot Ai where
you pair a person like Roxanne with a book. She
did Age of Innocence. I did the dowd Aching and
mine is about to come out. I think hers has
probably been out for a little while. The Doo is

(43:09):
all about that idea of you just have to work
with the way nature is. If you try and go
against it, you're going to lose.

Speaker 1 (43:16):
Every time, I had a plant that had died and
it had been really established, and then it over the
years in a previous home that I lived in, and
I talked a little bit about this in the book
The Rhododendrons in my previous home, and I was devastated
to watch them die and wanted to pull them out

(43:38):
of the ground after they had died, and it was
really hard. I felt like I was fighting with nature,
you know. It didn't want to come out of the ground.
And if pulling a plant out of the ground is fierce,
you know, so was everything else.

Speaker 4 (43:57):
Yeah.

Speaker 3 (43:58):
I don't know if you said this in a book
itself or elsewhere, but I put it under the notes
I have for the book, which is failure is fertilizer.
It feeds the next attempt. The deeper insight the unexpected path.
And I love that idea because it doesn't just say
just again, this idea that we mostly talk about with failures,

(44:18):
try try, try again. But I think that the wisdom
there is yes, try again, but as you point like,
maybe there needs to be a deeper insight before you
try again. Maybe there needs to be a different path
you actually have to be learning. It's not just keep trying.

Speaker 1 (44:34):
Right, And I think that it's really important to be
conscious about your failures and not just keep trying, because
if you keep trying to do something the same way
without understanding what led to the failure and what you

(44:55):
can do to improve the odds of success, I don't
know why would be different if you just keep trying
in the same way.

Speaker 3 (45:04):
Yeah, I think it's one of those really difficult things
about people who are trying to build anything. I'm thinking
of it in a business sense, having been in the
startup world for a lot of my life, but it's
really hard to know. It's like, do I just need
to keep going in this direction because it just takes
time and people are slowly coming on or is this
the wrong idea, the wrong direction? When do I pivot?

(45:26):
How have you thought about that in your life, Like,
do you have any way of sort of thinking through that,
whether it's a designer or in any way.

Speaker 1 (45:36):
I think it depends on who you're doing things for, okay,
and the bar that you need to be able to
reach in order to do something. If you're doing something
for someone else and you're getting paid to do it,
there's much less tolerance for failure. And that could include

(45:57):
your shareholders, it could include a board, it could include clients.
If you're doing something for yourself, I think you have
a bit more leeway. For example, when I started the podcast,
I was working a full time job. I was working
as a corporate executive, and I was making a good salary,

(46:22):
So I wasn't dependent on this other effort that was
really started as a labor of love. I didn't need
to monetize it, and I didn't need to do anything
other than really fulfill my own creative dreams and hopes
and aspirations. And to a large degree it's still the
case for me. I'm lucky that I can monetize it

(46:44):
in some ways, but I've never been dependent on it.
And when you take out the dependency equation, it gives
you a lot more freedom to experiment or evolve in
ways that don't impact others. If you're being hired to
make something for something else or for the public or

(47:06):
for profit, it does change the way in which I
think you approach anything, And ever so slowly, you know,
now that I'm in my six decade, I've tried to
eliminate the need to fulfill any obligation to the outcome

(47:29):
for others' purposes. And It's taken a long time. And
I'm very lucky, in privileged that I'm in a place
right now where I can do that more frequently. But
that's also a choice. You know. I'm not as comfortable
anymore fulfilling financial obligations. I don't want to live a

(47:50):
life anymore where I'm working to increase the market share
of products that I don't feel proud of doing. And
I did that for a very long time now that
I wasn't proud of them. I mean, I am very
proud of the work that I've done. I just don't
feel the need to redesign any more fast food restaurants

(48:13):
or over the counter pharmaceuticals or soft drinks or salty snacks.
And again, I'm very lucky that I was very successful
doing that, but there comes a time where you have
to decide how much more of this work do I
want to do in service of that work? And so
I feel extremely privileged to be able to take the

(48:34):
talents that I manifested and grew and developed over my
corporate career and now applied them to movements and efforts
that I feel are helping the world be a little
bit safer or a little bit kinder. And that's the
work that I'm trying to dedicate myself to doing. Now.

Speaker 3 (48:52):
Yeah, it's a really tricky thing. I mean, we started
this conversation with me sharing this magical day in New
York City, come into your studio, and me being like,
I wish I could do this full time, And now
I get to do it full time. And that comes
with a shadow side to it, which is that this
thing that started just because I wanted to do it

(49:13):
and loved doing it now provides a living for me
and for a couple other people, And so it's different.
And I think for me, the thing that I have
to sort of continually sort of do is like, yes,
I have to hold that there.

Speaker 4 (49:28):
It's real, It's true, it needs to.

Speaker 3 (49:29):
Be And I also need to turn as much of
my attention as I can to what about this matters
to me most deeply, and that actually is then what
ends up creating the best work. But it's always a
mixed thing. I wanted to ask you about your career.
You talk a lot about and you've advised a lot

(49:50):
of young people about their careers. And it's easy to
look at your career, maybe many people's careers, but I
can look at your career and I can see it. Okay,
it started, you know, down over here to the left,
and today it's up over here to the right, in
that all the things you just described are true, like
you are better able to do the work that you

(50:11):
want to do, You've had some degree of financial success.
So if I look at it, I go, okay, look
started down here to the left, ends up here to
the right, straight line up.

Speaker 4 (50:21):
That's not it, right. So I was wondering if you would.

Speaker 3 (50:24):
Share a little bit about some of the times that
you might have felt like, Okay, my career was going well,
and how all of a sudden it feels like uh, oh,
you know, or any sort of bumps in the road
or different things that sort of give us a little
bit more of the nature of the up and down
that happens in that chart if we zoom in on it.

Speaker 1 (50:45):
Yeah, I mean, I don't know anything that is just
a straight line up. I can't even imagine what that
would be like. I've graduated college in nineteen eighty three
and moved to Manhattan. I'm a native New Yorker, so
I wasn't that big a jump, and the first thirteen

(51:05):
years of my career there was some success there in
some highlights, but for the most part, it was a
lot of despair as I was trying to figure out
who I was and what I wanted to be. I
graduated with a degree in English literature, so I wasn't
really prepared for the big time, and at the time,

(51:26):
I wasn't in a place where I either could or
wanted to go on for a higher degree. I wanted
to live in Manhattan and be a working girl, so
to speak, and because I didn't have a lot of
training or a lot of guidance or any money, it
was really really hard for me. And I was also

(51:49):
grappling with a lot of unresolved trauma and was living
on my own for the first time in my life,
and I often say that I considered that first decade
of my career just experiments and rejection and failure and
bit of humiliation, and then quite serendipitously ended up in

(52:10):
the world of branding. You know, I had some skills
in design coming out of college because I worked on
the student newspaper and the editor of the section also
had to put the paper together, and that meant designing it.
And that's when I discovered my love of graphic design
and began to develop the skills that were required to

(52:30):
be a graphic designer. It was still pretty rudimentary. Although
I had, I think, a good eye and some good ideas,
I didn't at that time have the drafting skills that
were required in the eighties. I developed them, and that
was a good thing. Again, it was very serendipitous, a
fluke that I ended up in branding. And then, as

(52:54):
you were talking about earlier, discovered I had a natural
ability for it. My brain just understood the psychological underpinnings
of wanting to engage with products that made people feel
either better about who they were, gave them more social confidence,
made them feel like they were part of a bigger tribe,

(53:15):
were enjoying a moment that they were engaging with that
brand and what that did to our psychological makeup, and
though even that entry point was marked with difficulties. I
came into an agency that was mostly comprised of young
British guys, and I came in as a sort of

(53:37):
loudmouth female American that was challenging. For the first couple
of years that I was embraced mostly because I was
doing well for the company. I was bringing in a
lot of business, and so I was then finally embraced.
But then, you know, when I was bringing in the business.
Part of my original offer to join the company was
that I would begin to earn equity. I knew that

(54:01):
the senior partner was interested one day in selling the company,
and so I wanted to be part of that. And
initially there was some resistance, as there would be for
anybody asking for equity, and I had to say that
if I didn't get equity, and I don't know where
this courage came from, that I'd have to leave the company.
And I didn't want to leave the company because it
was the first time in my life that I was

(54:21):
really successful and happy doing what I was doing, and
at this point I'm in my mid to late thirties.
I didn't become a partner at Stirling until I was
thirty eight, and was terrified that they'd call my bluff
and say, okay, well sorry, you know, we don't want
to give you shares. And then I did get on
an equity path which became really important to my life.

(54:44):
But I remember that night going home and thinking, oh
my god, what have I done. You know, I made
this threat that I would leave this job that I love,
that I'm finally good at something, you know, from a
professional point of view, and then thankfully that worked out,
but there were a couple of moments in there where
I wasn't sure it would And working in new business

(55:06):
the way I did is a constant street fight because
you're competing with other agencies. You're at the whim of
what a client might or might not want. I was
the chief rain maker for a long time in the
division at Sterling that I was running. You can only
imagine what that pressure was like, especially for somebody that

(55:27):
is not only competitive but using their success to be
their self worth. And that is really challenging because if
you aren't successful, it's something. If you don't win a
piece of business that can just decimate whatever little self
esteem you've built. And so I had to get off
that hamster wheel. But that's a really long time and

(55:49):
I still grapple with that, not necessarily in rain making,
but just in any area where I have to prove myself.

Speaker 3 (55:55):
Yeah, I think that that is something that many of
us wrestle with it. I think we can better at,
but I don't know if it ever completely goes away.

Speaker 1 (56:03):
Yeah, I'll let you know. I'm still searching for that.
That's my holy grail, Eric, that's my holy grail. Just
to feel good as is.

Speaker 3 (56:12):
Well, that is sort of the ultimate way to be
because as we've said, you sort of can't necessarily make
what is aligned with the way you want it to be.
A certain ability to be like, okay, this is I'm
going to be okay with what is is the thing
many of us are striving for. I suspect that there's

(56:36):
a creature, though, who may be good at this is
Maximus Touretto Blueberry adept in this skill.

Speaker 1 (56:44):
Well, Maximus Toretto Blueberry, the little multipoo we adopted during COVID,
is really an example of what it means to live
in the moment to have utterly no self consciousness about
any of our bodily requirements and is proof that unconditional

(57:04):
love exists. So Max is not my first dog. Max
is Roxanne's first dog, and so it's wonderful to see
all of those realizations birth themselves in her, and the
realizations and the relationship she has with Max, which is
just heart bursting. I can't even explain it. But the

(57:26):
first dog that did that for me was my dog Duff,
and that was twenty five years ago. One of the
great loves of my life taught me what it meant
to feel loved unconditionally and to love unconditionally, and that
is one of the great great gifts to the world
that our pets can do for us. And so I

(57:49):
love to have my furry my furry family around me.
We have two cats and a dog.

Speaker 3 (57:55):
Before we wrap up, I want you to think about this.
Have you ever ended the day feeling like your choices
didn't quite match the person you wanted to be? Maybe
it was autopilot mode or self doubt that made it
harder to stick to your goals. And that's exactly why
I created the six Saboteurs of Self control. It's a

(58:15):
free guide to help you recognize the hidden patterns that
hold you back and give you simple, effective strategies to
break through them. If you're ready to take back control
and start making lasting changes, download your copy now at
oneufeed dot net slash ebook. Let's make those shifts happen
starting today one you feed dot net slash ebook. Well,

(58:39):
I think that is a beautiful place for us to
wrap up with the happy image of Maximus and your
wife and your old dog, and I think it ties
right back to kind of where we started, which is nature.
Dogs are part of nature, and there's a special type
of connection that comes from being in partnership with.

Speaker 1 (59:00):
Yeah, and also witnessing what grows and what develops and
what evolves with or without our participation.

Speaker 4 (59:09):
Well, Debbie, thank you so much.

Speaker 3 (59:10):
It's always such a pleasure to talk with you, and
I appreciate you joining us.

Speaker 1 (59:14):
Eric, thank you, Thank you so much for all of
your kindness and generosity to me, and thank you for
a really nice interview.

Speaker 3 (59:21):
Thank you so much for listening to the show. If
you found this conversation helpful, inspiring, or thought provoking, I'd
love for you to share it with a friend Sharing
from one person to another is the lifeblood of what
we do. We don't have a big budget, and I'm
certainly not a celebrity, but we have something even better,
and that's you. Just hit the share button on your

(59:42):
podcast app or send a quick text with the episode
link to someone who might enjoy it. Your support means
the world, and together we can spread wisdom one episode
at a time. Thank you for being part of the
one you Feed community.
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Host

Eric Zimmer

Eric Zimmer

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