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October 22, 2025 27 mins

We love to pretend we’re above jealousy – that successful, self-aware people don’t feel it. But that’s a lie. 

When bestselling author and Mamamia Out Loud co-host Holly Wainwright found herself wide awake one night, jealous of a close friend’s success, she realised jealousy wasn’t something to outgrow. It was something to pay attention to. 

Because jealousy doesn’t just make you small. It points to what you secretly want – the thing you’re scared to say out loud. 

In this episode, Holly and I talk about the strange power of envy: how it can shake your sense of self, clarify your ambitions, and even become the most honest career compass you’ll ever have. 

Holly and I discuss: 

  • The moment Holly recognised jealousy in herself and what it revealed about her buried ambitions. 
  • How jealousy can act as a signpost for what you really want – if you’re brave enough to look at it. 
  • The difference between ambition and competition, and how one can paralyse while the other propels. 
  • Why success metrics constantly shift, and how to define what “doing well” actually means for you. 
  • How to stay grounded and generous when envy or comparison start to creep in. 
  • The link between gratitude, perspective, and creative freedom. 

 

Key Quotes 

“You’re only jealous of things you really, really want.” 

“If I focus all the time on what other people are doing, that’s what paralyzes me.” 

Connect with Holly on Instagram and LinkedIn, listen to Mamamia Out Loud and Mid, and check out her latest book He Would Never here

Listen to Part 2 of this interview with Holly Wainwright here

 

My latest book The Health Habit is out now. You can order a copy here:

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
I used to think that jealousy was something you outgrew,
that once you hit a certain level of success or
self awareness, you'd be immune to it. But when Holly Wainwright,
best selling author and one of the voices behind Mama
Mia out Loud, told me about the moment she found
herself jealous of a close friend's success, I really felt it.

(00:25):
She told me that she couldn't sleep, she couldn't stop
thinking about it. And what shocked Holly most wasn't the
jealousy itself. It was realizing that it pointed straight to
something she'd buried, what she really wanted. In today's episode,
Holly and I unpacked what happens when jealousy creeps in

(00:45):
at work, and how facing it honestly can reveal your
truest ambitions, often the ones you're almost afraid to admit.
Welcome to How I Work, a show about habits, rituals,
and strategies for optimizing your day. I'm your host, Doctor

(01:09):
Amantha Imber. Holly, I reached out to you for this
chat because I heard you talking about jealousy, and I
guess an experience of jealousy that you had back in
twenty twenty one. I want to say, and I feel
like I don't hear women talk about that experience of

(01:30):
jealousy much at all in the media, and I want
to start with hearing about what happened back then that
caused you, who is not a very jealous person to
experience that.

Speaker 2 (01:44):
Yeah, it was a really interesting moment for me, because
you know, there are those even though when you reach
sort of the grown up page that I am, you
think you know yourself pretty well, right, And I think
one of the revelations is that, you know, we're constantly
finding out that these stories we've told ourselves about ourselves
are not true. And one of the stories that I

(02:07):
had definitely always told myself is that I was not
a jealous person in all kinds of areas of my life. Like,
I've never been a particularly jealous person in romantic relationships.
I mean, I've had my moments when I've needed to
have them, perhaps, but it's not a defining factor for me.
I've never been one of those people who kind of
covet what everybody else has. I've never considered it to

(02:30):
be a driver. And then what happened was in the
experience that I spoke about and wrote about recently is
that my co host on Mamma Mia out Loud, Jesse Stevens,
who is a very dear friend of mine. We've been
working together very closely for god eight years maybe nine,
like a long time, and she's much younger than me.
Anyone who listens to mom were outlaud would know this.

(02:51):
Exceptionally talented, incredibly clever, very hard working like I just
but also the loveliest. I adore her. She wrote her
first book now, I at that time had written I
think three books, I think. And one thing that happens
whenever an Australian author in particular writes their first book
is everybody tells them to temper their expectations. And nearly

(03:13):
always that's the correct thing to tell people. They're like,
don't think just because you've got a book deal and
just because your book's coming out, but suddenly you're going
to have millions of dollars and all blah blah blah,
like you know we do. It's often not that life changing,
you know. I mean, it is for you because you've
achieved something you've always wanted to achieve. But so I
remember myself, I'm meya are other co host obviously co

(03:35):
founder of MoMA Mia were very much like Jesse. This
book is amazing, but you know, just be cool, like
it's not much is going to happen anywhere. Jesse's brilliant
first books called Heartsick. It's a non fiction exploration of
heartbreak through real people's stories. It's so good. Before it
came out, it became the subject of an international bidding

(03:58):
war in the US. And obviously I tell this story
with Jesse's blessing, like, you know, don't think otherwise, you know,
So she got a significant financial and also obviously status
from that. It was very successful. It was a best seller.
I think it was optioned for screens. So basically all

(04:19):
the things that there was me and me are being
like these wise experienced older heads telling her to keep
her call. Everything went the other way. There were stories
about Jesse Stephens the next big thing in literature. Now.
The story I have always told myself is that I
would be delighted for my friend. And I was delighted
for my friend, but also I found this experience incredibly destabilizing.

(04:44):
I became someone I didn't recognize. I became so jealous
of Jesse's success. It affected my sleep. It affected my mood.
It was like intrusive thoughts. It was like I couldn't
stop thinking about how this had happened to Jesse and
it hadn't happened to me, and it really really unsettled me.

(05:06):
I kind of examined it over time. Obviously, I had
to realize that I had to act on do something
about this, and I did talk to Jesse about it
quite early on. I spoke to her well, not that
it was her problem to do anything with, but it
just felt like something you should discuss.

Speaker 1 (05:22):
How did you bring that up, though, Holly, Like that
feels like such a hard thing to bring up with
a close friend.

Speaker 2 (05:28):
You know, I can't even remember exactly how I did it,
but I remember because you know, what I didn't want
is I didn't want to be snyde about it. Like
I didn't want to be because I think that there's
a female trope about this, right. And one of the
other things is I've always, in terms of the stories
I've told myself, I've always really rejected the idea that
women can't be happy for each other successes, that they

(05:50):
have to tear each other down. It's such a cliche,
but you know that any group of women are going
to be intensely competitive. Again, I thought I was against
all of those, like, very much against all of those ideas.
I've worked with mostly women for most of my career,
and that has not been my experience broadly, that women
can't work together, can't cooperate, can't be happy for each
other's successes. But there was something about this, And what

(06:12):
I realized was it was like my deepest desire, I
guess is that there are lots of things I do
in my career that I love and I'm passionate about,
and I work hard, but writing a book is such
an enormous endeavor and it's so vulnerable, and you know this,
it's such a vulnerable thing to do, and you put
so much of yourself into it, respect and success as

(06:33):
an author. Particularly at that time, I was doing okay,
like it wasn't like I wasn't. But the success that
she was achieving, I realized, Oh, that's really what I want.
You know, that must be really deep down what I want,
because it's driving me crazy. It was literally driving me crazy.
So I think the way I said it to Jesse,
I can't remember exactly how the conversation went, but what

(06:54):
I didn't want to be was all happy on the outside, like, oh,
I'm so happy for your success on that, but with
that sort of snide must be nice, you know, Like
I didn't want to be like that, So I think
I told her. I think at some point I told
her that it was driving me crazy, and I think
we did, and this is something we often do. I
think we talked about it on the show, workshopped it

(07:14):
a little bit on the show, and then I just
let it be out there. Sometimes. I think it's interesting
because I'm sure people who work with us, or work
around us, or listen to us a lot at that
time probably loved to gossip about that and be like, oh,
Holly has a problem with Jesse or whatever, and it's
just not true. You know, I adore her. But what
it did for me is it really as I worked

(07:35):
through it and I spoke to some really like trusted
I didn't trusted people about it, and workshopped it a bit,
I realized that what it did for me is it
clarified that I was more ambitious than I thought I was,
that I was more competitive than I thought I was,
and it sort of signposted to me. I mean, I

(07:55):
don't know if it's quite the right word, but like
what my priorities were in a way, like somebody said,
I think I interviewed somebody who told me that you
can't be jealous. You're only jealous of things you really
really want. So there can be a guy down the
road who's got a beautiful, fancy car, and I'm not
in the least bit jealous because I don't care about cars.
I don't want a fancy car. It's not you know,

(08:16):
I'm not jealous of people who have mansions. I'm not
jealous of people who have Gucci handbags because it's not
my thing, but it very clearly signposted to me or
that level of respect and success as an author is
obviously what I very much want, and I think it
reshuffled my priorities and allowed me to be more bold

(08:40):
about what I wanted.

Speaker 1 (08:42):
Have you experienced anything like that since that intense jealousy
you know that you had those few years ago.

Speaker 2 (08:50):
No, I can honestly say I haven't. I think I
interrogate myself more about why I feel a certain way
about certain things. I think what's interesting and I'd love
to know what you think about this. I obviously am.
My work is very important to be different facets of
what I do. I like to take pride in it.
Obviously a large part of my identity comes from it.

(09:11):
But the different ways that you value, you judge success
is something I think you're always recalibrating right in your mind.
When I wrote my first book, obviously just having a
book with my name on it was success. And then it's, well,
will it sell? Will I get to write another book?
You know? And then it's we're making this podcast, but

(09:32):
will anyone listen to it? Will it be? I think
that we're all always questioning what our markers of success are.
And obviously the world we live in social media and
constant comparison culture and announcement culture influences this. But I
always when I talk to or interview really successful people,
I always want to know what their relationship with success

(09:53):
is about, that is like, and their relationship with competition
is like, because I think there's a trope that all
successful people are very competitive and that you have to be.
I don't know if I think that's true. Do you
think that's true, Amantha.

Speaker 1 (10:09):
I'm a very competitive person and I use that to
drive me. I find it quite motivating, whether that be
in my business inventium, when we're pitching on a piece
of work, which is quite unusual. Generally we don't pitch
for work, but when we do, I put even more
effort in to what I'm doing, into the proposal, into

(10:29):
the relationship building than I would if there wasn't that competition.
It's interesting. I think I'm pretty competitive in the creative
projects that I have going on in my life, whether
that be book writing or podcasting. And we briefly talked
about that before we hit record, because I'm curious on
your perspective around this. You said you interviewed Sally Hapworth

(10:53):
during the week, and she's obviously just had a book
out this week. I think it's like her tenth or
eleventh book tenth, and she's an incredibly successful writer globally,
and like I definitely when when I've got a new
book about to launch. So I'm working on my fifth
one at the moment. Like I remember, you know, with
the past two, which have both been with Penguin, I've

(11:16):
been really competitive about pre orders. I want regular updates
on the numbers. I want to know if the book
has made the charts in the opening week or two,
like all of those things. I find that quite motivating.
It's kind of terrible because I think I define some
of the success around the project around the numbers, when

(11:37):
I'm sure that there's many people that would say, well,
you need to look internally to find success. What do
you think about this?

Speaker 2 (11:44):
I find that really interesting too, because what most of
us are like that to a point, right. I mean,
I've worked in digital media for a decade and when
I first was working in digital media and we were
writing stories, and then I was running a team that
was publishing stories. We can see in real time in
that environment, how many people are reading, how long they're
spending on there, and the whole point is more eyeballs,

(12:08):
more time, more eyeballs, more time. There's literally a leaderboard
in the office. I don't know if there is now
at MoMA MIA. We've have to have had different relationships
with this at different times because it depends what the
metric that you're driving for. But there's literally a leaderboard
in the office where everyone can see how well their
story has done. So it breeds obviously a very I

(12:30):
think parts of it are healthier. Parts of it are
not relationship with understanding what people want and what they
read and what that volume means. And then when it
comes to a project that's so different, like writing a book,
I think that there are authors, and I'm sure this
translates to different areas of work who are obsessed with

(12:51):
the numbers and the charts and the first week and
the second week and the pre orders and the you know,
and then there are those who can just let it go.
And when I was talking to sell this week, she
was saying that she has always kind of let it go.
But when we interrogated that a little more, I think
that also comes with a certain level of success and
confidence that it's going to be okay.

Speaker 1 (13:12):
You know.

Speaker 2 (13:13):
I remember I interviewed Leanne Murriati for mid in the
second season. I think, and you couldn't have a more
commercially successful author her, And you know, Leanne Moriarty does
not need to write another word, and she's fine, you
know what I mean. She's had so many I couldn't
tell you how many New York Times Number one best sellers.

(13:33):
She obviously has had almost everything she writes made into
a movie. She's she's at the pinnacle of that kind
of writing. And she said she still very much cares
whether or not her new book next book is doing
as well as the last one. It's not that she's
necessarily hungry for I need it to do because I
think at the beginning of your career, you need everything

(13:54):
you do to do well in order to keep doing it.
Do you know what I mean? That's the metric really
is like I need to sell enough books or whatever
that I will get another book deal, or that I
will be allowed to do this again, or I need
to win that client so I can win another client
and another client. So the success is the point, right
That isn't the case. If you get to a level

(14:14):
of serious success, however, then I think you're almost competing
with yourself because you want to be I think that
was very much what Leam sort of said, is that
she wants to feel that she's getting better all the time,
you know, which is not about being in competition with
another author. It's about being in competition with her own skills.
And I think that's kind of what Sally was saying
to me in this conversation we had. She said that

(14:36):
she's less obsessed with individual numbers. As she puts it,
you know, say, this is a week of the year
that when we're talking that a lot of big books
have come out, some people will go to the shops
and buy that one today, but then there might buy
the other one three weeks time, four weeks time. So
does it matter who wins the week?

Speaker 1 (14:53):
Like?

Speaker 2 (14:53):
That's kind of like that view, and I think depending
on your relationship with competition, yes it really matters who
wins the week. But does that make the work better?
Does that make you a better writer, author, creator? Whatever?
I think what that whole episode of brief insanity did
for me when I became obsessively professionally jealous, was realized

(15:18):
that actually, I don't think competition does motivate me. I
mean it does to a of course, I'm competitive to
a point because I just don't think you can be
driven without having that engine of something. And I'm definitely driven.
But actually personal and professional jealousy and competitiveness to a
point paralyzes me. Is if I'm always looking at that

(15:39):
and going that person's doing better than I am, or
that book selling more than mine or whatever, it kind
of makes me smaller. It's hard for me to explain it,
but it kind of makes me freeze. I can't really
explain it, but it's almost like it's I think for
some people it's definitely a motivation, and for others, I
think it almost paralyzes you because you sort of feel

(16:02):
like I'm not gonna win.

Speaker 1 (16:04):
Jealousy can feel ugly, But for Holly it was clarifying.
Coming up. We shift gears into how ambition plays out
once you've named what you want. We talk competition, comparison,
and the strange paralysis that comes from watching others win.

(16:25):
If you're looking for more tips to improve the way
you work can live. I write a short weekly newsletter
that contains tactics I've discovered that have helped me personally.
You can sign up for that at Amantha dot com.
That's Amantha dot com. I'm curious when so your fifth book?

(16:47):
He would never which I loved. I feel like I
will often write to you when I finish your Books'll
be like, when's the next one out? Because I need
my holy fix? Like I just I love your book
so much. He wouldn't ever, I think is your best
one yet. I've had several people say that.

Speaker 2 (17:04):
It's also been my most successful. I don't want anyone
to listen to this and be like, oh, holy she's not.
That book has done very well and I'm very proud
of it. It was very hard to write.

Speaker 1 (17:17):
I heard you say that as well. Actually I think
on it might have been a mum of me out
loud episode. And I actually I loved when you said that,
because I'm about to submit book number five to my
publishers in three weeks time, and I feel like it
has been far and away the hardest book I've written.

(17:39):
I've just I've been in struggle Town in a way
that I just haven't with the other four books. The
other four books have been relatively straightforward. There's been some
challenges with the structure, but then I know I've sort
of nailed that within a couple of months have been
into the writing process. But this one has just, oh,
it's been really really hard.

Speaker 2 (18:00):
People always say it gets well. Actually I don't know
the authors say this, but other people, well, so it
gets easier. I have not found like writing books has
not gotten easier for me. It's it's very difficult every time.
It's just it's a very difficult thing to do. It
really is.

Speaker 1 (18:18):
So I want to know, then, with what you were
saying when he would never came out, which I want
to say, was that like four or five months ago?

Speaker 2 (18:26):
It was in at the end of April. Yeah, it was, Yeah,
it was Mother's Day release.

Speaker 1 (18:30):
Yet, what then does your competitive drive all lack thereof
look like when it's publication day, it's launch week. You know,
the publishers looking at numbers, you're positive, like, what are
you doing in that week?

Speaker 2 (18:44):
You know with regards to that, Oh no, I am
looking at numbers. Don't get me wrong. One of the
things that, as I was saying before about my background
in digital media, I care very much about lots of
people reading my work. You know, it's interesting because sometimes
I'll be at a writer's festival.

Speaker 1 (18:59):
You know.

Speaker 2 (18:59):
That's so interesting about the community of book writers is
it's so we compare books as if they're all the
same meal, you know what I mean, when really somebody
who's writing poetry and someone who's writing recipes, and someone
who's writing a heartbreaking memoir and someone who's writing a
beach read are all sort of thrown together as if
you're all doing the same thing, or someone who's writing

(19:20):
nonfiction someone who's writing and that's clearly not the case.
Publishing is a very diverse industry. There are lots of loves,
So I don't think we should be comparing around in
July and recipe to eats like I just don't think
that's a thing. Like neither of them are better or worse.
But it's not a thing. But sometimes when I'm a
writer's festival and I have a little bit of imposter

(19:41):
syndrome because I still feel sometimes that I'm not a
like a serious author because I write what they call
commercial fiction. The thing about commercial fiction is it's called
that because lots of people buy it and lots of
people want to read it. And I am not ashamed
of that, you know what I I mean, I don't.
To me, that doesn't mean it isn't good. In fact,

(20:03):
I think it's the opposite. I always say, and I'm
happy to say, and I don't care if it sounds
a little bit brash or whatever. It matters a great
deal to me that my books sell well and the
lots of people read them. There is no greater compliment
to me than when people say to me, I love
this book. I stayed up reading this book. I told
my friends about this book, Like that's what I want

(20:23):
to hear. I want. I think women's lives are difficult.
I want them to have as much entertainment and also,
you know, see themselves in these stories. That's what I
do and why I do it. So I very much
want the book to be successful and I will work
my butt off to sell you know, the books as
much as I can, and publishers like that. But I
think the thing about whether or not I'm deeply competitive

(20:46):
is it's not for me about is it going to
beat that one? Is it going to be this? You
know what I mean? It's more is it going to
do well? Is it going to grow? I want to
get better. I want to be able to write books forever.
So I think maybe for me, I am more comfortable
with the term ambitious, Like I'm ambitious for my writing,

(21:07):
I'm ambitious for my career. I'm ambitious for my books
doing well. Competitive to me means that you are immediately
comparing and trying to beat somebody else. And what I've
found and that episode that I was talking about, is
that that makes me a bit sick. Do you know
what I mean? It actually makes me a little bit.
I don't mean it makes me sick as in I'm

(21:29):
disgusted by it. I mean it literally makes me quite
unwell to focus too much on that. What I learned
through that is it was a very interesting exercise in going, Oh,
you are really ambitious, you want all these things. But
if I focus all the time on what other people
are doing and whether or not i'm better or worse
than them, and they're doing better or worse than me,

(21:51):
that's what paralyzes me. That's what makes me quite unhappy
and anxious. And I'm sure this is true for you too.
Is that whatever field you're writing in, if you're writing
with other people's voices and opinions in your head all
the time, that's paralyzing too, Right. If you're always like,
what's so and so going to think about this, or

(22:11):
those people on the internet are going to say XYZ
about this, that stops you from creating. So I think
what I've learned and maybe where I've landed is I'm
very ambitious for my career and my writing and whatever
I'm doing, I want to do it really well. But
it's not about winning. I think that maybe that's the difference.

(22:31):
Does that make sense? It does?

Speaker 1 (22:33):
I love the awareness that you've got to and I'm
curious as to how then that has led to action,
because if you haven't experienced that intense jealousy in the
last four years, what do you think you've done differently,
aside from recognizing just how horrible that that feeling was
for you.

Speaker 2 (22:53):
I think I check myself on it a lot, because
I think it's the most natural thing in the world
when you see people you know. As I said about
the idea that sometimes your jealousy is a really helpful
signpost to what your really secret desires are, and that
yours might be quite different from societies or what they're
supposed to be. But when I feel it coming, I

(23:15):
can check myself on it. And when I say when
I feel it coming, I don't mean that it's constant,
but the little things that you know. Now. I'm very
fortunate in that I'm now at a place in my
career where I do get asked quite a lot to
can you help promote this book or this author, or
will you write a blurb about this or will you
interview this person? And if I want to, my answer

(23:37):
is absolutely yes, because I think if I was frozen
in my place of envy and fear, I'm like, well,
I don't know, do I want to help them? Be successful.
Do you know what I mean? I have to be
like absolutely, I want to be generous. I want to
push myself to recognize or that slightly icky feeling I

(23:57):
have today about that person or you know the news
that so and so just got blah blah, you know
a screen deal or a I don't know, whatever. I
can recognize it and go, Okay, but you're writing a
book right now. How does any of that help make
this book better? You know? And so I think the

(24:19):
awareness of it has been helpful, and it's an ongoing process.
I think to call yourself out sometimes about the uncomfortable stuff.
I really want to be the person who's focused on
the work. I can quite easily, especially if I'm myself
feeling burnt out, feeling tired, feeling what's all this for?
Or whatever it might be, then absolutely I can be

(24:42):
much more prone to that kind of negative thinking and bitterness.
I think, no question. And I think that's why I
think sometimes it feels when you read or look for
advice from people who are really successful, you're often there's
a bit of you that's like, well, of course you'd
say that, because you you know you've achieved all the things,

(25:02):
but what I've learned from, as I say, meeting a
lot of people who've achieved all the things that you
might dream of, is that they don't feel like that.
People are always pushing themselves. I think driven people always
pushing themselves so they don't necessarily feel like they've ticked
every box. But yeah, no question. If I'm struggling, then
I definitely am less generous in every aspect. And I

(25:24):
have to check myself on that too, And so it's
such a cliche, but I have to check in with
being grateful, you know, I really do, because you know,
as you know, because we speak sporadically over years now,
I've made a lot of changes in my life. In
the last few years. I've moved out of the city.
I've got this sort of more quiet life and a

(25:45):
bit more spect well in theory I do, I don't really,
but I have more space and more I've done a
lot of work in understanding what I need to try
and keep myself calm and grounded in a world that's
very as we all know, moving incredibly fast and very
anxiety inducing. And sometimes it is a cliche, but when

(26:06):
I stop and go look look at this, you know
these were all things I dreamt about. And look at
my family and my beautiful kids who are growing up,
and you know, look at the place where we live,
and look at the fact I'm growing tomatoes in my garden,
and look at the fact I'm sitting talking to you
in my little shed that is my room of one
zone that I had literally wanted forever. You know, it's

(26:27):
a cliche, but it's true, is that you have to
pull yourself back otherwise you can. I think ambitious creative
people we're insufferable often, like we just it's just the more,
more and more, And it's not necessarily more money, more status,
but it's just like it's the constant anxiety of like
why am I not doing as well? As like it's

(26:48):
just shut up. You know, I've really got to check
in with that shut up voice.

Speaker 1 (26:59):
Nollie and I were having such a great time chatting
that once we finished this episode, we actually ended up
continuing the conversation and we talked a lot about energy
burnout and how Holly is struggling with portioning out her
energy correctly to the right projects, and so we worked
up some strategies that she could use. So what I've

(27:20):
done is packaged up that episode as a little bonus
episode for today that you can listen to right now
by going to your podcast feed and looking for the
second How I Work episode that dropped today. If you
like today's Joe, make sure you hit follow on your
podcast app to be alerted when new episodes drop. How
I Work was recorded on the traditional land of the

(27:42):
Warrangery People, part of the Cooler Nation.
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