Jennifer Romolini, author of the new book Ambition Monster, has had a big career, including leadership roles in print and digital media. She has been the girl boss-of-bosses, and now has insights to share.
Read her fascinating book, checkout her podcast (Everything’s Fine) and listen to her thoughts on how having a big career impacts your important relationships, as well as your physical wellbeing. I took away from it different things than you will, or perhaps someone else will.
One thing I understood better after reading this book and speaking with Jenn: We all had messed up childhoods, in different ways. We are all using the survival skills we learned and honed (for me: be strong, build consensus, hold your ground, stand up for yourself, etc.) that got us through traumatic childhood events. Yet these may or may not serve our purposes later, or now, as we navigate our daily lives. Did we fight to get what we want? Or did we fight to win high positions, and then realize that wasn’t what we wanted, at least not forever. Things shift.
The same emotional armor, or in Romolini’s case, human understanding, innate perception, observational and language skills that helped back then may prove effective to gain career success – but at what cost? Just because you can be the boss doesn’t mean you have to be the boss.
Her first step to “right-sizing” her career was prompted by a health crisis: She completely lost her voice. Not just garden-variety laryngitis but injuries to her vocal chords that eventually (when she kept talking against doctor’s orders) surgery and the potential of permanent damage to her ability to speak. Here she tells what she learned from her journey from the boardroom to the podcast booth, and what she never wants to see again for the rest of her working life.
This Monster Is Out from Under the Bed
Sometimes reading another person’s story and learning from their journey can be the best way to learn more about your own. This is true for anyone who chooses to read Jennifer Romolini’s latest book, Ambition Monster. She is so honest, thoughtful and reflective – and her story is so interesting – that even if you don’t relate to all of it, you will learn from what happens to her along the way. It’s like she goes and drags the monster out from under the bed. And suddenly it’s not so scary anymore. In fact you can make friends with it.
Romolini, who is the co-host of the podcast “Everything is Fine” with Kim France (who among other interesting things was the founding Editor-in-Chief of Lucky), is someone who brings perspective and insights to the events of her life and uses those insights to make YOU (and me and all of us) feel smarter for reading.
Hearing her tell stories from her career makes your understand your career, your own parenting history. (Both the way you were parented and the choices you make balancing a career and the choices you make around whether or how to raise kids). Careers come with choices and as you move up you may not enjoy yourself as much or feel as rewarded as you did when you were doing what you loved. Plus every decision about work has an implication at home. Checking in on your feelings about both is important, because you find yourself depleted or broken.
What Happens When You Move Up the Ladder
Read her advice here, which will help women of all ages and stages to assess how to have the carrer they want, and make the choices that will work for them now, later and in each “season” of your life.
And spend time with the podcast, which is directed at women over 40 but holds true for women of all ages as we grapple with who we want to be and how we want to treat ourselves, including our health, our careers, self-care, and how to negotiate the birthdays as they arrive.
Whether you want a big career or are still searching for your “purpose” and your family shape and attachments, listen to Jenn. She has stories to tell and we have lessons to learn.
What Advice would You give your younger self?
Jennifer Romolini: Slow your roll. Your career is not going anywhere. It will still be there when you get back (from whever you need or want to go).
More than anything, I would tell myself to stop worrying about the outside world and start worrying about an internal world. My biggest mistake through the years was really letting myself be guided by what other people thought I should do instead of really thinking about what I wanted to do.
Lucy Danziger: Your childhood was like a movie. Reading Ambition Monster is like reading a movie.
JR: I mean it was like a movie – they were very beautiful. They were very beautiful messes.
Who was your inspiration and why? (I’m guessing your Mom.)
JR: I think my mother was my style inspiration for sure. But in terms of an inspiration, I mean, I think that I had very few models until my inspiration sassy became A guidepost for me. The editors of Sassy were revealing a life that I very much thought, for the first time, that’s the thing I want!
LD: And what was that? If you could encapsulate what that life meant or said to you? I read Sassy, but not everybody who reads this will have.
JR: It was independent. It was a irreverent. It felt a little bit outside of the norm. It wasn’t giving you the messages that YM or Seventeen were giving at the time, it was teaching you to carve your own path and have some attitude. Ms. and Sassy were saying that. Who else was telling you to have some attitude – and that attitude was okay?
LD: But you know what? I love that because I think I grew up with a little too much attitude sometimes and I think I bristled against norms or conventions of what little girls should act like. I swore a Blue Streak and I was at the Tomboy and I think a lot of people thought I was a little too much. I think that was my way of projecting that I was a feminist – at the age of 12.
JR: Yes same. That’s right. I mean ultimately that got me into trouble right? Having that attitude. Nobody warned you about what was going to happen when you were started putting that attitude into the workplace.
A little sugar goes a long way. You’re gonna have to learn to have some bedside manor or you’re going to encounter problems and you’re gonna get a lot of negative reviews – and you’re going to intimidate men, which is going to be a problem for you. Those were the warnings we did not get. But I knew that I was not going to be the soft girl.
What Advice to You Have For Someone Who Wants a Big Career?
LD: You’ve done so much. And a lot of people probably look at your life and say “I could never do that. I could never lead the way she led. What do you say to somebody who actually wants a big career and they want to step into a big role a leadership position?
JR: I think that as long as your expectations of this career are right-sized then that is fine. So keep your expectations in line with what this career is going to give to you and how much it is going to take away from you. I think that’s fantastic.
But this idea that you can have this giant career and also be very present for your relationships in your life (whether you choose a partner or not) and also do parenting at the level that you might want to mother, then that’s a totally unrealistic enterprise.
It is unrealistic to think that you can do all of those things at once. You absolutely can’t. And if you understand that ‘I’m going to be dropping the ball here.’ or ‘I might not really see friends for several years.’ As long as you’re understanding that you can’t do everything at once. And that everything we do requires some sacrifice. There’s nothing that is perfect.
As long as that’s what you want and you’ve really gotten right with yourself and you’ve really said, ‘This is where I’m okay with the level. I’m capable of showing up for the things outside of work.’ Making those decisions, think of your time as a pie chart, and you only have so much of the pie chart… How big of a slice you want motherhood to be? I didn’t have a second child because I knew that that would create such an imbalance and I didn’t think I could handle it.
What happened when you lost your voice? What was that about?
JR: I love work but it’s always important to question those decisions and make sure you haven’t made a turn for money or status that is actually depleting you –and that the work is still worth the sacrifice. It’s a constant interrogation of those things.
I had taken a job I shouldn’t have taken, because it really looked good to the outside world. I knew it was not a good job for me and I had also written a book, so now I’m being asked to speak at conferences. I’m doing Keynotes. I’m doing this heavy job. I’m editing a book. I was doing everything right.
When you have a book come out, part of publishing the book is promoting it. So I’m speaking constantly. I’m in meetings all day. I never not talking. And I was on a stage. And I tried to get a word out. And I couldn’t get it out. It just was like my voice collapsed and then it went away. Then I started having all this pain in my throat, and then I was so busy, that I got annoyed by my body.
I went in and finally got a doctor to see me. At first another doctor told me, “You’re stressed.” and I was like, this is not just being being stressed. This chronic Laryngitis is not stress [alone] and I went to see a vocal cord specialist, and she told me, “You have polyps on your vocal cords, and you need to stop talking or they’re gonna start bleeding. And if they start bleeding you could paralyze your vocal cords, you could never speak again. We’re gonna have to operate. That’s where we’re at.
I was so far into workaholism that my reaction was: “I can’t stop talking! I won’t do that!” Even though I knew what the stakes were high. But I was so far into this work that I could not walk away. So I didn’t stop talking and they got worse. I got another polyp. And at this point my doctor was like, “Okay, we’re scheduling the surgery.” So I got the surgery and after the surgery I had to be silent for two weeks. And I knew this was for real this time.
I knew I couldn’t mess with this because Once you’ve done a cut on your vocal cords… if they touch or get scarred, you can really damage them for life. They really needed time to heal, so I had to embrace silence for two weeks. Living my life silently for two weeks – on work calls, dealing with the kid, dealing with my husband, everything! I had a little white board that I walked around with in my house. I even fought with my husband on a whiteboard.
So I had that time to slow down. And when you slow down, you can really see things. From an outside perspective. I was no longer a player. I was no longer in it, I was out of it and I started to see what was important to me. And what was not! And the job was a disaster and I realized that I hated the job.
So You Climbed Down the Ladder? You Can do that?
I couldn’t keep working at the job and trying to please people that were un-pleasable, who didn’t know what they wanted, who had big egos, who were callous, who didn’t give a s*** about me. And I was putting way too much energy into that. So in the balance of my life that job had to go and the big executive career had to go too, because that wasn’t what lit me up. I like creating things.
JR: The more successful you become, the less often you get to do the thing you love. Because the idea is like: You’re great at this! Now we’re gonna take it away.
LD: Right. For me, I love editing and writing and coming up with ideas. So you move up, and now they want you to care about KPIs and ROI and SEO.
JR: That’s such a perfect analogy! Because I like writing and editing. I love both of those things. I like working with writers. I like assigning stories. I like writing stories and I was just getting kicked Higher Up and it wasn’t fun anymore.
I was getting kicked higher upstairs and now I’m a paper pusher. I don’t want to look at one more deck in my life. I don’t give a s*** about that stuff. I like the work.
I’ve created a life for myself that I now do the work I love. But nobody says you can climb back down a couple rungs if you hate the work or you were unhappy at the top. Nobody does that, and I don’t know why. But that’s the thing about success: It’s not one size fits all.
That is really our problem with women. It’s like if you can do it – because we couldn’t for so long– then you are supposed to want to do it. So now the idea is if you can do it you should do it. If it leaves us feeling unhappy or empty or depleted and out of balance – or all of the things – it’s because there are so few of us. That we need the representation. That’s not the way to live a life.
“I was fatigued and bored at work, because the thing is about life, when you’re bored, why even be doing it? I would so much rather be scared. I live my life in a way that I want to be challenged and scared.”
Their are Seasons to our careers. The thing is I did all those board rooms and I had all those conversations and I fought all those fights and I was a good feminist and I was in there. The fact that I was fatigued and bored because the thing is about life when you’re bored, why even be doing it? I would so much rather be scared. I live my life in a way that I want to be challenged and scared.
JR: We have to normalize getting off the ladder and not look at his like ‘It’s over for her!’ It’s great because when you’re younger when you’re in your 30s and you just have all that fire and you’ve so much to prove and you’re just like ‘Yes!’ That’s the person who should be in our job. Not the person who’s checked out or who’s hoarding the power and overstaying their welcome.
If someone really doesn’t want it anymore, but they don’t want to give it up, then wew have to normalize that it’s not a big deal to step away! You’re not a failure and your career is not over, just because you don’t have an impressive Linked In job. Who cares about that?
You have to change the way we think about success. I think there’s joy on the other side. We need language around this, shedding the Ambition Monster. Because we don’t have [the words].
LD: Wow.
JR: . We only have this one very narrow vision of what success is. We don’t talk about the richness of life and following what you actually want to do. A couple years ago. I took this job in Ireland and it’s in the book. It was after I got off the big ladder and I got offered this job. It was such a bulls**t job. I was the Editor-in-Chief and Chief Content Officer or whatever of a weed site that was based in Ireland. Okay, it was these kids who were building an SEO play.
LD: That’s amazing.
JR: We would run stories like “Does Cannabis Cure Herpes?” No, but you’d write that story. Whatever the reason, I took that job. And it paid enough – more than my half of the bills, but it wasn’t anywhere near my big salaries of the past. But every two months, they sent me to Ireland for a week.
I got to Ireland for a week with these kids and I loved it. The other part of this job was that I only had to work from six in the morning till 2:00 in the afternoon. So I had time to pick up my child after school. I had so much work-life balance. It was an easy job. I could do it in my sleep. it was the best bridge for me because it creative financial security. But it didn’t take my whole brain and it gave me all this independence and I got to travel and going to Europe every six weeks or two months was transformative for me.
It was erotic in a way because I was just alone with time just walking the streets of Dublin. That was such a success for me and everybody told me it was a joke job. It’s gonna ruin your resume and I was like, no this sounds like fun.
LD: Fun is underrated when it comes to work.
JR: Right. But your enjoyment of work does not have anything to do with the external status. It has nothing to do with it.
Do you have a mantra or words you live by?
JR: Easy come, easy go. I have a tattoo on my arm that says that.
LD: What does that mean to you?
JR: : It means don’t get too attached to this opportunity happening.
Easy come at work: When everything is working, when the energy is good, when you’re involved in an incredible creative collaboration, when there’s a lot of green lights on a project and you can feel that it’s all going really well and it’s in balance and you’re working to your strengths there’s kind of nothing better. That’s when I love work. But it never stays that way forever so you need to be flexible and do what feels right.
JR: When things aren’t working, it may have to do with so many other things, like what is going on with your team, or other outside economic forces. If you’re in alignment with the work and your skills, that’s unique. But often it just doesn’t have anything to do with that. So don’t get attached to the so-called failure either.
Don’t get attached to a success. Easy come, easy go. It also means let’s just live a little bit with ease here. And this idea that there’s also not scarcity. We can really get caught up in a scarcity mindset when there’s abundant work out there for all of us, and there’s so much to be living. So that’s really about not getting stuck. Easy come, easy go.”
Follow Jenn On Instagram
Read her Substack: jennromolini.substack.com
And definitely order Jenn’s book, AMBITION MONSTER here.
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Navigating the ups and downs of work life is tricky. This advice will help you be smarter as you reach your professional goals.
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