Naomi Walkland and I have never met. But for a long time now, we’ve moved in similar circles and I keep finding myself in situations where her name comes in up conversation, and people keep tell me how much I’d love her and how I should really try to meet her.
Naomi and I both worked at the same dating app. And although she had left long before I joined, her legacy and impact were still felt throughout the marketing team. People would frequently reference Naomi as one of the best leaders the business had ever seen and would lament at how much they missed her. At a recent coffee catchup with ByRotation’s CEO, Eshita Kabra, Naomi’s name came up again. As an investor in ByRotation, Eshita told me just how brilliant she is, how supportive she is to the business and how I should try to get to know her. I made a mental note to try to meet her at some point and then a few days later, I had a notification to say that Naomi had subscribed to this newsletter. My eyebrows went up and my mouth fell open. Coincidence? Fate? Either way, I knew I had to get Naomi to tell me all about her hurdles.
Naomi’s Substack The Power of Quitting is one of my favourite newsletters. Born from Naomi’s own experiences of quitting a job that had a terrible environment and culture that made her feel like she couldn’t show up and be herself, she interviews brilliant women who have made a difficult decision to leave something behind, and digs into how they’ve pivoted, embraced change, and backed themselves into something new. And as someone who, as of this year, finally decided to not keep doing the things I’d previously been doing just because they were the things I’d always done, every interview is a reminder to listen to my gut when it’s telling me something’s not right for me – and to remember that I can always walk away if I need to.
Here, Naomi tells me all about her hurdles, including having to learn the big old lesson that achievement does not create peace. She talks about the perils of not listening to your gut during an interview process and and why interviewing needs to be a two-way thing. And Naomi also talks about why the people you work for matter just as much as the company name, and how some of her former work wives became some of the most important friendships in her life today.
Hiya Naomi. Please tell us a little bit about you as a person, and a snapshot of your life right now:
Hello Emily! Thank you so much for having me on the series. I have loved reading the other interviews.
My life feels very full at the moment. I am doing this interview off the back of my son’s fourth birthday party weekend – 20 children at our house. It was brilliant, chaotic and exhausting in equal measure. I work in marketing, which I have done for most of my career, and I also sit on the boards of The Marketing Society and Mothers2Mothers.
When I am not working, I try to keep things quite simple and spend as much time as possible with my husband, son and our dog, Rocky. I need to move most days to feel like myself, so I run and train, and have become slightly obsessed with HYROX over the last few years. At weekends I love cooking and baking, which is probably the thing that helps me switch off most. I read a lot too. I have just finished Selfish Girls and am now reading Cleopatra and Frankenstein. More than anything, though, I love spending time with the people closest to me. Give me family, friends, good food and a long conversation and I am very happy.
Q: Where in the world do you live?
I live in a village just outside Cambridge. We left London about five years ago, just after Covid. We were the total cliché, I know. But we are very settled out here now, and have the balance of city and country life as I’m in London a few times a week.
Q: How would you describe yourself as a person? Tell me who you are, where you came from, where you’ve been and where you’re going.
I grew up in North London. I moved out in my teens for school, came back to the city when I was a bit older, and stayed until about five years ago. I was raised by a single mother, and I always share that because it has genuinely shaped who I am. She has always worked, and she still does now. She is where my work ethic and my ambition come from.
So who am I? Hard-working, curious, and a big dreamer with a relentless attitude. My career has been in marketing and communications throughout. I started in luxury lifestyle PR, moved into lifestyle and tech, spent a good chunk of time as a consultant working across a range of brands, and I am now a chief marketing officer. Where am I going? Still have lots of big ambitious dreams.
Q: What were you like as a child? How would you describe how you showed up in the world, how you felt and how you interacted with your own life and the lives of others?
I was shy and quite anxious at times as a child, at least around people I did not know. With my close friends, I was often the most confident person in the room. It is funny watching my son now because he has exactly the same tendencies. He can be a little wary when he meets someone new and then become the most confident little boy in the world once he feels comfortable.
I had a huge imagination and was endlessly curious. I still am. As an only child, I spent a lot of time in my own company and became very good at entertaining myself. I had a small, tight-knit group of friends, loved sport, enjoyed school and was always happiest when I was learning or trying something new. There was a bit of a contradiction to me. I could be shy in some moments and completely confident in others, depending on how comfortable I felt. I was also very independent and probably matured quite early. I think that comes with being raised by a single parent and being an only child. My mum worked incredibly hard, so from a young age I would let myself in after school, make something to eat, get my homework done and take responsibility for myself.
Q. What are you like now? How would you describe how you show up in the world, how you feel and how you interact with your own life and the lives of others? What are the main differences between who you are now and your childhood self?
The curiosity, the hard work and the independence are all still very much there. The biggest difference is confidence. I am far more confident now and nowhere near as shy as I was growing up. I have learned to trust myself and back myself – even when I do not feel completely ready. I still thrive in close-knit environments though. My favourite place is still around family, close friends and people I can be completely myself with.
People often describe me as ‘driven’ and say there is an empowering energy about me, which always makes me smile because I do not think my younger self would recognise that description at all. That said, some things have not changed. I was an anxious child and I still have anxious moments now. The difference is that I understand myself much better. I know how to manage it, and I know that some of the same qualities that drive me forward – ambition, curiosity and caring deeply about things – can sometimes be the very things that create anxiety too.
Q: When you were younger, what did you want to be when you ‘grew up’?
I just wanted to work in business. I could not have told you exactly what that meant. My mum was a management consultant, and I simply wanted to be a businesswoman.
Q: What do you do for a living? Tell me your current job title and all the job titles you’ve previously worn in the past.
Most of my career has been spent in tech businesses. Today, I am Chief Marketing Officer at an automotive marketplace business and before that, I was Vice President of Marketing at a dating app.
I have had a lot of different job titles over the years, but they have all sat somewhere within marketing. I started out in PR and communications and over time moved into broader marketing, growth and leadership roles. My career has always been about helping businesses grow and understanding customers (I’m passionate about people, society and culture – I studied Anthropology).
Q: How do you feel about what you do? Does what you do define who you are? If so, has it always? If not, why not?
I have been on a real journey with this one and, if I am honest, I am still on it. For a long time I let my work define me, and I am still conscious of that pull now. I talk about it a lot. My Substack, The Power of Quitting, actually grew out of an event series I ran that explored pauses, pivots and identity – and so much of that conversation comes back to who we are versus what we do.
My work gives me a huge amount of energy. I genuinely love what I do. It challenges me, motivates me and gives me a real sense of purpose. But I work hard not to let my role become the whole of me. What I have realised over the years, though, is that I do not want my work to be the only thing that defines me. It’s a big part of who I am, but so are the other roles I play in life – as a wife, a mother, and a friend. The challenge for me has been learning to hold all of those things at the same time.
Q: Tell me about your best job ever. Why did you love it? What did it give you? What did it teach you about yourself?
My best job was my last one, and I absolutely loved it. I joined when there were fewer than 50 people, and getting to experience the journey from start-up to scale-up and eventually a publicly listed company was incredible. It was messy, exciting, challenging and rewarding all at the same time.
It was also the first time I had worked for a business whose mission I genuinely felt connected to. We were right in that post-#MeToo moment, with conversations around women’s empowerment, equality and representation happening everywhere, and it felt like we were building something that mattered. One of the campaigns I am proudest of launching is My Love Is Black Love. Growing up in London, I rarely saw people who looked like me represented in images of love and relationships, and when I did, it often did not reflect our experience. We wanted to celebrate the joy, beauty and diversity of Black love in Britain.
What I loved about that campaign was not the marketing. It was the impact. If even one young Black girl saw those stories and felt more seen, more confident or more willing to make the first move, then it was worth doing. That role taught me so much, not just professionally but personally too. I was given opportunities before I felt ready, learned how to lead, made lifelong friends and grew a lot as a leader. More than anything, it showed me what it feels like to do work that genuinely connects with people’s lives.
Q: Now tell me about your worst job ever. Why did you hate it? What made it so bad? What did it teach you about what you value in a job?
I had one role that was, without question, my worst. The telling thing is that my gut was off the entire way through the interview process, and I did not listen to it. From the moment I started, I did not like the culture. I did not feel I could show up and be myself and the environment was not great. So I quit. And quitting that role is what led to me starting The Power of Quitting, and to launching my consultancy. It was a real catalyst. It taught me how much the environment matters, how important it is to listen to your gut, and that the people you work for matter every bit as much as the company name. I always tell people now that an interview is a two-way thing. Get as much information out of them as they get out of you.
Q: How did you get to where you are today? What did it take? What decisions did you make? What was the path like? What hurdles stood in your way? Was it extremely difficult? What did you say yes to? What did you say no to?
I got here through a combination of hard work, ambition and a healthy amount of saying yes before I felt ready. I have always pushed myself outside my comfort zone. I have also been incredibly fortunate to have mentors and coaches throughout my career who saw potential in me before I fully saw it in myself. Their belief gave me confidence at moments when I needed it most.
There have been hurdles along the way. Every career has them. Different companies, different leaders, politics, timing, setbacks, moments of self-doubt. A lot of success comes down to things you can control, but some of it is also about being in the right place at the right time and making the most of the opportunities when they appear. What I do know is that I work exceptionally hard. I care deeply about doing a good job, I am a bit of a recovering perfectionist, and I tend to throw myself fully into the things that matter to me. Looking back, that combination of hard work, tenacity and backing myself before I felt ready has probably been the biggest driver of where I am today.
Q: Is the reality of where you are today different to how you imagined it would be? If so, how? What are the biggest differences?
Yes and no. Professionally, if you had told my younger self where I would end up, I would not have been surprised. I always had big ambitions and big dreams, and I worked hard because I wanted to build a career I was proud of.
What is different is how I thought it would feel. When I was younger, I probably thought success would feel like arriving somewhere. That there would be a moment where I felt completely confident, completely certain and like I had everything figured out. The reality is that every stage brings a new set of challenges, doubts and opportunities to learn. The older I get, the more comfortable I am with not having all the answers.
The other thing I never fully appreciated was how important the rest of life would become. My husband, my son, my friends, my family, my community. Early in my career, I would probably have described success almost entirely through the lens of work. Today, work is still incredibly important to me, but it sits alongside a lot of other things that matter just as much. So the destination is not wildly different from what I imagined. The definition of success definitely is.
Q: Who are the people you feel the most like yourself around? How did you meet them? What’s your relationship like? Why do you think they make you feel like this?
My husband and son are my world, and I feel most myself when I am with them. I am also very lucky to have some incredible friendships. I have never really been a big friendship group person. Instead, I have a handful of very close friends, many of whom I have met as an adult. Quite a few of them came through work. What started as work wives and a work husband turned into some of the most important friendships in my life. I am now godparent to one of my friend’s daughters, which probably tells you everything you need to know about how those relationships have evolved over the years. A lot of my closest friends live abroad, particularly in the US, so we make a real effort to see each other. One of my closest friends I met on a retreat last year and we bonded almost immediately.
What I love about those friendships is that there is no pretence. They know me professionally, personally and through some of the biggest moments of my life. They challenge me, support me, make me laugh and keep me grounded. They are the people I call when something good happens, and they are also the people I call when life is hard. The older I get, the more I value depth over breadth when it comes to friendships. I have never been someone with a huge friendship group. Instead, I have a small number of people who know me incredibly well and who I make a conscious effort to invest in.
Q: What’s the biggest hurdle you’ve ever had to get over? Why was it stood in your way? How did you get over it? Did anyone help you? What did getting over the hurdle unlock for you in your life? How do you feel about that particular hurdle when you look back on it now?
I think the biggest hurdle has actually been learning that achievement does not create peace. For a long time I thought the next promotion, the next opportunity or the next milestone would finally make me feel settled. The reality is that ambition can be a wonderful thing, but it can also become a treadmill. You hit one goal and immediately move on to the next.
There was a period after a friend passed away where I was forced to slow down and really examine how I was living. I was burnt out, exhausted and constantly chasing. Coaching helped me realise that I could be ambitious without making achievement my entire identity. I am still working on it. But I have learned that my worth is not tied to a job title or a milestone – and oddly, holding ambition more lightly has made me better as a leader.
Q: What’s a hurdle that regularly trips you up?
My ambition. I know that sounds like a strange answer, because ambition has given me so much, but it has a shadow side too. I care deeply about doing a good job. I set incredibly high standards for myself and I can slip into perfectionism. Sometimes I have to remind myself that not everything needs to be exceptional, and that sometimes good is genuinely good enough. I have learned that the same trait that helps me achieve things can also create anxiety if I do not keep it in check.
Q: What’s the best thing about your life right now?
Honestly, I feel completely myself. And I feel so blessed with my family and my friends. That is the best of it.
Q: Do you find life hard? If yes, why? If no, why not?
Not generally, no. But I would be lying if I said there have not been times when it has been genuinely hard.
Q: What’s the best advice you’ve ever been given?
My mum always used to tell me the Maya Angelou line. No one can make you feel inferior without your consent. It has stuck with me my whole life, and I come back to it constantly.
Q: What’s the worst advice you’ve ever been given?
Someone once told me I should leave the company I was at, which was a complete rocket ship at the time, to go somewhere more corporate and do an MBA. I am very glad I did not listen. The exciting, slightly uncomfortable path turned out to be exactly the right one.
Q: After your days, how would you like to be remembered by those who knew you?
As someone who had a real, positive impact on the people in her life, and on the wider world too. I am deeply motivated by leaving an impact.
Q: Who is the person you admire the most? What is about them that makes you feel this way?
The person I admire most is probably my mum. She taught me that hard work matters. That resilience matters. That if you want something, you go after it. So much of who I am today comes from watching her.
Q: What’s a secret you’ve always harboured, that you might like to share now?
I do not know if this counts as a secret, but I think people are often surprised to discover that I am actually quite a homebody. My job can look quite busy and outward-facing from the outside, and I spend a lot of time speaking at events, travelling and meeting people. But my perfect evening is genuinely being at home with my husband, son and dog, good food on the table, hair up in a clip, comfortable clothes on and nowhere else I need to be. That is probably when I am happiest.
Q: What’s one regret that you have in your life? (If you’re someone who says they have no regrets because everything that’s happened is what brought you to where you are today, tell me something that you’d go back and change – if it meant that nothing else would change as a consequence)
Honestly, I do not spend much time thinking about regrets. There are definitely decisions I would make differently with the benefit of hindsight, but every difficult experience has taught me something important. If anything, I regret some of the time I spent worrying. Worrying about outcomes I could not control. Age has given me a bit more perspective. Most things work out, and when they do not, you usually learn something valuable anyway.
Q: What is something that’s made you laugh recently?
Preparing for my son’s birthday party. There were four adults in the room: me, my husband, my father-in-law and my mother-in-law. Between us, we somehow managed to completely overcomplicate pass the parcel. We all had opinions, none of them matched, and we could not agree on how to run one of the simplest games in the world for a group of four-year-olds. After a heated debate about how to wrap pass the parcel, we eventually realised how ridiculous we were being and ended up all laughing.
Q: Well me the one great story you have to tell. Maybe it’s the story you always dine out on. Or maybe it’s your favourite funny story. Or the one your friends and family always ask you to tell.
How my husband and I met and our first date. We met on Bumble and our first date was meant to be a quick coffee. It turned into an eight-hour date.
Q: Tell me about the greatest loves of your life. (This could be a partner, friends, family members, a hobby, a job, a pet.) What made them so great?
My husband, my son and my dog, Rocky. They are my whole world. My husband is my biggest supporter, cheerleader and sounding board. Someone once told me that one of the most important career decisions you make is who you choose as your partner, and I think there is a lot of truth in that. He pushes me, backs me and keeps me grounded.
My son has completely changed my perspective on life. He brings so much joy, laughter and chaos to every day, and being his mum is the greatest privilege. And then there is Rocky, who is quite clearly the best dog in the world. He was our first baby and has been by our side through so many of life’s milestones. He is very much the glue in our family.
Q: Do you have any parting words?
I love that you are doing this. It is one of the best interviews I have done, and so refreshing. It was just lovely to have a real conversation.
This interview is part of the Hurdling interview series. You can find more of them here. You can keep up with Naomi, and see the work she shares, on her Instagram. You can also subscribe to her Substack The Power of Quitting here.
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