5 Powerful Women On The Career Risk That Paid Off
When these five founders and leaders chose uncertainty over security within their careers, they all discovered that the biggest strides forward often begin with trusting your own instinct. By NATASHA BIRD
Careers are rarely built on a single leap. Certainly, entrepreneurial careers require a series of risk assessments, probably a few steps back and definitely a lot of perseverance in the face of uncertainly or setbacks. For many women, those moments of weighing up the pros and cons of a bold decision carry extra weight. Research consistently shows that women are less likely to apply for roles unless they meet 100% of the criteria, while men will often go for opportunities when they meet around 60% of the given list. The same caution shows up in entrepreneurship and leadership, where women are often socialized to value security over a more dicey risk-reward strategy. Yet progress, both personal and professional, rarely happens without stepping into the unknown. Here, five incredible women reflect on the calculated risks that changed the course of their careers – and what happened when they chose conviction over comfort.
Clare Goodwin, founder and CEO of communications and talent agency CGC
What was the risk – and what made you take it in that moment?
“The risk was stepping away from a challenging, yet secure role at a company I genuinely loved – especially as I had a young family and the responsibilities that come with that. But I could see a clear shift happening in the media landscape: new brands were emerging, new platforms were reshaping how audiences engaged, and there was space for an agency that approached things differently. One rooted in storytelling, brand building and truly embracing new media.
“People close to me were understandably uneasy. They saw the stability I was walking away from. But I felt a quiet confidence. My intuition told me the timing mattered and that this window of change wouldn’t stay open forever. Earlier, I might not have had the experience or clarity. Later, the opportunity might have gone. So, despite the noise around the risk, I chose to trust that instinct and take the leap.”
What was at stake?
“I had no idea how to build a business. I hadn’t written a business plan. I didn’t have clients lined up. I was walking away from a secure job into complete uncertainty. If it didn’t work, I would have lost not only financial stability, but potentially credibility in an industry where reputation matters. But I wasn’t starting from nothing. I had a deep understanding of the industry, a strong reputation, meaningful relationships and an instinct I trusted. My gut told me there was space for something different and that I was capable of building it. If it failed, I would have learned. If it worked, it would change everything. And that possibility of the chance to build something of my own, on my terms, was worth the risk.”
Which part of the process was hardest – and how did you steady yourself through it?
“The hardest parts were the early days. They’re incredibly exciting, but also relentless. There’s no team, no systems, no safety net. You’re doing everything yourself: serving clients, pitching new business, running accounts, managing cash flow. The weight of it all sits squarely on your shoulders.
One of the biggest challenges was hiring. When you’re a tiny team, one wrong hire doesn’t just affect performance, it affects culture, morale and momentum. The stakes feel amplified. What steadied me was being intentional. I didn’t rush decisions. I thought everything through carefully. I trusted my instincts, not just in starting the business, but in shaping it. I said no to a lot of opportunities that didn’t feel aligned even when saying yes would have been easier financially. In hindsight, that discipline was defining. It shaped CGC and who we are today.”
Looking back, what did the risk give you – beyond the obvious rewards?
“Beyond the obvious rewards, the risk gave me confidence – real, earned confidence. It strengthened my belief in my own judgment. When you build something from nothing, every decision matters. You learn to trust your instincts, to stand by your vision and to take responsibility for the outcome. That process gave me a deep sense of self-assurance in my decision making. As a leader, clarity is everything. You need a clear vision and a consistent approach. You need the people around you to believe in where you’re going and why. Taking that initial risk and seeing it through gave me the conviction to lead with certainty rather than hesitation. The success wasn’t just external. It was internal. It allowed me to feel grounded and sure of myself in a way I hadn’t before.”
Michelle Kennedy, founder and CEO of women’s social networking app Peanut
What was the risk – and what made you take it in that moment?
“I was in a phenomenal role as deputy CEO at Badoo, and our group company Bumble was in rapid growth. I was well paid, really the most senior woman in the organization and able to have real influence. To walk away from that and determine that it was the moment to start something new was a huge risk. I lived with the idea of Peanut for almost three years before I took the leap to build it. I think that the longer I sat with it, the more I saw the opportunity everywhere, in every step, at every moment – I could see women needed this platform. They needed their own support network, their own product, their village.”
What was at stake?
“At the time, the biggest thing I stood to lose, I think, was my ego! When you are at the top of your organization, to step out and start again is humbling – there are no people to do things for you. You are the people. You are the recruiter, the FD [finance director], the marketeer. You do it all. You are unable to focus on anything else – it’s all-consuming and obsessional. That obsession and drive to make the world a bit better than I found it meant that I had everything to gain – but a little bit of naivety as to how hard it was going to be, how people were going to respond, and to have confidence in my own abilities definitely helped!”
Which part of the process was hardest – and how did you steady yourself through it?
“Starting a business is hard every day; that’s the truth. Even on the days you are winning, something happens and can make you experience an extreme low. The way we talk about women, women’s health, motherhood has changed and evolved exponentially (thank goodness). When I started Peanut, perceptions were so different – we weren’t talking about baby loss, about infertility, about isolation in motherhood. I often felt that Peanut was single-handedly carrying those conversations.
“I’ve also lived every iteration of trends for tech (NFTs, Crypto, AI), all whilst highlighting that what women – mothers – actually need is real-life, human connection. That required absolute obsession and dedication to understanding women’s lives. As women, we are multi-faceted, we are complicated, but resolutely, we are better united. That has underpinned every decision I’ve made at Peanut, and it’s how I steadied myself through every fad or trend that made anyone question the validity of what we are building.”
Looking back, what did the risk give you – beyond the obvious rewards?
“Risk gave me courage and, more than that, I believe it gave people around me courage – my children, my friends. The courage to believe that taking a risk is worth it, that if there is an issue or an opportunity out there, and you want to make change, you can be the one to do it, change it, fix it. Honestly, why not you? And, of course, risk gave me resilience. At this point, there isn’t a single element of rejection or disappointment I haven’t felt or experienced! But I know that what I do every day is leave the world a bit better than I found it. Peanut has made a positive impact on the lives of millions of women – and every day we work tirelessly to make sure that continues. I’ve never regretted taking that risk. Even on the hardest days.”
Becky Fatemi, executive partner at Sotheby’s International Realty and founder of Shadow to Shine
What was the risk – and what made you take it in that moment?
“There is never a perfect moment to take a leap. Leaving my job at one of London’s leading real estate agencies was probably the biggest risk I took in my career. For me, at the time, I was feeling a quiet discomfort – and that was the shift I needed to take the plunge. To the outside world, everything looked as though I was doing very well – I was number one in the company, felt secure and was earning well. But I had been there from 1998 to 2011, and when the founder of the business left, something shifted for me. He was such a visionary and a huge part of why I loved the business. Without that energy, I knew in my gut I was not happy anymore and wanted something more – and I had a rumbling ambition to do my own thing.
“The next big risk was leaving there without a plan. I went back and forth for months. Then, one day, I handed in my car keys and walked out. Setting up entirely by myself, with my own company, Rokstone, made it even riskier. I was moving away from a powerful, established brand and placing my faith fully in myself. Financially, emotionally and reputationally – and as a single mum – I felt very vulnerable. Furthermore, I was a woman of color in an industry that hadn’t always felt the most inclusive – but this made me even more determined to succeed. Eventually, the hard work and tenacity paid off. I went above and beyond for that first Rokstone client – and, even though I definitely didn’t make money on that initial transaction, the memory I left with the client and effort put in set me up thereafter. It reminded me to trust myself – and that has shaped everything I’ve built since.”
What was at stake?
“I had a phenomenal client book, a top office on Park Lane and the security of a bigger company around me. There was every chance I could lose visibility or that people might not follow.
“But I gained freedom and could build my own brand and authenticity. Rokstone allowed me to build something on my own terms, prioritize relationships and create my own legacy. Fifteen years on, after more than £8 billion in transactions with my team, that journey led to partnering with Sotheby’s International Realty, which felt like the perfect blend of independence and global reach.”
Which part of the process was hardest – and how did you steady yourself through it?
“The hardest part was going out as a woman on my own in an industry which was so male-dominated. There were not many women around me doing the same thing and very few people who looked like me in the rooms I was operating in. There was no clear blueprint to follow. There were moments of doubt, moments of being underestimated and times when I had to dig deep to find the grit and determination to have the confidence to shine.
“To this day, I surround myself with great people who inspire me and mentors to keep me steady. I had brilliant lawyers, accountants and people who believed in my vision. I focused on showing up, delivering for clients and letting the results speak. I have great friendships with clients and they come to me for so many things – not just property, but the best tips for so many aspects of their lives.
“The best piece of advice I received is from Virgil Abloh [the late fashion designer and entrepreneur]: “Each one, teach one” – meaning, share what you have with another, keep sharing, keep teaching. I’m not always easy to work for, but everyone I have worked with has gone on to do incredible things – and I’m so proud of them.”
Looking back, what did the risk give you – beyond the obvious rewards?
“It gave me freedom and control, but also purpose. I could choose who I work with, move at my own pace and be present as a single mom, which matters more than anything.
“It also created space for the things I care deeply about. Founding my charity, Shadow to Shine, was incredibly personal. It came from recognizing how isolating my own journey had been as a woman of color and wanting to give young people – particularly those without industry access – mentorship, confidence and real exposure to opportunity. It is about opening doors and making the industry feel more inclusive.
“My app that I created for creatives, BlackBook, builds on that in a different way. Co-founding a tech platform focused on bridging the UK’s creative talent gap has been about scale and impact. It connects emerging creatives with real opportunities, champions female-led innovation and challenges traditional networks that can often feel closed.
“Ultimately, the risk gave me agency. Not just to build a business, but to help create pathways for others coming through. Helping others grow, for me, has been the most meaningful return.”
Louise Roe, interior designer and founder of Copenhagen-based brand Louise Roe
What was the risk – and what made you take it in that moment?
“Up until 2018, we were going around all of the design fairs, building a stand and then tearing it down a week later. It took endless logistics and planning. I really wanted to open up my own physical space, where I could ground myself and where I could showcase my objects in a setting that was my own. A place that could have longevity, that we did not have to deconstruct each time. We had been looking at several spaces, but by chance we came upon the place in which my gallery resides now.
“It was double the rent of the spaces we were initially looking at (and even those were a high risk to begin with), which meant that we needed to take a huge financial leap – for which we could end up paying the ultimate price. When we got it, it was in a fairly boring state, but it was in this beautiful old iconic building that had an incredible façade – and I could definitely see the potential. This made me feel that I simply just had to do it. If I had waited, the opportunity might have been lost. I’m sure others would have advised me to wait and save up, but I felt that this space could really represent me and my vision. So, quite simply, I took the risk because I felt that this opportunity was too good to pass up.”
What was at stake?
“As I mentioned, this studio space meant undertaking a huge financial risk. If it didn’t work out, and we weren’t able to generate enough revenue to keep it running, we could have been in a very precarious position. Besides that, we had to stop going to design fairs. We had to go from gift boxes to more simple packaging – and it also meant that we could not grow our staff. The only staff we could hire was for the café that I wanted to have inside the studio. So my small team of four (including myself) had to dig deep to develop and grow the company with limited resources. We knew we would lose exposure at the fairs with all the buyers, and we could negatively halt the growth of the company.
“On the positive side, if it worked out, we stood to gain a lot. I could not only showcase my objects, but I could express myself and my brand and reach consumers directly. The space has six large windows facing the street, which meant a lot of exposure. And if the café did well, we could gain a lot of foot traffic, which meant people discovering my brand. It was very much a high-risk/high-reward situation.”
Which part of the process was hardest – and how did you steady yourself through it?
“Every day, looking at the finances and trying to keep us afloat was definitely the hardest. The pressure we were under to perform was immense and I was constantly looking for measures that would balance the books for the first two years. Thankfully, I have a very positive outlook, which helped me immensely through this. I have always believed in looking on the bright side and being confident in myself. So, basically, what helped me going through this was just believing in it. I always believed that the positives outweighed the negatives – even though the negatives meant taking a huge risk.”
Looking back, what did the risk give you – beyond the obvious rewards?
“Opening the Louise Roe Gallery, with The Roe bar inside, is the single most successful thing that we have done. The Gallery is now at the absolute center of everything that we do and has opened up incredible opportunities. It is a space that embodies everything Louise Roe is – enabling us to host both our everyday regulars, but also host our own events and launches, creating a community of friends and family that regularly visits and attends our events. On a more personal level, it made me more confident in my decision-making and made me believe in myself even more.”
Anna-Sophie Hartvigsen, co-CEO of finance and investment tech platform Female Invest
What was the risk – and what made you take it in that moment?
“I had just signed a contract with a top-tier management consulting firm, which had been my dream job for years. I had spent months preparing for the interviews and the salary was great; the path was clear. Everyone around me thought it was the obvious choice. At the same time, I had fallen in love with Female Invest. Back then, it was nothing more than a passion project. No money. No network. No safety net. What made me take the risk at that exact moment was knowing that if I did not try then, I probably never would. I was young and had very few commitments. It felt like a now-or-never moment, where choosing the safe option would mean closing the door on something I deeply believed in.”
What was at stake?
“I stood to lose everything that looked good on paper. A prestigious career, financial security, validation. I also risked disappointing people who cared about me and thought I was making a mistake. What I stood to gain was harder to explain at the time, but much more important. I had the chance to build something meaningful. To work on a mission I genuinely cared about. To see whether I could create my own path, instead of following the one that was expected of me.”
Which part of the process was hardest – and how did you steady yourself through it?
“Being a start-up founder is hard in every possible way. There is constant uncertainty and there are very few moments where you feel fully in control. The hardest part was trusting myself when there was no external validation and no clear roadmap.
“What grounded me was the decision itself. Once I chose to follow my passion, I committed fully. I reminded myself that this was the moment in my life where risk was possible. I knew that if it did not work out, I would still be able to rebuild. That perspective made the hard days manageable.”
Looking back, what did the risk give you – beyond the obvious rewards?
“Taking that risk changed everything for me. It taught me that there is no single correct way to build a life or a career – that you do not have to follow the conventional route to be successful or fulfilled. I also learned that the worst-case scenario is rarely as bad as we imagine. Failure would not have defined me, but never trying might have. Most importantly, I learned to trust my intuition and to believe that, with focus and persistence, far more is possible than we are taught to think.”