8 high profile women on their biggest failure, and what it taught them.

Few things in life are guaranteed, but failure - in varying degrees, in varying moments - is one of them.

We all fail. We probably all fail often, but failure is something we are all conditioned to shun and avoid.

In 2021, Mamamia is embracing failure.

The hope is to normalise things not always turning out how you wanted them to. We want to encourage women to take risks and put themselves out there, accepting failure as a possibility but not letting it stop you from pursuing your wants and needs. 

Because no one's journey to success is linear; there're forks in the road, and many dead ends. 

We asked a number of high profile, inspirational, successful women about their own experiences with failure, their relationship with failing, and how they move past their mistakes.

Failure sucks, but it doesn't have to mean the end of the road. And with the benefit of hindsight, you might even find yourself grateful for the lessons it taught you.

Samantha Wills, jewellery designer and author.

Image: Supplied.

When I first moved to New York City, I was so mesmerised by it all and very quickly lost sight of the brand's (Samantha Wills Jewellery) 'why'. Rather than staying true to what we did and finding a market that matched our authenticity, I changed the entire design language in one fell swoop. My thought process at the time was that I need to change the brand to fit into a higher-end market. Needless to say, it didn't impress the market I was trying to enter, and I pretty much demolished the brand in one season. It was without a doubt the biggest mistake I have made in business.


I had to sit in the demolition site of the brand I had just almost destroyed. I sat there and had to return to 'why' I started the brand in the first place. I had to regain the trust of our community, retailers, as well as our internal team.

My advice around this is to never change your brand (or person!) to fit into a market, embrace your truth and authenticity, and the market that is right will find you.

It taught me the importance of authenticity and how without it there is no longevity.

I have tried to separate failure and 'f*** ups'. For so long in my career I held such a tight view of a successful outcome. I would focus entirely on something I wanted to achieve, happening in the way I wanted it and in the exact time I wanted it to. I held so tightly to that, that I was unable to see anything else that was unfolding or presenting around me. 

I was so focused on what I thought 'success' was meant to look like, that if I landed anywhere outside of that framework, by my own standards it was a failure. This is obviously ridiculous - because often what we deem as a 'failure' ends up being replaced with something that we had not anticipated. This can be even better than the original vision.

Whereas a 'f*** up' is something that you get so wrong, goes against all your internal instincts and intuition, yet you persist with anyway. In my experience when you go against your intuition, the outcome is rarely a good time. 

My advice is to loosen the grip a little on what your exact vision is, don't let it go, but just loosen the grip a little. This way we can have a slightly more fluid framework that is not success vs failure, but rather allowing room for what is trying to present itself to us to find us.

Learning to trust ourselves and our intuition is the key to letting go on what we think an outcome should look like. Instead allow room for what is trying to make its way to us. I feel if we look at it like that it puts a whole different context on 'failure'.

Jessica Vander Leahy, model and writer.

Image: Supplied. 
I fail all the time, but I think that's only because I'm always excited to try my hand at new things. A few big flops I had were through my early modelling career. 


Basically I had a few big jobs and, maybe because I was too young or just unskilled, I choked. I was never booked by some of these brands again. It sounds silly, but it was a hit to the confidence any time I didn't feel like clients LOVED me, but those failures pushed my career in different directions. 

But all in all, would I change it? Probably not, because the thing about modelling is it’s not ~really~ the most solid career choice. That struggle I had as a young model made me go out and work on a few plan B's: I don't buy into not having some contingencies when it comes to your work. 

Now in my career I feel I can take more risks and enjoy the ride because I've worked other jobs and had training and experience in other areas - if no one ever booked me on a shoot again I would still be able to get a job. 

Had I been super successful as a teen model I might not have had that drive to go to uni or diversify my career. 

It taught me that failure makes you hungry. And while I don't think life should be driven by fear-based decisions, setbacks do test your passion for something. You can more easily tolerate being humbled by trying to do something that feels authentic to your purpose.

While I'm sounding all positive about failing, I certainly don't like it when I'm in the muck of it. It's f***ing hard to feel like you're sucking at something. But, if you fail and feel like you need to try again and again, when you do hit success you might discover there were so many learnings in those hiccups.


They're important - you just sometimes need perspective to see them like that, so hang in there. I hate to sound cliche but I think at the end of your life, the bitterness of knowing you didn't try will be harder to swallow than knowing you choked a few times trying to to suck the marrow out of life.

Maria Thattil, Miss Universe Australia.

Image: Instagram. 
It was the summer of 2016, I was in my last semester of my Master's degree and had just scored a commercial internship at a huge oil and gas company in the HR team. My four-year plan was to secure a position in the graduate program for three years after the internship, and then transition into a permanent HR role in the organisation. 

Despite bringing heart and soul to the opportunity, at the end of the internship, I was not successful in securing a graduate role. This was hard to swallow because it disrupted the four-year plan I was wedded to. I cried, stressed, wallowed and my confidence took a hit.

However, because life didn't go to plan, I ended up pursuing contract opportunities that were more flexible and allowed me to earn an income whilst dabbling in content creation as a hobby. Fast forward five years, and that hobby has grown into a platform that enables me to champion the causes I believe in and pursue 'extra-curricular' activities… like becoming Miss Universe Australia, a professional writer and speaker, and launching my first podcast.


My relationship with failure has evolved from fighting against it, to seeing it as a natural experience when you are striving. That job 'failure' ended up teaching me that hardship can be the gift of a lesson, that rejection can be redirection, and struggles can morph into opportunities. How you perceive things matters.

Khadija Gbla, human rights activist.

Image: Supplied. 

I have had many failures. In some ways, I feel lucky that my 'failures' have been very personal and happened behind closed doors. So I think the failure I want to share is the one I had years ago. I don't want to call it a failure. I want to redefine that term. I think when things don't work out, they are a redirection. Because I'm a believer that everything is based on our perception.

So when I won the Young South Australian of the Year (2011) award, I was on a high from that and the publicity. I thought to myself, "This is the time to manifest all the goals I've always had." One of those goals was to create a magazine for women of colour called Chocolate magazine. At the time, we didn't have any magazines that were dedicated to women of colour. All the major magazines were very whitewashed. Still in 2021, they are whitewashed. The diversity was lacking. When I read Dolly or Girlfriend, I didn't see myself reflected, so I thought I would solve this problem.

Anyway, that didn't go anywhere because I partnered up with somebody who was in it for the wrong reason. They had a background in graphic design, and I just didn't have the skills to manage it. I was utilising the award so much for advocacy, raising awareness for domestic violence victims and the impact on culturally and linguistically diverse women. It was such an honour and such a huge deal that this young, black, former refugee woman had been awarded this top award from our state. I wanted to make sure that I utilised that time to launch this big project, but it was just all too much at once.


So I failed at launching a magazine for women of colour. But like I said, I saw it instead as a redirection. I needed to focus more on being a voice, advocating and representing like I was already organically doing. The evidence was the messages from young girls of colour across Australia contacting me saying, "It was so great seeing somebody who looks like me, sounds like me."

So I did achieve my goal, I didn't fail. We have to redirect, relaunch, reevaluate our perception of how we achieve our goals. This is not the way that this needed to be, and that is okay. The image that we have projected our dreams, motivations and goals onto may not look the same in the end as it did in the beginning, but our core message is unchanged.  

I moved on by acknowledging that I did not manifest that goal in that particular format and that I have already paved a different way to still bring about the same result. I just needed to reevaluate what I wanted to achieve. If anything, it was a misstep on my part rather than a failure.

It taught me that you don't always have to create something. I think we live in a world that makes us believe we always have to create something. I didn't have to do that. I just needed to build on what I was doing already.

I am absolutely comfortable failing. It would actually be horrible if I succeeded at everything. How would I learn or grow? When I journal in my gratitude journal, I give gratitude for the things I failed at and the lessons I learnt from them. They have revealed my values and motives. So I am comfortable with failure because it allows me to redirect to what I need to be doing and presents an opportunity for me to do something else.

My advice is that your perception is the difference between seeing something as a failure or an opportunity. Your perception is everything. Don't just give gratitude for the things you have. Give appreciation for the things you haven't been able to accomplish. I genuinely believe there are lessons in the battles we haven't won, and the dreams we haven't manifested.

Isabelle Silbery, Gogglebox star and writer.

Image: Supplied. 
Failing at my marriage was a defining moment in my life. I was desperately trying to make it work purely because the idea of failing at a marriage felt so embarrassing. I didn't want to let my son down or my family down.


It took a long time to move on. I had to mourn the idea of how I thought my life was going to be first and let that go in my own time. Processing grief and failure is different for everyone.

I wouldn't change anything about this time although I wish I had known that there was a good life after divorce because at the time, it just felt like the end of the world. It taught me that if something doesn't work, it's better to have failed at it than to be deeply unhappy and stressed. Life is way too short to be scared of failure.

I embrace failure, in fact I expect it. I accept that I am forever learning and the learnings that come from failing makes it all okay. It's never easy to embrace the uncomfortable but once I learnt to step out of my own way, I've challenged myself in ways I never would have before.

Get to the deep root of your feelings around failure. If the fear of failing is stopping you in life, ask yourself - what's the worst that could happen if you did fail? Think back to your earliest memory of feeling like a failure and relive those emotions.

Choose to allow yourself the space to fail and let go of perfection and the expectations of others. You might find you are the only one in your way!

Shahni Wellington, NITV host.

Image: Supplied. 
O' let me list the ways! Something that sticks out in my mind is the time I submitted a personal piece for the anthology 'Growing Up Aboriginal in Australia.' Working mostly in news, it was the first time I sat down and wrote something personal about my identity and my own lived experiences, in what was my own writing style. I can still feel my stomach drop when I received the rejection letter.


In my mind I had handed my heart to a publisher, only to have it turned down for me being "too me". I took it so incredibly personally that I remember thinking I shouldn't have submitted anything at all.

Spoiler alert - it was a mistake email and I was in fact accepted for the book. In all of that though, I learnt a huge lesson that I shouldn't only pursue dreams for the glory of living them out. I loved writing in a creative way about how I saw the world, and whether it would be published by a company or my mum for the fridge (she offered) shouldn't hold me back from trying and putting myself out there.

I think my response in this situation said it all. I'd conditioned myself over the years to want to be the best, that it became debilitating. If I wasn't certain I'd succeed, I'd rather not be involved at all. While I still find it very challenging, I've been trying to see the strength that lies in vulnerability. I try to apply this to relationships, my career and really every other part of life. 

For me, it's about taking back my own power. Success can sometimes come in the form of simply being in the moment, trying new things and having the courage to take on a challenge. It's important to find validity and happiness in yourself, rather than judging your success on outside influences – whether it be acing the test, getting the job, making the team, the boy texting you back, or the publisher including your story.


Kate Morris - Adore Beauty founder.

Image: Supplied. 
It was maybe nine years ago, and I was overseeing a tech project that went absolutely pear-shaped. Our website wouldn't work properly, customers were livid, none of my staff could do their jobs properly. Every day for several weeks, I drove to work in tears knowing that the entire day would involve people complaining about this project I was responsible for.

I just kept turning up every day and trying to put out the fires and fix the problems, one by one by one. What choice was there? I certainly learnt a lot about what to avoid in those sorts of projects, especially around accountability. But then I also hired a Chief Technology Officer who would be better at all that than I was.

It's just one of many failures over the years, but each one teaches you resilience. The world doesn't end when something goes wrong.

I wouldn't say I'm comfortable with failure - it always stings a bit - but I do accept that it is to be expected from time to time when you're trying to do big things that nobody's done before. One of our core values at Adore Beauty is 'Always Growing', and that means we push ourselves outside of our comfort zone and anticipate that a lot of what we do might fail - but we keep trying.


Don't beat yourself up too much over failures. Try to talk to yourself as you would talk to a friend - you'd be kind and support her, not tell her she was useless! Failure is an amazing learning opportunity. Give yourself an hour of wallowing under the doona, then pick yourself up and have another go.

Sheryl Thai, CEO and co-founder of the League of Extraordinary Women, former founder of Cupcake Central.

Image: Supplied. 
One of my most memorable failures was when we were expanding our business from three stores to five. We had a mass exodus of staff leaving as we enforced new procedures too strictly and rapidly. The company culture changed and the existing team started to all hand in their resignations, which affected every part of the business from production to team happiness and productivity.

Whilst it was exciting to be expanding and opening new stores, we underestimated the adverse effect it would have on the team when we suddenly introduced new managers and updated procedures to allow for expansion. When staff morale was low and we had 10+ of our team move on, we were desperately low on bakers and it was highly stressful. The remaining team had to work longer hours, in a high stress environment and ensure that it was business as usual from the outside looking in.

It was about two-three months of working 18 hour days and having to step back into the kitchen to help with baking and getting orders out. We also had to hire a new team of bakers and front of house in a short period of time and train them all up.


At that point it was really taking each day as it comes, staying optimistic and focused on what we were trying to achieve. I had to keep reminding myself that it was temporary and this too shall pass, we'd be stronger for it.

I was also fortunate to have a group of entrepreneurs I surrounded myself with giving me perspective and sharing experiences of how they have dealt with similar situations. If it weren't for my EO community, my mindset and mental health would have suffered a lot more. They really helped keep me [keep] grounded and resilient when I needed it.

If I had the opportunity to do it again, I'd be more aware of change management processes, keeping our team informed with more open communication. Phasing in change is important and getting the team on board first before just rolling out what we thought would be best.

Communication is key. Leadership is the ability to have the foresight to understand what could go wrong and have a Plan B, C & D. Prevention is better than a cure.

When I was younger, I definitely had Type A personality traits and I would beat myself up for days, if not weeks, when I felt I had failed at something. Since starting a business, it's hard to not fail at something every week – so that was a steep learning curve, for me to rejig my mindset to see failure as an opportunity for growth rather than an experience that diminishes who I am and what I'm capable of.

Whilst failure will never be something I'm completely comfortable with, I sit with it and ask myself, 'What can I learn from this?' rather than let that negative self talk get out of hand.

Failure is not the opposite of success, it is part of success. Once you accept that you can't avoid failure in life, it makes it easier to face it, overcome it and grow from it.

Also, find like-minded peers that have achieved what you're hoping to in business. Joining EO Melbourne has been instrumental to my personal and professional growth. Just knowing you have a network of other successful business founders to share the ups and downs with is empowering.

At Mamamia, every day is International Women’s Day. We fund the education of 150 girls in school every single day with our charity partner Room to Read, and our goal is to increase that number to 1,000. To help support girls’ education in developing countries, you can donate to Room to Read and contribute to a brighter future. 

Feature image: Supplied/Instagram.