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Confident and Killing It with Tiwalola Ogunlesi

In honor of Women’s* History Month, we sat down with women-identifying Squarespace customers whose stories of strength, creativity, and success inspire us everyday. Based in London, Tiwalola Ogunlesi is a confidence coach and inspirational speaker who works to help other women find their voices and speak their truth. She chatted with us about self-love, her message to young women, and how she fearlessly faces the challenges in her business and in her life. 

SQUARESPACE: You founded Confident and Killing It in 2017. What made you want to create this platform?

Tiwalola Ogunlesi: Months into my first job I felt a bit lost. There was deep unfulfillment that came from being stuck in a job I hated. In the back of my mind, I knew there had to be more to my life than living on autopilot. In a search for a more fulfilling life, I began volunteering as a Youth Leader with a group of twenty 15-year-old girls. 

One day, I asked them to write down an area in their life they wanted to grow in. I got home, super excited to see what they had said until I opened the first piece of paper.

“I want to be more confident” 

“I wish I loved myself more” 

“I want to be more confident”

“I want to learnt to unleash my inner diva” 

And so it went on and on and on. ALL TWENTY GIRLS in the group had written in one way or the other that they wanted to be more confident and love themselves. I burst into tears not only out of sadness for them but also sadness for myself, as I remembered being a teenager and not loving myself. 10 years had past and it felt like the world hadn’t changed, another generation of young women growing up struggling to love themselves. 

That evening broke my heart. I could no longer be a bystander in life. It was time to start using my voice to stand up for women and girls. It was time to wake them up to their truth. Society has normalised self-hate in women and young girls and it is NOT ok! We all deserve to love and believe in ourselves but it’s like everything is conspiring against us to make sure we remain insecure. 

So with a fire burning in my heart and a deep sense of conviction, I decided to use social media in a more meaningful way by sharing positive content that inspired women and girls to wake up to their greatness. That’s how Confident and Killing It was born. It’s a self-love revolution that wakes women up to their worth, so they can be confident, unstoppable and dare to live the life they truly desire. 

SQSP: As a self-love advocate, how do you suggest women work on incorporating more empathy into the way they view themselves? 

TO: First of all, it’s important to know that your worth is intrinsic. Your worth doesn’t depend on where you’re from, how much money you have, the colour of your skin or what other people think of you. You don’t need to be perfect. You matter simply because you exist. So place value on yourself and don’t wait for your validation to come from strangers on the internet. 

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Secondly, you are not your thoughts. Your thoughts, feelings and identity are all different things. Just because you think or feel like a failure does not mean you are a failure. You are not your fear, anxiety or depression. You are worth, you are strength and you are purpose. Feelings come and go so don’t internalise your negative emotions or stay stuck in them. Be kind to yourself, you are beautiful.  

Thirdly, it's crucial to understand how powerful your mind is and how to program it for success. Your mind is a battlefield of conflicting forces. Your strengths and weaknesses are constantly fighting for your attention and whatever you focus on wins. So make it a priority to learn about your strengths. Write down your achievements, moments you’re proud of, skills that come easily to you and work that energises you. Read them everyday and make decisions from your strength not your weakness.  

In summary, believe you are worthy regardless of the circumstance; don’t internalise negative emotions as they are not your identity; gain a deeper understanding of your strengths and bring them to the forefront of your mind. 

This is not always easy to do on your own, so I would love to invite you to join me, Sharmadean Reid, Naomi Shimada and Poppy Jamie at the next Confident and Killing It event on March 29th where you can meet a community of women loving and supporting each other on their journey to feeling more confident and alive in life. 

SQSP: How does your identity as a woman influence the way you approach your career as a confidence coach and inspirational speaker?

TO: I come from a family of extraordinary women. My grandma, a Scottish woman, met my grandpa, a Nigerian man, in Oxford and moved to Nigeria with him in the 50’s by boat. It took her two weeks. She left her family and everything she knew for a life of adventure and uncertainty. She raised my mum with that same bravery, resilience and confidence, who then raised my sister and I in the same way. So everytime I get on stage to give a talk or run a workshop I don’t just come as myself, I come with the energy of all the amazing women who have inspired me and shaped me. I think that’s what really sets me apart. The self-help industry is mostly dominated by men and so when I come with my badass feminine energy and get everyone to dance to ‘Bootylicious’ as a warm up, it’s a magical moment a white man could never recreate. 

As a woman, I also understand the challenges other women face when it comes to being confident and daring to live life to the fullest. Having faced some of these challenges myself, I am able to connect on a much deeper level over our shared experiences. My talks and workshops have been described as relatable, transformational and inspiring and I believe it’s because I speak to issues women really care about and provide actionable tools that lead to real transformation. No fluffy stuff. I’m also not afraid to show up as my full authentic self. People have seen me laugh, cry, dance, act stupid, be afraid, be confident...I’ve shown it all and they are drawn to it. 

SQSP: What’s one piece of advice you would share with another woman looking to start an entrepreneurial project?

TO: The first thing you need to know before you start a business is yourself. Period. Think about what you’re passionate about, what your strengths are, what makes you feel vulnerable and what ways you are likely to sabotage yourself. You must first learn to master your mind, before you can master a business and build a team. Personal growth is a never-ending journey so you will never fully “arrive” but you must first believe in yourself and what you have to offer before you venture into entrepreneurship. 

Also, remember fear is just a negative thought of something in the future that hasn’t happened yet.  So, don’t let the fear of failure or fear of the future get in the way of your ability to take action on your dreams now. Instead of thinking “what if I fail?!?” make an intentional decision to change that thought and instead think -  “what if I succeed”. You never know where life will take you. Be bold and follow your curiosity. 

SQSP: If you could go back in time and tell the younger version of you one thing, what would it be?

TO: I would tell myself that in a world that thrives off my insecurity and negativity, loving myself and being unapologetic about it, is the most revolutionary act of all.

*We use an inclusive definition of “woman,” “women,” and “female” to encompass all people who identify as women in a way that is significant to them.

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