Lessons I learnt about Confidence from a Confidence Coach.

Kenny O
TOSS IT OUT
Published in
4 min readFeb 25, 2022

How to Make Scary Decisions in your Career and as an Entrepreneur.

Man using a pair of scissors to cut a piece of paper

First, a little background story, of course.

I’m Kenny, the Producer and Co-host of a lifestyle Podcast called ‘Toss It Out’. On Series 4: Episode 3 of the podcast, we interviewed Tiwalola Ogunlesi, Author and Founder of ‘Confident and Killing It’, and a Confidence coach specialising in positive psychology. Tiwa (AKA Tiwalola) started posting one minute inspirational personal growth tips on Instagram in 2017 because she noticed while volunteering as a Youth leader, that there was a cycle of self-esteem and confidence issues amongst the young women and girls she was working with. This issue concerned Tiwa greatly because it was an issue that she had dealt with in the past herself.

Today, Tiwa has built an engaging community online, offering one-to-one confidence coaching and ‘bagging’ multiple speaking tours around universities and companies in the UK. Her clients include huge names like Facebook, Google, Deloitte, Morgan-Stanley, and so on. So, we spoke to Tiwa and asked her to share all she knows about being confident, whilst also going through her own journey with confidence too. She said:

  1. Expecting to feel confident 100% of the time, everyday, is unrealistic. This is not how confidence works. Tiwa emphasises that Confidence isn’t perfectionism, instead, it’s being able to bet on yourself even when you don’t feel like it. Confidence is authenticity. It’s also the ability to celebrate your wins and have a level of trust in yourself, whilst acknowledging your struggle and failures as well.
  2. Learn to trust your intuition. Listening to your body and gut feeling is something we might have been hearing a lot about lately. Tiwa started to experience panic attacks going into work and she started to think maybe it was time to leave her job. She ignored these signs at first, but they started to get even more evident when she went into work one day and wanted to burst into tears while at her desk. She says you have to remember that “your life is your responsibility”. No one will live with the consequences of your actions more than you do. Tiwa reaffirms the importance of not being afraid to bet on yourself.
  3. Have a plan or have a mentor or have both. Tiwa didn’t have a business plan yet when she quit her job; however, she did have a mentor. This was someone who was doing something similar to what she aspired to do, so she decided to reach out. She would send her mentor pitch decks, asking for advice and guidance on this new journey. Tiwa says it is important to know someone who is ahead of you, doing what you want to do, so you can see what the future path looks like.
  4. Be Flexible and Adaptable. The journey may not be straight forward. As Tiwa’s new business started to take off, the pandemic hit and everything got cancelled. Every business plan, like in-person workshops, scrapped. She had to start from square one. ‘The thing about being an entrepreneur is flexibility and adaptability’ she said.
  5. Do what feels like THE NEXT RIGHT MOVE. This one sounded the most interesting to me. When the pandemic hit in March 2020 and Tiwa lost all planned in-person speaking gigs, she decided to partner with people in her industry who are also entrepreneurs for a webinar series titled ‘Killing it as an entrepreneur’. About 400 people signed up in just 2 days (I was one of them). This was HUGE. Because of the success of what was supposed to be a one-off webinar, Tiwa did the only logical thing: create another one, and then another one, and then another one. And then, Tiwa hosted webinars every other Sunday for about 3 months. These actions put her on the map and kickstarted her growth trajectory in her first year of being a full-time entrepreneur. “Take baby steps, project by project - you cannot plan too far ahead because life is unpredictable,” she says.
  6. Finally, how to get out of a rut and deal with imposter syndrome. If you find yourself feeling stuck, Tiwa says it is part of the process so acknowledge and embrace it. The key is to express and articulate your thoughts by writing them down or speaking to someone about it. That way you can either seek advice/help to resolve the issue or you might end up figuring out your next best move to take. If the narrative playing in your mind is a negative one, your thoughts lead to your feelings and your feelings lead to the actions that you take or don’t take. So having negative thoughts about how you’re not good enough, for example, leads to you procrastinating or retreating and not taking any actions. Find and articulate what your strengths are, and align your next actions or goals to them. For example, when imposter syndrome comes, use your strengths to challenge it. Your strengths are factual. For example, you are resilient. Remind yourself of how you’ve demonstrated resilience in the past. This is a trait that will allow you to bounce back from any drawbacks and being aware of this trait as a strength that you possess will allow you to succeed in the face of adversity as an entrepreneur. This is how confidence comes.

Above all else, a good entrepreneur should create value for people. Confidence will only get you so far. Tiwa believes that creating value for people grew her personal brand. Things happened organically in her business when she started creating value for people and businesses as one person recommended her to another. Trust the process, believe in your greatness, and you just might become unstoppable too.

Links mentioned: Toss it Out Podcast.

Links mentioned: Confident and Killing It

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