In this episode, I chat with Kenyan activist Ory Okolloh who has an active sense of pursuing curiosity with an appetite to see social change in the African landscape. 

With a wealth of experience in her career, Ory serves on the Board of Directors of several organisations including the Thomson Reuters Founders Share Company, Stanbic Holdings Plc and Stanbic Bank Kenya. She has also worked as Google’s policy and strategy manager and for numerous corporations and companies, including the Omidyar Network and Luminate Group in Africa, both of which are part of The Omidyar Group.

With the social development in Africa a strong driving force in her professional pursuits, Ory is one of the founding members of Ushahidi, a non-profit open-source software application designed to help give a voice to marginalised people.

Starting something & trusting your instincts

Throughout her career, Ory has faced a fear of failure, a fear of being broke, fear of screwing up, all mingled with feelings of Imposter Syndrome. Looking at her major moves now though - such as whether to go to Harvard to study law, move back to Kenya from the United States after he studies, or moving to South Africa to live with her now-husband - she’s realised that they were the right decisions in retrospect. 

At the time, though, they felt like there was potential for massive mistakes. Pushing through this, she has learnt to trust her gut.

“Over time you realise that nobody really knows what they’re doing. I keep waiting and I still feel like I’m not quite sure about what next. And I think overcoming that feeling is important. Because everyone is consistently trying to figure it out. And as you learn, you get better at making big decisions.“

Using the analogy of a child learning to walk - which they only do after falling countless times - Ory pointed out the hesitation of a wobbly start or fear of making a big life decision is natural. Only after consistently trying, you realise you can do it. And when you fall or fail, you realise it’s not so bad and you become bolder next time and learn to make bigger leaps.

And even then, the “what the hell am I doing?” feeling never really goes away, so it’s worthwhile just going for it anyway.

Seeking out failure: Post-traumatic growth

The concept of post-traumatic growth is based on the theory is that no matter how bad the trauma you experience, humans find a way to improve.

So, instead of shying away from failure, the shift towards internalising the mindset helps to take the big leaps and make bold decisions. With every failure, there’s a way to learn to be better so it’s worth seeking out the lessons. 

“After failing, you end up better, smarter, more resilient.”

In addition, if you don’t do anything or avoid starting something out of fear of failure, you’ll have failed before you even have the chance to try and you won’t have gained any insight in the process.

Breaking the norm and going against the status quo

From an early age, Ory had a supportive upbringing from her parents, and she attributes her nature to push the status quo now to her father. 

“I was quirky. I hated wearing dresses, I wanted to wear only certain kinds of clothes. I didn’t want my hair done in a certain way. I was never a girly girl. And I was their first kid, so you can imagine what they went through, in the environment they were in, without any experience or expectations. To their credit, they let me be and learnt how to nurture my curiosity.”

Later in life, her ability to question social “norms” continued. Not only in her career path, but in her interactions. In panels, if she’s asked how she balances her career with kids and a family, she refuses to answer if the same question isn’t posed to males of the panel. 

It’s not about making a statement, it’s about taking a stance and fighting for the values despite what society says.

Intellectually curious & the power of niche reading

“If you look at my resume, there’s a story that it tells but it’s a bullshit story. Of course, there’s a theme that I care tremendously about the continent and Kenya. And I want to be in places where my work is improving my country or creating opportunities so that more people aren’t dependent on luck. So there’s a theme, but everything else in between is all over the place driven by my intellectual curiosity. I get bored very easily, so I can’t do just one thing.”

Ory used to be apologetic about this “rabbit-hole” obsessive curiosity, but she’s chosen to embrace the variety of her intrigue. She balances her multi-interested curiosity with excelling at what she puts her mind to. 

As a child, Ory read a variety of books on a number of arbitrary topics - the books her mother could find was all the literature she had available - and would now rather read widely, picking articles that she knows that others haven’t found. 

“It forces me to up my game. Through this, I have learnt a lot of stuff. Some of it is neither here nor there, but a lot of it has improved me in terms of picking up new things and meeting new people. I’ve got opportunities as a result of the interesting topics I can discuss that others can’t.”

Beating “sacrifice fallacy” and time-blocking

Ory noticed that in the United States there seems to be a sense of security in being eternally busy. Likening it to a drug, there is a culture of time-filling, hyper-drive and power catch-ups rather than productivity and quality output. 

Africa, on the other hand, seems to have an approach which tends towards enjoying that there “are enough hours in the day" to do everything. If you break your day up, you have sixteen hours remaining after sleep and it’s up to you how you want to fill them. An eight-hour workday still leaves you with eight hours, so there’s time to exercise, socialise, and fill your proverbial cup with not-work things. 

Embrace your narrative

In closing, her advice is to embrace that you get to choose to own your narrative and let your life’s story speak for itself. There’s a culture of modesty, especially in South Africa, but putting your hand up and saying ‘hey, look I did it’ is part of embracing your success, which is so important in building something.

If you want to get in touch with Ory, find her on LinkedIn, on Twitter.