The Reality: Corporate to Full Time Side Hustling

Hey there! I decided to start a blog series called The Reality Series where I’ll be sharing insight (and lessons learnt) from my journey into the unknown, the life of entrepreneurship and discussing the different phases of the ‘side-hustle” from my lens. I’ll also be conversing with a few friends who are changing the game in their industries, and of course we’ll be sharing the highs and lows we’ve encountered along the way.

Chefchaouen, Morocco.


What Did I Get Up To?

So it’s been 9 months since leaving a top corporate job I dreamt of in my university days – all the feels are in this blog post. There was no complex formula to my exit besides a crazy urge to delve into the things I was deeply passionate for at that time. The blog was doing relatively well when it launched early this year and despite being proud of my blog statistics I wanted to build something more. I decided to spent my time in Southeast Asia discovering different approaches to building a travel based business.

Elephant Jungle Sanctuary, Chiang Mai
Elephant Sanctuary. Chiang Mai, Thailand

To my surprise, I returned from my solo trip around Southeast Asia in the spring with an opportunity to start up Wind Collective Trips under The Wind Collective, one of the best (and possibly only) millennial creative travel agencies in Europe (yes, self advocacy is a thing business owners – try it)!

Fes, Morocco. At our first ever group travel experience. Shot by @WilliamAdoasi

From May to August I spent a great deal of my time unpacking and packing suitcases, the airport became my second home and I ended up travelling to 5 countries and visited over a dozen cities.

It Wasn’t Always Fun…

All the travelling, the flexibility, the freedom but did I still make room for doubt and did the quarter life crisis kick in? Heck yes!!

All those questions…“What am I doing with my life!?”, “Should I go back into corporate work right now!?” or “Should I stay a baby girl (lol) and embrace each day as it comes!?”

Even in the bubble of what seemed to be a glamorous summer of launching group travel experiences with Wind Collective Trips, staying in luxury hotels, sponsored trips, bespoke hospitality and spontaneous adventures, there was still a blank space filled with worry. But you know what? I’ve learnt that’s It’s OK to have those thoughts for a second, a minute or maybe two…because what really matters is where we place those thoughts and how we transform the weight of worry into action. In Christianese, it’s how we place our trust in God to take the burden and fill us with hope.

Mykonos, Greece. Shot by @NigerianAbroad

I really don’t want this series to be limited to my experience as it’s one perspective. I want this to be more of a dialogue between entrepreneurs, creatives, professionals or if you are like me, dabbling between all three…let’s come together and support each other along the way.

But Wait, What Do We Do Once The Bubble Bursts?

I branded this as The Reality Series because there is a reality that many of us face while building a brand, a blog, a business, a side-hustle and pretty much anything that requires a shift in our comfortability.

The bubble will burst.

After your amazing launch, when the summer season ends, when the boom phase takes a pause, once the music stops; it will happen and it has happened to me. We hear it all the time but we simply need to keep the momentum going, whether fast or slow, and keep the real conversations flowing.

A group trip we organised to Marseille with @WindCollectiveTrips. Shot by @CleHunnigan

So Let’s Have A Conversation

Let’s get comfortable having an open dialogue when it comes to sharing our journey, both the highs and the lows so we can learn from each other.

What’s Next In The Reality Series?

I’ll be interviewing the forever smiling, intelligent and innovative duo featured in London’s most popular media outlets such as the Evening Standard, ELLE Magazine, VICE UK and Time Out Magazine. We’ll be discussing how to shoot your shot in this constantly evolving world of entrepreneurship and we’ll be hearing about the lessons they’ve learnt in their journey to becoming successful London business owners, so stay tuned!

Use the hashtag #myreality on social media to share a few lessons you’ve learnt from your business journey (it’ll help someone) and don’t forget to share this post.

Peace & Love

Doyin x

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