You might think you understand that the startup world is different than the ordinary world, but there’s some parts you can learn and others you just have to experience. This time we’ll be talking about the ‘Belly of the Whale’ moment of this journey. That’s the first time you realise you’re really doing this and turning back isn’t an option.

In Startup World there aren’t obstacles, only challenges that you haven’t found the edges of yet. Here it’s not about if but how you get things done. Sometimes you do need to constantly stop and ask yourself, ‘How did I get here and what am I doing again?’ It’s crucial that you set your mission statement by the time you’re in the belly of the whale. It’s all too easy to get distracted by the newness and novelty at every step from here. If you haven’t figure it out by now, choosing to explore the answer to a question in life by way of a startup business is a journey, not a singular endpoint.

Recently I had a friend recount an instance where he had to explain the concept of ‘entrepreneurship’ to a group of people who didn’t have that word in their language. The best he could describe was thusly, ‘a person who assembles a crew and builds a boat to voyage to an island that nobody’s ever been to but they’re pretty sure should exist.’ I love that analogy! In this sense, it’s all about figuring out how to plot a course to a location that you’ve never been to and there is no existing map.


The thing about uncharted waters is that you can never be completely prepared.

You just need to be ready to face daunting, alien, demanding situations to the best of your ability. This is a core skill of the startup founder. Luckily, this is something that’s conceptually teachable but you still have to go out and practice it to build your mental adversity muscle. 

The concept of the belly of the whale in Joseph Campbell’s understanding of mythic structures is all about that petrifying moment when you awaken to the possibility of the existence of worlds within worlds. And you figure this out by accidentally finding yourself in one of these other worlds. This is most often an event like your first major pitch opportunity (for partners, cofounders, early customers, etc.). This is the first moment you realise, “Oh crap! I’m doing this now regardless of how ready I am.”  Sometimes these moments are big, dramatic and there’s time to brace for it but there’s many instances where they sneak up on you from a series of seemingly innocuous events. 

So how can you be just honest enough with yourself to prepare for the unknown but not let yourself be overwhelmed by fear or doubt? Here’s how some of our startup founders thought about it.

As Michael the founder and CEO of CrowdPleaser explains, “My startup journey was preceded by a lot of doubt, as I’d imagine a lot of other founders have found as well. Coming from an enterprise software engineering background, I knew I could face the technical challenge but that’s a very small part of starting up. As corny as it sounds I had this [motivational] photo on my cubicle at my old job. Following these rules helped me build the hunger, determination and motivation to give my own startup a shot and to not look back. ”

Cas McCullough Founder of Writally recounted a very poignant ‘belly of the whale’ moment she had just last year. I think it’s just the right combination of relatable and inspiring.

“Last year, I scraped together a few grand and flew to the Philippines for the Tropical Think Tank, an event that attracts highly motivated and highly successful entrepreneurs from all over the globe. I didn’t feel like I would fit in at all because my business was only small and at the time, mainly just me, but I wanted to meet some of my heroes and grow my business into something more. So I pulled myself together and showed up, completely nervous and full of anxiety.

Much of that week I had to battle with my inner critic telling me that I was just a struggling single mother, or just a part time consultant or just … fill in the blank. I realised that one of my biggest challenges was dealing with that little voice not the mechanics of running a business.

That event changed something for me. Being surrounded by amazing, highly successful people showed me it was possible and that it was “normal” to have success. It was a turning point.

I just made a decision … “why not me?” Yes, I had a lot to work through and a lot to learn, but everybody starts out at zero.

When I won the Collaborate competition earlier in the year, I couldn’t believe it! I still can’t. There’s a part of me that says “you don’t deserve this” and I battle that feeling every day, especially when I am faced with a gazillion dirty dishes, a pile of laundry that hasn’t been folded since March and the ups and downs of parenting 3 boys, but every day it gets a little easier. Being a part of BlueChilli has really opened my eyes to the amazing opportunities available to entrepreneurs. There is life beyond the struggle and now when I hear that little voice, I tell it where to go!”

The biggest challenge is taking that leap that puts you in the belly of the whale. Founders do it every day. While they don’t all raise a massive series A round or scale into a persisting corporation, that’s not a legitimate measure of success. It’s about building your grit muscle to pick yourself up and keep trying when the world around you is a perpetual landscape of chaotic opportunities.

From here on out I’m curating a conversation on these topics in a dedicated Slack team. You can request an invite and join the conversation by emailing with Founders Journey Slack in the subject line.


Filed under:   challenge   competition   founder   founder's journey   startup   startups   tips