FYI there isn’t any playbook for success
Success rarely follows a straight line. From unexpected career pivots to evolving ambitions, this story challenges the idea that passion must come first, and instead argues that opportunity, adaptability and persistence are what truly shape the journey.
By Aaron B. Gibson, CEO of Hurree
Keegan Caldwell is one of those remarkable people who appear to have seen and done it all. From a marine biologist to partner at a top patent law firm, his journey isn’t just fascinating, it’s reflective of the reality of success, twists, turns, surprises… nobody could’ve planned it, not even Keegan.
It’s a path that every successful entrepreneur is familiar with. Not that everyone starts as a marine biologist, but very few end up where they thought they would when they first began. Myself included.
Before my CEO Founder life, I had zero clue where I was going. Traditional education wasn’t for me. I left school after my GCSEs, and I thought I’d end up joining the army or becoming a mechanic. Fast forward to 2026, over 10 years later, I’m now coming into my own company every morning, a dog-friendly office, so my 4 pups get to join, sitting down at my desk and taking calls about our data analytics platform and AI.
Not even remotely close to where 16-year-old Aaron thought he’d end up. It was all trial and error.
Despite the copious number of success guides being pushed on social media by the CEO-bros of the world, the reality is that there is no actual playbook to success. Keegan and my journey are proof of that.
During a recent chat on the SaaSy AF podcast with Mr Caldwell, he said something that stuck with me: Everyone says you have to pursue something you’re passionate about, but I think sometimes we get the order wrong.
When you start a business, there’s this huge misconception of ‘start as you mean to go on’, but the reality is your journey is going to change direction many times. As Keegan put it, it can be better to choose opportunities that enable the life you want at that time, and allow passion to follow later.
Focus on taking the best opportunities as they become available. Passion often grows through progress, not the other way around (both mine and Keegan’s journeys are a testament to that).
Success is unpredictable, and exclusively chasing passion can sometimes lead you into dead ends.
This narrative may not fit neatly into the polished CEO-bro journeys we’re used to seeing online. They present success as moving from A to B. In truth, it feels more like starting at C, jumping to G, backtracking to E, and somehow ending up at B anyway.
Whether you agree with this perspective or not, talking with Keegan made one thing clear: there is no playbook. No universal routine. No magic 5 am wake-up formula that guarantees anything.
Having an idea of where you’re going doesn’t mean you’ll end up there.
So don’t get caught up in what success is supposed to look like. Enjoy the journey for what it is. Let your passion evolve. Focus on finding joy in the process, not just the success.
