I once built a framework to teach 400 people how to make decisions faster. It was one page. The entire thing rested on a single question: can you walk back through this door?
At TravelPerk, we'd hit the stage where decision-making velocity was becoming the bottleneck. Not because people were stupid. Because they were cautious. Every decision, no matter how small, was being treated with the same weight. Someone wanted to open an entity in Singapore. The proposal went through layers of review, legal consultation, leadership alignment. Weeks passed. The actual question was whether we needed a full entity or whether a contractor arrangement would achieve the same goal. One of those is expensive and hard to undo. The other costs almost nothing and can be reversed in a week.
We wrote it into our operating principles. Bezos had already articulated it beautifully: Type 1 decisions are irreversible, one-way doors. Make them slowly, carefully, with full information. Type 2 decisions are reversible, two-way doors. Make them fast, with 70% of the information you wish you had, and course-correct. What we added was a practical heuristic: look for the highest impact decision that can be taken at the level of reversibility you can approve. In other words, decompose the big scary decision into a smaller reversible one that moves you forward. Don't ask for permission to open a Singapore entity. Ask for permission to test the Singapore market with a contractor.
In a counterintuitive way, giving people a framework and guardrails for decision-making didn't slow them down. It freed them. The problem had never been that people couldn't decide. It was that they couldn't tell which decisions needed the heavyweight process and which didn't. Once they could, things moved.
Then I co-founded Oliva Health and started making decisions where the framework was no longer theoretical.
The decision to diversify from mental health into leadership coaching... two-way door. We could run both product lines. Low cost to test. We tested, it worked. The realisation that coaching isn't a tech business and can't scale to global impact... that wasn't a decision at all. That was a one-way insight. You can't un-know it once you see it. And the decision to build readywhen.ai as a separate brand, a clean break from Oliva... that was as close to a one-way door as it gets. New name, new product, new positioning. The old product lines still run well under Oliva. But the bet on where we put our energy is made.
What I didn't expect is how differently the framework applies at ten people versus four hundred.
At TravelPerk, the problem was that people used heavyweight processes for lightweight decisions. At readywhen.ai, the problem is the opposite. Every decision feels irreversible because resources are so scarce. A wrong hire is three months. A wrong product bet is the quarter. The instinct is to deliberate more, wait for more information, make sure.
But actually (and this took me longer to internalise than I'd like to admit), early stage is the most two-way-door environment you'll ever be in. You haven't shipped to millions of users. You haven't signed enterprise contracts. You haven't hired 500 people around a specific architecture. You can change almost anything. Last month we made three significant decisions in under a week: a GTM pivot to revenue-close leaders, an ICP heatmap as our primary analytical framework, and a clean break from our legacy platform. All reversible. All made with roughly 70% of the information we wanted. All correct so far, and if they're not, we'll course-correct before the cost compounds.
The paradox is that the smaller the company, the more reversible your decisions are, and the more irreversible they feel. The framework I built for 400 people is more useful at ten than it ever was at scale. I just have to keep reminding myself to use it.
I'll leave you with Bezos: "If you're good at course correcting, being wrong may be less costly than you think, whereas being slow is going to be expensive for sure."
The door swings both ways. Walk through it.