When There’s No Second Chance
- Michael Rickwood
- 4 days ago
- 3 min read
Updated: 3 days ago
Most of the work I’m focusing on today lives in a narrow, uncomfortable space.
It’s the space where decisions are made in public and reputations shift in minutes. Where a room quietly decides whether to trust you, fund you, follow you, or move on without you.
And where, more often than we like to admit, there isn’t a second chance.
I didn’t learn this from books. I learned it from experience. By watching good work fail because it was poorly prepared and poorly framed. Like a key presentation at a pivotal career moment that dies in silence. By seeing strong ideas sink because the moment was misread, and the audience didn’t forgive because a lot of investment had been made by all involved. By discovering, sometimes painfully, that being “mostly right” is often the same as being wrong when the stakes are high. This is particularly true in Europe, where the silent code of risk aversion does not reward last-minute sprints or people trying to iterate live in front of a room when expectations are already set. The frustrating thing is that this outcome can appear when we underprepare. It can also appear when we overprepare.
Critical moments don’t announce themselves. They look like meetings. Pitches. Panels. Town halls. Boardrooms. Keynotes. They look ordinary. Until they aren’t.
Over the years, I’ve seen people come to these moments fully aware of what’s at stake. They prepare. We work. We refine. They practice. I give feedback. And sometimes, the result is a real shift. I remember working with one young underwriter at the World Bank in Washington DC for a pivotal event celebrating 30 years of MIGA (the guarantees arm of the bank). A few focused sessions later, his visibility inside the organisation changed. Today, he holds a more senior role. He knew that the moment was critical. He gave everything.
But I’ve also seen the other side far more often. At events, in interviews, in online trainings that quietly crash and burn. Pitches that are forgotten the moment they end. Moments that should have opened doors, but instead closed them.
What’s striking is that these failures are rarely about talent.
They’re about gaps in the system, small communication breakdowns, and assumptions left untested. Friction is avoided because it feels uncomfortable. Everyone thinks the work is “good enough”. No one wants to be the person who slows things down or names the risk. Then the moment arrives. It doesn’t hold. And once it’s over, the story freezes. Someone has to carry the cost. Intentions don’t matter anymore. Only the outcome does.
What decides the result in those moments is not brilliance alone. It’s alignment. Clarity. Timing. Judgment. The discipline to choose what to say and, just as importantly, what to leave out. But the critical thing to remember is that we can rarely do this alone; taking sufficient distance from exterior human feedback is critical. AI can help us as a sparring partner, but it falls woefully short of nuanced human feedback.
Working with founders, leaders, and teams, I keep seeing the same pattern. People don’t fail because they lack ideas. They fail because the signal gets lost. Because the message is technically correct but strategically misaligned. Because they prepare content, but not the decisions.
Vortolo exists for that edge.
For the moments where you don’t get to “fix it later”. Where communication isn’t performance. It’s a consequence.
That’s the work that I am obsessed with.
From noise to alignment.
From intention to impact.
From hoping it lands to knowing why it will.
We learn from failure its true, but big failures can be time costly and more often than not, avoided.
Give yourself every chance. First time.
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