It probably won’t surprise you—at least not once you’ve met me—that I’m a planner. My name is Vanessa Riley, and I’m a serial planner. There isn’t an outline I don’t love, nor a spreadsheet that doesn’t call my name. If I could design a map of a map of a map of systems accompanied by a flowchart—I’d consider it bliss. Come to one of my book events and ask what kind of person or writer I am, and I’ll often tell you: I’m a nerd’s nerd, a meticulous nerd. That’s right—pocket protector-level nerd. I love formulas and systems. I love figuring things out and then optimizing them.Why? Because we only get so much energy, so much time, and so many resources in this life. I want every ounce I give to have maximum effect. If you can show me how to reach more people, make more impact, or spark more meaningful change, I’m listening. I’m all in.But what happens when the plan doesn’t work?Devastation. Armageddon. World War 3. In other words, I don’t take it well.Yet I listened to Meghan Sussex, yes Meghan Markle on the
Emma Grede’s podcast, Aspire, talking about failing as winning.It sounds crazy at first.I mean carefully charted course falls apart. How is it winning, when something completely unexpected hijacks your progress and leaves you scrambling? For those who “pants” their way through books—that is, write without plotting—this kind of disruption might just feel like a quirky detour. But for a planner? It’s devastating.Life is unpredictable and messy. You pour energy into structure and logic and find out the world has other ideas.And if the detour is because of people— you know the ones who don’t behave the way you think they should. Those people who’ve bought into that notion called free will, it can be devastating.You don’t know who to trust. Or if you should trust it all. If the past year has taught us anything, it’s that people often act in ways that defy their own interests. They cling to ideals or narratives that make sense only to them. And we have to let them. As a famous poet, Bobby Brown used to insist, that’s their prerogative.For those of you who know the chaos of watching a plan implode, I see you. I’ve lived that upheaval, and I want to offer a few steps I’ve found helpful:1. You did your best.Even if the outcome wasn’t what you expected, you gave it your all. The plan didn’t play out perfectly, but you showed up. You tried. And it’s OK to take a moment to lick your wounds.2. Mourn what was built and what was lost.It’s perfectly valid to grieve the work, the dream, or the strategy that didn’t survive. Tend to your mental health. Sometimes, starting over means burning what didn’t work to the ground. This can feel extreme, but it’s also freeing. When ego is stripped away, what’s left is humility, hunger, and a wide-open future.3. Learn the lessons.Every failure teaches us something. Maybe you trusted someone you shouldn’t have. Or maybe you missed an opportunity to include a partner who would have made all the difference. The lesson might be to trust more wisely. One of the best lessons is to pay attention not just to the bottom line, but to everyone on all sides.4. Stopping is not quit.Unless you’re physically in the grave, the game is not over. You might feel tired. You might feel lost. But you are not done. Separate the strategy from the strategist. It’s not a failure if you’ve learned to do better.5. It’s okay to begin again.Being brand new is not failure—it’s freedom. There’s a joy in learning, in discovering new spaces, in making new connections. Walking away and choosing the right season to begin again is a