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 win.

6. Accept that all spaces aren’t meant for you.

When I look at that portrait of Ruby Bridges (The problem we all live with), as she’s being escorted by guards to integrate a classroom—people are screaming, writing nastiness on walls. But she and her parents decided that was the place for Ruby to be.

Honestly, I don’t know if I’d make the same call. Ruby’s treatment was horrific. Adults who should be protecting children were monsters in plain sight.

That’s hard. I’d question if that sacrifice is worth my peace?

Sometimes, the brutal truth is that the path you planned wasn’t yours. Stopping doesn’t mean you lost. It might mean you’re closer to the path that you’re meant to take. And in this day and age, that place needs to be loving, edifying, and safe. You have to feel you can bring all of you, not just fragments. Not just 50% of your gifts. All or nothing.

Writers know this well. Sometimes, we have to throw out what doesn’t work. I deleted 50,000 words from a manuscript that wasn’t working. That kind of heartbreak required ice cream and chocolate, and maybe a few deep sighs—but it made the book stronger. With my upcoming novel Fire Sword and Sea, the original plan didn’t hold. It took me two years, and several rewrites, to get it right.

Because I’m writing about real people—Pirates Jacquotte Delahaye, Michel Le Basque, Anne Dieu-Le-Veut, Laurens De Graaf and others from the 1600s—I owe it to them, and to my readers, to go the extra mile. You have to be will to pay the price to create value, something of lasting meaning.

If it’s worthwhile, it’s worth the effort. A good book is worth the effort. And you? You’re worth everything it takes to reach your dreams.

You know those dreams—the ones that keep you up at night, the ones you see in vivid color when your eyes finally close. These dreams call to you for a reason. And I believe you can do it. I’m counting on you. I know you can win.

Books to help you on your journey:

Meghan Sussex recommends Atomic Habits by James Clear. It’s is a practical guide to transforming your life by making small, consistent changes that compound into remarkable results.

When Things Fall Apart by Pema Chödrön

– Wisdom for moments when your plan shatters and you need spiritual grounding

.

Burnout: The Secret to Unlocking the Stress Cycle by Emily Nagoski & Amelia Nagoski

– For the serial planner who’s burnt out and doesn’t know why. It’s a guide to recovering your energy and agency.

This week, I’m highlighting Parnassus Books through their website and Bookshop.org

Help me build momentum for Fire Sword and Sea—spread the word and preorder this disruptive narrative about female pirates in the 1600s. This sweeping saga releases January 13, 2026. The link on my website shows retailers large and small who have set up preorders.

Show notes include a list of the books mentioned in this broadcast.

You can find my notes on Substack or on my website, VanessaRiley.com under the podcast link in the About tab.

Let’s keep rising and creating together—like, subscribe, and share. Stay connected to Write of Passage.”

Thank you for listening. Hopefully, you’ll come again. This is Vanessa Riley

This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit vanessariley.substack.com/subscribe

If you don’t recognize the phrase “Sexual Chocolate,” then you might be too young or too sheltered—or simply overdue for a viewing of Coming to America. The phrase hails from a hilarious moment in this 1988 cult classic when Prince Akeem (played by Eddie Murphy) attends a church service in Queens hoping to find a “good woman.”

He does find one—but not before the audience is treated to a cringe-worthy performance by a band called Sexual Chocolate, fronted by the deluded Randy Watson (also played by Eddie Murphy in disguise). Randy sings off-key, struts like a super star, and owns the moment.

He even drops the mic to a silent crowd. Except one diehard fan leaps to his feet, clapping and shouting, “That boy is good. That boy can sing!”

It’s iconic, ridiculous, and strangely affirming. Because in a world that’s often silent—or even worse, critical—every writer, every artist needs their own version of that one fan in the crowd. Every writer needs a little Sexual Chocolate.

In today’s publishing landscape, the pressure to produce, perfect, and promote your work can be overwhelming. The road is long, the milestones are often invisible, and the validation? It’s often non-existent.

And even those at the top of their game need well wishes and love. I send some now to Ali, a real advocate who has people so pressed that find fault over ridiculous things. Ali, you are love and light. Signed, your Atlanta Hype woman.

That’s where your hype person comes in. We need a cheerleader, someone who sees your potential even when your proses are shaky, your plot is flat, your characters are still finding their rhythm. These cheerleaders shout encouragement when you feel invisible. They believe in your words—even before they’re ready for the world.

But this kind of fandom isn’t just blind praise. We have rules.

Rule #1: Be Sensitive.

A good hype person knows the difference between when a writer is ready to hear feedback and when they just need a boost. Some days are for critique; others are for comfort. Sometimes what we need most is for someone to say, “Keep going. I see you. You’ve got this.”

Rule #2: Be Strategic.

Cheering doesn’t mean enabling bad decisions. Don’t let your writer friend send out a draft that isn’t ready. Don’t let them self-sabotage by skipping the hard (but necessary) parts of the process—like working with an editor, developing a marketing plan, or cultivating industry relationships. Praise their progress, yes. But also give gentle nudges to help them remember to do the work that success requires.

Rule #3: Know Their Creative Love Language.

Every writer is fueled by different things. Some need words of affirmation. Some need gifts (like good chocolate, please and thank you). Some need a like or share of a post. Some need you telling one person or one library about their books.

Others need quality time—just someone to sit with them in the mess and say, “You’re not alone.”

The truth is, even the strongest voices waver. Even the most confident writers have moments of doubt. That’s why it’s more important than ever to be a person in someone else’s corner. Check in on your writer friends. Call up the creatives. Remind them they’re not crazy for chasing the dream, battling blank pages, or daring to tell a story that hasn’t been told before.

So today, be someone’s fan. No matter how off-key they feel, your belief in them might be the thing that gets them through.

Now say it with me: That writer can write.

Some books to help us be better encouragers are:

Keep Moving by Maggie Smith it’s

a collection of affirmations and reflections that feel like encouragement from a friend.

Untamed by Glennon Doyle is especially for women creatives, teaching how to step into your power—and to surround yourself with people who cheer for you, the fully realized version of yourself.

The Light We Carry by Michelle Obama is not just for writers but this beautiful meditation offers hope and helps us navigating tough seasons.

This week, I’m highlighting Kindred Stories through their website and Bookshop.org

Help me build momentum for Fire Sword and Sea—spread the word and preorder this disruptive narrative about female pirates in the 1600s. This sweeping saga releases January 13, 2026. The link on my website shows retailers large and small who have set up preorder.

Show notes include a list of the books mentioned in this broadcast.

You can find my notes on Substack or on my website, VanessaRiley.com under the podcast link in the About tab.

You can guess my love language? Go ahead and like this episode and subscribe to Write of Passage so you never miss a moment.

Thank you for listening. Hopefully, you’ll come again. This is Vanessa Riley.

This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit vanessariley.substack.com/subscribe