June 24, 2025 • 11 mins
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 wor
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:06):
Welcome to the Rite of Passage with Vanessa Riley, the
podcast where storytelling meets passion in every page turns into
a new adventure. I'm your host, Vanessa Riley, and together
we'll dive deep into untold histories, reflect on current events
through a historical lands, share behind the scenes writing insights,
(00:29):
and explore the ups and downs of the author's journey
from rich historical novels to unforgettable characters to pop culture's
intrusion on the written word. Hey, we're going to explore
it all. So grab your pen, your notebook, and let's
begin our journey through the written word. Let's start your
(00:54):
right of passage. When the plan falls apart Professions of
a serial planner. It probably won't surprise you, at least
not once you've met me, that I'm a planner. My
name is Veness Riley, and I am a serial planner.
(01:15):
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 at consider it, bliss come to one
of my book events and what kind of person or
writer I am? And I'll often tell you I am
(01:39):
a nerd 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
(02:03):
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? Arma gittin World worth three.
(02:30):
In other words, I don't take it well. And I
listened to Meghan Sussex, Yes, Meghan Markle on the Emigreds
podcast Aspire, talking about failing as winning. It sounds crazy
at first, I mean, carefully charted course falls apart. How
(02:53):
is it winning when something completely unexpected hijacks your progress
and leaves you scrambling. For those who pants their way
through books, that is right without plotting. This kind of
disruption might feel like a quirky detour, but for a planner,
(03:14):
it's devastating. Life is unpredictable and messy. You pour your
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
(03:37):
called free will, it can again be devastating. You don't
know who to trust, or who you should trust, if
you trust at 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
(04:00):
that makes 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
(04:22):
steps I've found helpful. Number One, 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 okay to take
a moment to lick your wounds. Two, mourn what was
(04:44):
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
(05:05):
left is humility, hunger, and a wide open future. Number three,
Learn the lessons. Every failure teaches us something. Maybe you
trusted some one you shouldn't have. Maybe you missed an
important opportunity to include a partner who would have made
all the difference. The lesson might be to trust more Wisely,
(05:29):
one of the best lessons is to pay attention not
just to the bottom line, but to every one on
all sides. Number four. Stopping is not quitting unless you're
physically in the grave of the game is not over.
You might feel tired, you might feel lost, but you're
(05:49):
not done. Separate the strategy from the strategist. It's not
a failure if you've learned to do better. Number five,
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 and making new connections. Walking away and choosing the
(06:13):
right season to begin again is a win. Number six,
Except that all spaces aren't meant for you. When I
look at the portrait of Ruby Bridges as she's being
escorted by guards to integrate a classroom, people are screaming,
writing nastiness on the walls, but she and her parents
(06:38):
decided that 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, you know, I'd question
(07:01):
is that sacrifice worth my piece? Sometimes the brutal truth
is that the path you planned wasn't yours. Stopping doesn't
mean you lost, might mean you're closer to the path
that you're meant to take. And in this day and age,
(07:21):
that place needs to be loving, edifying and safe. You
have to feel you can bring all of you, not
just fragments, not just fifty percent of your gifts, all
or nothing. Writers know this well. Sometimes we have to
throw out what doesn't work. I deleted fifty thousand words.
(07:44):
You heard that, fifty thousand 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
(08:09):
and several long rewrites to get it right. Because I'm
writing about people, Pirates Jacquetta de la Haye, Michael Labaz
and Delivered Laurence de Graft, and others from the sixteen hundreds.
I owe it to them and to my readers to
go the extra mile. You have to be willing to
(08:31):
pay the price to create value, something of lasting meaning.
If it's worth while, 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,
(08:52):
the ones that keep you up at night, the ones
you see in vivid color when your eyes finally close.
The dreams call to you for a reason, and I
believe you can do it. I'm counting on you. I
know you can win. Here are some of the books
(09:15):
that can help you in this season. Mesic in Sussex
recommends Atomic Habits by James Clear. It's a practical guide
to transform in your life by making small, consistent changes
that compound into remarkable results When things fall apart by
Pima Chordan. Wisdom for moments when your plan shatters and
(09:40):
you need spiritual grounding. Burn Out The Secret to Unlocking
Stress by Emily and Amelia Nagasaki. This is for the
serial planner who's burnout and doesn't know why. It's a
guide to recovering your energy and your agency. This week
I'm highlighting Pernussus Books. Do their website and bookshop dot org.
(10:05):
Help me build momentum for fire Sword and See Spread
the word and pre order this disruptive narrative about female
pirates in the sixteen hundreds. This sweeping saga releases January thirteenth,
twenty twenty six. The link on my website shows retailers
large and small who have set up preorders. Show notes
(10:26):
include a list of the books mentioned in this broadcast.
You can find my notes on substack or on my
website Vanessaurilly dot com under the podcast link in the
about tab. Let's keep rising and creating together like subscribe
and share, stay connected. To write a passage thank you
(10:52):
for listening. Hopefully you'll come again. This is Vanessa Rile.
Oh what
Welcome to the Rite of Passage with Vanessa Riley, the
podcast where storytelling meets passion in every page turns into
a new adventure. I'm your host, Vanessa Riley, and together
we'll dive deep into untold histories, reflect on current events
through a historical lands, share behind the scenes writing insights,
(00:29):
and explore the ups and downs of the author's journey
from rich historical novels to unforgettable characters to pop culture's
intrusion on the written word. Hey, we're going to explore
it all. So grab your pen, your notebook, and let's
begin our journey through the written word. Let's start your
(00:54):
right of passage. When the plan falls apart Professions of
a serial planner. It probably won't surprise you, at least
not once you've met me, that I'm a planner. My
name is Veness Riley, and I am a serial planner.
(01:15):
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 at consider it, bliss come to one
of my book events and what kind of person or
writer I am? And I'll often tell you I am
(01:39):
a nerd 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
(02:03):
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? Arma gittin World worth three.
(02:30):
In other words, I don't take it well. And I
listened to Meghan Sussex, Yes, Meghan Markle on the Emigreds
podcast Aspire, talking about failing as winning. It sounds crazy
at first, I mean, carefully charted course falls apart. How
(02:53):
is it winning when something completely unexpected hijacks your progress
and leaves you scrambling. For those who pants their way
through books, that is right without plotting. This kind of
disruption might feel like a quirky detour, but for a planner,
(03:14):
it's devastating. Life is unpredictable and messy. You pour your
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
(03:37):
called free will, it can again be devastating. You don't
know who to trust, or who you should trust, if
you trust at 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
(04:00):
that makes 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
(04:22):
steps I've found helpful. Number One, 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 okay to take
a moment to lick your wounds. Two, mourn what was
(04:44):
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
(05:05):
left is humility, hunger, and a wide open future. Number three,
Learn the lessons. Every failure teaches us something. Maybe you
trusted some one you shouldn't have. Maybe you missed an
important opportunity to include a partner who would have made
all the difference. The lesson might be to trust more Wisely,
(05:29):
one of the best lessons is to pay attention not
just to the bottom line, but to every one on
all sides. Number four. Stopping is not quitting unless you're
physically in the grave of the game is not over.
You might feel tired, you might feel lost, but you're
(05:49):
not done. Separate the strategy from the strategist. It's not
a failure if you've learned to do better. Number five,
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 and making new connections. Walking away and choosing the
(06:13):
right season to begin again is a win. Number six,
Except that all spaces aren't meant for you. When I
look at the portrait of Ruby Bridges as she's being
escorted by guards to integrate a classroom, people are screaming,
writing nastiness on the walls, but she and her parents
(06:38):
decided that 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, you know, I'd question
(07:01):
is that sacrifice worth my piece? Sometimes the brutal truth
is that the path you planned wasn't yours. Stopping doesn't
mean you lost, might mean you're closer to the path
that you're meant to take. And in this day and age,
(07:21):
that place needs to be loving, edifying and safe. You
have to feel you can bring all of you, not
just fragments, not just fifty percent of your gifts, all
or nothing. Writers know this well. Sometimes we have to
throw out what doesn't work. I deleted fifty thousand words.
(07:44):
You heard that, fifty thousand 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
(08:09):
and several long rewrites to get it right. Because I'm
writing about people, Pirates Jacquetta de la Haye, Michael Labaz
and Delivered Laurence de Graft, and others from the sixteen hundreds.
I owe it to them and to my readers to
go the extra mile. You have to be willing to
(08:31):
pay the price to create value, something of lasting meaning.
If it's worth while, 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,
(08:52):
the ones that keep you up at night, the ones
you see in vivid color when your eyes finally close.
The dreams call to you for a reason, and I
believe you can do it. I'm counting on you. I
know you can win. Here are some of the books
(09:15):
that can help you in this season. Mesic in Sussex
recommends Atomic Habits by James Clear. It's a practical guide
to transform in your life by making small, consistent changes
that compound into remarkable results When things fall apart by
Pima Chordan. Wisdom for moments when your plan shatters and
(09:40):
you need spiritual grounding. Burn Out The Secret to Unlocking
Stress by Emily and Amelia Nagasaki. This is for the
serial planner who's burnout and doesn't know why. It's a
guide to recovering your energy and your agency. This week
I'm highlighting Pernussus Books. Do their website and bookshop dot org.
(10:05):
Help me build momentum for fire Sword and See Spread
the word and pre order this disruptive narrative about female
pirates in the sixteen hundreds. This sweeping saga releases January thirteenth,
twenty twenty six. The link on my website shows retailers
large and small who have set up preorders. Show notes
(10:26):
include a list of the books mentioned in this broadcast.
You can find my notes on substack or on my
website Vanessaurilly dot com under the podcast link in the
about tab. Let's keep rising and creating together like subscribe
and share, stay connected. To write a passage thank you
(10:52):
for listening. Hopefully you'll come again. This is Vanessa Rile.
Oh what
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