"How do I choose the right creative challenge?"

📨 Ask An Ex-Planner

Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.

Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.

Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #23. ✨

☀️ How was your week?

🎶 Getting to know you 🎶

Would you do me a quick favor? Hearing your personal stories of uncertainty, life transitions, and new beginnings has been so impactful that I’ve created a dedicated, evergreen thread for us to get to know each other! (As a bonus, knowing more about you will help me write a more useful, enjoyable newsletter.)

Whether you’ve been reading along quietly, or chatting regularly in the comments section, I’d love to hear a bit about you—whatever you’re comfortable sharing. Take a moment to introduce yourself here:

Welcome to the community! Let's get to know each other.

On to today’s letter!

📨 Ask an Ex-Planner

Life is full of change, transition, and uncertainty—all things that are better navigated together. So in this column, I hand over the mic in order to address what you’re struggling with or curious about.

Want me to respond to your question? Make an anonymous submission right here—or just reply to this email.

Dear Maddie,

I write to you about not so much a setback as a question of choosing the right challenge.

I left a career in journalism with the plan to become a book author. But I've spent months looking into each of various promising ideas, then ultimately rejecting them as not quite the topic to keep me inspired for several years.

Thoughts on finding the right, and write, focus for such a long-range conundrum?

–Would-Be Caro

Dear reader,

At its heart, the question of choosing the right creative challenge is one of discernment. In a world with infinite stories to tell, what’s the right one for you?

It’s also a question about commitment. Maybe you can select a story that feels like the right fit today, but does it have the staying power to feel right two years from now?

Yes, that means asking whether a topic has enough meat on its bones to warrant a long simmer.

But it’s more than that. A few years from now, your life—and the world around you—will have taken turns unimaginable from your vantage point today. Who will you be then? How might the topic have evolved? How can you know that you’ll still be compatible?

The resident expert on discernment and right-fit commitments in your own life is, of course, you. But here are some thoughts to guide your self-inquiry:

• ✅ Consider the process.

• ✅ Harness the power of experimentation.

• ✅ Seek alignment above all else.

✅ Consider the process.

When it comes to so many challenges, failure can hold rich life lessons.

However, if you’re seeking a book deal, delivering your promised manuscript is…kinda non-negotiable. For this type of challenge, the advice to “detach from outcomes!” isn’t particularly helpful.

So instead, for each potential path, prioritize thinking about what the process looks like, in as much detail as possible. Because completing a creative challenge—achieving your desired outcome—will mark a single moment, but the day-to-day process is what you’ll be living through.

In your example, you need to choose between a handful of book ideas, each containing a unique set of ingredients.

Maybe they all require research. But one topic might require you to log the bulk of your research hours in the library, where others require more interviews with living experts—in different professions, walks of life, and locations.

How do you want to spend your days? What kinds of people do you prefer interacting with, in which settings?

In the pursuit of any compelling creative challenge, it’s easy to ignore the daily implications of a goal you’re jazzed about. But your daily experiences are the mosaic tiles that form the bigger picture. Allow them to guide you.

✅ Harness the power of experimentation.

When scientists have questions, they test their hypotheses by conducting experiments. Only then do they draw conclusions—or revise their hypothesis for the next test.

We would all do well to apply the scientific method to our own goals, and spend more time experimenting with big challenges before committing to them.

We date our partners before marrying them, right? You might consider dating your book topic before marrying it, too.

I know what you’re thinking. Your background research, plus the process of writing a book proposal, constitutes an experiment—right? While both are necessary and important, I humbly submit that neither one quite fits the bill.

An experiment is a low-stakes sandbox to test whether or not you actually like creating the thing you might commit to.

I’m advising you to create a creative sandbox because I’ve experienced the benefits of one. Writing a newsletter has allowed me to experiment with different perspectives on my topic, and confirm that yes, I actually do enjoy writing about it week after week.

As a journalist, you probably had plenty of opportunities to experiment with topics on a small-scale basis before committing to them. You might’ve written a few shorter articles with a limited scope before embarking on big, page-one features, or a series of pieces that explored a single topic in depth.

Do that now!

Your experimental writing can be public (Substack, as you know, is a cozy home base for journalists like you), or stay totally private. What matters is that you do it somewhere.

No need to stop experimenting after you’ve committed to a book topic. Consider keeping the doors of your “idea laboratory” open to write about other, unrelated subjects on the side.

It might be a pressure-release valve for your writing life—and your manuscript.

✅ Seek alignment above all else.

When you’ve chosen a creative challenge that’s “in alignment,” you’re pursuing something that’s consistent with your deeply-held beliefs.

To be clear, there’s nothing wrong with choosing a book topic because it’s intellectually interesting or piques your curiosity, because it’s marketable or the story’s engaging. But if you’re unsure whether something will hold your attention for years, you have a better shot if it’s aligned with your core values.

At some point, the once-motivating prospect of fulfilling your creative dream will feel…well, considerably less inspiring. It might even begin to feel like a slog.

If you’ve chosen a challenge rooted in some form of meaning or purpose—whatever that looks like for you—you’ll have a backup fuel source when that initial excitement fades.

💬 What do you think?

I’m curious to hear from you. What would you like to share with the reader who wrote in?

Had your own plan-in-flames experience? Taking a leap into the unknown? I’d love to hear more. Just hit “reply” to get in touch, or introduce yourself here.

Warmly,
Maddie