How should I tell my money story?

Avoiding the three biggest traps of personal finance writing

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 #18. ✨

☀️ How was your week?

Scenery from a 2011 photo walk with Jacqui, captured on Kodak Portra 400 film

No shame in a little nip/tuck. You might have noticed a minor facelift to this newsletter’s online home!

As you already know from this edition, I’m a bit obsessed with film photography. So when my writer friend—and fellow film geek—

Jacqui MacKenzie

joined Substack, memories of a photo walk we took together (pictured above) inspired me to dig through my Adobe Lightroom archives.

Moving forward, I plan to feature more of my film photography in this space—a change I’m rather excited about.

On to today’s letter!

How should I tell my money story?

Cascade Pass, captured on Kodak Portra 400 film

As a financial planner, talking with other people about their money stories felt totally comfortable. In fact, it could be downright fun.

When it comes to talking about my own money story? In public? Well, that feels a bit more fraught. But it’s time to figure out how to tackle the topic. And not just because it’s the subject of my professional expertise.

It’s because my own experiences of loss and transition have fundamentally changed how I think about, and use, my own money.

These changes are central to the mission of this newsletter. If I don’t write about the changes to my own relationship with money, I’m not telling the full story.

If you’ve explored the corners of the Personal Finance Internet, you’ve seen bloggers share almost everything about their money: detailed spending reports, net worth charts, and all the specifics about their investment portfolios.

That’s not the approach I’ll be taking; keeping my personal writing sustainable means not giving myself one oversharing-induced vulnerability hangover after another.

But just as importantly, I don’t find that kind of financial writing to be particularly helpful. And that’s because it feels designed to route readers directly into one or more of these traps:

• The comparison trap,

• The relatability trap, and

• The (dis)connection trap.

We can’t always avoid triggering these traps, but caring personal finance writers should be mindful of them. As they say in the Spider-Man franchise: with great power comes great responsibility.

Here’s how I think about each of them.

💰 The comparison trap

When I began serving financial planning clients who’d received large tech IPO windfalls, I was sure it’d trigger my insecurities.

After all, I’d worked at a nonprofit for years, and had taken a pay cut for my current role. I was content with my life; still, I was talking with folks my age in very different financial circumstances.

It was a recipe for comparison and envy, but it didn’t pan out that way. Why not?

There were too many variables at play to allow for neat comparisons. Apple, meet orange.

Those variables included each client’s income, fixed expenses, spending habits, location, educational path, career choice, relationship status, family background, and kids—or the lack thereof. Their current circumstances could be explained by the compounding effects of countless decisions and sheer luck.

And each client had their own personal definition of what constituted enough. I had clients with (comparatively) much less who had a sense of calm and abundance around their money. I also had multi-millionaire clients who felt like the walls were closing in on them.

The more I learned about each individual client, the less sense it made to compare myself to them—or to compare one with another.

Still, inclinations toward financial comparison are totally normal. So I’ll offer gentle reminders that my own unique mix of variables is so fundamentally different from yours that comparing our money stories is, truly, beside the point.

💰 The relatability trap

Appearing “unrelatable” is the cardinal sin of sharing online. But what does it mean to be financially relatable or unrelatable, really?

If you and I were both newly-minted adults, “relatability” would be more easily achievable. There’s no such thing as an even playing field when it comes to money, but at least our differences wouldn’t have had decades to compound.

But at thirty-six, as I list the different “chapters” of my money story spanning adulthood so far, I find that there are more than a dozen.

Since receiving my diploma in that shapeless polyester gown, each ensuing year has opened a distinct new installment in my money story, with its own challenges, opportunities, and lessons. Wild! The same is probably true for you.

And because our money stories don’t unfold in lockstep, relatability is a moving target. If I wait to achieve maximum relatability before writing my money story, I’ll never begin.

💰 The (dis)connection trap

The primary reason I write this newsletter is to facilitate connections: to remind other people that they’re not alone, whatever their own five-year-plan-in-flames experience looked (or looks) like—and to remind myself of the same thing.

Writing in a way that invites comparison, or inspires feelings of profound unrelatability, is inherently disconnecting—exactly what I don’t want in this space.

And yet the only way to guarantee avoiding either trap means avoiding the subject of personal finance entirely. Deep down, I know that’s a cop-out.

I hope learning from each other’s money stories allows us to find points of connection, even where the plotlines of our stories diverge.

So when I begin writing the chapters of my money story, I’ll do so in a way that’s as useful as possible.

For each twist and turn in my unique story, I’ll share the universal habits, practices, skills, and projects that proved most helpful—and talk about what I might do differently with the benefit of hindsight.

And I’ll write each chapter with these three truths in mind: that financial differences don’t have to inspire comparison. That relatability is a moving target. And that, if we’re lucky, talking about money can bring us closer together, rather than driving us apart—regardless of where we’ve been, where we are, or where we’re going.

💬 What do you think?

I’m curious to hear from you. When you read someone else’s money story, what type of sharing do you find most helpful?

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