Investing in myself on a $32k salary

What financial self-advocacy looked like at 24

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 #27. ✨

Investing in myself on a $32k salary

A mural in Chicago’s Pilsen neighborhood, captured on Kodak Ektar 100 film

For years, I worked as a financial planner. The irony? My life hasn’t unfolded according to plan. In this series, I share what helped me navigate each chapter of my money story with resilience and flexibility, no matter where life took me.

Here’s what you’ll find in this edition:

• 🎬 Setting the scene of where I was, financially, at age 24

• 🎁 The gift I gave myself during this time

• 💰 The investments I made in myself

• 📚 The biggest lessons I took from this chapter

🎬 Setting the scene

Having paid off my student debt, I move to Chicago unencumbered—and unemployed.

Scrambling to fix the second issue, I land an entry-level admin role at Northwestern University’s business school. At $16.50 an hour, over 37.5-hour workweeks, multiplied by 52, I’m raking in…just over $32,000 a year.

Gulp.

That’s a 20% pay cut from my last job—but hey, my monthly debt payments are gone! And Chicago’s cost of living is lower than D.C.’s! These are the things I tell myself whenever I feel a rising sense of panic.

Over the next three years, though, I’ll learn to make big-city life on a small salary work…and I’ll even manage to invest in myself along the way.

🎁 The gift I give myself

When my boyfriend and I tour the spacious one-bedroom on Bryn Mawr Avenue, we’re taken with the hardwood floors and gigantic windows, and my God, the location: above an adorable coffee shop, two blocks from Lake Michigan.

It’s far from the trendy neighborhoods closer to the Loop—which is the only reason it’s affordable.

When that live-in boyfriend becomes an ex-boyfriend, things become a bit less affordable. My half of the rent doubles, to $1,050. I learn the rule of thumb that says your housing expenses should be less than 28% of your gross income; they’re now 39% of mine.

Because I am madly in love with the apartment, I renew the lease anyway.

How do I make this expenditure a gift to myself, rather than a burden? I make it as central to my life as it is to my budget.

I host chaotic BYOB happy hours after work, welcoming colleagues bearing six-packs through my front door. The more, the merrier!

By necessity, I limit my restaurant spending—but I make elaborate dinners for friends at home, testing recipes from my cookbook collection. (Though I wince whenever ingredient costs stray too far outside my weekly $50 grocery budget.)

There’s a lot I have to give up. I have friends who take taxis—and, once iPhones enter the picture, Ubers—all over the city. No matter how late my nights end, you’ll always find me heavy-lidded on a bus or the El for the hour-long ride home.

But there’s a lot I gain, too, like the pride stemming from my successful DIY home decor projects. (As I write to you from 2023, I’m sitting at the same hand-me-down desk I sanded and painted back in 2011.)

💰 The investments I make in myself

I decide that I’m ready to figure out how I might build a career, rather than a series of jobs.

At this particular moment, with a year of consistent blogging under my belt, I know one thing is true: I love stringing together words and photographs, and improving at both crafts gives me energy.

I follow that energy, spending $335 on a Beginning Digital Photography class at the local arts center. I delight in my weekly assignments and fledgling Photoshop skills.

On a whim, I pick up my old 35mm camera and slip into a full-blown love affair. You know how it goes, right? One innocent thing (a few hours in the university’s darkroom) leads to another (scouring eBay camera auctions long after bedtime).

I spend $99 on a starter medium-format camera, to make sure my feelings are real. Obsession confirmed, I upgrade to a $600 camera body and $390 lens. My new loves, film and development, earn themselves a precious line item in my budget.

All those hours I’ve spent on public transit, conserving twenty bucks here and there?

Totally worth it.

Scenes from Quebec, captured on Kodak Portra 400 film

When I find out that the Film Is Not Dead workshop is coming to Chicago, it’s not a hard sell; I’ve been binge-reading attendees’ glowing reviews for months.

FIND, as the traveling photography workshop is known to true believers, has a cult following. And I’m thirsty for Kool-Aid.

But first, I have to jump through two mental hoops:

1. This is a workshop for professional photographers; I’m still very much an amateur.

2. More vexing? The $2,300 cost, which represents a full seven (!) percent (!!) of my annual income.

These facts should deter me from grabbing my debit card—but as before, I follow the energy.

FIND Chicago portraits, captured on Kodak Portra 800 film

Attending FIND turns out to be a definitive moment in my creative life.

• I shoot portraits for the first time, and gain confidence in posing subjects.

• I watch other attendees’ portfolio reviews, which teaches me how to show my own work.

• I learn how to craft photographic essays with a beginning, middle, and end in my blog posts.

• I leave with a comprehensive editing workflow.

• I begin a relationship with a professional film lab, where I learn how to communicate with the people scanning my film.

Most importantly, I build lasting relationships with my fellow attendees—ones that don’t end when the workshop does.

I use these new skills, these seeds of artistic confidence, to shoot portraits of any friend who asks. “I love your photos,” they say. “Can you take one of me?”

The answer is always yes, which is how I find myself shooting a dear friend’s wedding.

My friend’s wedding, captured on Kodak Portra 400 film

Ultimately, though, I don’t become a professional photographer. I love the creative outlet so much that I want to shield it from the hard choices involved in running a business.

And yet! The years I spent practicing—and the thousands of dollars I invested in learning the craft—buy me important life lessons.

📚 This chapter’s biggest lessons

As I move into the next chapter of my money story, here’s what I take away.

Spending on my passions is usually worth it.

If a piece of equipment, book, workshop, course, or coach helps me grow or refine my skills, it tends to be a valuable investment.

It pays to know what “enough” looks like.

That knowledge is meaningful whether I’m flush or strapped for cash.

It also helps me find creative ways to nurture my priorities when money’s scarce. Figuring out which expenses to cut can be a creative act; creativity, after all, is born out of constraint.

Keep the pilot light burning.

In my twenties, my career choices veered away from creative entrepreneurship. But that little flame of desire kept flickering in the background, like a pilot light.

As I write to you today, it’s burning brighter than ever.

💬 What about you?

Let’s meet in the comments section for your hot takes:

• What’s the best investment you’ve made in yourself?

• What lessons came out of a time when money felt scarce?

• What’s your biggest DIY project success—or your most hilarious fail?

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