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Okay, time 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?

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Most of the best investments in myself have been books. Still the best bang per buck I can think of.

I’m glad this story didn’t end with you becoming a professional photographer. The value of investing in our enthusiasms is not talked about enough. Thanks for that.

Also you have a great reading voice. ⭐️

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100% agree about books being incredible investments. Where else can you get a lifetime of wisdom distilled into a digestible package, all for under twenty bucks?

Glad you enjoyed the punchline—I totally agree that our hobbies and creative pursuits are well worth investing in, regardless of whether or not they become careers. And speaking of hobbies: thanks for the kind words about my audio efforts!

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Maddie,

Thank you for sharing! Your takeaway on finding what is "enough" is THE QUESTION I find myself struggling with the most!

I am reading the book, Christian Atheist by Craig Groeschel, and he wrote how he has struggled to find what is enough:

"I always told myself, one day when we have a certain amount saved, then I'll feel secure. Yet each time I cross that imaginary line of security, my line moved. What before seemed like more than enough suddenly didn't feel like close to enough.

After serious prayer and reflection, I realized what I was doing. I was placing my trust and money instead of in God...

When my Christian Atheist let go of those false promises of worldly pleasures, it was easier for me to pursue God. And pursuing God I became strangely content. That was enough."

Thw word that hits it for me is CONTENT... That is literally the one word I feel most of us (myself included) is ultimately pursuing.

How to achieve contentment? That's the ultimate question now isn't it? 😉

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It's such a joy when a subject I'm mulling over starts appearing in lots of different things I'm reading. It's so cool to hear that you're thinking through this topic, too—because as you correctly note, achieving contentment really *is* the ultimate question! Thanks so much for sharing this reflection, Jordan.

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Same same re: the imaginary line.

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I appreciate the idea of giving gifts to ourselves even during leaner times. It reminds me of a recent Planet Money episode with Maria Bamford (in which she is radically honest about her finances). She recalls going to a debtors anonymous group (or some such gathering) and learning that it's not necessarily better to live a totally spartan life while trying to get out of debt. Because then, once you're out of debt, you're more prone to overspending. Those little gifts even when it seems like you can't afford it can be part of a healthy long-term strategy.

This essay also resonated with me because I'm in a similar transition at age 48. After 20 years in higher ed, I gave up my career so our family could move closer to relatives. Unfortunately, that move also led to a divorce (in progress), and so my initial plan of embracing independent writing without a particular income goal is no longer viable. I launched a book coaching practice in March that is growing slowly, and I'd love to see it reach a viable threshold in 1-2 years. But I'm also applying to other positions along the way to keep my options open. I may be an unlikely reader for your series, but I appreciate it. Some of these principles apply regardless of age or stage of life.

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Joshua, I'm so glad you shared your story here—it's wonderful to "meet" you! I'm wishing you success as you move forward with your career transition, and peace as you move forward with your relationship transition. I know from personal experience that it's a lot to navigate at once!

And I completely agree that these principles are applicable across many life stages; I'm in a totally different place now than I was at 24, but still carry everything I learned back then. So: you're not an unlikely reader whatsoever.

Going to download the Maria Bamford episode immediately...it sounds like a juicy one, based on the extremely on-point lesson you shared. Thanks for the rec!

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I can’t think of any big investments in myself. Probably more like mini-ones along the way. I think the bigger one I remember is after my mom died I needed and wanted to get away by myself. About 6 weeks later I went to Hawaii with a training group and swam, biked and ran around the Big Island. It felt very healing. My mom even made an appearance in the night one night. Scared the bejesus out of me at first, but she came to tell me she was ok. ❤️

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With time, I think that mini-investments compound into bigger ones! And this sounds like a particularly cathartic one at a particularly important moment.

I'm so glad you took yourself on this retreat, Kim—and it sounds like your mom was clearly cheering you on the whole way. 🥰

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A bit late to this post (just finding it now). I really appreciate your takeaways. The biggest lesson that came out of a time when money felt scarce for me was that money is not everything (once your basic needs are met). I had this realization when in my late 20s I felt like I had "made" it at a fancy job in DC, living alone in the center of the city only to realize I was the unhappiest I had ever been. I thought back to my 22 year old self, scraping by and realized that version of myself yes had way less money but I had a job that gave me purpose and an amazing community of friends. That lesson has shaped the way I structure my life and approach my career.

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Thank you so much for sharing your story! As someone who also felt deeply unhappy at the “peak” of her career, this resonates deeply.

I’m so glad you took meaningful lessons from this moment and applied them to all your career decisions that came thereafter. ☺️

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Hey, I’m sorta similar to you. At 21 I moved to Chicago with no job and no debt. But i was interviewing for an admin job at Northwestern. I didn’t get it, so I started working at Whole Foods instead, making hardly any money. Unfortunately I didn’t care that much because I’m not much of a spender anyway. (I say unfortunately because I wish I was a bit more motivated to make money lol.)

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Loran, I love hearing about the overlap between our two stories. And as someone who went on to work in finance—but has *never* been driven solely by the prospect of earning more—I can totally relate to your note!

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I don’t know why I never thought of investing in my creativity as “investing”. I just put it in the category of “frivolous spending”. If I think of my energy and where I draw from it - it’s my art! Thanks for re-framing this for me. ☺️

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I’m incredibly happy to have helped reframe this for you, because it’s a perspective I feel super-strongly about! The world needs more of you and your art. 🤗

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If it's fueling any part of you, it's always a worthy investment. Love this, Maddie. I suppose my big investment in myself (which I'm still paying off) is my BFA in film from a private art school, which I loved attending. I got close a time or two on being the writer/producer I expected to be, but I treasure that experience, even though I'm no longer on that career path. When I was my brokest, I stashed cash. Anything under my weekly budget was set aside for bigger purchases. And, each week, I bought flowers for my garden ($4 plants). I was so poor and so rich at the same time. My first book was my biggest DIY project! LOL. Learning about printing and distribution, trying to get it into big stores. That was fun. xo

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Oh, this is such a lovely set of reflections, Sandra! "I was so poor and so rich at the same time"—I know *exactly* what that feels like, and I can picture you nurturing your $4 flowers with such TLC. I'd be fascinated to hear about the process of getting your first book out into the world sometime!

Love that your film degree was a formative part of your artistic life, even though you're not working in the industry. My brother has a similar story about film school, so I know that it can inform your creative life and career in a multitude of interesting ways!

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Thank you, Maddie. Happy to share the book stuff any time (I think we need a Zoom/wine date). Much easier (and cheaper) now. CalArts was a wonderful womb for artists. Had the best time. Regret nothing (but the 9% interest). And, sadly, I murder plants. Either with too much love or not enough. But, for a brief period, my garden was lovely. It was a stressful time, but I was also happy. Every little achievement meant so much. xo

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I love all of this. ❤️ Fellow plant murderer here who echoes your Zoom wine date suggestion!! 🥂

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The best lesson I learned from my post-college days was to strike a balance between enjoyment and frugality. I had to watch my spending; I had no choice. But there were times when I agonized over whether I should go out with friends, which, after a few drinks, can get expensive. But looking back, I am so glad I did. Those are the memories I remember today. Sometimes in the moment, we look at things from purely financial terms without considering that we are investing in future happy memories.

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I'm so glad you mentioned this. It's a lesson I *wish* I'd been wise enough to have learned much sooner! This is the kind of stuff that pays major joy dividends for years to come—a worthy investment indeed.

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So good to hear your voice, Maddie, and love how keeping your apartment (near Lake Michigan 🤩) was the gift -- and you made it work as a gift not a burden. ❤️

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Thank you, Jolene! 🤗 I remember plenty of walks from Edgewater into Andersonville during those years...such a wonderful corner of the city.

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