🎁 The gifts you gave yourself this year

I asked—and boy, did y'all answer!

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 #34. ✨

A quick scheduling note: I’m taking the last two weeks of December off, so this is the final newsletter of 2023 for free subscribers (you’ll hear from me again on the first Friday of 2024!). Paid subscribers, you’ll receive one more edition next Friday.

On to today’s letter—which is so packed full of goodness, you’ll have to click “View entire message” to expand this email (or simply open it in your browser).

The gifts you gave yourself this year

Icicles on evergreens, captured on Kodak Portra 400 film

I signed up for Substack—the platform that hosts this newsletter—on Friday, January 20, 2023. That was three and a half weeks before my mom died, seven weeks before my layoff, and twelve weeks before I mustered the energy and courage to publish my first letter.

Standing at the precipice of a new creative project and multiple life transitions, the only thing that accompanied my uncertainty was anxiety. Would I run out of things to write about? Would anyone read my writing? If they did, would they judge me?

I look back on my anxious self with compassion, so consumed by fears of what might go wrong that I couldn’t recognize the possibility that things might go right.

And boy, did they ever. I gave myself the gift of writing headlong into fear, and that resulted in a supportive community of readers (yup, that’s you!)—and meaningful friendships with other writers, too.

Today, some of my writer friends gamely agreed to answer the following questions, ones I’ve been reflecting on all year:

• ⬇️ What’s the best gift you gave your Present Self in 2023? Think: a delightful item or experience that gave you joy in the moment.

• ➡️ What’s the best gift you gave your Future Self in 2023? Think: a kindness that you’ll definitely appreciate down the road—but one that wasn't necessarily fun.

Please enjoy the crowdsourced wisdom of their responses below! I hope something here inspires you to give more gifts to both your Present and Future Self next year.

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An A+ start to the day.

This year,

Kimberly Warner

of

Unfixed

“discovered the poet Rosemerry Wahtola Trommer. Her glimmering poems, always both weighted and soaring, leave me reflective, hopeful, grateful to exist. So few months ago I subscribed to her daily poem newsletter and decided to begin each day not with a frenzy of emails, but the necessary, life-giving pause of her work.”

I love reading as I drink my morning coffee, so I’m taking inspiration from

Nishant Jain

of

The SneakyArt Post

: “This year I have read more new authors than any other single year. My world is larger and more beautiful for reading the works of Salman Rushdie, Chitra Banerjee-Divakaruni, and Byung-chul Han, among others.”

Cait Flanders

of

Explore Within by Cait Flanders

had an award-winning response: “This will sound ridiculous but houses for the wild hedgehogs that live in my garden. Watching them toodle around every day brings me a ridiculous amount of joy.” The only thing better than reading while drinking coffee? Watching hedgehogs toodle around while drinking coffee.

I couldn’t agree more with

Jenovia

of

JENOVIA'S WEB

, whose gift was “making my walks in nature non-negotiable. Often, I will plan my whole day around them. Moving my body whilst being out in nature heightens my creativity and consciousness. I'm able to be my best self when I've gone for a walk outside.” 

And

Aliza Sir

of

platonic love

knows that the best start to the day happens when you’re well-rested: “Sleep training my son. (Shout out, Taking Cara Babies! #NotSponsored, but wish I were.) I’ve always been a high sleep needs person – so for me, that was absolutely critical. I feel like it’s only made our bond stronger.”

Clothing (and accessories!) that made you feel amazing.

Holly Starley

of

Holly Starley's Rolling Desk

bought “a soft denim jumpsuit from Cider, buttons down the front, tie at the waist, slightly wide legs. Rotate earrings, shoes, or shirt when it’s chilly, and I live in it whatever the occasion; living in a van makes single-piece, no-thinking-required wardrobe items dreamy.”

And

Sue Deagle

of

The Luminist: Personal growth through grief, loss & death

bought something that felt equal parts grounded and lofty. “This year I decided to take my milestone birthday - 55! - into my own hands, delighting myself with a cool new pair of reading glasses. They represent my practical self (old people need help reading!) and my aspirational self (red=bold!). Now every time I wear them, I remember both who I am and who I want to become.”

Sophia Le

of

The Write-Life Balance

bought “this cashmere sweatshirt from Quince. Throwing a bit of caution to the wind because my 4-year-old is constantly covered in paint, but this fabric is so buttery soft.” 

Aliza Sir

treated herself to “this Patagonia puffer jacket that I purchased with a gift card, then split the difference with myself. It’s soft, warm, and packs up so small. No regrets!”

Experiences and time spent with loved ones.

Wendi Gordon

of

Changing Lives

saw The Boss in concert, and gushed: “I’ve been a fan since I was in high school and their concerts have been the best nights of my life!” (As a fellow Bruce Springsteen superfan, I lived vicariously through Wendi’s report.)

Jordan | The Wealth Letters

of

The Wealth Letters

invested in his family by taking “a full week off of work during my busy season to spend time with my girls.”

And

Jeffrey Streeter

of

English Republic of Letters

took “a trip to Paris with my fiancée.” I mean: 😍!

Day-making upgrades.

Christopher Anselmo

of

Hello, Adversity

sprung for this satisfying upgrade: “A new Kindle. I use it all the time! My old Kindle was about 12 years old and it was sloooooow. The battery would also overheat and die out after an hour, which drove me nuts.”

I’m inspired by

Jolene Handy

of

Time Travel Kitchen

, who’s going all-in on glamour in 2024. “One of my closest friends gave me ‘Shiny Brite’ Christmas ornaments from the 1940s she’d recently inherited, still in their original boxes, knowing I’d love them. They are a special gift that needed a special tree, so I bought myself a little artificial flocked spruce and set it up on my bar cart—it’s harder for my cat to get to it there. My neighbor saw the tree and he said it looked glamorous, and that’s a word I’m taking into the new year.”

When

Aja Frost

of

platonic love

and her partner moved into their new place, “one of its primary draws was we could both have our own offices. I spent a ton of time scouring Facebook Marketplace for vintage pieces that would make the room both comfortable and beautiful. My favorite purchase was a wide, elegant wooden desk with plenty of drawers and room for me to spread out my pens, notebooks, screens, etc. It makes me happy every time I walk in to start working.”

All the #goodvibes.

I cheered for

Mariana Calleja Ross

of

The Feel Good Life

, who wrote: “This year has been one of massive life changes for me: changing countries, continents, and ways to connect with my beloved ones. I'd say the most meaningful gift I've allowed my present self in 2023 is saying yes to love. For myself and others. Allowing it all and saying yes to life.”

Kathryn Vercillo

of

Create Me Free

was all about the gift of creativity. “I allowed myself to reduce my workload and take on debt so that I could write full-time on Substack and go to grad school, something that has truly been a treat.”

Sandra Ann Miller

of

A Sassy Little Substack

gave herself happiness. “I spent the entirety of 2023 working on being authentically happy (none of that toxic positivity garbage), and I am!”

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Investments in your physical surroundings.

Kimberly Warner

offered a peek into the future of her backyard. “My future self, hopefully with two good growing seasons ahead, will be enjoying a 1/4 acre backyard monarch butterfly way-station. After two years of solarizing the grass and an autumn of back-breaking soil management, I finally planted thousands of seeds after our first frost, with visions of migrating monarchs already dancing in my head.”

And

Jenovia

“cleared out the past in order to focus on my present and future” in a task she described as daunting and emotional—and a relief to have completed. She combed through “over 20 years worth of personal life stuff in three different storages in three different states. Gathering all of my past lives, keeping what I needed and throwing out the rest, has allowed me to be fully rooted in my current life.”

Investments in your education…

Jeffrey Streeter

“invested in myself and took a copywriting course. It was hard work, but I already feel the benefit in terms of my paid written work. It will help me pay the bills (including that trip to Paris 🙂)!”

Kathryn Vercillo

cited the monumental undertaking of grad school: “I certainly am enjoying a lot of it along the way but there's plenty I don't enjoy in the moment.”

…and investments in fledgling creative projects.

Many writer friends cited the projects they launched this year as the best gift to their Future Selves; nothing, after all, inspires more pride than actually doing the thing that was previously an intangible glimmer of your imagination.

Wendi Gordon

built a website to help those struggling with their mental health.

Mariana Calleja Ross

launched her newsletter, which marks “the first step of [an entrepreneurial journey] I have envisioned for more than a decade.” Embarking on a long-held dream—particularly one that’s in service of others!—is always an extraordinary gift.

And

Aliza Sir

and

Aja Frost

have already published more than 60 issues (!) of their newsletter in 6 months (!!)—but their efforts have inspired so much support that Aliza reports, “We have no plans to slow down in 2024.”

You 👏 love 👏 to 👏 see 👏 it!

Adjustments in your relationship to movement.

Each morning,

Sandra Ann Miller

’s first alarm “goes off at 4:30 AM, my second goes off at 4:45...and all so I can exercise in a less-rushed way before work. Future me had better appreciate this sacrifice!”

Sophia Le

sprung for “a yoga-inspired strength training plan from Axios Coaching. Jace's expertise combined with the technology of the Volt Fitness app actually gets my grumbling self out of bed to do a workout. Still waiting to become one of those people who adores exercise…” (Relatable.)

Cait Flanders

credits “regular strength training and daily stretching” as her biggest gift. “I do like it,” she says, “but I'm mostly doing it for Old Lady Cait.”

And

Aja Frost

offered a refreshing perspective for anyone—myself included—who’s had to soften a too-rigid grip on their relationship with exercise.

Her gift? “Letting go of my reliance on exercise to feel like I ‘deserved’ to feel okay or eat what I wanted to! (Technically, I started making progress on this in 2022, but the work is ongoing.) It's been an incredibly freeing shift; I no longer wake up every morning dreading the punishing Peloton classes or hour-long Stairstepper routines I needed to do. Now I go on walks (no matter the weather), which are not only easier on my body but give me opportunities to talk on the phone, listen to podcasts, or music, or simply take in the beauty of Boston!”

And finally: so many glorious intangibles.

• Clarity. In August,

  Christopher Anselmo
  left his job “to write full-time and take the rest of the year to contemplate what's next. I had a nagging feeling that my career was starting to veer off track and I felt I owed it to myself to figure out what I really wanted to do.” Newfound clarity on your life’s path? Priceless.

• Attention. In 2023,

  Nishant Jain
  “started paying more attention to colours in my environment. It was painful in the moment because all the old fears of ‘ruining my sketchbook page’ came back. But after a couple of nervous starts, I find myself happier about my work and the process of its creation.” (Observe the beauty of October and November’s entries here!)

• Presence.

  Jordan | The Wealth Letters
  said “no to more business so that I can have the increased ability to be more present in my daily life (especially with my wife and daughters).”

• Permission.

  Holly Starley
  offered herself, and the rest of us, the following wisdom: “Be yourself, sweet thing (kindness in self-talk being an older gift I’m getting better at receiving). That your words are weapon was never your own refrain and never true. Be your generous self in search of emotional honesty on the page, and share it, lest you break your own heart believing your silence is a gift to anyone.”

💬 What about you?

Let’s meet in the comments. Looking back at 2023, what’s the best gift you gave your Present or Future Self? Do you have any special gifts planned for 2024?

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