Your Five-Year Plan is a newsletter about embracing lifeās profound uncertainty.
Maybe your own plans went up in flames; maybe youāre considering a big, scary leap. This is your trusty companion while youāre writing the next life chapter.
Welcome to the conversationāand to the adventure that unfolds when your plans go sideways. This is letter #34. āØ
A quick scheduling note: Iām taking the last two weeks of December off, so this is the final newsletter of 2023 for free subscribers (youāll hear from me again on the first Friday of 2024!). Paid subscribers, youāll receive one more edition next Friday.
On to todayās letterāwhich is so packed full of goodness, youāll have to click āView entire messageā to expand this email (or simply open it in your browser).
The gifts you gave yourself this year
I signed up for Substackāthe platform that hosts this newsletterāon 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 couldnāt 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, thatās you!)āand meaningful friendships with other writers, too.
Today, some of my writer friends gamely agreed to answer the following questions, ones Iāve been reflecting on all year:
ā¬ļø Whatās the best gift you gave your Present Self in 2023? Think: a delightful item or experience that gave you joy in the moment.
ā”ļø Whatās the best gift you gave your Future Self in 2023? Think: a kindness that youāll definitely appreciate down the roadābut 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.
An A+ start to the day.
This year,
of ādiscovered 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.āI love reading as I drink my morning coffee, so Iām taking inspiration from
of : āThis 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.ā of had an award-winning response: āThis 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.ā The only thing better than reading while drinking coffee? Watching hedgehogs toodle around while drinking coffee.I couldnāt agree more with
of , whose gift was āmaking 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.āĀAnd
of knows that the best start to the day happens when youāre well-rested: āSleep training my son. (Shout out, Taking Cara Babies! #NotSponsored, but wish I were.) Iāve always been a high sleep needs person ā so for me, that was absolutely critical. I feel like itās only made our bond stronger.āClothing (and accessories!) that made you feel amazing.
of bought āa soft denim jumpsuit from Cider, buttons down the front, tie at the waist, slightly wide legs. Rotate earrings, shoes, or shirt when itās chilly, and I live in it whatever the occasion; living in a van makes single-piece, no-thinking-required wardrobe items dreamy.āAnd
of bought something that felt equal parts grounded and lofty. āThis 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.ā of bought āthis 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.āĀ treated herself to āthis Patagonia puffer jacket that I purchased with a gift card, then split the difference with myself. Itās soft, warm, and packs up so small. No regrets!āExperiences and time spent with loved ones.
of saw The Boss in concert, and gushed: āIāve been a fan since I was in high school and their concerts have been the best nights of my life!ā (As a fellow Bruce Springsteen superfan, I lived vicariously through Wendiās report.) of invested in his family by taking āa full week off of work during my busy season to spend time with my girls.āAnd
of took āa trip to Paris with my fiancĆ©e.ā I mean: š!Day-making upgrades.
of sprung for this satisfying upgrade: āA 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.āIām inspired by
of , whoās going all-in on glamour in 2024. āOne of my closest friends gave me āShiny Briteā Christmas ornaments from the 1940s sheād recently inherited, still in their original boxes, knowing Iād 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 cartāitās harder for my cat to get to it there. My neighbor saw the tree and he said it looked glamorous, and thatās a word Iām taking into the new year.āWhen
of and her partner moved into their new place, āone 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.āAll the #goodvibes.
I cheered for
of , who wrote: āThis 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.ā of was all about the gift of creativity. āI 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.ā of gave herself happiness. āI spent the entirety of 2023 working on being authentically happy (none of that toxic positivity garbage), and I am!āInvestments in your physical surroundings.
offered a peek into the future of her backyard. āMy 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.āAnd
ācleared out the past in order to focus on my present and futureā in a task she described as daunting and emotionalāand a relief to have completed. She combed through āover 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.āInvestments in your educationā¦
āinvested 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 š)!ā cited the monumental undertaking of grad school: āI certainly am enjoying a lot of it along the way but there's plenty I don't enjoy in the moment.āā¦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.
built a website to help those struggling with their mental health. launched her newsletter, which marks āthe first step of [an entrepreneurial journey] I have envisioned for more than a decade.ā Embarking on a long-held dreamāparticularly one thatās in service of others!āis always an extraordinary gift.And
and have already published more than 60 issues (!) of their newsletter in 6 months (!!)ābut their efforts have inspired so much support that Aliza reports, āWe have no plans to slow down in 2024.āYou š love š to š see š it!
Adjustments in your relationship to movement.
Each morning,
ās first alarm āgoes 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!ā sprung for āa 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 exerciseā¦ā (Relatable.) credits āregular strength training and daily stretchingā as her biggest gift. āI do like it,ā she says, ābut I'm mostly doing it for Old Lady Cait.āAnd
offered a refreshing perspective for anyoneāmyself includedāwhoās had to soften a too-rigid grip on their relationship with exercise.Her gift? āLetting go of my reliance on exercise to feel like I ādeservedā 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!ā
And finally: so many glorious intangibles.
Clarity. In August,
left his job āto 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.ā Newfound clarity on your lifeās path? Priceless.Attention. In 2023,
āstarted paying more attention to colours in my environment. It was painful in the moment because all the old fears of āruining my sketchbook pageā came back. But after a couple of nervous starts, I find myself happier about my work and the process of its creation.ā (Observe the beauty of October and Novemberās entries here!)Presence.
said āno 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).āPermission.
offered herself, and the rest of us, the following wisdom: āBe yourself, sweet thing (kindness in self-talk being an older gift Iām 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.ā
š¬ What about you?
Letās meet in the comments. Looking back at 2023, whatās 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? Iād love to hear more. Just hit āreplyāĀ to get in touch, or introduce yourself here.
Warmly,
Maddie
If you haven't answered these questions in today's letter: looking back at 2023, whatās the best gift you gave your Present or Future Self? (And if you have, you're welcome to let us know if you've got any special gifts planned for 2024!)
Maddie,
What a crowd-sourced piece of positivity!
This is what it's all about...why we are here.
Thank you for all you do and share with us readers!