Your Five-Year Plan is a newsletter about embracing lifeâs profound uncertainty.
Maybe your own plans went up in flames; maybe youâre considering a big, scary leap. This is your trusty companion while youâre writing the next life chapter.
Welcome to the conversationâand to the adventure that unfolds when your plans go sideways. This is letter #34. â¨
A quick scheduling note: Iâm taking the last two weeks of December off, so this is the final newsletter of 2023 for free subscribers (youâll hear from me again on the first Friday of 2024!). Paid subscribers, youâll receive one more edition next Friday.
On to todayâs letterâwhich is so packed full of goodness, youâll have to click âView entire messageâ to expand this email (or simply open it in your browser).
The gifts you gave yourself this year
I signed up for Substackâthe platform that hosts this newsletterâon 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 couldnât 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, thatâs you!)âand meaningful friendships with other writers, too.
Today, some of my writer friends gamely agreed to answer the following questions, ones Iâve been reflecting on all year:
âŹď¸ Whatâs the best gift you gave your Present Self in 2023? Think: a delightful item or experience that gave you joy in the moment.
âĄď¸ Whatâs the best gift you gave your Future Self in 2023? Think: a kindness that youâll definitely appreciate down the roadâbut 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 âdiscovered 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.âI love reading as I drink my morning coffee, so Iâm taking inspiration from
of : âThis 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.â of had an award-winning response: âThis 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.â The only thing better than reading while drinking coffee? Watching hedgehogs toodle around while drinking coffee.I couldnât agree more with
of , whose gift was âmaking 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.âÂAnd
of knows that the best start to the day happens when youâre well-rested: âSleep training my son. (Shout out, Taking Cara Babies! #NotSponsored, but wish I were.) Iâve always been a high sleep needs person â so for me, that was absolutely critical. I feel like itâs only made our bond stronger.âClothing (and accessories!) that made you feel amazing.
of bought âa soft denim jumpsuit from Cider, buttons down the front, tie at the waist, slightly wide legs. Rotate earrings, shoes, or shirt when itâs chilly, and I live in it whatever the occasion; living in a van makes single-piece, no-thinking-required wardrobe items dreamy.âAnd
of bought something that felt equal parts grounded and lofty. âThis 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.â of bought âthis 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.â treated herself to âthis Patagonia puffer jacket that I purchased with a gift card, then split the difference with myself. Itâs soft, warm, and packs up so small. No regrets!âExperiences and time spent with loved ones.
of saw The Boss in concert, and gushed: âIâve been a fan since I was in high school and their concerts have been the best nights of my life!â (As a fellow Bruce Springsteen superfan, I lived vicariously through Wendiâs report.) of invested in his family by taking âa full week off of work during my busy season to spend time with my girls.âAnd
of took âa trip to Paris with my fiancĂŠe.â I mean: đ!Day-making upgrades.
of sprung for this satisfying upgrade: âA 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.âIâm inspired by
of , whoâs going all-in on glamour in 2024. âOne of my closest friends gave me âShiny Briteâ Christmas ornaments from the 1940s sheâd recently inherited, still in their original boxes, knowing Iâd 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 cartâitâs harder for my cat to get to it there. My neighbor saw the tree and he said it looked glamorous, and thatâs a word Iâm taking into the new year.âWhen
of and her partner moved into their new place, âone 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.âAll the #goodvibes.
I cheered for
of , who wrote: âThis 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.â of was all about the gift of creativity. âI 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.â of gave herself happiness. âI spent the entirety of 2023 working on being authentically happy (none of that toxic positivity garbage), and I am!âInvestments in your physical surroundings.
offered a peek into the future of her backyard. âMy 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.âAnd
âcleared out the past in order to focus on my present and futureâ in a task she described as daunting and emotionalâand a relief to have completed. She combed through âover 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.âInvestments in your educationâŚ
âinvested 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 đ)!â cited the monumental undertaking of grad school: âI certainly am enjoying a lot of it along the way but there's plenty I don't enjoy in the moment.ââŚand 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 âthe first step of [an entrepreneurial journey] I have envisioned for more than a decade.â Embarking on a long-held dreamâparticularly one thatâs in service of others!âis always an extraordinary gift.And
and have already published more than 60 issues (!) of their newsletter in 6 months (!!)âbut their efforts have inspired so much support that Aliza reports, âWe have no plans to slow down in 2024.âYou đ love đ to đ see đ it!
Adjustments in your relationship to movement.
Each morning,
âs first alarm âgoes 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!â sprung for âa 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 exerciseâŚâ (Relatable.) credits âregular strength training and daily stretchingâ as her biggest gift. âI do like it,â she says, âbut I'm mostly doing it for Old Lady Cait.âAnd
offered a refreshing perspective for anyoneâmyself includedâwhoâs had to soften a too-rigid grip on their relationship with exercise.Her gift? âLetting go of my reliance on exercise to feel like I âdeservedâ 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!â
And finally: so many glorious intangibles.
Clarity. In August,
left his job âto 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.â Newfound clarity on your lifeâs path? Priceless.Attention. In 2023,
âstarted paying more attention to colours in my environment. It was painful in the moment because all the old fears of âruining my sketchbook pageâ came back. But after a couple of nervous starts, I find myself happier about my work and the process of its creation.â (Observe the beauty of October and Novemberâs entries here!)Presence.
said âno 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).âPermission.
offered herself, and the rest of us, the following wisdom: âBe yourself, sweet thing (kindness in self-talk being an older gift Iâm 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.â
đŹ What about you?
Letâs meet in the comments. Looking back at 2023, whatâs 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? Iâd love to hear more. Just hit âreplyâ 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, whatâs 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!