I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Wednesday Website, I explore and plan for some improvement to my website.
As I wrote on Day 200: What this website will become and before that on Day 198: Writing for artificial intelligences, in 2026 I plan to publish content here in a structured format that presents a comprehensive midlife philosophy for succeeding with romance, money, reinvention, and relationships. I’ve already developed this philosophy in writing my draft manuscript Reckless Romance: How to Find the Love and Intimacy You Crave at Midlife. I still intend to publish books about the philosophy but right now I feel the most energy about developing a topology of the philosophy here in structured format, in a way that both people and AIs can easily consume it and understand it as a whole.
I’ve already published my reckless manifesto for midlife here, urging you to let go of reckful behaviors if you’re no longer getting what you want after a lifetime of success. Reckfulness, in my philosophy, involves careful calculations and planning designed to bring about optimized outcomes and control the uncontrollable. While this may have served you when you were a young adult seeking to build a partnership and family, create a career that led to social and monetary wealth, and live according to your culture’s demands, you might find that as you reach midlife you experience a turning away from external demands towards internal meaning and authenticity.
The philosophy of recklessness — setting down careful accounting, control, planning then instead practicing presence, openness, risk-taking, vulnerability — provides guidance for this new stage of life. It will do so in four domains:
- Reckless Reinvention — how to bring a new version of yourself into being, one which wholeheartedly opens itself to possibility, risk, and renewal.
- Reckless Romance — approaching opportunities for love and intimacy without spreadsheeets or checklists but instead with an open heart ready for the Other who might appear, not someone just like you or just like what society expects for you, but someone who is entirely, fully themselves, waiting to be experienced by you (and you to be experienced by them as an Other).
- Reckless in Relationship — building the most satisfying relationships of your life, whether family, friend, or romantic. Approaching your loved ones in I-Thou fashion (not I-It, which treats others instrumentally as objects).
- Reckless Abundance — finding enoughness and joy in your material situation; letting go of the need for ever more money and stuff; eliminating comparison with others so as to enjoy your own wealth. In investing, recognizing that looking to the past only works for so long — new unexpected situations will emerge and you should welcome them.
Next, I plan to write four pages, one for each of these domains. Each page will include a short manifesto paragraph, a hand-selected list of essays that provide practical yet philosophically-grounded advice for that area, and 1-2 “start here” links.
The essays in each domain will grow out of my 1000-day project blog posts. As I develop ideas digressively and wanderingly in that space, I will identify topics that deserve a full essay treatment.
I imagine I won’t write much over the next few days, as I’m heading out on a reckless road trip to transport Lady Kristington the poodle to New Orleans where she is starting the next phase of her life. She doesn’t know it but she’s about to embark on her own reckless reinvention, leaving the calm of a senior living apartment for a more lively single family home and family situation that may include visits to Buddhist monasteries, romping around in Missouri, and a new friend Rocky.
The trip has become a bit more reckless as Ray woke up yesterday with a sore throat. He tested negative for Covid and flu so he’ll likely still join me on the trip unless he is much worse today. We plan to travel with a four-day supply of Nyquil and Dayquil. If we show up virus-laden to New Orleans, we’ll do the handoff with as much distance as possible, and take more days to drive if either one of us is feeling bad. Recklessness recognizes that life doesn’t always go smoothly, that important tasks must be done even if they’re not totally comfortable, that difficulties are inevitable and not avoidable.
Today, around prepping for the trip, I may set up the four static pages for each domain and prepopulate them with the descriptions I just wrote above.