Judging by the cottage industry of books and videos hawking strategies for “Getting Things Done”, most people seem to be overwhelmed by how much they have to do. My challenge is the opposite; I have a hard time coming up with what to do next. Even when I get into something (like so many of my landscaping projects in Fresno), no matter how exacting I am with each step, no matter how much of my seemingly limitless time that I expend, ultimately I reach the end, and then once again I have to wrack my brain to invent another project, often more elaborate, sometimes more fringe, to occupy my time.

On a few occasions when I didn’t know what to do next, I lent myself out to friends, bringing the same intensity and passion and attention to detail to their projects as I would my own. This had a mutually beneficial effect, as it helped to break their inertia (nothing like an eager friend at the ready to vaporize procrastination) while giving me a host of novel, bite-size problems to solve without having had to define the overarching project. These are what Daniel H. Pink refers to as “Goldilocks tasks” in his book Drive, “challenges that are not too hot and not too cold, neither overly difficult nor overly simple” that help one achieve a state of “flow”. It was only by giving my fatigued “project generation engine” some room to breathe that potential future projects started again to percolate in the back of my mind.

Working on someone else’s project is a great strategy for “self-unblocking”, but one has only so many friends and neighbors, and they have only so many applicable projects (let alone available non-work time) that I started brainstorming with another friend (and former colleague) about a Craigslist-like service to connect neighbors with skills to neighbors with projects. No money exchanged, just support, tools, know-how, and camaraderie. I don’t believe in the “good old days”, but I do think that our modern life, in particular the boundless mobility we possess to seek new jobs in new places, has come at the cost of close serendipitous bonds with the people who happen to live around us (because so many of those bonds are formed when we’re young). Now I am loathe to suggest that this is a problem that can be solved by software alone, but if there were a service with offline community-building as its first principle, well maybe, just maybe, it might escape the horrible fate of today’s social media hellscape. Though I’d be willing to help build it, really I just wish it already existed so I could turn to it when I lose the thread on what to do next.

In the time-honored tradition of dogfooding one’s own ideas, at the end of October I created a post on the Monterey Bay Craigslist under “skilled trade services” (at a cost of $5) to offer my assistance, free of charge, to anyone who needed help with a DIY landscaping or renovation project. It was fun to write, but the instant I hit “Publish” I felt naked. What had I just done? What would people think? It occurred to me afterwards that there’s a name for this feeling: vulnerability. When so much of “adulting” seems like code for “guarding against appearing vulnerable at all costs,” I almost forgot how exhilarating it can feel at the same time.

I’m not sure what I expected to happen, but you can probably guess how it turned out. Crickets. I heard absolutely nothing for days, such that I almost forgot what I’d done, until I got a brusque request 8 days later. “I need a concrete gutter 18 in wide by about 20 ft long for drainage away from the house give me a call.” The tone (not to mention lack of punctuation) suggested that they didn’t quite appreciate the spirit of my listing, and I worried that in my overwrought attempt to explain my offer while also appearing as non-threatening as possible, perhaps something had got lost in translation. So to clarify, I replied, “Just to be clear, I’m interested in assisting folks with their do-it-yourself projects, as in, lending an extra pair of hands, but not doing all the work myself,” and never heard back. A few days later I got another request, and this time it seemed like they had at least read my post because they wrote, “I have never seen a listing quite like yours,”—which I consider to be high praise, perhaps I should brand my marketing strategy as “security through verbosity”—but then they continued with, “I do a full background check on anyone who is invited to work with me, I would require a photo of your drivers license to verify identity,” suggesting that maybe they were looking to hire someone for a job that they were being paid to do (or maybe they just wanted to steal my identity). I sent a reply to clarify (without a photo of my drivers license), and once again I never heard back.

Just before my post was set to expire, I received a request that restored my faith in the experiment. Someone was looking for help in dismantling a dilapidated shed on their homestead property with the goal of rebuilding it later as an accessory dwelling unit. We chatted on the phone and it was very clear they understood the spirit of my post, such that I felt totally comfortable driving half-an-hour for a tour of their property and said shed. Of course this was right before Thanksgiving, so a combination of holidays and wet weather has put the project on hold until the new year, but it did convince me that my oddball idea had legs. So I revised my post and paid $5 for another month. I got an email 9 days later from someone who needed help preparing their front yard for drought tolerant landscaping. And this time we actually set a date. Super nice guy, he just needed help leveling the yard and removing the top layer of sod and weeds, exactly like something I did in Fresno. So we spent one morning in December shoveling like mad and managed to get about two-thirds of his front yard leveled. But more important than the progress we made was the fact that he could start to see a light at the end of the tunnel while I got to spend a few blissful hours not thinking about what to do next.

Update: Curious how my experiment turned out? Check out Accidentally Unretired.