Side Hustles

As a writer, a consultant, and a dad, you could argue that all my hustles are side hustles. I’m a multi-faceted hustler. And that’s why I found myself Friday morning, after dropping my kid off for volleyball camp, casing a little trail system two miles up the road. There I found all manner of magic, skinnies, a seesaw, a bunch of twisty, technical single-track, and very few humans. Even in this work-at-home age, most folks are actually working during the hours I am side hustling.

In the realm of life hacks, side hustling a quick ride is the most level up bulls*%t I can recommend. I do NOT recommend taking on more jobs or selling your time to a company that can’t be bothered to have a health plan or contribute meaningfully to your retirement. I understand, needs must, but your time, in my occasionally humble opinion, is worth far more than they’re offering.

Because the aforementioned volleyball was a multi-day affair, my initial casing of the wooded joint yielded a fun spin there with my wife the next day, and on day three, I put the needle back on that record and danced like no one was watching.

Out of town sports trips are a good chance to scope out the dirt in some other town or find a bike path you haven’t ridden a thousand times. All-day tournaments don’t require your presence for every single moment. Your kid is busy. They’re with friends. Do the sane thing and squeeze in a bike ride. You won’t embarrass your progeny with your cringey presence, and neither will you resent having wasted a day sitting in a camp chair staring at your phone.

This strategy is not limited to all day errands like soccer/volleyball/lacrosse/basketball/baseball tournaments, track meets, spelling bees, space camp, LARPing sessions, the Ren faire or a laser tag birthday party. It works quite well for boring, local errands too.

The other day, I needed to go, in person, to see my insurance agent. There is a major artery that would take me there in short order, but I dropped down through my neighborhood in the opposite direction, picked up some dirt through a patch of woods, skitched over to a rail trail, and took that most of the way, including some small bits of single-track. I was just as sweaty when I pushed the door open and said, “Is Judy here?” as I would have been if I’d battled traffic to get there, but I was approximately eight-times as stoked.

When I drop my car off at the mechanic, I eschew the ride back they sometimes offer in favor of a bike on the rack and the long way home through the Arlington Great Meadow, the back of Wilson Farm, and the bit of Sutherland Woods that backs up to the bottom of my neighborhood. Picking up the car later allows me to reverse this course, a rambly twofer. Or is this a BOGO? Both?

Even if I just need to run to the grocery store for dinner supplies, I can rail the steep hill at Robbins Farm, bridge across to Menotomy Rocks and do a couple laps of the hill and pond there, before the four-block detour to the store. I prefer to side hustle on the way there, since I’ll be returning (all uphill) with a back-sack full of produce and other comestibles.

I’ll tell you sincerely, I miss bike commuting. OK, not every crosstown trip was fun, although when I worked at Seven I could get a lot of the way there in the woods. But I miss that enforced, daily on-bike time. It was my base fitness, my mental floss, and my constant connection to the bike, until…well…you know what happened. Developing and incorporating the two-wheeled side hustle took me some time discover, and hey, it’s not always possible, but I bet, if you look at your life, at the waking hours at your disposal, you could find time for a bit of this side hustle too. This one comes with no health or retirement benefits either, but you’ll resent it a lot less than most of the other varieties.


An eBike for errands can be a good way to get the side hustle in without all the sweat and fatigue.

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