We’re catching up on blog posts after a busy past month! In real time we’re in San Diego, about to leave with 100+ other boats on the Baja Haha Cruiser’s Rally heading to Mexico. This post will cover our whirlwind three weeks back in the Bay Area in September and October.
When we left you last we had just hosted a boat warming party in Aquatic Park, right on the city front. We had a lovely few days anchored there catching up on sleep, going on runs in the city, and meeting some fellow sailors. We were back home, but being anchored out made it feel like we were still cruising. After a few days we picked up anchor and sailed the final leg back to the Berkeley Marina. We’d done that sail so many times when we used to live in Berkeley on the boat, and it felt just like old times drifting home on the tailwinds coming through the Golden Gate.
With the boat safely tucked away in the marina, our top priority was reconnecting with our bay area friends and community. We spent time on the couch in our old apartment, had lovely dinners, and laughed & chatted with our craft club crew. We got our butts kicked by a fun reunion workout with our old neighborhood workout group. We slept over at friend’s apartments and relived the casual closeness of having roommates as we brushed our teeth together and got pastries in the morning. Jeremy got to go to a friend-hosted music festival and Maddie taught beginner sailing at the Women’s Sailing Seminar. We had some spectacular sunsets, shockingly warm weather for Hardly Strictly Bluegrass Festival in Golden Gate Park, and got to see the dahlias in bloom. We had beers with our old boat neighbors in the Berkeley Marina and shared tales from cruising life. We’d really been missing our community and this visit filled our cups!
Unfortunately, in addition to all of the nostalgia and community that came back upon our return to Berkeley Marina, we also found ourselves reverting back into the stress that we were feeling the last time we were there, frantically getting the boat ready to go. That tension came roaring back almost immediately, with a big to-do list of boat work scrawled on our whiteboard, Jeremy picking up a bunch of in-person work while he could go to the office, and plans to knock out all our doctors appointments and errands and social reconnection before we left again with no planned return. It was almost physical, the way the Bay vibrated with a trembling urge to pack as much as possible into our days. We found ourselves up at night with racing thoughts, our minds trying to keep up with the pace of city life after months of quiet anchorages in the PNW and a long, wild passage down the coast.
That feeling is, in many ways, a defining pulse of the Bay Area. It’s the birthplace of the optimization mindset: a city built on striving toward the future, often at the expense of feeling at home in the present. That outlook subtly pervaded our educations and early careers, and brought us many skills and gold stars, alongside no small amount of anxiety. Returning to the hustle felt like slipping into an old skin: we packed our days, we multitasked, we scheduled every evening to make sure we ticked as many boxes as possible. There’s something we genuinely love about that mode— it’s energizing and social, it feels like coming home to an effective and engaged version of ourselves and a world of opportunities ripe for the picking.
And also, it sucks. It’s antithetical to mental clarity and quietude, to the project of just living (as Jeremy’s therapist once encouraged him to try) as a human being rather than a human doing. To thrive in that environment seems to require jettisoning whatever stillness and contentment we’d learned out on the slow ocean. Our friend Nicole, who left SF around the same time as us to hike the PCT, remarked that returning to the city requires a constant sharding of attention. It feels like splitting a clear but simple mirror into a glittery disco ball— a tantalizing jumble reflecting a dozen things at once, but none of them very well or very long.
Still, there was much joy in the acceleration, especially when it came to people. After months of isolation up north, we dove into the social world we’d missed. We crammed weeks full of people we love in the Bay, and it struck us how many of them have come to feel like lifelong friends. We’ve spent enough life together in this important chapter of our 20s that there’s shared history, touchstone stories, little phrases or mannerisms we’ve taken from them and melded into ourselves. For all the fun and excitement of making new friends in a dozen different places as you travel, that precious depth is hard to attain without roots and commitment. Realizing that left us with the warm but slightly aching knowledge that we’ve built something real here, and that leaving it again will always carry some loss.
The dissonance of feeling both rooted and restless— knowing we want to go and also that we’ll miss what we’ve built— weaves into the dissonant attraction and repulsion we feel towards SF’s busyness more broadly. The culture of the Bay is so alive, so about something, and yet it often feels antithetical to the kind of quiet clarity we find offshore. To live in one world seems to require letting go of what the other teaches you. Finding that we love both of them leaves us unsure about what we will want our life to look like when the sailing chapter is over.
Jeremy had a moment while we were back that brought this into focus. At a contact improv class in Berkeley, he met a guy who’d just moved from Bellingham — one of the towns we’d spent a lot of time in up north. Bellingham represented much of what we loved about the Pacific Northwest: it felt slower, more rooted, less busy. When asked how he’d liked it, the guy said, “Honestly, I kind of hated it. When I moved here I realized I hadn’t felt inspired in three years. Nobody was doing anything.”
That felt like it neatly summed up the double-edged sword we had been grappling with. The same stillness that feels nourishing from one angle can feel stale from another. The same busyness that’s exhausting and sharding is also the engine for interesting things happening. That tension can’t be escaped, but it’s also a source of joy in transition; the good parts of both of these states can only be appreciated in juxtaposition to their counterparts.
This chapter in the Bay left us with more questions than answers about what comes next. When we eventually return from this sailing chapter, we now have enough of a trial run to know it will be complicated. We’ve seen too much of both worlds now to ever belong fully to either. There’s a version of us that feels most alive in motion, and another that feels most at home among friends, routines, and projects. The trick, maybe, is to pepper our life with chapters that swing back and forth, so that we can always appreciate both what we’re leaving behind and what we’re returning to.
With all of that in mind, it surprised us both how calm we felt as we left the Bay to sail South. We woke up at 6am to time the tides under the Golden Gate Bridge and shuffled around in our slippers, getting the boat ready as the Berkeley hills glowed a deep blue. As we motored out of the Berkeley Marina the huge harvest moon lit our way with a shimmering path West as it set over the hills of Marin. By the time we reached the bridge it was lit up bright red in the morning sun, and we glided peacefully under the span, hollering up to hear the echo of our voices bouncing back to announce our departure. We remarked how much more confident we felt leaving this time around. Even though there were arguably more unknowns this time, including no plans for when or if we might return, we felt more sure than ever that this is the life we want to be living.
Until next time,
Maddie and Jeremy (and Tardigrade)
PS- if you want to support our journey by buying a print of any photos from our adventure so far, check out the Sailing gallery on Jeremy’s print store:
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