Since Kelly was driving me, we could leave any time on Sunday and I could tarry tying up the last loose ends before I left: I put my gigantic mint-colored cabinet on the street, dropped off a couple boxes at my brother’s, bought guitar strings, and got cash from the bank. I even had time for one last brunch with my friends and a shower before I left.

As a parting gift, Kelly bought me a bottle of Maker’s Mark from the store on the corner, known in our household as Corner McRip-Off. As soon as I saw him exit the store, gripping the narrow neck of a brown paper bag, I had a hunch of what it was. Then I saw the fake red wax on the inside which confirmed my suspicions. We got to-go coffees from the cafe kitty-corner to Corner McRip-Off and drove off.

The drive down was silent and uneventful. We stopped once to take a pee because of the coffees we downed at the beginning of the drive. Kelly’s offer was a courtesy, but I got the feeling he wanted to see me off. We didn’t need to exchange any words because we both understood each of us were in a transitional period in our lives. We are also old enough to know how the world changes and it’s not good or bad but the way it is. We had been living together on Jackson Street with two other roommates for the past two years; two of the most fun years of my life. Kelly had a near nervous breakdown when he first moved in. I don’t know if the diabetic symptoms caused his anxiety or vice versa or if there was something else that caused the two. Whatever the cause, he was suffering from them both. He read the symptoms online. Numb feet, dumb legs, then blindness. He was saying that his feet felt numb and probably thinking what would come next. With some time off his new job, a couple of visits home to Sacramento and a little help from his friends, he got over it all and we started to have a blast.

After a few more months, Kelly started dating his long time friend from college, Sarah. They had been hanging out all the time since he moved to the city. So much so that, one time, when Sarah was with her family and talking to Kelly on the phone, she passed it around for everyone to say “hi”: mom, dad, grandma, and sister. I encouraged him to ask out Sarah, saying that they were pretty much already going out as it is. After some missed opportunities and involvements with people they never liked as much as each other, things worked and they started dating. But, like I said, not much changed; they were already best friends to begin with.

On October 1st Kelly moved out of 1363 Jackson Street and in with Sarah. I was now the oldest tenant in our revolving door apartment. Crystal, the only tenant who was there when I moved in, moved out 4 months earlier to be with her boyfriend in New York. A year earlier, Vivek, who was also there when I moved in, moved in with his girlfriend, Becky, who was also a brief tenant before she moved to Texas and back to be with Vivek. Kelly actually moved in when Becky moved out. I felt stale. I had lived there for two and a half years and probably lived with 10 other roommates and sublettors in the same building. Crystal was a teacher so she’d rent out her room for the summer months. There was Liz, the unemployed smoker from Pittsburgh; Tucker, the HP consultant who liked to play Wii; Lee, the high school science teacher from an Indian reservation in Montana; Shane, the law school-dropout bartender; Emilie the MIT student who interned at Apple. When I left there was Cesar the Italian cook from Jersey, Lisa the unemployed paralegal from Long Island, and Caroline the ex-office worker aspiring dog-walker. Kelly and I lived with Caroline for a year. She was a permanent resident and a fixture at 1363 like I had been. I felt bad moving out on her as I’m sure Kelly felt bad moving out on both of us. But after venting to Crystal over the phone I think she understood. I had been talking about quitting my job and traveling since before she even moved in. We came to terms with the situation and I made sure not to leave behind any unwanted garbage like the gigantic mint-colored cabinet.

Kelly had Pet Sounds playing in his CD player. It’s a sappy adolescent album whose greatness I’ve only recently discovered. Most people will recognize the zippity-doo-dah love songs like Wouldn’t It Be Nice and God Only Knows, but there are songs that deal with some heavy emotional topics on that album. When I listen to Here Today, I think of the six odd fleeting relationships I’ve had over the last year and how none of them made sense. I Know There’s an Answer, offers a possible solution if not inspiration to find one. Don’t do life alone and get out of your safety zone. Then there’s Sloop John B which is a happy song about a homesick sailor, which seems like an allegory for something.

We arrived in Santa Cruz after the sun set. We stopped at the first Mexican joint we found and ate the burritos we’d been craving the whole drive. The dinner, like the drive, was speechless. We griped about the Sunday blues. He would be going to work the next day. We cleared our trays and navigated our way to the Santa Cruz Harbor. Captain Gary emailed me directions on how to get to the harbor, including helpful landmark cues that you don’t get from Google Maps like, “go right at Betty’s Burgers.” Just like he said, I saw Crytal Blue Persuasion at the bottom of the hill at the end of the pier. There were tools, hoses and electrical cords strewn about in preparation for the voyage. Kelly helped carry my bags to my berth and said, “I better get out of here.” He had nothing to do on the boat and needed to get back to San Francisco at a decent hour, besides, we had just spent a serene two hours silently saying goodbye and closing a chapter of our lives.

There are many ways to travel and I’ve done most of them: airplanes, cars, trains, buses, and bicycles. All that leaves is motorcycles, boats and hot air balloons. Boating (more specifically, sailing) is probably the least popular method of transportation due to its expensive and inconvenient nature. It is also the most romantic (or so I’m hoping). Being propelled without motor on the open ocean and nobody and nothing but who and what’s on the boat. Historically sail boats were the only efficient way to transport cargo and men would labor on them for a meager wage. Now sailboats are toys and men sail them for recreation, paying for the opportunity.

I first learned to sail in 2001 when I took sailing lessons at Mission Bay with my dormitory suitemate. Neither of us had a car so we rode the 34 bus down La Jolla Shores Drive to Mission Bay. We got off at Santa Clara point and walked to the Mission Bay Aquatic Center, a rec center set up for the area colleges. The first type of boat I sailed was a Sabot, which our instructor described as a “bathtub”. I think he was describing the shape of it because a real bathtub would sink. It’s a simple boat with only one sail. Anyone sailing in one looks a little foolish but it helped me learn the points of sail and how to steer using a rudder and tiller. After some more classes we moved up to a larger boat, the Holder 14, which has a jib and centerboard. We also went out on a Hobbiecat once or twice.

Mission Bay Aquatic Center didn’t have any keel boats. Or if they did, they were few and we couldn’t take them out. And if we did, we would be sailing in Mission Bay, which used to be a marsh called False Bay until it was dredged and renamed somthing more marketable. Looking at the bay, this makes sense. It’s peculiarly shaped, shallow and still murky.

Once we finished our basic and advanced sailing classes at MBAC, my friend found out about the Navy sailing center in Point Loma. Since my dad’s a retired army officer, I had a US Armed Services ID card that gave me access to military bases and their facilities. They had Catalina 22′ and 27′ boats for rent, but we would have to complete their training program to take them out. We took the courses and started sailing in San Diego Bay.

There were countless days in the office at my old job where I sat in my swivel chair wondering, “Is this as good as it gets?” I won’t restate the tragedy of offices and office drones because it’s been done before and I’m sure you have a first hand experience in such an environment. My anxiousness got so bad that I convinced myself that the most foolish thing that I could do was NOT quit my job and go sailing. When I told my dad my plans, he pondered a bit and said, “I think it was Thoreau who said, ‘Most men live their lives in quiet desperation.’” He was right. Up to that point I had been living my life in quiet desperation, taking the safe route that I’m supposed to take instead of the fun, risky route that I dream about when I’m sitting in a meeting pretending that I’d still be in the room even if I wasn’t getting a paycheck.

Not exactly a year ago, a good friend of mine, Bridget O’Brien was killed in a car accident with her husband. She was driving her husband’s band, the Electric Jellyfish, through Ohio when she swerved to miss a deer. She was an inspiration to everyone who had the luck to meet her. This became blatantly apparent from reading her memorial website and attending her funneral where there weren’t enough seats in the chapel for bereaved to sit. I am still shaken by her death and inspired by her life. She died doing what she loved and saw more of the world at 26 than many people see in their entire life. Her death taught me that life is short and it’s never too late to seek adventure regardless how crazy it may be or how old think you should behave. I know I am making her proud, but I’m doing it in my typical slow style.

I have no ties. I have no car, no mortgage, no girlfriend, no kids. I barely have any furniture. And what I have only has utility value to me; I couldn’t sell it to anyone for an amount that’s worth my while to arrange a sale. One girl I told this to looked at me with a frown and said, “That’s sad.” I think I planned it that way, though.

I’m going to miss all my family and friends, especially during the holidays. To this, I say, you always have to miss something. There’s no doing anything where you’re not missing out on something else. I would say I can catch everyone when I get back, but after Bridget’s death, I realize it’s not a safe assumption, but it’s a pleasant one so we’ll leave it at that. And San Francisco. I will miss San Francisco. But she too will always be here with her buildings and her bums and her jobs.