*Disclaimer: This is a long one, skip if you don't want to read approximately…

Disclaimer: This is a long one, skip if you don’t want to read approximately 1 chapter

And you may find yourself in another part of the world… And you may ask yourself, “Well, how did I get here?” -“Once In A Lifetime” -Talking Heads

That is the subject of today’s musings. While waiting for my morning coffee yesterday, the barista and I started chatting, and the inevitable question came up after I said I’m passing through on a sailboat from Chicago enroute to the Bahamas… “Wow, so how did you get here?”

A question I’ve been asked by every bartender, barista, and beekeeper (I did meet one!) from Paducah to Apalachicola. One that I almost feel guilty answering sometimes. How does someone who is 30, just leave life on land behind and sail off?

Well. How DID I get here?

I could go back to the very very beginning, but we don’t have time for that. So I’ll give you the sparknotes version. My parents met at a Regatta (sailboat race), my mother was there to meet my dad’s roommate, but it was a classic case of “I Saw Her First”. Yadda yadda yadda some 35 years later they are still married, round of applause for Mary Beth & Jim. I used to tell my charter clients “I only exist because of sailing”

By 6 I was in sailing lessons on an Opti Pram, hating every second of it. I still remember coming down the drive every morning to the boat ramp in Lake Forest and my mother saying as she looked out at the lake “You’re the luckiest boy in the world” In many ways, she was probably right, but at 6 I could just groan and roll my eyes.

Fast forward to 15 or 16. Something made me realize that if I knew how to sail, I could take my friends out without adult supervision. Being able to do any “adult” activity without an actual adult was all any of us actually cared about in high school right? Like driving, but on water… I started taking sailing seriously. I fell in love with it shortly after. It was like falling in love with an old friend you never paid much attention to. My very own “When Harry Met Sally” but Sally had sails instead of a skirt.

Around that same time I was starting to look for my first car. Setting the bar for the rest of my life by never doing things the easy way, I searched for what would be my first car restoration project. It ended up being a 1974 Ford Gran Torino. In the first of many gestures from family and friends that encouraged me crazy schemes, my father agreed to fly with me to Winnipeg Canada the day after thanksgiving to drive this $800 car home through the tundra. He then helped me with completely restoring it, body, paint, interior, engine, etc… He taught me everything I know about fixing stuff and tackling a big project. That car, taught me about resilience, more times than I can count. After 10 years of ownership, the car is now prowling rural France. Bonjour, Huggy Bear. Fast forward to college and beyond. I made a decent career out of producing entertainment tours. But I always found a way back to the water. When I wasn’t on the road turning some of the finest arenas and stadiums of America, Canada, Mexico, or Australia into a Monster Truck playground, I was back in Chicago teaching sailing.

One thing has always been a constant in my life, sailing…

So when I reached a fork in the road, a touring job opportunity in LA or staying in Chicago with my then partner (next time you see me, ask me about the time I cold emailed Arthur Fogel and got a job offer out of it), I chose Chicago.

I ended up leaving the touring industry completely and took a role running Chicago Sailing. Up until COVID closed it in 2020.

At this point in my life, every job, and every formative experience had been something that either; I didn’t want to do (sailing lessons at 6), or something I had been advised against (taking a job with Monster Jam while still in school). Every part of my life that I look back on now with a fond memory of, started as something I didn’t want to, or was told not to do.

So here is where the story of this trip to the islands really begins to develop.

November 2020. I had just been laid off from Chicago Sailing. No idea what I want to do next. I get a call asking to captain a catamaran delivery from St. Thomas to Marco Island. Sure! Make a couple bucks and go do some open ocean sailing which always clears my head. So off I went. Now, this trip is worth a whole separate post in and of itself, so I’ll skip the details.

Something happens when you are 100+nm from land in any direction, with 1,200nm to go. There is no internet, no phone, no texting, no Instagram. It forces you to be present. I distinctly remember sitting at the helm as the boat rocked and rolled, staring up at the milky way and thinking “every decision I have made in life, has led me to this moment, on this boat, at this point in time.” Whoa, trippy dude. Anyone who has been in the middle of nowhere and just stared at the sky for a few hours and let their mind unwind knows what I’m talking about. If you don’t, go get in your car, find a campground in the middle of BFE, take an edible and just stare at the sky for a few hours. Trust me it’s aweome.

Anyways. I had this, let’s call it “Chicken Noodle Soup For The Soul” of a sail. I came back to a cold and blustery Chicago with a reinvigorated sense of purpose and life. I promptly ended a relationship that I had determined was not good for me or my mental health.

So what do you do when you are laid off and newly single in the worst season to live in Chicago? Well if you are me you search for a project. I had sold Naida, the 1935 Grebe I lived on for 3 summers and I needed something to tinker with all winter. So off to Craiglist-land I went. There was one listing that really got me going. A 1969 Rolls-Royce Silver Shadow, just outside Detroit, asking price 3k. Why? Because who doesn’t love a Rolls, and because after selling Naida one night I thought to myself “I miss having something to varnish” God’s honest truth. A roller has plenty of pretty burl wood to varnish.

I PROMISE this is where we start to answer the “How did I get here” question.

So again, against everyone’s advice, and my better judgment, I rented a Uhaul trailer, and off to Detroit I went. Some haggling later, I was on my way home with my $2,000 Rolls-Royce. Now, it’s important to mention at this point, that while my friend Nick Naber thought this idea was absolutely ridiculous he was the only one brave enough to dive into the abyss with me. The next day Nick ALSO rented a Uhaul trailer and dragged back to Chicago a $1,000 1986 Jaguar XJ-6.

So naturally, it became a competition. Nick’s “Maggie” vs. My “Lady Edith”

His car ran, drove, and stopped under it’s own power. He had a head start over my Roller that hadn’t been driven in 10+ years and didn’t run. As I dug into Edith’s mechanical heart, it became worse and worse. Bad fuel pump, seized valves, bent push rods… What was supposed to be a tune-up, became a whole top-end rebuild. It didn’t end there. Everything on a Silver Shadow is about 10x more complicated than a typical car from 1969. A high-pressure hydraulic system that ran the 6 brakes calipers, and the suspension. A very early version of an “automatic climate control” that didn’t work. Stuck electric windows, rust, electric seats that didn’t work, the list goes on…

Being a recently single Type A busybody with seasonal depression during a Chicago winter, this car kept me sane. Literally. It gave me a reason to get out of bed every day and leave my apartment. I had victories, and losses. The over-complicated 1960s Rolls-Royce technology was the perfect puzzle to solve. It challenged me every day. The gear selector in a Shadow is electric, not a linkage. The actual motor box that shifts the transmission is more complicated than an entire Ford Gran Torino. The fuel pump? Imagine how complicated a fuel pump could be, then multiply that by 5. For 6 months, 7 days a week I would get up, walk the dogs, drive to the (unheated) shop and lay on the cold dirty concrete slab of a floor and try to fit another piece into this rusty puzzle.

Each system on the car was a puzzle to solve (and an expensive part to order from England). I ended up meeting some interesting folks along the way, people I am now thrilled to call dear friends. The world’s leading Rolls-Royce restorer Rodd Sala, and his team (Hi Jimmy!) at Park-Ward Motors. The look on Rodd and Jimmy’s faces when I dropped off the heads and quote “some of the worst condition calipers I’ve ever seen” then explained to them I was doing a restoration of a $2,000 car with the plan to drive 1,000 miles around the lake was priceless.

Oh I’m getting ahead of myself, while all of this was going on Naber had the brilliant idea of adding a driving component to the challenge, a trip around Lake Michigan. Yes, the idea for Lap The Lake actually came from him! I’ve always said he was the smarter of the two of us, I’m just the crazier one.

As we mentioned our plan to other car enthusiasts interest grew, to the point I decided to make an actual event out of it. Well, a website later, and after several cold emails (always worked in the past for me, so why not now) I ended up with 49 teams entered and Hagerty as the title sponsor for the 1st “Lap The Lake Rally”. Fun fact, I had never done a road rally. So I just made it up as I went a long.

It was such fun that when I opened registration for 2022 it sold out with twice the teams (100). At this point, I realized I had something I could replicate elsewhere… At the same time, I had just entered a purchase agreement for Gypsy. The wheels started turning in my head…

So in June 2022 I quit my fairly new to me job with Xtreme Xperince to pursue this rally thing and my desire of sailing in warm weather 12 months a year full time. Shoutout to everyone at XX, it’s a great company, and I loved my time there but like the song says “Brandy, you’re a fine girl, but my life my love and my lady is the sea”

Striking it out on my own hasn’t always been smooth or easy. In fact, most of the rallies I planned for 2022 were canceled. Gas prices and inflation scared off most folks. But I learned a lot and recalibrated for 2023.

So. How did I get here? Because after a few interesting career choices and being laid off, I did the stupidest thing you could do. Bought a $2,000 Rolls-Royce to restore, then asked a bunch of people to drive around Lake Michigan with me.

But that’s not really all. I was lucky enough to have an excellent friend that instead of just saying “You’re crazy” had the gall to say “You’re crazy, I’m in, also what if…” and a family that have always enoucraged me, even when they (or I) can’t see whats around the corner from one of my crazy schemes.

If you want your life to be interesting, make interesting (sometimes stupid) choices, and better yet, surround yourself with interesting people. You may just end up sailing from Chicago to the Bahamas.