My 60th birthday odyssey itinerary

Midlifers!

The countdown is on. In less than a week, I set off for my very own personal odyssey, inspired by not only the recent Odyssey movie (which I loved) but also my entree into a brand-new decade. Since the latter only happens a handful of times in our lives (two hand-fulls if we’re lucky), I really wanted to find a way to commemorate the event. Sixty needed a proper welcome.

It started with no clear plan, the way many of my larger life initiatives have begun — marriage, children, writing. It’s been a lot of putting one step in front of the other and hoping for the best.

My birthday getaway starting point was a few days in Vermont with my kids, staying at a dear friend’s place in Stratton. There’d be plenty of room for everyone to sleep, lots to do in a great location.

Then, the owner of my beloved Maine cabin, where I’ve been staying in the last few years, asked if I could switch my dates, which would push it close to the Vermont excursion.

Rather than driving all the way up to Maine, back to New Jersey, and up to Vermont a few days later — and after a ton of hemming and hawing — I decided to take two full weeks of work and combine the two trips.

And then, like Odysseus finally getting off the beach of Troy after 10 long years, my entire vacation horizon opened up.

Instead of going right from the cabin, which is about an hour north of Portland, to Vermont and waiting a few days for my kids to arrive, I started looking into what else I could do for a few nights. And I was all over the place. At one point, I even considered going all the way up to Acadia, which has been on my bucket list for 20 years. Or maybe Monhegan Island? Or should I spend a few nights in Woodstock, VT before heading south to Stratton?

Earlier in the week, I decided to book an Airbnb for two nights in Rockland, Maine, about 90 minutes north of the cabin, and a spot that’s been on my radar the last few years. It’s right in town, overlooking the harbor, and an easy walk to the Farnsworth Museum — which is what is really bringing me that far north.

I’ll stay there Sunday and Monday nights after I leave the cabin on Saturday, but there was no availability for that Saturday night. That gave me pause, since I don’t like not having a very clear itinerary when I travel. I don’t like leaving things to chance. A good friend went to France with her family a couple of years ago with zero hotel reservations and I can’t even tell you the amount of anxiety that gave me.

But as I considered clicking the RESERVE button for those two nights at the Airbnb, I thought back to a recent conversation I had with a woman I had worked with and admired. I had reached out to her to feel out if she might be interested in doing some consulting work but really, it was a great excuse to catch up. She is a traveler, and she told me all about going to two World Cup games this summer and an upcoming cruise to Alaska. I told her about my Maine odyssey and trying to figure out how to spend those few extra nights and she said, “Why not just wait and see what you feel like doing?”

Then she told me how she and her husband had gone with their then-young son to some European country and went where the wind took them. “If we liked a place and wanted to say another night, we did,” she told me.

Reader: contrary to what I said earlier, I’d really like my whole life mapped out. And preferably, with every stop along the way one that I have personally approved. Of course, I know exactly what my life should look like, I just don’t always know how to get there and I really wish things could just stay on course with my fantasies.

Not for nothing, Odysseus thought the same thing. When he set off from Troy to sail toward home, he immediately deviates from his initial course, thinking he knows the best way to get there — even though all his men are like, “Yo, where are you going?”

And trouble ensues. There are one-eyed giants and a three-headed monster to contend with. A swirling whirlpool in the middle of the sea to navigate. And finally, he ends up stuck on an island for seven years trying to forget everything that had just happened to him. He’s forgotten all about his wife and son, how much he has missed them and his burning desire to get home to them.

It’s not until Odysseus finally stops trying to control the situation and gives it all up to the gods, that he is finally able to make it home. You see him in the movie lying on a raft of cobbled together wooden planks and surrendering to fate. The swells are pummeling the raft and the planks are barely being held together and Odysseus lowers his head and lets the water wash over his face. He’s given up all control — and eventually washes up on the shore of his Ithaca, his home.

Can you tell I love the Odyssey? It’s the original source of not just the Hero’s Journey, but so many great metaphors — and ones I’ve used thinking about my own experience. How alcohol was my own Calypso who I adore but who also kept my trapped and unable to move forward. And then there’s my never-ending quest to find “home.”

And while I am not saying that not having one night booked in advance was especially brave, I did notice a mind shift when I booked the Rockland cottage. I spent some time scrolling through VRBO and Airbnb looking for cute cabins or inns for that single unreserved night, but nothing felt right. For a hot second, I did fantasize about a room at a seaside resort with a hot tub on its balcony overlooking Penobscot Bay for $1,500/night.

But I channeled my former coworker and decided that an opportunity would present itself.

Midlifers: Give me ALL the recommendations. Where to eat. What to see. All the must-do things along Maine’s midcoast.

Yesterday morning, like any good phone addict I picked mine up and immediately opened Instagram. I didn’t scroll far before I saw that a friend had commented on a post about The Lost Kitchen’s new(ish) lunch service. “Oh,” I thought, “I wonder how far that is from Rockland?”

Do you know The Lost Kitchen? Hidden in a restored mill in Freedom, Maine, it has become one of the most sought-after dining experiences in the country. With reservations awarded through an annual lottery, it’s achieved near-mythical status.

I went to their website to learn about lunch and saw STAY as one of the dropdown options. I plugged in my one date, pressed enter, and found that one of the three cabins onsite was available that night. And, it comes with breakfast the next day.

I clicked SUBMIT and immediately texted my bestie to crow about my incredible luck. All day, when I remembered what had happened, I got such a wave of excitement. It not only checked all the boxes for what I had thought I wanted, it went beyond what I could have even imagined.

With that new decade sparkling so close on my horizon, I found myself listening to a lot of Oprah this week. What can I say? I’m always looking for inspiration and meaning, and even though she’s really delivering the same handful of messages over and over, I often hear them in different ways, depending on where I am.

Cleaning up my kitchen early this week wearing my giant headphones, I listened to Oprah talk about how God has a dream for all of us. “And my advice to people is to lean into that dream and stop trying to dream it for yourself.”

It’s always bigger than anything you could have dreamed for yourself.

I’m always telling God what I want (a romantic partner, to write a book, retirement security), but I am very rarely thinking about what God wants for me. Interesting and slightly mind blowing.

So now, I’ll go from the cabin to The Lost Kitchen for a night and then head to a cottage on Rockland Harbor to watch the sailboats before heading to Vermont to spend a few nights with my kids and celebrate 60.

And, not to brag, I’ll set sail on my voyage this Thursday and spend two nights in Harwich Port on Cape Cod with my lovely college friend before heading off to Maine.

Not bad for someone who's been stuck a few times and battled some monsters along the way. Who thought she knew everything and slowly discovered she had so much to learn. And while trying to find home, realized that she had become home for her four children and they, in turn, have become hers.

Midlifers: Since I’ll be traveling this upcoming week, I’m taking some time off from posting here. To keep up, follow me on Instagram and I’ll see you here soon.