When I finished my last day of work, I envisioned an idyllic few months before we threw off the lines. I’d sleep well, get up early, see the kids off to school with a smile, exercise every morning, switch between afternoons getting boat and home prep done and romantic afternoons with Doug, and cook great dinners every night. It never occurred to me that the transition from work to getting ready to sail would be anything but easy.
I was wrong. The transition was harder than I thought. But with time and friends with a willing ear and sage advice, things worked out. I didn’t exercise much and we still went out to eat too much, but we’re a few weeks away from leaving, and the house and boat are almost ready. And I learned a few lessons for next time I face a life transition.
It Took Time to Find My New Groove
My pre-transition life was hyper-busy. 10 – 12 hour days with meetings from start to finish were the norm. After work was kid-driving (Doug did way more of that than me!), making dinner, and family errands. Throw in exercise, friends, concerts, kid activities, etc. and it felt like there wasn’t a moment to spare. Life moved fast.
Then all of a sudden life moved slow. Really slow. It was shocking to my system. Instead of being productive with all this free time, I struggled with how to organize my day at a more reasonable pace. Some days I just wanted to go back to bed. And that was quite confusing. I was supposed to be loving this easy new life!
It took time to find a new groove where I plan my day, accomplish things at a good pace, but also give myself permission to read the paper, chill out, and not always be productive. In hindsight, it shouldn’t have been surprising that it took some time to get into a new pattern, but it was.
It’s OK to Sometimes Miss My Old Life
I was excited to start this new life chapter; to head back out for a year of sailing and to share such a great experience with the kids. I was 100% all in. So, it was surprised to sometimes also miss work. Wasn’t I supposed to be excited?
I definitely missed the people. I worked with a lot of really fun, passionate, interesting people. Yes, there were a few jerks too, but mostly a lot of good folks. I miss their friendship and mental stimulation.

I also sometimes miss the action and the impact. While cleaning out my basement does bring a certain measure of satisfaction, it’s not the same as closing a big deal that will help a nonprofit or university do more. Or helping an employee shape a fulfilling career.
I felt odd missing my old life while jumping into my new life. Some days I had to remind myself that the action and impact will come once we set sail. There will be storms to conquer, interesting cultures to learn about, and hopefully watching the kids grow through this experience. But in the meantime, I’ve given myself the OK to miss work sometimes too. And I’m working on learning to enjoy the small pleasures – sort of.
I Had to Relearn Doing More on My Own
I quickly realized how much I relied on others to get things done, both my team at work and Doug at home. Right after I stopped working, Doug left for a month to sail the boat from the BVI’s to Annapolis. In one fell swoop, I lost my team and Doug! I was on my own for anything that had to get done.
It took a little re-learning to get back at it. I hadn’t realized how much I’d gotten into the habit of too often being the one to think up the idea, but then having others execute the solution. I found the decision-making more fun and had to relearn working through the “dirty work”. Unfortunately, I still have very little patience for administrative duties. Luckily, Doug takes on most of that.
Downsizing Can Be Emotional
I really looked forward to cleaning out all the “stuff” we’d accumulated at home over the years. I blamed it on our hyper-busy schedules, but we had done a horrible job of giving away or throwing out things we no longer used. Our basement, garage and closets were full of baby stuff, kid stuff, clothes, books, and junk! Getting rid of it was going to be freeing. And it was, mostly, but not always.
The kid books may have been the hardest. So many memories of Erin and Andy’s childhood are locked up in those books. Giving them away was officially saying good-bye to those long-gone days and long-gone little kids who are now teenagers. I spent more time than I’d like to admit re-reading old kid books and reminiscing, and then being annoyed by not getting enough done that day.

It also took me a few tries to get through packing up and giving away my work clothes. How many office clothes would I need when I got back? What should I keep and what should I pitch? That led to the unanswered question of What’s Next for me when I return. That led back to Missing My Old Life. You get the idea. I ended up having to pack in waves. First, the easy stuff; clothes I didn’t wear anymore went into a charity box, and clothes I loved were packed in a bin to keep. Then I’d wait a few days and try again, adding a few more clothes to each group. Much more painful than expected, but it eventually got done.
I spoke to a number of friends about how my transition was harder than expected (thank you friends!). And it turns out that my transition from boat to living on a boat isn’t much different than other transitions. I heard similar stories about becoming a stay-at-home parent, retirement, sending a child off to school, etc. Given that this will certainly not be my last transition, maybe I’ll be better prepared next time. And for now, I’m glad it’s almost done and we’re about to head out.