Welcome to Sabbatical — an exploration of the future of work, designing your life, and travel. Sent every month-ish. (Submit your sabbatical story for a future issue here.)

See last month’s issue here. Since then, 36 totally chill people have signed up. That's 182 subscribers. Woo! If you dig these issues, please forward along to any travel-loving, career-pondering friends!

Programming note: I’ve left my full-time job to focus on creative pursuits like this newsletter and spinning up a publishing house to publish more cool stuff online. The feedback about these lil’ issues has been amazing and subscribers like you were part of the reason I felt comfortable making the move. ❤️ 

Now let’s get to the issue, it’s a fun one.

Today's Itinerary

• The Note: Living Your Life in Seasons

• The Debrief: Frances Benjamin

The Note: Living Your Life in Seasons

Take a second and imagine the trajectory of your life. Which direction does it go?

No, literally, the direction? Is it going left? right? out? up?

Chances are you see your life as something that progresses linearly. Something that builds on itself. There’s a reason we climb career ladders. We aspire to marry up. We want to build a life by setting a solid foundation.

In 2024, life and careers don’t work that way. A framework used by several past interviewees that I find myself using: you’re living your life in seasons. Each phase of your life serves a different end. Sometimes it is a restful season. Other times, it is a season to work and amass wealth and knowledge. Sometimes you are focusing on family. Other times, yourself.

The key is knowing what season you are in and why you are in it. Be purposeful and unapologetic about what season of your life you are in. This means getting FOMO and letting people “pass you” while you are resting. Sabbaticals can be difficult when you see your peers getting promotions or accolades that, deep inside, you think you could have had.

It also means missing out on some things you would find short term fulfilling in service of some larger goal. Most entrepreneurs of massive businesses point to birthdays missed, health sacrificed, and hobbies left unexplored.

In this issue, we profile Frances who thought she was in one season, but was quickly pulled into another.

She worked in hospitality during the pandemic. She raised a daughter as a single mom and she was the sibling that lived closest to her elderly parents.

But just as she was getting underway for her long-planned sabbatical, her family was rocked by tragedy, and she was pulled back home. She began to question her plans, her place in her family, and whether she was “too late” to take the trip of her dreams.

She had every reason to restart her “old life” — but she pushed on. And on the other side was a “lightness” that began her newest phase, one centered around flexibility and family. 

In this Debrief, we see yet another example that hitting pause on your life may not go exactly as you planned it.

The Debrief: Frances Benjamin

Tell us about your sabbatical. When was it and why did you do it?

I tell people all the time that the pandemic was a blessing to me. In 2020, I was the general manager and also an HR director of a casino and two small hotels in the Virgin Islands. I was also a single parent to a high schooler.

And basically I had three jobs: two at work and one at home. When the world stopped, everybody stopped working, but I didn't. The infrastructure of my company still had to keep going. The bills still had to be paid. So I still worked and I still got paid. 

My daughter was in 10th grade at the time, and I knew obviously that in the next couple of years she would be leaving and going off to college. And so I decided at that time to take a sabbatical, while I have the luxury of still earning an income and the flexibility of being able to travel with my daughter. 

I got really serious and I hunkered down and I paid off all my debt except for my mortgage. I saved as much as I could. At one point, I was saving about 50% of my income. And on June 3rd, 2022, I left my job.

Did you wait for your daughter to move out of the house before doing this?

I wanted her to experience some of it with me. When she finished high school in June of 2022, we signed her up to start university the following January. So instead of spending the Fall semester at school, she traveled with me.

You very easily could have just dialed back your responsibilities or found another job or moved and kept working. What was appealing to you about taking this break?

It's just important to take a break. And I don't mean take PTO or take a vacation, because it's not the same. You know, a break really needs to focus on you and what you want for yourself and not for an employer.

I wanted to travel and experience different cultures and different environments. I come from a very small island community [in the Virgin Islands]. And travel has always been very important to me, especially having a child. I felt, and I believe still do, that travel is a big educator. And so I always wanted to not only do that with my daughter, but also for myself. 

Tell me about how you approached your trip. 

Initially, because my daughter was going to be with me for the remainder of 2022. We had a dog that we couldn’t take on the trip. And so we flew to Atlanta, dropped the dog off with my sister.

Then my daughter and I went to Mexico and traveled to a few places in Mexico for a while. And the plan was after we left Mexico, we did some house sitting in California, and then she wanted to go to New Orleans and Colombia before she started school in January. 

How did being a single parent impact your planning here? 

The world of your kids is greater than where they happen to live.

The biggest part of their education and their growth is through the experiences that they get. Those experiences are outside of the bubble that you're in or they're in in their schools and stuff like that. 

I look at it as the experience, not only for myself, but the experience and the education that I’m giving to my child and exposing them to the world outside of where they live.

You said “the plan was” like it didn’t work out that way.

It didn’t. We left Mexico, I believe, in September, and when we were housesitting in California I got a call that my mom was on life support. We had to go back.

The day after we landed home, we had to take her off of life support and she passed away. So the trip ended. As difficult as it was, it gave me the opportunity to spend a lot of time with my 83-year-old father and to make sure that he was okay.

I struggled a lot. Do I continue what I had started? Or do I stay and make sure that my father is okay? And so ultimately, I decided that I would stay until the end of the year. I knew the holidays were coming. I didn't want him to be alone on the holidays and stuff like that. I knew my daughter would be going off to college in January.

In January, my father and I dropped her off in Savannah. And we went back to the Virgin Islands. 

And the feeling came back again. It's like, “Are you gonna not continue this journey that you started out? What are you gonna do?” 

I have this promise to myself, where every year on my birthday I have to wake up in a place that I have never been before. My birthday is in February. And so now here we are in the beginning of the year and I'm like: What am I going to do? Am I going to continue? Am I going to stay? 

And then my dad said, “What are you talking about? You have to go, you have been planning this thing for two years and you know I can take care of myself.” It was difficult for me. I still struggle because he and my mom were joined at the hip, and now I'm leaving him alone. He was like “No, you gotta go.” And so on January 31st, I got on a plane to Thailand.

I had to start over.

How did losing a parent while you're thinking of this journey affect the way you approach it? 

One of the things that I had to remind myself of is that I had done a lot to prepare for this moment and I had shared it with my parents and they were aware and they knew how important it was to me. 

It made me feel like “it's time for you to start thinking about you and what you want because all this time as a single parent you've always taken care of someone else.” 

But as my parents aged, I questioned myself. But since these people that I care for: my daughter, my parents, know how important this is to me and know that this is something that I want to do. 

I just kept wondering, when are you going to stop and put yourself first?

What’s interesting is that, the very moment you're ready to expand your horizons, you have this moment where you actually have to come back home and focus on family. But once everyone else was settled I bet returning to your journey felt … lighter?

100 percent, much lighter. It was like weight lifted off. Absolutely.

So let's talk about the fun breezy light period where you're gallivanting all around the globe. How did you think about it? How long did you intend to go?

I started out making a list of places that I wanted to go. Not necessarily planning strictly like April I'm going to go here, May I'm going, you know what I mean? After a month in Thailand I headed home, stopping in Doha to take advantage of their stop over program, and I came home to check on my dad and he was okay. So I left again.

I went to Paris, it was okay. And then I went to Morocco. I had been to Morocco before and I really liked it. And I ended up doing a group trip and I met a bunch of women. It was great. But then I had an accident.

What was the accident?

We were on a tour of a museum in Morocco, and I misstepped at a fountain and I fell. It was awful. I was freaking out because I thought I had messed my knee up again. I ended up having to get the doctor to come into the hotel and I was put on crutches.

Luckily for me, I was surrounded by other women that just really stepped up and took care of me. I was preparing to go to Lisbon, and it turned out that a lot of the women I met were going to Lisbon as well. And they took care of me. I don't know if you've been to Lisbon, but it's a lot of hills and a lot of cobblestones so that was a little difficult.

They pushed the wheelchair and they carried my bags. One of them went with me to the ER. I mean, it was amazing. Luckily it turned out not to be anything serious. 

Tell me about the end. When did you decide to stop traveling and how?

I called it at the end of 2023. When I got back to Atlanta, I decided that I would travel more within the US. And one of the things that I started doing when this whole thing jumped off was house sitting, so I would book house sits in different parts of the US. I booked some sits in Miami. I booked sits in Savannah. 

I booked a three-week sit in NYC that allowed me to catch up with friends, hang out, and take in the city vibes without having to pay for accommodation. Housesitting is the ultimate travel hack!

How does housesitting work? How did you find houses? How did you get introduced to this?

It's amazing. I use Trusted House Sitters. House sitting is huge in places like the UK and Australia. Those are probably the biggest areas. People post that they need a house sitter in this location for this amount of time. Some of the house sits that don't include pets. They can be dogs, cats, horses, whatever. You have a video interview and then if there’s a match they hire you. 

You have to the location on your own. But once you get there, you don't have to pay for accommodation. You water their plants, you walk their dogs. And I'm a dog lover, so it just kind of was a natural thing for me.

How did you fund this trip?

I saved a lot of money and I sold a lot of my stuff, like my car. I created buckets of savings, and I had money specifically for travel. I had a bucket of money just to pay my mortgage. I had a bucket for courses I wanted to take. I did not work, but my house became a huge income generator because I rented it. And a third of the rental covers my mortgage. So the rest of it is mine. So that was a big help. 

Initially, I thought I would spend, I don't know, maybe 60 grand for the year? And I ended up spending less. 

Most people come home because they run out of cash, but it feels like you came home because you were ready. So tell me about what it felt like to be ready.

One of the things that made me feel ready was that I was kind of tired of living out of a suitcase. I wanted to get back the feeling of sleeping in my own bed and cooking with my own pots and stuff that weren't mine. 

Because, again, my daughter was in Savannah so I chose to settle there. It kind of reminds me a little bit of where I'm from. I am very winter averse [laughs].

How did your life change post-sabbatical?

I am not a typical sabbatical age, as you can probably tell [points to gray hairs].

I knew there was no way that I could go back to work and living life as I knew it for the past 30 years. And so it was never really my intention to go back to that full-time hospitality business.

Recently, in the last couple of months, I have taken a step back into that world and started HR consulting and started consulting other women about taking a career break. And so I'm building that for myself now, but with no intention of going back to the old life.

So it's not quite a retirement. It's not even a semi-retirement. It's kind of like you're still working as much as your capacity allows. It's just that flexibility seems to be the most important thing.

Flexibility is of the utmost importance. My dad is still back home. And so I need to be able to get there if I need to get there. And I know that working a nine to five for whomever would not always give me that flexibility. My dad is 85 and he lives alone. If I need to get there, I gotta get there.

Travel is also very important to me. There are so many places still on my list so having portable work is a must.

Given your focus on taking care of your family, you alluded to having a little voice in your head saying, “You’re being selfish!” How did you handle that?

For me, what I had to tell myself was, “You've taken care of people all your life. You've done it. Take something for yourself. Keep something for yourself. You are worth it.” 

You made the sacrifices. At what point are you going to reward yourself?