Sabbatical #4: Passive vs Active Careers

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

See last month’s issue here. Since then, 14 totally chill people have signed up. That’s more than 100 subscribers! Woo! If you dig these issues, please forward along to any travel-loving, career-pondering friends!

Today's Itinerary

• The Note: It’s Never Too Late

• The Recommendation: Hut-to-hut in Switzerland

• The Debrief: Rachel Bicha

The Note: It’s Never Too Late

When we are early in our careers, our knowledge of what our working (and non-working) lives can look like is limited. We lack context.

If your mother was a freelance graphic designer, you’ll be more aware of what it is like to work for yourself than, say, the person with two parents who had a “traditional” corporate 9-to-5. If your father was a powerful CEO, you have a better idea of what it takes to climb the ladder (and the costs and benefits of doing so). Steph Curry has natural talent, but surely having the context of his dad playing 16 years in the NBA helped him realize what was possible. 

As we advance in our careers, we meet different kinds of people. We cross paths with different sectors of the economy. We gain an awareness of what is possible. 

When I talk to people about taking sabbaticals, they sometimes lament that they “missed their window” or that they’re too deep into their careers to press pause. On the contrary, the bigger the contextual gap between when you started your career and where you are now, the more helpful a sabbatical can be.

Taking a sabbatical later in your career means you are more aware of what is possible. Whether you want to change course or hop back into your previous career, your cumulative connections and talents make it possible.

Sure it’s difficult to press pause mid-career with “more to lose” and more to manage. But we’ve seen already that you can take your entire family on sabbatical. You can do it as an entrepreneur (see below). You can leave a promotion on the table.

The more career experience you have, the more fruitful your break will be.

📍 The Recommendation: Hut-to-Hut in Switzerland 

If you’re craving peace and a few days to sit with your thoughts, consider a multi-day hike in the Swiss Alps. The mountains are dotted with huts where you can spend the night — so whether you need two days or two weeks to fully unwind, plan the route that works for you. Just be sure to book your huts ahead of time to make sure you have a spot.

Twirling around like Julie Andrews is optional but encouraged.

🎟️ Book your huts.
🗺️ See example routes.

The Debrief: Rachel Bicha

Rachel Bicha’s five-week sabbatical was an end rather than a means. The solopreneur started her own business in part to allow her to take extended breaks. We touch on how we’re not as indispensable as we think (and why that’s a good thing).  

Let’s start with just the overall shape of your sabbatical. Where'd you go? What'd you do? 

One of my big goals working for myself was to be able to take a sabbatical, just because I'd never done it before. I started planning it in February 2023 and I took five weeks off in August 2023. 

The first week, I was just settling in. I went to Switzerland and Austria for two weeks, and then I had a week where I was traveling in New England. And then the first week of September was kind of like reflecting, getting ready to go back to work to Boston.

When I got back, I pretty much went back to the same thing I was doing before. But I feel like I had a different outlook on it in terms of how I wanted to structure my days, and what kind of projects I wanted to take on.

Why was taking a sabbatical an important part of being self-employed? 

I felt like I fell into my career. When I graduated college six or seven years ago, I got a marketing internship. And after a few weeks there, they offered me a full-time position. I took it and liked it so much that I stayed there for four years. It was at a travel company, which was awesome — until Covid happened.

I then switched to this B2B tech company, which wasn't a good fit for many reasons. And then I thought I needed to work for myself. I’d fallen into these different roles based on what I thought I needed at different points, and a lot of it had to do with factors external to myself. 

I wanted to take time to figure out what I wanted to do, separate from these external things. Of course, money is always a factor. Of course, the economy is always a factor. But what are the factors that I'm bringing to the table? And then, obviously, it also just sounded really awesome. [laughs]

So it's almost like this passive career versus an active career, right? 

Especially in the tech space, I think there's a lot of pressure to always be growing and always be moving up the ladder. Maybe taking five weeks off is more important than an extra $10k. 

Did you have any kind of process going into the sabbatical?

I didn’t want to think about work at all. I just let everything run in the background and tried not to overthink it too much. I went to Austria and Switzerland. I did a hut-to-hut hike for two weeks (see “The Recommendation” above). It was more than 70 miles. No wifi, no cell service. I had a little satellite phone to tell my mom, “I'm okay, I made it!” 

That true disconnection was important. And I tried to hold on to that. Before I left I felt like, “Oh, my gosh, what if everything burns to the ground and I don't even realize I'm not even there?” And of course, I came back and nothing had happened. Maybe, unsurprisingly, when I came back the second week of September and I sat down, I kind of felt like, “Yeah, I know what I want. I want more time that feels like THAT.”

Did you have any moment of doubt? Like, “Am I doing this the right way?”

We spend a lot of time having other people tell us what they think we should do. Part of this was clearing a space where I could hear my own thoughts without somebody else's voice. If nothing else happens, at least I'll have done that. 

Your sabbatical is particularly interesting because it wasn't such a dramatic outward change. You resumed your business when you returned. It seems like it was more of an inward change. So what was that change?

There’s something that happened to me that stuck with me during that multi-day hike. I noticed after a week or so that I'm up in the morning and I'm trying to get out the door as fast as I can. I'm packing up, I'm eating breakfast, I'm getting my shoes on. 

And I'm watching all these other people around me, Germans and Swiss, and they're just like sitting on the porch drinking coffee in the sunrise. After a week or so, I kind of started to feel like,” Hey, how come I'm the only one in a rush to get out the door here? Are they only hiking five miles a day? What am I doing wrong?”

After I kind of realized that, I said to myself, “Okay, tomorrow I'm not going to rush. I'm going to go this German route. I'm going to sit on the porch and have my coffee.”

And I just didn't look at the clock, and I just tried to slow it way down. I had my leisurely breakfast, and I got my shoes. And when I finally got out the door, I looked at the clock, and it was only 15 minutes later than all the other mornings when I had to rush and try to get out the door. And that was such a light bulb moment for me. 

I wasn't even saving any time. I was just stressed the whole time. And when I came back, I thought “Oh, my God, this is my whole life rushing around, being stressed, trying to get these deliverables out, and do I even need to be stressed about it? I could just do everything at a leisurely pace and it would be okay.” So that was a really big takeaway for me. 

How did that filter into your day-to-day work?

Now, when I work, I try more to accomplish two tasks. I have two priorities or goals for the day and that's it. And if I finish them at 2 p.m. That's great, then I just stop. 

I also thought a lot about the types of work that I wanted to do. I realized little things like having a balance between the strategy offering and the writing offering allow me to create the kind of pace that I want. I realized that there were a couple of clients I had taken on because I was concerned about the finances or how it would look in my portfolio, and I wasn't enjoying working on them. 

Why did I start my own business if I'm going to keep on doing work I don't enjoy? Wasn't the point to be able to pick work that I like to do? 

I didn't blow up my life or move somewhere else or do something crazy, but I think probably for a lot of people, it's those little mindset things that kind of change the direction of your ship over time.

Much like adjacent dreams, you were adjacent to control of your time and your stress. But you didn't quite commit. Sounds like it took a little bit of reflecting to do that.

It's easy to be self-employed but to carry over that employee mindset. Having the sabbatical shook me out of that. I can take five weeks off in a row, what else can I do? What other options are available to me that I just haven't considered or haven't even seen as a possibility? What if I took six months off in a row? Who says I can't? Who's going to stop me? 

How did you pay for your sabbatical?

My base expenses like rent and utilities were about $3,500 a month. I needed to have that banked specifically for August. So as I was planning out my spring, I just took on that much more work to cover it.

The whole trip was probably, $2,200 to $2,300, including flights. So I needed $5,500 for the month. In the beginning, it felt like, “How can I not make any money for a month?” But then when I broke it down, it came down to just taking one additional strategy consultation. Turns out, one strategy consult equaled a sabbatical. 

What advice do you have for people considering this?

There’s a desire to optimize a break like this. You’ll ask yourself, “How do I get the most out of this time? How do I make this the most productive sabbatical I've ever had?” That desire is just so deeply ingrained in us. Don't try to make it productive. 

Don't try to be an ultra-journaler and figure out your whole life. Do something unproductive. Waste some time. Spend three weeks learning how to play the accordion or go on a really long walk. Whatever! Waste some time and see how it feels to not be productive and see how that changes you. We need a little bit more of that.