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Sabbatical #5: Important things are hard

(But they can also be awesome)

Welcome to the fifth 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, 10 totally chill people have signed up. That's 120 subscribers. Woo! If you dig these issues, please forward along to any travel-loving, career-pondering friends!

Today's Itinerary

The Note: Important Things Are Hard

Social media can feel like the world’s most obnoxious upselling salesman.

“Oh did you look up running shoes? HERE ARE VIDEOS OF ULTRA MARATHONS.”


When it comes to designing your life, the phenomenon becomes particularly frustrating. If you’re interested in starting a business it won’t be long before you are served a steady stream of people who claim to run one-person businesses making millions. If you want some parenting advice, it won’t be long before some dude with 11 kids on a farm will be telling you how to create Cheerios from scratch. And if you look into taking a sabbatical, you’ll see a steady stream of people who tell you how easy and fun it all was.

But nothing important is easy. Sabbaticals make for great social media content. But the act of removing everything from your day-to-day life and putting it back together can come with some pain.

It’s in that context I’m happy to share Melissa’s story. Don’t worry, her story has a positive ending, but the path to get there was not what she expected when she set out on her journey. There was some unfortunate timing, like when she returned just as the deepest recession in her industry’s history began (aka the “software as a service (SaaS) recession”).

That blue line is an index of SaaS companies.
Melissa’s sabbatical ended at the bottom of the market.

So goes risky uncertain things like entrepreneurship. Or quitting one’s job to travel without something lined up on the other side. This stuff is not as reckless as most people think, but there is risk. It is difficult.

Sabbaticals demand that your life open up to new experiences. Though there’s no guarantee those experiences are always pleasant. Or predictable.

Important things are hard, and a sabbatical can be the most impactful period of your life. Expect some bumps.

The Debrief: Melissa Dorsch

Melissa Dorsch in 🇫🇷

Melissa took nearly one and a half years between full-time gigs. But that wasn’t necessarily the plan. First, there was the canceled wedding and then there was the historic contraction in her industry. See how she navigated all of this and ended up better off on the other side.

Why take the break?

I was at my previous company for five and a half years doing workplace operations, events, and culture work. It was one of the fastest-growing startups at that time. I loved it. It was amazing. But the pandemic really threw a wrench in all of our workplace plans. 

I was sort of a one man show doing way too much by myself. It just felt like time. On top of that, I was also planning a wedding. I had some trips planned over the summer. I was about to enter my last big employee stock vesting window and so I was like, “This is my time. I'm so ready to go”.

Where did you go?

I left the company on April 1, 2022 and almost immediately went to Costa Rica for two weeks with my friends and my partner — that was amazing. Then we had a month-long trip to Italy planned for later that Summer. The first few weeks I just kept thinking, “This is great! How nice! I can sleep in! I can take my dogs on walks whenever!”

But then it started to have an impact on my relationship. A lot of my identity was tied up in my day-to-day work ethic and I was starting to be a little bit depressed.

Three months into the sabbatical, we broke up.

How did that impact the sabbatical?

I wanted to distract myself. I wanted to take advantage of the money that I had saved, and ended up on my “Eat, Pray, Love” journey. I went to the south of France and Monaco by myself. Visited some friends and went to places like New York, San Francisco, and New Orleans. I would come home for a few days and then go on another trip. 

I didn't feel like I was running away from my problems, this is what I wanted to do anyway. I just thought I would have been doing it with a partner. But by January 2023, nine months into the break, I felt like I was finally ready and in the right mental health space to start looking for work. And that's about when the tech market plummeted. 

We saw so many layoffs, so many people are looking for work in the Workplace and Events industry. I ran my own event planning business for a while, but I missed being a part of a team so I started looking into full-time work. I finally landed myself in, I think, exactly where I was supposed to be, with a startup called Circ in October 2023.

Why did you take the break versus just hopping into your next thing?

I've been working since I was 14 years old. I moved out when I was 17. I didn’t go to college. I worked really hard to get here. Why not do this while I'm young enough and before I have children? Why not take this time to sort of evaluate my next step, see what I want to do, take what I felt was a well-deserved break? 

I wanted to see what fell into my lap, and what the next steps were. Especially because work has such a huge bearing on the rest of your life.

Melissa Dorsch in Hawaii

How has the role of work in your life changed before you went into this versus after? 

I used to be the kind of person that was accessible 24/7. In facility management, that is going to be a thing and you're going to be working after hours to an extent. But I was too reachable.

I'm now better about setting boundaries. I now say things like, ”I'm going to get to this on Monday” rather than working on a weekend, for example. I have been in a way better headspace since. 

Do you feel like the break and allowing all that stuff space to breathe resulted in all these latent things coming to the service? Maybe you realized your relationship with work wasn't what you wanted it to be? Or the relationship with your partner wasn't what you wanted it to be? We can all paper over our issues by staying busy each day.

I think once you have space from anything, you're going to be able to see a lot of the things you maybe didn't see before. I had a really hard reset on life after that breakup. My mental health really plummeted and I definitely attribute that to the change in my career and not having something that's distracting me all the time. 

I can’t stress this enough, it's really important to take a step back sometimes. It doesn’t have to mean that you're changing careers or taking a sabbatical. But take a mental health day every once in a while when you need it. Not everyone struggles with mental health, but a lot of people struggle and don't even realize it.

How did you pay for your sabbatical? 

I started at the previous company pretty early on, and did really well as a result when they went public. I put a lot into savings at first and then hired a financial advisor to help me do some goal-setting. I also had previously purchased some real estate and sold a house right around this same time for a healthy profit. So when it was time to leave, my financial advisor and I had planned for what that would mean financially. 

But, I also thought my sabbatical was going to be a little bit shorter, so I definitely tapped way more into those savings than I wanted to. But luckily, I didn’t have to sell my house to travel or anything. 

You ate into that savings a little more than you would have liked, but you weren't, like, panicking up against the wall necessarily yet?

If you plan to take a sabbatical, be very weary of the market, of whatever you're working in. So if you're working in housing and there's a housing crisis, or if you're working in tech and tech takes a nosedive, it can be a little bit tough. 

If I could have changed one thing, it would have maybe been nice to have something lined up already, just slightly further into the future.

If someone were to come to you and say “Melissa, I’m fried. I want to take a break like you did.” What would you say?

Don't be scared to take a little bit of time off, and don't get scared by my story.

If you're not going to do it now, you probably won't ever do it. Take the leap. Just set budgets, goals, and expectations, not only for yourself but for your family or the people around you, and have good resources around you, say for example if you do end up needing to move in with friends because you couldn't find another job. Don't isolate yourself during the time off because work is such a social thing.

It was freeing to take this break. My stress levels got better, my skin got better, my hormones evened out. I was just so much less stressed on a daily basis. 

Did you do anything purposeful like meditation or a journal or checking in with friends?

I did journal, I did meditate, I do Pilates, I was able to just enjoy the sunshine. 

I listened to a million podcasts, and kind of stayed up to date on LinkedIn. I wanted to know what people were doing. I was still networking to an extent, I didn't want to completely fall off the earth, especially because mine was such an extended time off that I wanted to still stay relevant. 

Don't worry about a gap on your resume. If you can explain it in any way, anything from travel to being a caretaker for someone to spending time with your family, I think it's super important to do those things and hopefully companies with similar values will be totally on board with that as well.

Yeah, in a purely tractional way, when I’m hiring someone and I see they’ve taken a break, it’s relieving. I now know they won’t up and leave because they have taken their big trip already.

I was so ready to hit the ground running and just do good work and just get back into the workforce again and be a part of a team. I don't think it would have been the case had I gone straight from my last job into something else. I came back refreshed and rejuvenated, for sure — and I was just excited to work again.

The Recommendation: Food Tours as Stop #1

When you arrive in a new city, how do you get a lay of the land? Consider starting with a food tour. It’s a quick way to get oriented, meet several locals, and get additional historical and cultural context about the place you are about to explore.

Also, it’s delicious.

🎟️ Next time you’re in Nice, Melissa recommends this one.