Sabbatical-Curious? 5 Reasons A Sabbatical Might Be The Best Time And Money Investment You’ll Ever Make

The Great Resignation isn’t over, no matter the state of the economy. Workers across all industries and positions are leaving their jobs for greener pastures, including those in SaaS, sales management, and B2B tech.

For many, a chief reason for leaving is because they’ve had enough with living to work. Instead, the focus becomes working to live—less Great “Resignation” from their jobs, more a Great “Rethinking” about their jobs.

Part of that rethinking process often involves taking a sabbatical, an extended period of absence from the working world. Sabbaticals are also known as “professional pauses” or “temporary hiatuses,” but in addition to being a period of rest from work, they can also be fulfilling in many different and surprising ways.

To gain insight behind the myriad decisions to take a sabbatical, we interviewed professionals in the SaaS and startup space to learn about what led them to taking time off.

1. A sabbatical to build a startup

Sometimes an idea is too good to pass up, and you need time to mull over the potential for a new company and product. And sometimes, that means you take a break from one job to start another.

Michael Tuso is the former director of revenue performance at Chili Piper, a lead conversion app. He left his job in 2021 to take a year-long sabbatical in preparation for building his own startup.

One worry that Michael had was finances: how do you support yourself if you’re not working?

But as Michael put it, “Your bank account never has quite the amount you want in it before you quit your job.” If you’re not going to do it now, when are you?

To work things out, Michael saved as much as he could and moved to southern Oregon, where living costs were half of San Francisco. During his preparatory year, he did a lot of professional soul-searching, looking for answers to important topics like:

  • The type of company he wanted to build.
  • The employee experience he wanted to provide.
  • The relationship with his cofounder that he wanted.
  • The work/life balance he wanted to strike, namely, not being a stressed-out CEO projecting his own stress onto his team.

The best place for Michael to receive guidance on those topics was simple but not readily obvious: getting advice directly from CEOs as mentors.

“Finding mentors was a game changer for me. It made the leap from an employee who reported to a CEO to an entrepreneur who no longer had a boss much easier,” said Michael. “Their advice, having been an early stage CEO themselves, made me progress much faster—it helped me give a blueprint for how to approach the huge task of building a business.”

By talking to other CEOs and gaining critical feedback on his plans, Michael was able to use his time off wisely. Sabbaticals don’t have to be goal-oriented, but for those looking to accomplish something new, setting intentions and seeking out feedback helps you stay on track.

2. A sabbatical to change your career

Maybe you’re not looking to start a business, but you’re still feeling the itch to try something new professionally.

That’s what happened to Chester Liu, the former vice president of commercial sales at Allego, when he felt his work/life balance begin to spiral out of control. He was working 14-hour days, putting off doctor visits, and realized he couldn’t even schedule coffee with friends. Something had to change.

He went on a sabbatical in early 2022 to evaluate what he wanted to do with his life. During his time off, he learned a new programming language, launched an app in the Google Play store, and came to an important personal realization.

“I’m a technologist,” Chester said. “I love building great products. And when you’re in sales and marketing, you’re on the receiving end of the product, you have less influence over ‘what is the company is actually building.’ So that’s why I decided during my sabbatical to also get a product management certification and redirect my career in that direction.”

One impetus for Chester’s openness to a new career direction was an experience he had at the MIT Sloan School of Management. He had a dinner conversation with a local Boston entrepreneur, the founder of Sycamore Networks, who told him that he’d known nothing about networks before he’d founded that company. But he’d brought together great people to build it, and succeeded.

Why did this founder pursue something he had zero experience in? Because one of his core principles was to reinvent himself every 10 years to do something different.

Looking back at his own life, Chester saw that he’d spent 10 years in academia, 10 years in engineering, and 10 years in sales and marketing.

Now it was time for his next 10 years in product management, combining his technical and business expertise to launch the next chapter of his life.

3. A sabbatical to combat burnout

Of course taking time off can be just that—taking time off when you feel burned out.

For Ben Chambers, former senior director in sales compensation at Databricks and New Relic, his decision to hit pause on his career was a long time coming. He’d hit the ground running professionally, working full-time straight out of undergrad—all the way up to just a few months ago. Counting the full-time jobs he’d worked every summer while in school, he’d worked through 25 straight summers without a break.

So he decided it was finally time for his summer vacation.

“I think what mentally changed for me was accepting and prioritizing that life is too short to keep trudging down the same path.” Ben said. “So I’m taking a breather and exploring what I want the next phase of my life to look like, both work-wise and outside of work.”

Ben has used this time off to explore alternative formats for work outside of full-time employment to achieve the work/life balance that he wants. He is launching an advisory and consulting practice focused on his subject matter expertise in sales compensation, in addition to helping launch a craft pastrami shop in his neighborhood. Exploring these different avenues has allowed him to reflect on and revisit his fundamental relationship with work.

“That has been therapeutic, in a sense, by pulling the ripcord without a clear plan in place for what is next,” Ben said. “It has given me the time and headspace to be more receptive to new possibilities and directions for the next phase of my life.”

4. A sabbatical to travel

Many people dream of quitting their jobs, and taking off to travel and see the world. But those who actually do it are few and far between.

Kim Orlesky is currently the VP of sales at ConvergentIS, a business technology platform, but back in 2014 she left her position at American Express’s global corporate payments division to see what more life—and the world—had to offer.

It was not an easy decision to make. American Express told her she’d have to leave her position if she wanted to go, and her family told her that if she left the corporate world, she’d never get back in.

Thankfully, Kim was ready with a response for any potential future employers ready to say no to her based on a six-month gap: “That’s probably not a company I ever want to work for.”

She traveled to 17 different countries across Australia, Asia, and Africa. In fact, her trip turned out to be far more than just time off. Kim said that traveling for six months was one of the best investments of time and money she’d ever spent. She got more out of her sabbatical than her four years of postsecondary education, including:

  • Learning to push herself out of her comfort zone, by going to countries where she didn’t speak the language.
  • Learning to write, by blogging about her travel experience, which turned into influential LinkedIn blogs later.
  • Learning that it’s okay to not have everything prepared/analyzed in a spreadsheet. Some of her best memories were unplanned, like listening to folks in Cambodia telling her to visit the pink dolphins, and then just going to see them.

Kim said that most of all, she learned to listen to people, trust them, and be open to anything. That influenced her the most when she returned from her sabbatical and started her own business.

“I knew that no matter what, things would always work out,” she said. “And only the times when I have things purely planned, will I ever face disappointment. Whereas if I’m completely open to what the outcome is and release and surrender to whatever will happen, I will, no matter what, gain from it.”

At the end of the day, as Kim put it, “If you want to have an interesting life, then go lead an interesting life.” Spending time at the beach is still a perfect vacation, but sometimes your more unexpected travels—like seeing pink dolphins in Cambodia—become key moments in your life story, and ones you want to share with others.

5. A sabbatical to start a family

It’s easy to get caught up in the momentum of work. If starting a family is a personal goal of yours, a sabbatical can be a way to help you prioritize this.

That’s what happened to Eric Lindroos, a sales enablement manager at Gong, a revenue intelligence platform. He loved his work, and still does—but he also always wanted to be a father. And so, he has started a journey to surrogacy fatherhood, which can take about one to two years. Because the first few months of the surrogacy journey can be demanding, he has taken a sabbatical to relax, recenter, and devote his time to the early stages of his surrogacy journey. This time off is crucial in his eyes.

For Eric, remembering the reason why he was working in the first place was key. He’d only gotten into sales to save enough money for his surrogacy journey. After four successful years of working on sales enablement at Gong, he needed to force himself to take time off if he was ever going to do it.

Taking a break from the professional world and pursuing fatherhood was Eric’s way of challenging himself and living the life he wanted. But as he told us, that looks different for everyone.

“I would just encourage people to challenge themselves. And maybe that challenge is going out with a group of strangers to have drinks, and that’s outside their comfort zone. Or maybe the challenge is going on an excursion by themself. The challenge, it’s the same for all of us. It just maybe looks different,” said Eric.

If you’re considering a sabbatical, what challenges do you think you’d want to overcome? There’s only one way to find out.

Five key insights

  1. If not now, when? Like Michael said, you might never feel ready to quit working, but with a little planning, you can definitely be ready.
  2. Don’t be afraid of publicizing your sabbatical. Chester made his sabbatical public on LinkedIn, and recruiters who contacted him during that time were impressed by his confidence and honesty.
  3. You can always go back. As Ben told us, “Just do it, and if you don’t like it, you can get back to work.” If you’re in an in-demand field, there will always be employers who need your services.
  4. You don’t even necessarily have to quit your job. Kim met a woman who told her company she was considering a sabbatical in Portugal, and her company was happy to have her work overseas from there. The time zone difference actually worked in their favor.
  5. It’s okay not to have a plan. Eric recalled his grandmother’s wise words that have served as the backbone for his choices: any decision you make is the right decision in that moment. Trust yourself, communicate with those you care about, and get ready to learn a lot about yourself.
Rohma Abbas
Rohma Abbas
Managing Editor

Rohma is the Managing Editor at OpenView. She works closely with OV's contributing writers, freelancers, and internal experts to help them find just the right words to tell their story and provide the best possible reader experience to OV's audiences.
Scott Wilson
Scott Wilson

Scott is a contributing writer at OpenView. He works as a web and data developer at a consulting firm, creating personalized solutions for businesses through CRM integrations, customized apps, and database architecture. He is also an aspiring beekeeper.
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