It’s a weird switch to go from being hyper-scheduled and that feeling that your time is not your own, to an infinite stretch of time with zero threat of work-related emails, calls or texts. But that’s exactly what I did in March this year, when I decided to take a career sabbatical after seven years working at the cutting edge of US edtech.
I’m not a half-in-it person: my personality is such that I tend to operate in extremes. I grew up in rural Ohio and was the first in my family to go to college, after I was recruited to play volleyball by the University of Chicago. I then went onto work in edtech before starting my own business aged 29 – when I co-founded and became CEO of the peer-to-peer student engagement platform Wisr.
According to the National Center for Education Statistics, just 41% of full-time college students in America earn a bachelor’s degree in four years – leaving a lot of wastage amid other 60%. Our idea at Wisr was to narrow that drop-off by connecting students with sophomore or alumni mentors online – particularly in the early stage of the student life cycle, before freshmen turn up on campus.
My plan was to travel the world, talk to new people, learn about new industries
When the global pandemic struck in 2020, our platform really took off – in the first six months of lockdown, we quadrupled our revenue as we helped clients like Brown University and their partner, EAB, work out how to engage prospective students without the anchor of in-person events. This challenge eventually led to EAB acquiring Wisr in March 2021. I stayed on for two more years working in a managing director role on a different product line. But earlier this year, I decided that I was ready to move on.
The idea of doing a career search while working full-time was really unappealing to me. I realized that, since I was lucky enough to have the means, I should take a sabbatical – using six months off work to reflect and reset. It was something that my mentors had been advising for a while.
My plan was to travel the world, talk to new people, learn about new industries and maybe even come up with a new business idea. But I was scared by the idea of having nothing to do in my downtime. I know it’s a privileged problem but when you’re used to running so hard for so many years, and your company is all-consuming, the prospect of months of free time stretching ahead is intimidating.
That’s when I started researching adventures and came across the story of Radha Vyas, Flash Pack’s co-founder and CEO, on Instagram. I’m a sucker for female-led companies – I am always on the look out for them in my role as an angel investor – and Flash Pack’s trips sounded dreamy.
My Argentina adventure created a nice transition into my new sabbatical life
I decided to kick things off by joining an adventure to Argentina. I couldn’t imagine day zero of my sabbatical without being surrounded by people or activities, so Argentina – with its adventurous mix of ice-hiking, kayaking and mountain trekking – provided the perfect antidote. Rather than sitting around at home waiting for emails to come in, I knew I would be busy the whole time. It created a nice transition into my new sabbatical life.
The entire trip was awesome and beautiful. There were some really standout moments, such our first night in El Calafate, when we took an evening walk to dinner in an ancient cave. We were surrounded by the light blue water of Argentino Lake, in this breath-taking landscape near Los Glaciares National Park.
Later on in the holiday, a sinus infection meant I had to skip the all-day trek to the foot of Mount Fitz Roy. I didn’t mind, though, because I ended up having this very cool cultural experience instead, whereby I learnt how to cook lamb over an open fire with Marco, the owner of the Laguna Condor Mountain Hut where we were staying.
He didn’t speak English and I didn’t speak Spanish and so we just sat there for hours, drinking beers around the fire and using Google Translate back and forth as he showed me a recipe he had learnt from his own grandfather as a teen.
Me and three other girls ended up becoming close friends
The group was awesome, too, and we had a lot of fun exploring together. There were even a few other people on sabbaticals of their own. Me and three other girls ended up becoming close friends and we’re meeting up again later this year for a road trip across America.
After returning from Argentina, I traveled with Flash Pack again – this time to Bali. I’m not a particularly spiritual person so I was looking to push myself out of my comfort zone with this choice; to see where it might lead me.
Unlike Argentina, the Bali trip set a more relaxed pace and I had plenty of time to reflect. It was uncomfortable, but I got used to it and I felt really relaxed afterwards. It gave me space to move on from harder parts of my time at Wisr that I hadn’t said goodbye to.
Our group joked about the destination being a little woo-woo, but sometimes I think you need that element in life. For example, the day after we went for a meditation session with a local Hindu worshiper, I suddenly got loads of inbound leads from interesting people; ideas that I hadn’t considered before. I was hoping that something like that would happen – that getting spiritual would unlock something for me – but I didn’t really believe that it would.
My brain feels so much clearer now
In my old life as a founder and CEO, I only took time off around the holidays or long weekends. I never paused long enough to find time for international travel. And since we were a startup, I also spent a lot of my free time cold calling and doing software demos.
I think the hardest thing about life as a CEO is that you can’t let your guard down. You have to be the number one champion of your brand at all times; for your investors, for your co-workers and for your customers. In the early years, we had some really difficult times when we were just trying not to run out of money.
I’m realising now how much fun it is, and how much clearer my brain feels, when I’m not in a co-founder or senior management role. The freedom to travel has given me that, along with more confidence to set out solo. For example, recently I rented a van and headed to the Utah national parks. I went without a plan or someone to go with, which is not something I’d have done in my previous life.
I think my career gap adventures have also taught me about the power of meeting new people, and making friends around the world. I feel extremely fortunate to have generated so many new friends from my trips – people I can travel with, and whom I’d happily host back home. It’s nice to realize you can build new friendships in such a short space of time – and with people at a similar life stage, who share a love for travel and adventure.
For founders or other people like me who are on the cusp of a major career exit, I’d say go for it – lean into this exciting transition phase. You’d be surprised with what your brain comes up with when you’re around other creative people, making new friendships and with the space and time to think.
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Images: courtesy of Kate Volzer and Flash Pack