Millennials are beginning to choose jobbaticals over jobs and bar tips

True founders are able to envision a world vastly different from today. They leave their social construct with ease and play in long-term thinking. They can still play offence in the face of daily information bombardment while the rest of us digest sugary news. And they find truth in first principles rather than consensus.

All else equal, the farther their hypothetical world is from our current state, the greater the opportunity. Or in simple terms, the delta to the existing experience drives value creation. The opposite end of the spectrum is derivative thinking.

My favourite part of being a VC is discovering these rare people. One such person is Karoli Hindriks.

After spending time with her you feel a dishonest conversation embeds the employer-employee relationship. The world is full of employees expected to commit themselves to employers who don’t commit themselves in return. There are no lifetime employees rather ‘at will’ employees who at any moment for any reason can be fired. Previously, employees traded loyalty for a career ladder. Both sides saw a permanent relationship so they’d both invest in it. But now companies are in survival mode. Globalisation and technology have caused a race to the bottom.

Neither side trust each other. Employers don’t promote or train from within. Instead, they lay off and hire. Employers just don’t have the excess equity capital to invest in employees. It’s now a pull and plug model of expertise. Most employees feel they have to take a job at a competitor to advance their careers. Employers lose their most valuable people while retaining B players. Employees fail to invest in their current position because they’re looking outside for the next ladder rung. No one invests in the long-term relationship.

Millennials starting their careers face a broken model. And are now choosing journeys over jobs according to Karoli Hindriks. The five-day 9-to-5 workweek was invented by Henry Ford in 1926. But since then the end-to-end manufacture and delivery of goods and services has completely changed. And yet most employees still follow the same pattern of working 9-to-5, Monday through Friday, at the employer’s location.

Karoli Hindriks is the founder of Jobbatical, a marketplace for international career adventures. She grew up and lives in Estonia. She has twice been a nominee for the Europe’s Young Entrepreneur award. And Karoli is also an alumnus of Singularity University.

Jobbatical is a word made up of “job” and “sabbatical”. It means a professional career break where people use their skills and knowhow to work on an exciting project in a new team in a new environment. Most people who try to live a year overseas are stuck behind a bar and not able to easily contribute their real skills abroad. Vacations can be inspirational but rarely provide practical new skills and experiences for your career. Here’s a little more background on jobbaticals:

Paul: How is work now viewed by this new generation entering the workforce?

Karoli: We are experiencing interesting times. On one hand we have a traditional framework from a century ago, which kind of defines what “jobs” are: being present at certain times at a certain location at a certain desk. This is what we were taught and anybody operating outside that framework gets questioned at the family dinners: “But where do you actually work?” or “What is your real job?” (leaving out the comment “…besides the mumbo jumbo you do which does not sound like a serious job).

Yet, for many jobs today work starts as soon as you open your laptop or gadget. Plus, we have a generation growing up, who witnessed during the financial crises that the definition of a “real and steady job” is kind of a hollow promise even if you have followed the dotted line towards success (college + grad school + safe corporate job), as many people who have followed those dots still lost their jobs. That kind of has brought up the question: 1) Why do I have to follow the traditional framework just because my manager says so even if that does not make any sense? 2) If I can lose my job anyway then why not work on something I actually care about and in a way that enriches my life?

Paul: How do you view geography as it relates to the workforce?

Karoli: That is another interesting topic. If you think about the definition of “my circle of friends” and what it might have meant for your parents then it was most probably people from the area where you lived.

When you look at our circles today then it runs in the vertical of similar interests across different geographies. And it starts from the fact that previously in childhood the friends you had were collected from the playground, whereas now you have a buddy from France, Japan or the US with whom you play Destiny.

People are becoming more and more comfortable about other cultures, ethnicities and countries. That means joining a team in another country is becoming just as easy as changing jobs within your city, with a bit of the adventure adrenaline on top of it.

Paul: What is Jobbatical and how does it plug into this macro view?

Karoli: At Jobbatical we connect tech and business talent to mainly one year opportunities in the emerging cities of the world. The fact that people are more comfortable working across borders itself opens up a whole new talent pool for companies in the remotest places of the world.

Hiring talent that used to be the privilege of the nerve centers of the world (London, NYC, Silicon Valley) becomes possible for a small town in Australia just because people are much more open to exploring. If we agree on a decent commitment — you join their team for a year, help to get from A to B and see if they both want to move further with that professional relationship.

Paul: Who uses Jobbatical and what did they do before Jobbatical?

Karoli: For companies we take away the hassle of identifying the right skill sets as well as convincing talent to move to a new country. The talent using Jobbatical already has the readiness to relocate and in many cases they have also identified where they want to go.

For the talent, well, let me tell you a story. In 2012, after having a 10+ years experience behind me of building teams and 6+ years of building up television channels from scratch, I wanted to take my experience to a new environment — to give what I had learned in exchange for getting a glimpse of a new culture. I soon realised that my ‘best’ option was working on a farm in outback Australia, which was not quite what I had in mind.

With Jobbatical we really want to give people a chance to take the skills that they have worked hard to build and let them fulfill their travel aspirations.

Paul: What is your background?

Karoli: I had an early start in the entrepreneurial journey. I founded my first company at the age of 16 (officially becoming the youngest inventor of Estonia).

I was lucky to have my late father Paul. He had a very entrepreneurial mindset. When I told him about my school project idea, instead of asking me to focus on my studies and find a safe job, he suggested that I go to the patent office. I did and this was the beginning of quite a journey!

Altogether I have founded three and directed five companies in the media, marketing and recruiting fields. I also led the launch of seven television channels in Northern Europe (including National Geographic Channels, MTV, and Fox entertainment). In that sense I have been building teams and companies since high school.

Paul: Where would you like to see Jobbatical 5–10 years from now?

Karoli: I believe Jobbatical will help organisations to redefine how they build their teams. In 5–10 years teams will be more diverse and task oriented. It will not matter what passport you have. It’s only your skills and what you’re good at that matters.

Cross border hiring will be as seamless as hiring a next door neighbour, except that your next door neighbour most probably does not have the right skill set to help your business go global. It will be normal to have 7–10 jobbaticals in 10 years instead of 1 job for 10 years. Joining and leaving companies will be much less dramatic than today, as people who come in and then leave build a network of ambassadors for the organisations. By that time the smart countries will have realised how easing up the immigration regulation will define success in the war for talent and thus the success of their economy. As author Jacob Morgan said: “When it comes to the future of work, ‘late adopters’ are the same as ‘out of business’. I believe we will see how well it applies to countries.

Paul: What are the challenges facing Jobbatical and how can people out there help?

Karoli: If you are building a platform for a model that did not exist before then there are constantly things to work on. But none of the challenges are big enough to shadow the joy of people already changing their lives through our platform like Andrew, Thiago or Nikki. When I as a founder hear those stories then all the challenges are forgotten.

Karoli: If you ask how people can help then the biggest help would be looking at the world with an open-minded view. Encouraging collaboration across the borders. I sincerely believe that the world and business will be booming if it is easy for people to move around, exchange ideas and learn about other cultures. That is something I had already made my mind up about when I graduated high school in the US during my exchange student year.

You can learn more about Karoli and Jobbatical here.



AirTree is a venture capital fund that supports the most ambitious Australian and Kiwi tech founders. First round, multiple rounds.

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AirTree is a venture capital fund that supports the most ambitious Australian and Kiwi tech founders. First round, multiple rounds.