My First “Jobbatical”

(Or The 3 Ws of Changing Careers)

If you look for career advice, you will find many books and articles that try to provide clarity to the growing population of educated adults that frequently ask themselves:

“What should I do next?”

Most of this advice, while well-intentioned, is usually broad and difficult to know exactly how to apply. In their attempt to provide structure and predictability, they forget the nature of the career transition process…

It’s chaotic. Exciting. Uncertain.

It’s always wise to follow some principles: meet more people, learn new things, make time to think and plan, take calculated risks… However, we eventually must jump accepting that we won’t know where we’re going to land. The best first guess we can make for the question “what should I do next?” is simply “something else,” and get moving.

I had recently stepped away from the startup I founded nearly three years ago. When I made the decision, I knew that the future was going to be positive, but also unpredictable (as most growing periods are). As long as I had courage and curiosity, I knew I would be ok.

Cut to now. I’m publishing this essay from the airport in Buenos Aires, before flying to Tallinn, Estonia, for a three month “jobbatical” at a startup I discovered only two months ago.

Of the many times I’ve changed careers, joining Jobbatical is the most straightforward one so far. I wrote this essay to share what I’ve learned about changing career directions, why to do so, what to expect, and where to look.

When is a good time to change careers?

We should change when the things that matter to us in our work are missing, and there’s no reason to believe they can (re)appear.

Great careers are fueled by two factors: Inner motivation and working with the right people.

Inner motivation is important because working on what matters to you makes you work harder, which brings better results and rewards. Don’t underestimate re-igniting your motivation as a valid reason for change. As Karoli Hindriks, the Founder of Jobbatical, says, “nothing is worse than working on nonsense.”

What motivates you does not necessarily have to be outward focused. It’s honorable to want to fight poverty or cancer, but sometimes it’s hard to achieve without having the right skills and experiences to make an impact. It’s ok to be passionate about learning and growing while we identify the problems we care about.

Once you know what motivates you, 99.9% of the time you are going to need help to achieve it. The media loves to create narratives around the Michael Jordans and Elon Musks of the world. They embellish them to look like superheroes, but the full story behind any great career is one of regular humans helping each other succeed. Whether you prioritize learning, challenge, money, adventure, stability, or changing the world, always make sure you surround yourself with the right people to help you achieve your goal.

When you are no longer working alongside the right people on something that motivates you, it’s time to shift.

Why should I change careers?

I can’t think of a single example of a successful, life-long career that didn’t go through different stages, each with its own tradeoffs and rewards. These are five potential benefits of changing career directions:

1. Time for a personal strategy

Depending on the goal, almost anything could be a good or bad decision. Most people take steps going after short term, tangible rewards, without thinking about the foundations they are setting up for the long term. Pursuing a high salary could provide the stability you need for your family in your 40s, but it may affect how many different things you learn and experiences you get exposed to in your 20s.

Starting from the opposite end — “what do I need to know and have to become or achieve X?” — is a more resilient professional strategy that demands serious introspection.

When we face a career change, we can stop in our tracks and ask ourselves the important questions to make sure that everything we do is aligned with our long term goals.

For example, if I wanted geographical stability or to ramp up my savings, taking a short-term gig in a country where I know almost no one would be a sub-optimal decision. However, for me, 2015 is a semi-sabbatical year of exploration of new trends in employment. Add that Estonia was the first country to offer digital citizenships to foreigners, and Jobbatical became a no-brainer.

2) Learn new skills

Everyone agrees that picking up new skills is a good investment. Being good at more things means being able to understand the complex, communicate ideas more clearly, and solve bigger and more diverse problems; this is how we get better compensation for our work.

However, in order to learn something new, we must postpone working on what we already know so we can work on learning. Acquiring new skills means sucking now, so we can be greater in the future.

When we have been doing the same thing for a long time, the fast-learning, low-risk periods are over. You are expected to deliver your best results. Most organizations have a hard time justifying paying employees to learn new things they are simply curious about, not knowing clearly how it will impact the organization.

Similarly, running a startup has a tendency to make you focus on the present. You are immersed in keeping things moving, maintaining happy customers, and sharing your mission with the world. It’s hard to spend too much time investing in skills you’re not good at. Resources are tight and survival is the priority. Some investments are too long term for startups to consider.

When we take a job with more responsibility, or in a different environment, or in a new field, we get the opportunity to leverage our experience, while still accelerating the new things we learn.

3) Meet new people

Who you know is as important as what you know (maybe more). Other people are the best source of information, proven methods, and new opportunities. Having a vibrant network, and knowing how to tap it, helps us understand what’s important, what works, and what’s possible.

Similar to skills, when you have been doing the same work for a long time, the rate at which we diversify our network decreases. Solving problems usually means working with the same people for long periods of time.

However, sometimes we need different people in our lives if we want to advance. One of the most common patterns I see among the people I went to school or college with is that those with conservative social lives in their adulthood have the fewest career options.

Six years ago, I met a full-time traveler and writer (and very good friend), Colin Wright. He was the first blogger I met in person. Hearing about his work, projects and ideas changed my view of the world forever. Since then, I never stopped trying to expand my social horizons. I learned that people are the embodiment of ideas and values. They inspire us because they are possibility made reality.

Also, knowing more people grants you empathy: the ability to understand and share the feelings and perspectives of other people. This is key to communicating what you know effectively. Without empathy you’re stuck in a rigid and fragile career because you can’t get other people to do what you consider important.

If your network is stagnant, consider shifting careers to meet many new people fast. When you are doing something new, you have a new story to share. You have new information and ideas, which are very valuable in a competitive and fast-paced, changing world. Everyone wants to know what’s hot, everyone wants an edge.

“The best way to put distance between you and the crowd, is to do an outstanding job with information. How you gather, manage, and use information will determine whether you win or lose.” — Bill Gates

4) Have more good ideas

My old mentor, Gerry Garbulsky, would say that an idea is a new lens for seeing the world. When you change your professional context, you bring your old lenses with you. When you change roles in a company, or switch industries, or move to work in another city, you become a bridge between your old and new world. Your mind starts to play and see life through new lenses that connect what you knew with what you’re learning.

New lenses are the essence of innovation.

Why should we pursue innovation in our careers? Because the world is changing more and faster than ever, making our lenses outdated quickly and often. The paradox is that the best way to achieve sustainable growth in our careers is to embrace the uncertainty of the future. We need to put ourselves in situations where we can have new and better ideas frequently.

The key is not to look for ideas directly, but rather make career moves with calculated risk that increase the odds of stumbling with new ideas. As Steven Johnson says: “there are good ideas and then there are good ideas that make it easier to have other good ideas.”

A career shift is the latter.

5) Gain objectivity

When you work for the same company for too long, or with the same people all the time, it’s easy to lose touch with the outside world. It’s easy to think too highly of your ideas, your methods, and your impact.

This is not necessarily bad. Solving any important problem requires some degree of focus and blind faith in your theory of how the world works. If you’re always absorbing, you’re rarely executing.

However, when we do need a change, we are forced to come out of our bubble and face that unforgiving judge: the market. Most things we want in life are behind other people who will judge us before giving it to us. Time, money, jobs, information, support, romance, you name it. If you have any ambition in your life, you can’t be a spectator of the market. You have to get in the ring.

Every now and then, better professional opportunities come unsolicited your way, making the process simpler and your market value more apparent. But when you decide to pursue a career shift because your present situation is not satisfactory, you have to convince the world that you are valuable enough to get more than what you currently have.

After stepping away from my startup’s operations, I had 50+ conversations with close allies and mentors. We talked about what they were doing, why I was changing directions, what they thought I should pay attention to, potential opportunities and threats in my future, and more.

This was hard. I had to let others judge me —so they could help me— by what they thought I could do with what I had.

Talking with them BEFORE making any move was a great decision. They helped me see my blind spots, and where I was standing. It’s hard to know where to go without knowing our starting point.

This is why shifting careers, while temporarily uncomfortable, can be a sobering decision with lasting benefits: it’s better to face the pain of growth head on than stay in a bubble and learn one was unprepared for the waves of change once the bubble bursts.

And rest assured that all bubbles burst.

Where should I look to change careers?

If you believe that the next step in your career should be to launch your own business, there’s already plenty of content out there that can help you with that path, so I won’t cover it here.

However, if you’re in the much larger group of people where the next best step for you should be working with/for someone else, it’s worth having some heuristic to know where to invest your time. Reid Hoffman, Ben Casnocha and Chris Yeh, in their practical book The Alliance, help us identify where to look for those that want to keep growing: organizations willing to have honest conversations about the future.

If you want your next career step to be a fruitful one, you should be part of a culture that promotes vulnerability and creative collaboration. Your plans should factor in your context as much as your motivations. You want to identify organizations that:

• Understand the fast pace of change and unpredictability of our times, while still being committed to investing in the future.
• The irreplaceable value of entrepreneurial employees to adapt and get stuff done in front of adversity and uncertainty.
• Acknowledge that lifelong loyalty cannot be asked or given anymore.
• Accept that ambitious and hard working employees will always try to improve their situation.
• Want to develop a mutually beneficial alliance with you, regardless of your future with the organization, instead of seeing the relationship as a transaction of time and money.

This is the new way for organizations and talented employees to invest in their relationship and take the risks to pursue bigger returns. However, this is not easy to find.

Most companies today still lack the risk tolerance and entrepreneurial leadership to “walk the talk” when it comes to having honest conversations. They understand they have to be vulnerable, but their actions show their resistance.

Even more damaging, they still see employees as a resource to be allocated or cut, like revenue or office furniture, instead of owners of a key perspective in any evolving organization. Alas, as Paul Graham says: “Increasingly you win not by fighting to get control of a scarce resource, but by having new ideas and building new things.”*

Which brings me back to Jobbatical, and what got me so interested in them: bringing together highly talented people with sincere, forward-thinking companies. Here’s an excerpt from Jobbatical’s ‘How It Works’ page:

“There are professionals who are seeking new inspirational locations and teams in order to leave their current careers for a short-term combined work and travel experience. We connect them to employers seeking to hire for short stints. […] By providing short-term professional gigs, Jobbatical creates a unique opportunity to build up the working relationship with the talent. It gives a chance for both parties to get to know each other, the style of work and team spirit.”

Kudos to Jobbatical for leading the way in helping talent and companies start their relationship with honesty about their future. This is exactly the kind of conversations that I want to help grow, and I can’t think of a better place to start exploring the next stage of my career.

Wish me luck!

Thanks to Florencia Di Sarli, Isabel Hirama, Gia Castello, Léa Peersman Pujol and Karoli Hindriks for their powerful feedback and help with editing, and to Rocío Hedman for the illustrations and design thinking.