How to design the ideal career sabbatical

Last week, many people wrote to say that both the non-linear career and sabbatical struck a chord with them.  I got a lot of questions about how exactly to go crafting a sabbatical as you’re contemplating what you want to do next in your career.

I’d be lying if I said it’s easy and that everything made sense to me at the time.  But like most things, repetition leads to learnings and, eventually, a blueprint.  I’m happy to share some of the design principles I’ve used to decide how to spend my time exploring and learning at every fork in the road in my career.

Don’t follow your passion, but instead follow your value

You hear it everywhere - follow your passion.  That’s really bad advice.  Why?  There’s a lot of reasons.  First off, your passion is probably something you love to do.  Many times it's a hobby or a way for you to unwind or relax.  It’s usually where you go when you’re trying to escape the stresses and pressure of your job.  So what happens when you turn your passion into your job?  Uh oh.  Nowhere to turn.

But more importantly, your passion is really important to you, and something you’re probably not willing to compromise on (rightfully so).  And at the end of the day, don’t want to pay you for something you care a lot about.  They want to pay you for something they care a lot about (usually something around solving a problem of theirs).  So instead of following a passion, understand what value you can create and then learn about people who are interested in the value you can create (aka customers).  

So, how exactly do you learn about these people?  Good question.

Chase relationships, not titles or brands

If you have the luxury to take some time to figure out what’s next for you, don’t scour the websites for titles and companies that you admire.  Instead, learn more about the people in those roles, what they do outside of their day jobs and ways in which they continue their professional development.  It may be charitable work, industry work, board service, volunteering.  Join those groups and communities.  Start slowly building your networks in these areas.  The barrier to entry to these communities is most likely lower than if you were to apply for a role at your dream company or your dream title.

Don’t forget to be authentic and honest.  Every week, set a goal to grow your network by a few people.  Over time, you’ll start to learn more about people you admire and want to emulate.  You’ll learn about how they broke into the industry or company and how they work to support others making that same jump.  People tend to want to help one another.  Lean into that.

Ok, great.  You want to add people to your network, but why would they want to add you to theirs?

Don’t be afraid to offer your help and expertise…FOR FREE

Yep, I said it.  It’s okay to offer your support or expertise for free.  In fact, it’s the best way to show you’re serious about working.  You show initiative and work ethic and now have given your chance to show the quality of your work.  And it never has to feel desperate.  Be transparent and share that you’re looking to connect with people as you break into a new industry and that you have time to offer your services of “x, y, and z” to people and brands you admire.  Discuss projects and be clear on how much time you have.  Sell your value and be honest.  People rarely turn down free, quality help.  Trust me.

If you’re having trouble jumping over the hurdle of working for free because you’re too senior or you think you’re giving your value away, think back to when you paid for college.  You gave away tons of money for the chance at a quality job prospect 4 years later.  Now you’re just giving away a few dozen hours for the chance of a quality job prospect down the road.  Not a bad trade off.

When faced with choices, use the Regret Minimization Framework

Back in 2009 when I had just accepted a Fellowship offer, I was given the opportunity to enter my name on a (very) shortlist for a role at an NFL team.  There were a number of factors at play, but in the end, I asked myself which decision I’d least (and most) regret passing up 15 years later.  In the last decade, I’ve told this story many times and always thought of myself as a pretty smart guy, coming up with this cool framework on decision making.

Turns out Jeff Bezos used this framework way before me and even gave it a name.  

Oh well, maybe I was the second person to use this (ha!).  

These are four design principles that have helped me navigate the numerous career sabbaticals I’ve taken along the way - and the ones still ahead up the road. Understand your value, slowly build your network, offer that value to help solve problems, and find a framework that helps you make decisions.