How to De-Risk Your Sabbatical

Welcome to Sabbatical — where we help ambitious people like you take a mid-career break. Since last issue, 55 people have signed up. Woo!

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One of the most common questions I receive in my sabbatical coaching (totally free! Schedule a session here) is “What should I do to prepare for a sabbatical?” Which is another way of asking, “How can I feel good about the risk I’m taking?”

Like most adventures, you’ll never be 100% ready, and that’s part of the fun. Sometimes, you must leap and a net will appear. 

However, I usually work people through five “layers” of preparedness to help. These are known areas, proven by speaking with dozens of people who have taken sabbaticals, where there is some amount of risk.

You do not need definitive answers for each one. Indeed, some of them you can only make educated guesses. But considering each one and having a strategy or a rough idea can be enough to feel good about taking the leap.

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Layer One: Identity. 

Are you ready to feel adrift?

This is for all of you overachievers: who are you without your career? Who are you without the doing?

Most people start with the financial considerations (see next layer), but this is more important. What you do for a living is a core part of your identity — it’s one of the reasons “So, what do you do?” is a standard cocktail party opener. 

When you are considering taking a break from working, a core part of your identity is now in flux. The space created by temporarily removing your career can be difficult to internalize before you do it.

Be comfortable with the idea that you will not know how to describe yourself or that you will be met with a blank stare when you do. At least, be comfortable with being uncomfortable.  

Layer Two: Money. 

Do you have the savings for the kind of break you want?

Sabbaticals are sometimes described as “mini retirements.” Much like a retirement, you need to be honest about the lifestyle you’d like to maintain during your break and consider the length of time you expect to take off. Things to consider:

• The length of time of your break

• Do you have a condition that requires medical insurance or expensive prescriptions?

• Do you want to travel? To where? And what is the right balance of price and comfort?

• Are there side projects or businesses you want to start that may require investment?

• How much of a buffer do you have if you have a sudden unexpected expense such as a large home repair?

Don’t forget to bank in time to enter the next phase of your career, whether that’s finding a new job or starting your own thing.

Consider Melissa’s story, after her break she ended up taking longer than she expected to find her next move. Luckily, she had the savings on hand to weather the delay. 

See this video for a breakdown on the four ways people pay for a sabbatical: Savings, flexible work, secondary income, a windfall. 

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The four ways people afford sabbaticals. Still curious? Drop a comment and ill make sure I get you an answer when I do my next batch of ... See more

Layer Three: Employment. 

How confident are you that you could come full circle?

There’s a truism in investing circles: “Nobody can time the market.” You can’t know what’s coming around the bend like, say, a global pandemic. But using your best judgment, do you believe that, if you had to, you could find a job similar to the one you are leaving? That if none of your exploring and self-discovery yielded anything, you could end up roughly back where you are now?  

This mental exercise is a good way to prepare yourself to take the risk of a long-term break. If everything went wrong and you didn’t find some brand new way forward, could you land roughly back where you started? If you are a nurse do you think you could find another nursing job, even if the location and salary weren’t an exact match?

The answer doesn't have to be “yes”, but knowing the answer helps you take the long-term break with eyes wide open and helps you understand how long it would take you to find a job when you return. 

For example, if you are a C-suite executive, you may be able to find another job. But given executive hiring cycles can take months, you have to bake that into your “re-entry” plan.

Consider Amanda’s story, where she ended up back in a similar role in a similar industry, but with a few changes to her approach. 

Layer Four: Goals. 

What does a “successful” sabbatical look like to you?

It’s important to be honest here. Some take the definition of sabbatical that is grounded in academia, where you take a break to produce something. Others have a simple goal of recovering from burnout. Or maybe you want to end your sabbatical knowing your next career step.

Especially if you’re an ambitious person who likes to plan and strategize, you may benefit from seeing what bubbles up during your break. 

For example, when considering his sabbatical, Len purposefully focused on rest above all else: “Because if I had a goal and then I didn't achieve it, then I would have failed sabbatical. And can you imagine anything more demoralizing than failing at rest?”

Layer Five: Discovery. 

Are you ready for some uncomfortable introspection?

Especially if you travel during your sabbatical, you are taking a very full life and removing your community, your career, and your home. What’s left is what I affectionately call “The Abyss.” When you create an absence, you allow some latent feelings or thoughts to come to the surface.

Sometimes this is good. Maybe after years of working alone, you remember you always loved working with people and perhaps your next career step should focus there. Or maybe you realize your bank pain comes from all the hours at the computer. 

For example, with some space to think, Rachel realized that she had been subconsciously rushing things, often for no reason.

Sometimes this can be difficult: Maybe your focus on your career has damaged relationships in your life, and it took taking a break to realize that. 

This can be uncomfortable and bracing, but it’s the work that makes taking a sabbatical worthwhile.