How to Plan Your Sabbatical
By now, you know a sabbatical isn’t just a vacation. In Newsletter #2, I laid out what a sabbatical really is: a strategic pause, a chance to reset. In Newsletter #3, I walked through the signs it might be time: when success feels hollow, when your body and mind wave warning flags, when the quiet question “is this all?” refuses to go away.
Now comes the practical question: How do you actually plan one?
A sabbatical doesn’t happen by accident. It takes intention, and yes, some logistics. But don’t let the details overwhelm you. Planning is less about creating a perfect blueprint and more about building just enough structure so you can step away with confidence.
Here’s how to start.
Step One – Name Your “Why”
Before anything else, get clear on why you’re stepping away. If you don’t have a strong “why,” your sabbatical risks becoming an expensive detour instead of a life-giving reset.
Ask yourself:
What do I need space from right now?
What do I want to return with when this pause is over?
Your “why” will keep you steady when doubts creep in or people question your choice. It’s the compass that makes everything else make sense.
Step Two – Define Your Duration and Boundaries
Not every sabbatical is a year-long odyssey. Some are a month. Some are three. The length matters less than choosing a time frame that stretches you without breaking you.
Alongside duration, decide on your boundaries. Are you going fully offline? Will you check in occasionally with work or family obligations? Being clear about these lines up front prevents guilt, misunderstanding, and scope creep once you’re underway.
Step Three – Prepare the Practicalities
This is where intention meets reality. A sabbatical won’t succeed if the basics of your life unravel behind you. Think through three essentials:
Finances: How much do you need? What expenses can you cut? Where’s your cushion for surprises?
Work: Will you negotiate leave, design a clean handoff, or make a full exit?
Life at home: Health needs, family responsibilities, community obligations—what has to be handled before you step away?
You don’t need every answer nailed down. But you do need enough of a plan to step away without leaving chaos in your wake.
Step Four – Choose the Form
Sabbaticals aren’t one-size-fits-all. Some people travel, immersing themselves in new cultures and environments. Others stay local, using the time for deep rest, personal projects, or creative pursuits. Many do a mix of both.
The form matters less than the intention. What matters is creating conditions where you can pause the usual script and give space to what’s been buried under busyness.
Step Five – Create a Gentle Framework
One of the easiest mistakes is turning your sabbatical into another project, with color-coded calendars and to-do lists that feel like work. The opposite mistake is going in with zero plan, which often leads to wasted time and frustration.
The sweet spot is a light framework: a few daily or weekly anchors that keep you grounded without boxing you in. Journaling. Walking. Limiting screens. Setting aside time to learn something new or revisit a passion.
This is the scaffolding that supports renewal—not productivity theater, but presence.
Common Pitfall to Avoid
The biggest danger isn’t poor planning. It’s confusing escape with intention.
If your sabbatical is just a way to dodge responsibilities, debt, or hard conversations, you’ll return to the same issues you left. The power of a sabbatical lies in leaving with purpose—and preparing to return with clarity.
Reflection for the Week
If you’re considering a sabbatical, start with these questions:
What excites me most about the idea of stepping away?
What scares me most about it?
If I wanted to begin six months from now, what would I need to put in place today?
Write your answers down. Don’t overthink them. Sometimes the first scribbles on a page hold more truth than all the overanalyzing in your head.
Closing Thoughts
Planning your sabbatical isn’t about scripting every moment. It’s about creating just enough stability that you can step away, reset, and return renewed.
It’s not quitting. It’s reclaiming. It’s not about drifting aimlessly—it’s about realigning when the old course has gone stale.
If this stirred something in you, forward it to a friend who’s been talking about “needing a break.” And if you’re new here, subscribe so you don’t miss what’s next.
Fair Winds,
Captain Rickman