The tipping point
Real-life stories from people who describe how they went from 'I'm not quite sure if I should go on sabbatical' to 'hell yeah, I'm obviously going'.
Over the past few months I've been busy building a self-paced module to help people who are thinking of going on sabbatical and are struggling to make the decision. This has been a year in the making and I was recently able to tap into exactly the right kind of energy to build it, as I just quit my job to go indie.
Many of you who read me will have stood there, at the fork in the road, looking at your two possible futures knowing fully well you can't both go on sabbatical and not go. Maybe you're standing there now, and you’re realising just how difficult it can be to decide to overhaul your life, in the hope that something good will come out of it.
The module I'm making will give people who feel stuck or anxious a space where they are guided into making a decision that is aligned to what they truly want to do and who they truly want to be, deep-down.
If that's you, this will give you structure at a time when things might feel chaotic. You'll hear stories from others and get invitations to reflect, at a time when you might be struggling to calm the noise in your head and listen to what your heart has to say. And you'll find peace of mind knowing that you’re engaging with a process that’s been thoughtfully crafted by someone (me) who’s made the decision twice already, and who's guided dozens of others on their own journeys.
I know how valuable it is to hear about other people's experiences, their fears and their hopes, and how they came to a decision. So I've been recording podcast-like conversations with thoughtful humans who have already made that decision, so they can share their story and help anyone who is standing at that fork in the road.
One of the most difficult parts of the process to describe is the tipping point, the moment where you go from 'I'm not quite sure just yet' to 'hell yeah, I'm going on sabbatical'. So I asked every podcast guest to share their thoughts with me on that topic, and today I want to share some of those stories.
Sriram had been thinking about going on sabbatical for more than a year, to heal from burnout, focus on health and spend more quality time with his family. He has set money aside and wasn't too worried about how difficult it would be to find another job at the end of a sabbatical, but somehow he wasn't quite ready to take the leap.
It's only when he spoke with two thoughtful internet strangers who had already gone on sabbatical that it finally became obvious to him that he had to go. In those conversations, he shared his hopes, talked through his thinking, and felt comforted that other reasonable humans had taken the leap before and didn't regret it one bit.
There was a clear 'before' and 'after' for him.
Bruno already knew he was ready for a big life change but he wasn't quite sure what or how, so he'd been looking for new professional opportunities and new places he could move to.
He’d already heard about sabbaticals in the past but the idea of him going on a sabbatical only crossed his mind when he listened to a podcast on the topic with
, and me.As Paul, Michelle and I shared our sabbatical experiences, Bruno not only realised the change he was looking for could be in the shape of a sabbatical, something actually clicked for him in the moment, and he just knew going on sabbatical was the answer he’d been looking for.
He went on to have a few conversations with the people who'd be most impacted by his decision to take time off before making any formal decision, and as soon as they gave him their support, he started preparing for his adventure.
Yujia laughed as she told me she actually carried out a proper 'alternatives, risks, and mitigations' analysis, like any reasonable corporate person would do.
She'd had this nagging feeling inside of her that she needed to take a break but couldn't quite get herself to take the leap, despite knowing deep-down that it was what she wanted. It's that analysis that made her realise that the downside of going on sabbatical was actually pretty light. As she put it, the worse case scenario is "you lose 6 months of income and skills that you would have gained".
The downside is known but limited. On the other hand, the upside is unknown but infinite. In that sense, sabbaticals are like positive black swans i.e. they're highly impactful events which have a limited downside and an infinite upside.
For Yujia, this felt like a breakthrough, and she went on sabbatical less than two months after this realisation.
Everyone's story is different.
Yet everyone can point to a moment when the seed was planted and a moment when things clicked and they knew they had to go. The amount of time that goes by between those two moments is highly variable. For the most decisive people—like Yujia— it will only take a couple of months, and for others one or two years.
For those who are standing at the fork in the road right now, this might feel terribly long. It is—and that's because the whole process is iterative.
Also because it's a decision in which you need to involve your head and your heart. Things will only fall into place once they're both aligned.
And my advice—to anyone who’s interested in hearing it—is to best not ignore the fork in a road if it’s right in front of you.
Once the idea of going on sabbatical has been planted inside of you then it’s not going to go away. What might have started off as a light-hearted fantasy will likely become a nagging thought that you get to hear on an increasingly frequent loop, as time progresses. So you owe it to yourself to give yourself the space to properly consider it as an option, and think about how you would shape an experience that fits your risk appetite, your hopes, and your life circumstances.
The last thing you want to do is let time go by without making a decision, and end up with one of those big life regrets when you're older.
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More about sabbaticals: whether you're thinking of going on an extended break from work or you’ve already taken the leap, you are right in the middle of an experience that can transform your life in a truly meaningful way. It’s exciting of course, but it can also feel scary, lonely and a bit overwhelming at times.
I’ve created two playbooks to help you on your journey:
Thinking of a sabbatical will give you everything you need to consciously decide if going on an extended break from work is the right move for you
On Sabbatical is a self-paced digital experience with insight, structure and resources to turn your sabbatical into a life-changing experience