Feeling Lost in Your Career? Why Transitions Feel So Unsettling
Photo by Aron Visuals on Unsplash
The recurring theme in the gift sessions I offered in September (see LinkedIn post) was this: people were exploring or contemplating a transition, navigating career dissatisfaction, or trying to make sense of changes in their lives.
For those thinking about career transitions, one thing stood out. Most of them — like many of us brought up in middle-class Indian families — had a clear, set path: join a good college, get a great job, and for some, add an MBA in between. Even when we didn’t have the exact plan, we knew the direction — or at least where to look for clarity. (Often in what Sharma ji ka beti/beta was doing.)
For me, for the longest time, a cousin who joined IIT before me was that compass.
And then, there comes a point of disillusionment: Is this what I was aiming for? Why don’t I feel satisfied or fulfilled after reaching where everyone wants to be? Does it even feel like me anymore?
Sometimes, priorities shift too — after having a child, facing a health scare, or simply wanting to spend more time with family.
At such junctures, we start to feel lost. The compass we had is no longer useful, and the compass others are following doesn’t feel like ours either. We may even wonder if this feeling is just temporary, something that will eventually pass.
It can feel like a pendulum: on one side, holding on to what we’ve achieved; on the other, letting go to find what truly aligns with our heart and soul.
That’s the beauty of transitions — and what draws me so deeply to working with people navigating them.
In his book Transitions, William Bridges makes an important distinction between change and transition.
Change is situational, what happens on the outside (a new job, role, city, manager, or family situation).
Transition is psychological.
He writes: “Transitions start with letting go of what no longer fits or is adequate to the life stage you are in… The transition itself begins with letting go of something you have believed or assumed — some way you’ve always been or seen yourself, some outlook on the world or attitude toward others.”
This is why transitions are often hardest for high-achievers. Not because they aren’t smart or hardworking, but because the rulebook they followed no longer works. There are no “right” answers to the questions they’re asking, no set guidelines — they have to write them on their own.
The famous nine-dot puzzle is a great analogy here. You’re asked to connect nine squarely arranged dots with four (or fewer) straight lines, without lifting the pen or retracing any lines.
If you have never seen this puzzle before, go ahead and try it before you scroll ahead.
At first, it feels impossible because we imagine a boundary around the dots, assuming we must stay within that square. But the solution only becomes possible when you step outside the perceived boundary.
That’s what life transitions are like too. We could either feel frustrated that our old compass no longer works, or feel excited about the possibility of discovering a much bigger space to play in.
Zen meditation teacher Henry Shukman captures this beautifully: “Any true journey is a journey into the unknown. If we are really developing or truly growing in this life, we will always be moving into what we don’t know yet… So we can let go of the need to know or to understand, because that’s how new discoveries are made.”
What would it feel like to free ourselves from the need to know?
As you enter the unknown (even if only in your inner world at first), you could either feel lost — or see it as the great adventure of a lifetime.
During such times, I often come back to the idea of Wonder. Maria Popova, in The Marginalian, defines it as:
“That edge state on the rim of understanding, where the mind touches mystery… our best means of loving the world more deeply. It asks of us the courage of uncertainty because it is a form of deep play… inherently open-ended, without purpose or end goal, governed not by the will to win but by the willingness to surrender to the experience and be transformed by it.”
🤔Reflect (inspired by what my brother once shared):
Would you rather be lost — aware that you’re trying navigating your way — or truly lost — not even knowing you may be on the wrong path?
PS: If you found this helpful, you may also enjoy a recent contemplation I wrote on one of my own mini-transitions here: Is it still aligned? Reflecting on purpose, plans, and growth
If you’re curious about working together, you can learn more about my coaching here.
