How to Make a Career Shift When You’re Afraid of the Unknown

Photo by Dan DeAlmeida on Unsplash‍ ‍

I feel deeply grateful for the kind of subscribers who read my newsletter. Almost every issue brings me one or two thoughtful replies, and that makes the whole process feel even more meaningful. (Though the primary motivation remains that writing helps me clear the clutter in my head and brings clarity to my own thinking.)

One of the posts that brought back the most reflections was: Feeling Lost in Your Career? Why Transitions Feel So Unsettling.

Different parts resonated with different people, depending on where they were in their own journeys. But one response stayed with me and nudged me to elaborate on their insight.

Referring to a passage, about sitting in a period of uncertainty and ambiguity, they shared:

“I have been feeling lost for quite some time, but it gave me a perspective that if I make the jump, I have nothing to lose. But if I don’t, I may miss out on the adventure of a lifetime. Why play safe when you can afford to play with risk?”

The passage they were referring to was:

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.


Now, the level of risk one can take is deeply personal. It depends on circumstances, responsibilities, and one’s own internal appetite for uncertainty.

But irrespective of that, stepping into the unknown during transitions feels uncomfortable for most of us. Often, we make decisions through strategy or instinct, or some combination of both. Those who have relied heavily on strategy tend to feel the most discomfort because strategy provides a sense of control. You can plan, prepare, create experiments. But there’s only so much you can strategise. There’s only so much you can do.

Interestingly, during these phases, people may not be clear about what they want to do next, but they become increasingly clear about what they don’t want. This clarity often comes from sensing what no longer feels aligned… a deeper tuning into who they are becoming.

And if we could focus on who we are, and who we want to be - that can become the anchor. In a way, that becomes the new strategy. 😀
It can help reframe the uncertainty as an adventure and make us feel more prepared to make (or even contemplate) the jump.

Take one of my clients as an example. Despite having achieved everything one could hope for, including an Ivy League MBA, they “knew” a career transition was coming. When we started, they were certain about one thing: they wanted clarity before quitting. “I can’t just sit and figure it out,” they said.

So we began with alignment - what feels like them, and what doesn’t. We explored identity, not action.

In one session, we used an analogy:
They were underwater, holding on to an anchor. They knew it wasn’t helping them go where they wanted, but the destination still wasn’t visible. So the plan was: hold onto the anchor for now, explore the currents, notice where the water (their natural inclinations) was taking them, and understand how each direction felt. And once they felt comfortable navigating the water, or could see even a hazy glimpse of the next anchor, they could let go to swim in its direction.

But midway, they paused and said:
“This anchor won’t let me explore fully. It’s actually what’s holding me back. So even though it’s scary, I think I need to let it go.”

The work of navigating the unknown still continues for them. But letting the past go, metaphorically or psychologically, and shifting the anchor from doing to being, to self-belief, is what ultimately sets us free.

And yet, these mindset shifts are a journey of their own. You can’t will them into existence, but work towards them!

If you’re navigating a similar phase, you can begin by gently noticing:

  • Where might the flow of life be leading you? What excites you?

  • What’s a thought or fantasy that keeps returning? What about it feels energising?

  • What about the present no longer feels like “you”? What would need to change for it to feel aligned?

You don’t need to act on any of these right away. Just start noticing. Awareness has a way of opening doors you didn’t know existed.

If you want to read more on transitions, pair this with:

  1. What If Unhappiness Isn’t A Problem To Fix

  2. Is It Still Aligned? Reflecting on Purpose, Plans, and Growth

If you’d like some support in navigating through your drifts, I’d love to support you. You can learn more about my coaching here.

Next
Next

What Really Makes Us Happy? Rethinking Happiness and Fulfillment