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8 questions to ask yourself at a crossroads

One of my clients, who like many of my clients, is at a crossroads trying to figure out what’s next, has recently shared with me a beautiful quote by author John Holt:

“The true test of intelligence is not how much we know how to do, but how do we behave when we don’t know what to do.”

We are culturally wired to lean on ‘learned knowledge’, to be valued for how much we’ve mastered, but what if it’s what we do, the decisions we make and how we make them, in those critical crossroads moments, when we are in the unknown, that matters most?

Life is a series of decisions, of sliding door moments strung together, and we get to choose how we show up for ourselves and navigate through those pivotal moments .

Some of those fork-in-the-road moments are circumstantial, some are self-imposed and some we don’t see coming. A door closed out of the blue, a plan didn’t work out, or our feelings about a path we’ve been on changed.

The bottom line is we all encounter these moments in life when we don’t know what to do.

The questions that Holt prompts us to reflect on are What do I do when I don’t know what to do? How robust is my toolkit for those moments? How helpful are the actions I turn to? Where do I seek answers? Who is in the room with me (metaphorically speaking) when I make decisions?

When we don’t know what to do, there are things we can do that are supportive, empowering and helpful, and then there are things we can do that don’t serve us, that aren’t helpful.

Thinking we’re supposed to know, for example, is extremely unhelpful.

Other strategies/tools I’ve found unhelpful are making endless pros and cons lists, asking for everyone else’s opinion, turning a decision over in our minds a million times and playing out all possible scenarios.

On the other hand, when I don’t know what to do, sometimes I go to explore new things/experiences. I seek inspiration. Often, I ask for an answer, a direction, guidance, some shift – and then wait for it to come in some form. Other times, I go to a coaching session, to use words to help make something buried and vague come to the surface. All of these things help.

And what’s been a great companion for me in the past decade is journaling. When we journal, especially when we use the stream of consciousness writing technique, we can "bypass" the type of thinking that often gets us stuck and access our inner wisdom, instead.

I invite you to use the following questions as journaling prompts when you need them. Some may resonate more, some less, take the ones that feel right for you and leave the rest.

And remember, answering these questions in writing is very different from “thinking about '' them. Writing opens up space for different things to come up, that often won’t come up through “thinking”.

8 questions to ask yourself at a crossroads:

  1. What am I afraid to let go of?

  2. What do I truly want?

  3. What matters most to me?

  4. What are my big dreams?

  5. What would bring me joy?

  6. What does my soul/heart want me to know?

  7. What decision or choice feels most “resonant”?

  8. What would the ULTIMATE version of me choose?

Some answers may feel surprising or even mysterious. You don’t have to understand your answers right away. Over time, their meaning will emerge for you. When you don’t know what to do, what do you do? What is in your toolkit? And what might you like to add to it? Any interesting journey will take us again and again to the crossroads of not knowing. To be human is to be uncertain, to not know. And what we do from there makes all the difference. Love, Naama P.s. If you’re at a crossroads trying to make a decision about what's next, I’ve written a post a while ago where I shared 5 tools to help you make decisions without overthinking, you can read it right here.

P.p.s. If you’re at a crossroads and crave support and guidance, in my Life Transition Experience program I support you in finding your way forward. I walk alongside and guide you to find your direction.


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