Defining better questions (and answering them) is a critical component of success in the business and academic spheres. Einstein famously said, “if I had an hour to solve a problem, I’d spend 55 minutes thinking about the problem and five minutes thinking about solutions.”

How might we extend this questioning to our own lives, facilitating improved self-awareness and clarity?

If you’ve ever partnered with a good therapist or coach, you’ll notice that they rarely give you any answers. Instead, they’re skilled questioners who seem to find the perfect sensitive points to poke, prompting you to insight.

Therapy is a dialogue. We can use journaling as a tool to enter into a similar deep conversation with ourselves. A good practice is to use curated question sets for reference, which provide starting points for these discussions.Three heuristics come to mind when thinking of how to find the right questions to answer:

1. Find the “soft” points. When you poke the right spot, there’s a little bit of give; a subtle gravity draws you deeper. Follow that impulse.

2. The disgust or repulse response. This is the opposite of the above - the immediate adverse reaction usually signals an area worth exploring, although it may take some courage to go there.

3. Anything that points towards yourself and away from the “shoulds” and “ought to’s” of others. “To know thyself is the beginning of all wisdom”.

Your journaling will probably not replace a good therapist, as you are by definition ill-equipped to identify your blind spots. However, it’s a great starting point. And remember to be kind to yourself. No therapist or friend would entertain your self-flagellation, so neither should you.