Socratic Coaching dialogue (real-life) about a difficult career decision

Richard van der Linde
3 min readDec 24, 2023

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Client: I’m not uncertain about whether I should leave my job to pursue a risky business idea. How can I determine what’s the right decision?
> Me: That depends, what are your leading principles for decision-making?
Client: What does that mean, leading principles?

Me: Every person bases their decisions on their beliefs about right or wrong, what is desirable and what mechanisms are at play that determine if you achieve what you desire. Once you become familiar with yours — perhaps from past decisions — we’ll have the answer to your question. So, what do you normally value when making decisions?
> Client: I like to be fair and honest and challenge myself to be the best version of myself.

Me: Got you. How do you feel about taking risks? Is more risk always better, as a way to challenge yourself?
> Client: Not really, I guess there is a point at which adding more risk makes the challenge too big for its purpose.

Me: Excellent. So, how do you know when you shouldn’t add more risk?
> Client: It just wouldn’t feel right.

Me: Okay, so feelings are a significant indicator for you. Now, can something also feel too easy?
> Client: Yes, it certainly can.

Me: Can you describe for both scenarios how that would feel, too easy and too challenging circumstances?
> Client: If it’s too easy, I would describe the feeling as unengaging or boring. Conversely, in a situation that’s too challenging, I feel nervous and restless.

Me: Good. And you know that because you could, sort of, feel it, am I right?
> Client: Now you ask, indeed, I did feel that. Perhaps not as intense as in a real situation, but certainly I got a sense of how it feels.

Me: Great. So, now we know when it is too much and when it is too little challenge for you. Would you agree that the right amount of challenge still makes you feel a little uncomfortable — more similar to when there is too much challenge than when there is too little?
> Client: I agree.

Me: Could you differentiate between discomfort from a suitable challenge and one that’s too much?
> Client: I think so.

Me: Okay, so with this framework in place, imagine now how it would feel to quit your job and start that risky business. Where would you place the amount of challenge you feel?
> Client: To be honest, based on my level of discomfort, I would rate it as too challenging.

Me: Well, I believe that answers your initial question. We could explore other aspects or unknown factors related to your business idea. We could also look into increasing your tolerance level for discomfort. But if this already feels like a resolution, then we can leave it at that.
> Client: Thank you, I know what to do next. This has been very helpful!

Socratic coaching

This is how Socratic coaching looks like. Sometimes, it may require examining your fundamental beliefs to make seemingly simple decision. But, after a few such inquiries, you begin to recognize your patterns and you can apply them universally.

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Richard van der Linde

Suggesting nuances that can make complex matters simpler. Bottom line of my writings: life is all about breaking the identification with the voice in our head.