What Coaches and Mentors Can Learn from Designing Your Life
Guiding other people can quietly narrow into steering them toward the path that worked for you, or toward the one "right" answer you're sure of, rather than helping them find their own. Designing Your Life offers a useful correction, both for how you work with others and for your own development: get curious about what's actually going on for the person in front of you — and for yourself — test small steps before pushing for big leaps, and stay honest about what you value in this work rather than assuming you've already got it figured out because you're the one giving advice.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
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The core lessons, applied to you
Get curious about what's actually going on — for them and for you
Instead of assuming you already know the cause of someone's stuck feeling because it resembles something you once went through, ask specific questions before offering a specific answer.
A mentor assumes a mentee's dissatisfaction with his job just means he needs to push harder, because that's what worked for the mentor at a similar point. He keeps encouraging more effort on the same track for months, never asking enough questions to notice the actual friction is a mismatch between the mentee's daily tasks and what he's good at, not a lack of effort.
In your next session with someone you're guiding, ask two or three specific questions about their actual daily experience before offering any advice, and notice what assumption you were about to skip past.
Encourage small steps instead of big leaps
A large, all-at-once plan is exciting to design but easy to abandon after one hard week; a small, testable step is more likely to actually happen and teach you both something.
A coach builds an ambitious full overhaul plan with a client in one enthusiastic session — new habits, new schedule, new goals, all starting Monday. By the following week the client has abandoned nearly all of it and feels like a failure, when a narrower first step would have been far more likely to stick.
When you and someone you're guiding land on a direction, break it down to the smallest next step that could realistically happen this week, and check in specifically on that one piece before adding anything else.
Get clear on what you actually value in this work
It's worth separating what worked for you personally from what you value about the practice of guiding others — the two aren't always the same thing.
A coach keeps recommending the same career framework to every client because it's the one that worked for her, without noticing that what she actually values in her own work is helping people ask better questions — not necessarily arriving at her particular answer.
Write down what you value most about doing this work — the moment in a session, the kind of change you want to help create — and check whether your recent advice to others has actually been serving that, or just repeating your own story.
Help people imagine multiple paths, not just the one you took
Rather than pointing the people you guide toward a single correct path — especially the one that worked for you — it helps to actively invite them to picture two or three genuinely different directions and notice which one actually fits their own situation, since the path that worked for you was shaped by circumstances that may not be theirs at all.
The person you're guiding may want a confident, single answer right now, while genuine curiosity means sitting with more open questions than they'd like. Hold both by being direct about the process itself — telling them you're helping them test possibilities rather than handing down a verdict can ease the discomfort of not getting an instant answer.
Name one thing, honestly
What's one piece of advice you give often that comes more from your own path than from what the other person has actually told you?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
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Run this for seven days
Write down what you value most about doing this work — the moment in a session, the kind of change you want to help create — and check whether your recent advice to others has actually been serving that, or just repeating your own story.