What Coaches and Mentors Can Learn from Farsighted
Coaches and mentors are often the ones other people turn to precisely when a decision is too big and too unfamiliar to make alone — a career change, a relationship decision, whether to leave a stable path for a risky one. The trap is subtle: it's easy to help someone narrow to the option that matches your own values, or to walk them through only the future you'd want for them, without realizing you've substituted your map of the situation for theirs.
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
Help them map their whole situation, not yours
When someone brings you a big decision, it's tempting to reason from the factors that would matter most to you in their position. But their situation involves people, constraints, and considerations you may not share — a family obligation, a financial cushion or lack of one, a local job market you've never worked in. Before offering a view, help them map the fuller landscape of their own situation, not the one you'd imagine for yourself.
A mentor advises a mentee to take a bold, high-risk career leap, reasoning from what worked well in the mentor's own past. The mentor never asks about the mentee's financial obligations or lack of a safety net, and the advice, while well-intentioned, ignores what actually makes the decision risky for this particular person.
Before offering guidance on a big decision, ask the person to walk you through everyone and everything it touches in their life, not just the parts they led with.
Help them picture more than one way it goes
People bringing you a big decision often arrive having already pictured one future — usually either the hoped-for outcome or the feared one, rarely both. Part of your value is helping them sketch several different, plausible ways the situation could unfold, including ones they haven't let themselves consider.
A coach helps a client prepare for a major transition by focusing entirely on the client's stated fear of failure, reinforcing a single worst-case scenario. They never help the client picture a middle scenario — partial success requiring adjustment — which turns out to be closer to what actually happens, leaving the client unprepared for anything but total success or total failure.
In any coaching conversation about a big decision, ask the person to describe at least two different plausible outcomes, not just the one they're most afraid of or most hoping for.
Make sure you're not their only outside voice
It's tempting, as a trusted mentor, to let a mentee treat your view as the outside perspective they need. But you're one person with your own blind spots, and a genuinely good decision usually benefits from more than one source of outside judgment. Encourage the people you mentor to seek a second perspective, even when they're inclined to stop at yours.
A mentee makes a major decision based entirely on one mentor's confident advice, without seeking any other outside view. The mentor's blind spot in that particular area, never surfaced by a second opinion, turns out to matter a great deal.
When advising on a major decision, explicitly encourage the person to also talk to at least one other person whose experience differs from yours.
Keep an honest record and review it afterward
The best mentors keep some record, even a loose one, of the advice they've given on big decisions and what happened afterward, because that's the only way mentoring judgment actually improves over time rather than staying a matter of instinct and confidence.
Helping someone map their full situation and imagine multiple futures can feel like it's slowing down a person who's anxious and just wants a clear answer. Resist the urge to shortcut it — a rushed, single-scenario conversation often leaves the person less prepared, not more reassured.
Name one thing, honestly
Think of someone you're currently advising on a big decision — are you helping them map their own situation, or quietly steering them toward the one you'd choose in their place?
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
When advising on a major decision, explicitly encourage the person to also talk to at least one other person whose experience differs from yours.