A few months ago, a close friend came to me in real pain. One of the pillars of his life was fracturing. He was terrified of it falling apart. He didn’t want to lose what he had spent more than a decade building and had put all his love into. He asked me directly for advice. He came to me, I think, because he believed I would tell him something true and helpful.
At first, I didn’t want to say anything. I played it off with platitudes and a bunch of “meh, you’ll be fiiinne”. I am often asked for advice, yet I have a long-standing reluctance about giving advice. I’ll spend most of this post explaining why. But this was my friend. Someone I love and care for. And his fear was so raw, so present on his face that I saw him like I see my own son, and my reluctance gave way. I told him to lean in. To stop managing the situation from a safe distance and instead be fully present in it — authentic, vulnerable, speak this truth gently but remain boundaried. I gave him my observation, which I preceded with the fact that I am looking from the outside and I can’t truly diagnose the situation, but I told him to sit with the uncertainty and stay in for as long as he could. How long, he asked. Give it time, six months I proffered. I believed, and still believe, that this was the right orientation for a person struggling with what he was going through.
What happened next slapped me in the face like a bag of bricks.
Over the following days, something shifted in him. Not towards patching up this pillar of his life. Toward clarity. The man who had come to me terrified of losing this amazing thing he had built, decided to unravel it himself. He went from gripping the pillar with both hands to letting it go. Completely.
I still don’t know what to make of it. I’m not sure it was wrong. I’m not sure it was right. What I know is that I watched my own advice travel through another person’s life and arrive somewhere I never anticipated, carrying weight I didn’t intend, touching parts of him I couldn’t see.
That’s the thing about advice. It never stays the shape you gave it.
Why People Ask
Before we talk about what happens when advice lands, it’s worth sitting with why people seek it in the first place.
The simple answer we like to go to is that people want guidance. They’re facing something hard, they don’t know what to do, and they hope someone else does. But I’ve come to believe that’s rarely the full picture. It’s the lie believed to preserve the hidden truth.
When someone asks for advice, they are almost always also asking to be relieved of something — the weight of not knowing, the discomfort of sitting with an open question, the anxiety of genuine uncertainty.
Advice feels like solid ground. A path paved by someone else can be stood on, at least for a moment, without the whole body shaking.
The psychologist Erich Fromm called this the “escape from freedom.” His insight was that genuine freedom (the freedom to choose, to author your own life) is experienced by most people not as liberation but as burden. It produces isolation and anxiety. And one of the most reliable ways to escape that anxiety is to hand your path forward over to someone else. An authority, an expert, a wise friend with a beard.
This is not weakness. It’s deeply human. But it means that the moment someone asks you for advice, they are often not really asking you to solve their problem. They are asking you to take the weight of their uncertainty off them, even briefly. And if you take it, if you give the advice, you have done something to them that neither of you fully recognizes. You’ve made their path yours. And however that path goes, some part of you will carry that. Not because it’s your fault. But because you made it your business.
The Invisible Lens: Projection
Carl Jung gave us a word for something that happens constantly in human relationships, mostly without anyone noticing: projection.
In simple terms, projection is the unconscious act of placing something from inside yourself onto someone outside.
In projecting, you attribute to another person a quality, a feeling, or a capacity that is actually a reflection of your own inner world.
We all do it. It’s not pathology. It’s the method of how the psyche manages what it cannot yet hold consciously.
When someone projects wisdom onto you, the mechanics are roughly this: they encounter something in you (your history, your willingness to sit with hard questions, your stature) that resonates with a quality they sense but haven’t fully claimed in themselves. Something in them knows their path. But they haven’t yet trusted that knowing. So they place it outside themselves. They put it on you. And then they ask you for it back.
“Everything that irritates us about others can lead us to an understanding of ourselves.” — C.G. Jung
The reverse is equally true: everything we idealize in others, the wisdom, the clarity, the groundedness we seek, is often a quality we are not yet willing to own in ourselves.
This is why people in my circles tend to come to me for advice. I don’t think it’s because I’m wiser than they are. It’s because something in the way I engage (the questions I ask, the pace I keep, the willingness to name hard things directly) reflects back a quality they are reaching toward. They project onto me a certainty I do not possess. And then they ask me to hand it back to them.
The trouble is: when you accept the projection, when you play the wise, bearded elder, you don’t give them the thing they actually need. You deprive them of it.
Because the thing they actually need is to find their way to their own knowing. To stop borrowing clarity from someone else’s face and find it in their own.
Advice, received through the lens of projection, almost never does what it appears to do. It doesn’t transfer wisdom. It confirms the receiver’s belief that the wisdom lives somewhere outside them. And that belief is the very thing keeping them stuck. And that’s a wild, wild thing to say and to see. And yet, that’s exactly why people go to motivational seminars and listen to the amazing Tony Robbins tell them they can do it! So they can package that feeling from their projection, handed back neatly by Tony, for them to carry into their lives for a little bit and then go right back to where they were before, and then repeat the cycle the next time his circus is back in town.
The Shape of Uncertainty
There is an old story from the Taoist tradition that I find myself returning to often. It goes something like this:
An old farmer’s horse ran away. His neighbors came to console him. “Such bad luck,” they said. The farmer replied: “We will see.”
The next morning, the horse returned, and with it came a dozen wild horses. The neighbors rushed back: “What wonderful luck!” The farmer said: “We will see.”
That afternoon, the farmer’s son tried to tame one of the wild horses and was thrown. He broke his leg. “Such terrible luck,” said the neighbors. “We will see,” said the farmer.
The following week, soldiers came through the village to conscript young men for war. The farmer’s son, with his broken leg, was spared. “How fortunate,” the neighbors said. The farmer said: “We will see.”
What makes this story worth reading again and again is not the twist. It’s the farmer’s refusal to give-in to the uncertainty prematurely. He doesn’t know if things are good or bad. Not because he’s passive or detached, but because he understands that life unfolds across a longer horizon than any single moment can reveal. The neighbors, always certain, do not sway the farmer’s resolve to stay in uncertainty.
I’m living my own version of this right now. My son is five. We’ve applied to six private schools — the kind where if he gets in, he’ll likely be there from kindergarten through twelfth grade. All six give their answers on the same day. Our first choice feels like the right fit, the porridge is just right – it’s got a little bit of everything we value. And it’s the closest drive for daddy and daddy cares a lot about that. The others are all genuinely great — one has a campus built for athletics, one is academically intense, one is deeply rooted in community and diversity. We want what’s right for him. We just don’t know what right looks like yet. And here’s what I keep coming back to: even if we get our first pick, I still won’t know. His life will unfold the way it will unfold, shaped by teachers and friendships and moments I can’t anticipate, inside whatever walls he ends up in. The school we’re hoping for might be exactly right. It might be the thing that costs him something we can’t currently see. So, we will see.
My friend pulling apart his own pillar in life might be the worst thing that ever happened to him and everyone involved. It might be the moment that saves a life. It might bring people closer, it might pull people apart. I genuinely do not know. I have my own strong feelings and I’m contending with it. But I have stopped pretending to myself, that the advice I gave was right or wrong. It moved through him and became something altogether unrecognizable to either of us from that moment we shared. That’s all I know.
This is not a comfortable place to stand. But I think it’s an honest one.
Why Advice is Two Cents
I’ve arrived, through years of reflection on my experiences with adversity and loss, at a position that life advice has very little value. I work hard to give very little of it and I seldom ask anyone for it.
This isn’t false modesty. It’s not that I think I have nothing to offer. It’s that I’ve watched advice, my own and others’, move through people’s lives and consistently land somewhere other than intended. The problem isn’t the person giving it, but rather the very nature of advice.
First: advice is always drawn from someone else’s life. When I tell you what I would do, I am telling you what I, with my history, my wounds, my particular relationship to risk and loss and love, would do. That person is not you. The advice that saved me might undo you, not because it’s wrong in the abstract, but because it was built for a different soul.
Second: advice, by its nature, skips the most important part. The most important part is not the answer. It’s the process of arriving at the answer — the sitting with uncertainty that the rockstar Jungian analyst, Marion Woodman, described as “holding an inner or outer conflict quietly instead of attempting to resolve it quickly.” The slow and uncomfortable clarification of what you actually value takes time. When someone gives you their answer, they rob you of that priceless process. You get the destination without the journey, and the journey was the thing that would have transformed you into who you sought to be all along.
Third: as we’ve already seen, advice passes through the distorting lens of projection. The person receiving it is not hearing what you said. They’re hearing it through who they believe you to be, which is mostly a fiction their own psyche constructed. We don’t see things as they are. We see them as we are. So the advice gets filtered, magnified, twisted. It arrives in a different shape than you sent it.
“I would like to beg you, dear Sir, as well as I can, to have patience with everything unresolved in your heart and to try to love the questions themselves as if they were locked rooms or books written in a very foreign language.” — Rainer Maria Rilke
He was saying, with great care, that the answer is not the point. Learning to live with the question is.
The Advisor Question
I want to draw a distinction here, because I think it matters.
There is a real and legitimate role for advisors, and it’s worth being precise about what that role is and where its limits are.
A good advisor is someone with deep expertise in a specific domain: M&A Finance, contract litigation, SaaS product strategy, consumer electronics go-to-market, cloud security architecture. When you bring an advisor into your orbit, you’re not asking them to weigh in on who you are or what your life should look like. You’re asking them to apply a concentrated body of knowledge to a well-defined problem. That should be genuinely useful. The best advisors I’ve known are extraordinarily disciplined about the limits of their expertise. They know what they know and they know where it ends and to say so.
But I watch founders reach for advisors — and mentors, and investors, and friends like me — for questions that are not domain specific to their tenured skillset. They’re sitting with something that doesn’t have a right answer. Something about whether to push forward or let go, whether a relationship has run its course, whether the company they built still fits the person they’ve become. They ask for advice on these questions because the questions feel unbearable, and because having someone else weigh in makes the unbearable feel momentarily more manageable.
No advisor can help with these questions. Not because advisors aren’t smart. Many of them are extraordinarily smart. But because these questions are not information problems. They’re not solved by more data or a better framework. They live in territory that expertise cannot reach.
This is where the advisor role ends and something else begins.
The Mirror
I became a coach not despite my reluctance to give advice, but because of it.
I have spent years sitting with people in the hardest moments of their work and their lives. Founders who built something real and then felt it slowly hollowing them out, myself included. CEOs who couldn’t understand why they kept recreating the same conflicts with different people, myself included. Leaders who had every external marker of success and felt, underneath, like they were running from something they couldn’t name, myself included.
What I noticed, repeatedly, was that these people (myself included) didn’t need other peoples’ answers.
They needed to see themselves more clearly.
They needed someone to hold up a mirror, not a flattering one, not a cruel one, but an honest one, so they could see the patterns they were living inside, the beliefs they were defending without knowing it, the story they’d been telling about themselves that had stopped being true.
That’s what coaching, at its best, is. Not advice. Not answers. Not even guidance in the conventional sense. It’s a particular quality of attention, rigorous, unhurried, willing to sit with what’s difficult, that allows another person to see what they couldn’t see alone.
Jung understood this. His whole psychology was built around the idea that what we cannot see in ourselves does not disappear. It reappears in our life, in the form of the circumstances we keep recreating, the relationships we keep damaging, the patterns we swear we’ve broken that keep returning – and of course, of course, it greatly impacts our careers. The work of becoming more conscious, more aware of what’s actually driving you, is not intellectual work. You can’t think your way to it. You need a relationship, a genuine encounter with another person, to bring the full you into clear view in the form of a mirror.
The Tao Te Ching puts it differently, and perhaps more simply:
“To the mind that is still, the whole universe surrenders.”
The coach’s job is not to speak wisdom into the room. It is to create enough stillness, enough safety, enough honest presence, that what the client already knows can surface. Most people are so busy managing their own anxiety, keeping up appearances, seeking validation, running from uncertainty, that they never get quiet enough for their deeper knowing to be heard.
The coach doesn’t give you anything you don’t already have. The coach helps you hear yourself.
What Changes, and How
I want to be specific about this, because I think it’s misunderstood.
When people imagine coaching, they often imagine something like a sophisticated version of advice: a smart person helping you think through decisions, offering frameworks, asking good questions that lead somewhere the coach already sees. And perhaps some coaching is like that – it’s a free market. That’s not the intent of my coaching work.
The kind of coaching I’m drawn to, and the kind I practice, goes to a different layer. It starts from the premise that the struggles leaders bring to coaching are rarely what they appear to be on the surface. The co-founder conflict is rarely just a conflict about decisions. The burnout is rarely just exhaustion. The inability to delegate is rarely just a management problem. These are the outer expressions of something happening at the level of identity — who the person believes themselves to be, what they believe they deserve, what they’re afraid to want, what they’re using the company to prove.
Working at that layer is slower. It asks more of the person. There are sessions that feel like nothing happened, and then something shifts weeks later in a conversation with a board member, co-founder, or a spouse and the person can’t explain why. The changes are not always traceable. But they tend to last, because they’re rooted in something real and the person goes through a transformation.
I’ve watched founders stop recreating the same conflict with different people, myself included. I’ve watched CEOs release a grip on control that had been slowly strangling their companies for years, not because someone told them to delegate, but because they’d done enough inner work that the compulsion to hold everything simply loosened, myself included. I’ve watched people whose companies were performing well finally let themselves feel it, instead of moving immediately to the next threat – myself included.
These are not small things. They’re the things that change how a person leads, how they love, how they inhabit their own life.
One Last Note on Advice
I still don’t know if what I told my friend was right.
I’ve turned it over many times. I’ve looked at the advice itself, lean in, be authentic, speak truth, be gentle but boundaried, and I believe those things. I still believe them. But I also know that my belief in them, and my love for him, and my reading of his situation, were all limited by who I am and what I can see from where I stood. He took what I said and carried it into his own interior, where it mixed with everything I couldn’t see, and arrived somewhere I didn’t expect.
Like the farmer, I will see, over time, what happened in my friend’s life and whether the path he’s on is one he can build something good from. So will he. And we will see what happens with my dear son, as we soon accept some school as our second home for the next thirteen years. Nobody knows yet.
What I do know is that the most useful thing I can offer, to my friend, to the founders I work with, to anyone sitting with something genuinely hard, is not my answer. It’s my presence. My willingness to sit with them in the not-knowing. My refusal to hand them a certainty I don’t possess.
That willingness is a different kind of help. It’s slower, and less satisfying in the moment, and it doesn’t let either person off the hook. But it points toward the place where real change actually lives: inside the person asking the question.
Further Reading
Memories, Dreams, Reflections – C.G. Jung
Letters to a Young Poet – Rainer Maria Rilke
Holding the Tension of the Opposites – Marion Woodman