How and When to Give Advice

In some ways I’m professional advice giver these days. I talk to people monthly and help them make big decisions that will impact their lives greatly. I also do events where 7-10 people join me somewhere and we try to plot the course of their next few big moves. Giving advice is an enormous responsibility, especially when you know it’s likely people will follow through on it, so it’s something I take very seriously and to which I have given a tremendous amount of thought.

That wasn’t always the case, though. When I became a professional gambler in the early 2000s, I tried to convince all of my friends to do it. I was enthusiastic and proactive, but nobody listened to me, even as they saw me do well. The same thing happened when I learned about pickup a few years later.

Those two events were a huge lesson to me. I’d heard that people won’t take advice unless they ask for it, but I had cracked two major problems that all of my friends had, and I was absolutely flabbergasted that none of them took my advice.

Now I give no advice unless someone asks, or if I have the type of relationship where there’s an assumed openness to advice. I’d say that that group of people is 10-15 in size maximum.

Not only is there no point in giving advice when someone doesn’t ask for it, it can actually be a negative thing. If someone comes to you and wants to vent or isn’t ready to take action, your giving of advice will be seen as tone-deaf and may even make them resent you. I’ve made the mistake of advising people to break up with someone when they didn’t ask me, and then I could feel a little bit of tension afterwards when they stayed with them.

Give advice when asked directly. If you’re not sure, offer to offer advice in a way that makes it very easy to say no: “If you’re open to advice I have some thoughts on the situation, but it seems like maybe you’re working on it by yourself and don’t need input.”

When giving advice it is important to put it in context and explain why you’re giving that advice. This appeals to peoples’ intelligence and allows them to decide whether the advice is good or not. For example, sometimes I can tell people, “I’m telling you to do this because I was in the same situation and have a similar principles as you, so I am very confident it’s going to work.”

Other times I have to take the opposite tack. At one event someone asked me about parenting and I had to say something like, “I’ll give you advice but all of it may be totally worthless because I’m not a parent and my experience is only from observing my own parents, others’ parents, and from reading books about parenting. You will have to match the advice to your experience to see if any of it is of any use.”

I would much rather come off unconfident or even unhelpful than to betray false confidence and have someone go down a path that may be wrong for them. I also want them to understand where I’m coming from and why I’m giving advice so that they can filter it and adjust it if their premise is a little bit different.

Last, I want to make sure that my advice solves the problem they care about, not the problem I would have were I in there shoes. For example, sometimes I tell people to stay in school or stay at jobs, even though I would never do those things personally. They may not be valuable for reaching my goals, but they can absolutely be the right tools for other people’s jobs. It took me a long time in life to realize that my goals weren’t right for everyone.

I love giving people advice and I think of it as an art and a science. Every month I give advice that has the potential to steer someone’s life course drastically, and I take that responsibility very seriously. Good advice can change someone’s life, but only if it’s wanted and presented in a way to be of maximum utility to the receiver.


Photo is some early cherry blossoms from my last trip to Japan before quarantining at home.

I hope everyone is doing well on quarantine! I’ve been doing a lot of random backed up projects and am learning about 3D modeling and printing.

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