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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.

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