2.) Develop an awareness of, and pay attention to, your mental health throughout your life.

You know about it and recognise it when you have a cold, or scrape your knee, but too many people, both men and women, are walking around with undiagnosed depression, anxiety, and other extremely common mental health issues. If you are struggling, see a doctor, who can refer you to a specialist – it is one of the best things you will ever do for yourself.

So failing often is a very good piece of advice. I wanted to add something to that too. That is not to leave any crumbs behind when it comes to relationships, career, or society. That means, whatever you do, leave on good terms and leave a good trail behind on your past impact. A failure can be falling short of a quota but make sure it is not a work relationship problem where your rep is on the line (cheating, scam, greed). Fail gracefully and be honest with yourself. Because if you leave enough crumbs behind you, unfortunately all you attract in life are rats (energy-killers, poor relationship, hard job-seeking,etc…)

I thought about this for a long time. I think my challenges with women have come from one place…and I’m not pointing fingers or placing blame. Being shamed or teased for liking a girl. You remember when you were young and a sibling or in my case, my mother, would say “What is that your girlfriend. Ewwww!” It always made me embarrassed. I began to associate attraction to a girl as something to be ashamed of.

I would tell my son to never be ashamed of what he is feeling and to understand that it is normal to be attracted to someone. You have a right to talk to anyone you want. I would tell him it’s no big deal if you are rejected. Don’t worry about the number of times it doesn’t work out…look to the times when it does.

Finally I would tell him…be proud to be a man. Being a real man is a great thing to aspire to be. If it doesn’t work out there will never be any doubt that the pleasure was worth all the pain.

Whenever we go through something rough, like a bad breakup, a tough situation at work, and so on, we have a tendency to think that it is all our fault. That this is happening to us because there is something fundamentally wrong with us–that if we were ‘good’, the sun would be shining on us all the time.

I’d want my son to understand that this isn’t the case. He is going to go through storms just as every good man before him has. It’s less personal and more universal. The way he handles them and the way he handles himself is a very big measure of him as a man.

I want him to understand that he won’t always be able to come through as he would want. I also understand that everyone respects someone who handles disappointments and setbacks with poise, because we all will face them.

–I want him to understand that he will face rejection from women, some that he are really into. He will approach a woman and he will flub it. He will take her on a date and she won’t feel it for him. He will get into a relationship with a woman he is really into, and she might leave him. And he will feel searing pain that might last a long time, due to biochemical reactions beyond his control. That doesn’t mean that he isn’t a good man. It is more about how he handles her rejection.

–I want him to understand that he will face challenges and obstacles on the way to achieving his dreams. And even that not all goals will come true. Not everyone can be the next LeBron James, and not everyone can be a Division I college athlete. I want him to give it his all anyway. And to also understand when he cannot do any more and when it is time to stop.

–I want him to understand that there are others who will try to use their power to intimidate him–physical or financial (e.g., a bad boss). I want him to learn to deal with confrontation as a mature man.

Great question!