Here is a good formula for living a life with as few regrets as possible: Always help when you can.
Once, many years ago, I saw a young woman walking in the rain, looking cold. I was about to pull over to offer her a ride, but I let fear get the best of me. I was an adult man and she was a teenage girl, and I feared the risk of my intentions being misinterpreted. So I didn’t speak to her, and instead drove off.
I’ve thought about that once a week for two decades. I tell myself all sorts of stories – we were in a populated area, not a lone stretch of wilderness highway, so she probably wasn’t walking far. She could have gone into any store for temporary shelter if she was really in distress. Maybe I even misinterpreted her look as distress; she could have just been wet but perfectly content to experience the rain.
I tell myself those stories as a defense against the guilt of regret. Because my brain also tells other stories – what if she was in real danger, and you didn’t help? What if she was trying to get away from someone? What if she was walking in the rain because she was disoriented or in deep emotional distress? The potential answers to those questions haunt me.
In all the years since, I’ve never once regretted helping someone. Those little gestures – grabbing a door for someone, offering to carry something, helping someone pick up something they’ve dropped, offering a hand if they’ve fallen. None of those have ever turned out bad. I’ve never been burned by any of them, or lost time or effort I couldn’t afford.
In fact, all those little gestures have brought me much joy! As a result of that pattern I’ve made friends, held babies, found new friends for my children, and all sorts of other boons – not to mention the great happiness in my heart that comes from living your life that way. I’ve never had a moment of awkwardness or embarrassment or anything else negative as a result of trying to help. But I’ve had two decades of guilt and regret from the notable time that I didn’t.
Even if someone ever did respond poorly to my offer of help (and no one ever has!), it would be easy to shrug off, since I know I was just trying to help and my intentions were good. So there’s almost no way it could turn out badly.
I try to offer advice rarely, instead just “living my life out loud,” talking about my experiences, and letting people take what lessons from it they will. But in this instance, I will offer the advice very genuinely: Help people. Build it as a habit to give those small bits of assistance whenever you can. Your life will be so, so much better for it.
The Opportunity Machine 