Dear Son, The Good Guy Doesn’t Always Win


Dear Son, The Good Guy Doesn't Always WinAs we celebrated my son’s 15th birthday, I was thinking a lot about what I really want him to know in order to help him become a successful human being. What words of wisdom do I have for him as he makes his way to adulthood? What have I tried to protect him from through the younger years and what does he need to hear from his mom before the world socks it to him in a not so motherly way? I’m sure if we all sat down and made a list of things we want our children to know there would be approximately 50 million things on that list. How do we pick just one?

I decided to start with the thing that still bothers me as a 41-year-old adult. Perhaps if I’d learned it a little sooner I wouldn’t have been so surprised by it.

We start using the word ‘fair’ very early on in our children’s lives. They hear it from us at home. They hear it from their friends on the playground. They hear it from their teachers at school. And before we know it, they’ve started saying that well known phrase in their whiniest voice “Mom….that’s not fair.” Being the primo parent that I am, I would usually yell something back like “well, life isn’t always fair, buddy!” and the conversation would end there with a huff and a stomp off (by both of us). I realize now as he’s gotten older and doesn’t use that phrase nearly as much, that I never really explained to him what I meant or why I was so grumpy about it.

It’s probably time he knows.

Dear Son,

I would tell you that there’s really no such thing as fair because the good guy doesn’t always win. Actually, the good guy rarely wins because the good guy usually puts everyone else above him. The good guy won’t step on other people to get to the top. The good guy usually doesn’t like confrontation so he will bend and flex as much as humanly possible to keep the peace. So it may seem like the good guy gets the raw end of the deal and often, the good guy goes to bed at night wondering when it pays off to be the good guy. (Mom hint: sometimes you may not ever see it pay off, son.)

I would tell you that people won’t make decisions based on your feelings. People are selfish. People make their decisions based on how THEY feel and what THEY want…not how you feel or what you want. People get mad. People hold grudges. People want revenge and people want to feel superior, so people will flex that superiority with no thought of how you will feel about it. (Mom hint: good guys are people too, son, so you will feel all these things at some point too.)

You might ask me about rules and laws, right son? Aren’t rules and laws put in place to keep things fair? Don’t rules and laws protect the good guy? You’re right, son, but people don’t always feel like the rules apply to them. They break those rules or ignore those laws because their agenda is more important to them than anything else. Sometimes there are consequences to breaking those rules, but oftentimes there aren’t because the people on the other end of the rule or law are the good guys. And remember: good guys often let things slide to avoid confrontation. Good guys take the high road. (Mom hint: sometimes the high road is lonely, son. Take it anyways.)

But it’s not all bad, son. Good guys have a lot going for them too! Good guys make the world a better place. Good guys are loyal. Good guys surround themselves with other good guys and they all work together to do good things. They don’t always come out on top and sometimes it might even seem like they rarely “win,” but in the long run, it always pays off to be a good guy. (Mom hint: good guys make their mommas proud.)

So even though life’s not always ‘fair’…and it’s not even always good…YOU can be fair and YOU can be good. Don’t base your actions on the actions of the people around you. If someone is unfair to you, be fair back to them. If someone is unkind to you, respond to them with kindness. Take the high road and learn to lose with dignity.

Remember son: it’s not IF you lose, it’s WHEN, because I raised you to be a good guy and good guys…well, I think you get the point.

Happy 15th year from one good guy to another.

Love, Mom

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Hey, Hey! Amanda here. Wife to KJ and proud mom to my 3 boys: Noah (14), Nash (4), and Banks (6 months). I'm a forever Carolina girl that moved to Knoxville in 2003 and have called it home ever since. When I'm not wrangling children or writing for personal therapy, you'll find me stressing about what's for dinner or compulsively moving things around my house (some call that decorating). I could also be found listening to true crime podcasts or sneaking in new Halloween decor because it's my favorite holiday (give me all the spooky vibes). Motherhood is an adventure; let's go on it together! I hear it's easier that way.


  1. Love this! So true life isn’t fair but glad you’re teaching your 15 year old that he can overcome unfairness by being strong & not counting on fairness but by being “His Best Self.” Good job Mom🙌💕


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