Supernatural's Dean Winchester is a hero. Like everyone else, Dean isn't perfect, and made various mistakes throughout the series, especially when it came to the Mark of Cain, keeping secrets from Sam, and trusting the wrong people. However, from Dean's mistakes and victories alike, or even just from moments in his life, audiences can pick out valuable life lessons.
Keeping classic rock on hand during long road trips is certainly one of those lessons, as well as the importance of never giving up, despite the obstacles ahead. Always being prepared for anything, as well as memorizing pop culture references are also noteworthy life lessons that Dean Winchester offered to audiences over the years.
Relationships With Parents Are Complicated
Dean grew up too soon after his mother was killed; John placed a lot of responsibility and burden on his shoulders, between teaching him to hunt and making sure Dean was always there for Sam. Dean was always loyal without question to his father, but it often came at a cost, especially when he was placed in the middle whenever John and Sam would fight. Plus, John told Dean before he died that he might have to kill Sam if he couldn't save him; that's certainly a big burden for a parent to place on their child.
When Mary came back to life, Dean's relationship with her wasn't the greatest either, as she certainly wasn't the mom he remembered when he was little. In any case, relationships are complicated, but Dean made his peace with both of his parents and loved them, even if things between them weren't perfect.
Always Play Classic Rock, Especially On Long Road Trips
One of the things that makes Supernatural so iconic is its soundtrack, many songs of which are classic rock songs from bands like ACDC, Metallica, Eric Clapton, and more. As Dean decreed in the series pilot, "driver picks the music, shotgun shuts his cakehole." Dean is usually driving, so Sam is subjected to many hours worth of classic rock with Dean singing along.
While Sam complains every once in a while, he obviously loves it, especially given the time he and Dean sang Bon Jovi's "Wanted Dead or Alive" while in the car. It makes the many hours on the road fun, and for Sam and Dean, it created good memories.
Keep Pop Culture References Handy
Whether or not anyone else was listening or even understood them, Dean was full of fun pop culture references throughout the entire run of Supernatural. From Scooby-Doo to Dead Poets Society, Dean loves film and television and has a perfect reference for any given situation.
It usually provided a lighthearted moment, which was welcome in a show like Supernatural given the monsters and serious situations the Winchesters were usually up against. His vast knowledge of pop culture is a beloved quality of his, and audiences can learn to make references of their own to lighten the mood in their own lives. Even if they're the only ones that pick up on it, it can be entertaining to them, much like it was for Dean.
Always Be Prepared
While audiences aren't necessarily walking into creepy houses or preparing to battle terrifying monsters on a regular basis, they can learn to still be prepared for anything, especially from Dean. Dean had everything he needed in any given situation, whether it be hunting, fixing Baby, or helping Sam.
Audiences can apply the same preparation techniques in everything they do, whether it be a job interview, a wedding, or even a relaxing evening at home, complete with movies, popcorn, and candy. Dean even had snacks; in Supernatural Season 1, he had M&M's while he and Sam were out looking for a wendigo that actually helped Sam and Ben find him after he'd been taken!
Don't Keep Emotions Bottled Up
Dean wasn't one to share his feelings easily. Looking back, Dean could have benefitted from having a few more of those moments, especially with people he trusted and cared about.
It took Dean a long time to open up to Sam about what Hell had really been like, and Dean rarely let others comfort him when he was at his breaking point. He would wait until everything became too much and then explode in anger. He might have experienced less stress and found comfort in others if he had spoken up about what he'd been feeling, even if that didn't come to him naturally.
Always Unapologetically Be Yourself
Dean never pretended to be anyone he wasn't; unless he was on a case, of course. Even when he lied about his background and name though, he was still himself in that sense that he loved food, pop culture, and proved his strength and intelligence at every turn as he looked into whatever the threat was.
Dean had a goofy side that he would show now and then, and while he would embarrass Sam with his table manners, Dean never apologized for his behavior or personality. He was confident in who he was, as well as his abilities, even if he did have doubts from time to time.
Life Is Too Short For Regrets
Dean had plenty of regrets in his life, especially when it came to former girlfriends like Lisa that he really cared for. Ultimately, Dean didn't end up with any of them by choice; with Lisa, he had Castiel erase her memories of him to keep her safe. It was obvious that Dean truly regretted that, given Lisa and her son Ben were his family and he gave up on his opportunity to have a normal life free of hunting.
If anyone knows how short life really is, it's Dean, and each time he died, he had regrets. In any case, from Dean's experiences, audiences can learn to take opportunities when they come, so they can avoid making the same mistakes that Dean did.
Things Are Not Always As They Seem
Dean didn't initially believe in angels, unlike Sam. After he discovered angels were in fact real, he certainly didn't like them. While audiences know that he eventually became best friends with Castiel, Dean and Cas had a rocky start.
Dean's animosity and skepticism towards angels at the time certainly didn't help matters, but the fact that Castiel came to be an ally, and then friend, helped matters greatly between the two. Castiel always came through for the Winchesters; he made a few mistakes along the way, but no one, not even angels, are perfect. Still, Dean learned a great lesson from Castiel in that not everything is as it seems, and sometimes friends are made in unexpected places.
Family Is Everything
Dean is the best brother; he pretty much raised Sam while John was hunting for his wife's killer, and he always made sure Sam was taken care of, even in adulthood. Dean would go to the ends of the Earth to help Sam, whether it be trying to find a way to spring him from Lucifer's cage, using an angel to cure Sam, or any other of the various things that Dean did over the years to ensure his brother's health and safety, even if Sam didn't necessarily agree with him.
Dean goes above and beyond the call of duty; family is important to him, and he shows them that in everything he does.
The Importance Of Never Giving Up
Dean has been to Hell and back, literally. Yes, there have been many times in his life when Dean has declared that he's done, and even told Sam to give up on whatever they were trying to accomplish, whether it be beating Chuck, or even removing the Mark of Cain from Dean himself.
The thing is, even when Dean was at his lowest point, he always found a way to fight back; he might have felt over it, but between himself, or Sam, or one of his friends, Dean always found a way to gather up enough strength to carry on. By not giving up, Dean did a lot of good for the world and showed audiences the importance of never giving up.