The show Friends hasn't been on air since 2004, and yet fans love to rewatch the series and rediscover their love for the characters and relive some of the laughs they've had with them. While Chandler has his ups and downs, he's among the most lovable of the group.
He didn't always make the best choices in life (he dated Janice more than once and kissed his best friend's girlfriend), but he did make some that ultimately affected his life path in the very best way. Small or big, these are the decisions that were bound to leave a lasting mark.
Kicking Out His Roommate
For a while, Joey moves out from his shared apartment with Chandler, so he gets a new roommate, named Eddie. However, things with his new roommate don't quite work out as well. It soon turned out that Eddie was a bit unusual, like watching Chandler while he slept and accusing him of sleeping with his ex-girlfriend.
In the end, Joey helps him out of the awkward situation and moves back, and it's clear that kicking Eddie out before he did something weirder than just watch Chandler sleep was the right decision.
Breaking Up With Aurora
Chandler has a brief romantic entanglement with a woman named Aurora, who he believes is way out of his league. Unfortunately for Chandler, he soon discovers he's not the only one enjoying Aurora's company.
It's hard for him to accept that he doesn't want to be one of Aurora's many lovers, and prompts her to "lose the other guys". Despite realizing that he enjoys a part of their relationship, he ends up breaking up with and it was one of the best decisions he ever made for himself. If he had stayed with her, it would undoubtedly effect the respect he had for himself and his sense of self-worth in the long run.
Breaking Up With Janice
Chandler's relationship with Janice was a recurring joke in the first seasons. Often, it seemed Chandler was stuck in a relationship with Janice because he didn't have the courage to break up with her. His inability to face it forced him to fly to Yemen to avoid telling her the truth, which was problematic at the least.
After developing actual feelings for Janice, Chandler was happy in their relationship. But when he found out Janice had a chance of reconciling with her ex-husband, he told her to go back to him and reunite their family. Letting someone you love go is never easy, Chandler also came from a broken family, and knew the trauma that can often come with it. He didn't want to play a part in breaking up another family. Even if it was painful at first, he gained the peace of mind he wouldn't otherwise have.
Not Allowing Monica To Spend Their Savings On A Wedding
Chandler was always the most money-savvy out of all of the six friends. He has a steady well-paying job throughout almost the entire show. Not always being the character with the most spine, it would be expected that Chandler would cave into Monica's demands that they have the wedding of their dreams and spend his savings nest on that.
In a rare turn out of events, Chandler puts down his foot and argues that the money he spent years saving up would be better spent on their future lives. Many couples go into debt to finance their wedding but Chandler knew it wasn't the right way to start their lives. The decision ultimately paid off - as they got two kids instead of one, so they sure could make good use of that money.
Supporting his friends
Chandler was often the most reliable character and always tried to support his friends. This is especially clear with Joey, as Chandler is often seen paying the bills for both of them and even financing some of Joey's headshots when his career wasn't taking off.
He was continuously a good friend to all of his friends. Now, supporting one's friends should never be something people do because they expect something in return, but you "reap what you sow", and Chandler can count on the support of his friends back in return.
Quitting Smoking
Smoking was his worst habit. While Chandler doesn't smoke for the entirety of the show, he is shown struggling with it multiple times. He first relapses when he's teaching Joey how to smoke for a role and hides his habit for a while before getting caught by his friends.
His addiction makes him do some pretty hilarious stuff like taking a puff out of a stranger's cigarette and even hiding a cigarette in his desk at work until his friends ultimately help him kick the habit. Smoking is unhealthy, so by quitting he likely extended the length and improved the quality of his life (not to mention he saved a lot of money).
Owning Up To His Mistakes
When Chandler pursues Joey's girlfriend Kathy and then lies to him about it, it hurts Joey a lot and compromises their friendship. It was admittedly one of the worst things he's done to Joey.
In order to save their friendship, he agrees to spend six hours of Thanksgiving locked in a box to prove how sorry he is. Chandler proves to Joey how sincere he is by staying quiet in the box even while Kathy breaks up with him. Despite Chandler often being sarcastic, he cares deeply about his friends, and if this cost him his friendship with Joey, he likely would never have forgiven himself.
Being Himself
Some people might say that Chandler just can't help himself - that's the way he is. But at another glance, it seems that Chandler at some point made a conscious decision to just be himself. He goofs around and drowns in self-deprecating humor and often says stuff he isn't supposed to share with other people.
But his friends know all this about him and love him anyway. So it can be argued that the decision he makes every day to be himself has very real consequences. His personality attracts the right kind of people into his life, ultimately making his life different than it would be if he acted fake with people.
Quitting His Job
Chandler has a steady job and financial stability throughout the show when most of his other friends don't. But as everyone rises through the ranks and improves their careers, Chandler feels continuously stuck in his job and decides to risk everything to pursue something that will not only pay the bills but also inspire and fulfill him.
He quits his job, which is one of the most unexpected things to happen on Friends. Not only does he have to deal with less money coming in, but is also starting out with people that are half his age. This was the bravest thing Chandler ever did, and the right decision. If he had stayed at his old job, he would likely have been miserable for the rest of his life, but taking this risk allowed him to find his passion and consequently happiness.
Overcoming His Commitment Issues
One of the recurring jokes on Friends is Chandler's inability to have a long committed relationship. His commitment-phobia starts to present a real problem when Chandler falls in love with Monica. That is the one relationship he doesn't want to ruin. It would not only affect his relationship with Monica but likely his friendship with everyone else.
He could have gone through his life going from one empty relationship to another, but as one of the biggest signs of growth, Chandler manages to get through it. By communicating with Monica and slowly getting to a place where he's ready for that next step, overcoming that fear was likely the decision that had the most lasting impact on his life. Finding his home in a person he loves filled his life with a sense of purpose and belonging and played the biggest role in his future happiness.