Why Some People Regret Trying To Improve Their Social Skills
Many people realize they have some social weaknesses, work to overcome them, and are happy for having done it. Like they know they're generally shy, feel out of their element in group conversations, and are nervous about public speaking. They put some time into improving in those areas, see their efforts pay off, then move on to other things.
A subset of people who try to improve their social lives look back on it with regret. They feel like they wasted their time, pursued the wrong goals, or approached the whole project with a faulty mentality. They may feel totally unsatisfied with that period in their life, or be able to acknowledge they got some benefits from working on their people skills, but not as many as they hoped before they started the whole undertaking.
Here are some core reasons someone may feel regretful about trying to enhance their social skills. Hopefully reading it may prevent you from making the same mistakes. If you've already made them, maybe it will validate that you're not alone in having some second thoughts about trying to correct their supposed problems in this area.
They bought into a false message about what was wrong with them, and tried to change socially to correct it. The process of trying to transform amplified their sense of being shameful and broken. They later realized they were okay as they were
For example, someone is naturally reserved, likes spending time alone, has non-mainstream hobbies, and doesn't care about partying. Growing up they repeatedly received the message that these traits made them a boring loser. They believe they have to overhaul their personality and social style to be happy. They want to be liked and have friends, so they decide to change. A part of them is even excited to do it, since they've truly swallowed the narrative that they're flawed. Only a smaller piece of their mind feels reluctant and resentful about the endeavor.
Over the next year they honestly try to become a more outgoing, broadly appealing party animal. There are flashes of success, but many moments of failure. They're not good at being that kind of person. They don't like it. It feels forced and unfulfilling. Other people don't seem to respond well to them when they try to put on that persona. They feel like even more of a defective reject. They're trying to morph into what society wants, but they can't.
Eventually they realize there's nothing wrong with their natural personality and inclinations. Plenty of people are just like them. There are lots of ways to build a satisfying social life without having to sell out who they are. Just because their culture constantly sends them a message, it doesn't mean it's true.
It's great that they've reached a place of self-acceptance, even if it's later in life than they would have liked. However, now they look back unhappily on all the time they wasted trying to be someone they're not. At best they can point to some practical skills they learned, that they can strategically use as needed. At worst they felt like they picked up a bunch of extra shame and self-criticism from it all.
Their goal was to be accepted by a certain type of person, who wouldn't naturally click with them
For example, a cerebral, quirky guy was often picked on by fratty jock types while growing up. The mistreatment hurt, and on an unconscious level he believes if he can turn himself into someone frat bros like, that will make up for all the bullying he survived in school.
He works hard to become palatable to sporty frat guys. It might be that his changes are superficial, or maybe he deeply tries to adopt their values and worldview. Maybe he succeeds in winning them over, or he could fall on his face. Either way, one day he realizes it's not worth his time to try to mold himself to fit in with people he has nothing in common with. He shakes his head at all the time he spent trying to appeal to them.
They mistakenly believed becoming more socially savvy would fix problems that aren't actually about interpersonal skills
Someone's real issue may be anxiety, depression, unresolved childhood trauma, a lack of self-compassion, or dozens of other things. These problems can impact social functioning. It's not uncommon for people to think, "If I can just get over my shyness, insecurities, and poor conversation skills, my life will be in a way better place."
They work to improve their confidence and communication skills. If they succeed the initial rush of having friends or feeling more self-assured may make them feel better for a while, but it wears off. They belatedly realize weak social skills isn't their root problem, and their unresolved baggage is still making them miserable. Again, they may be okay with improving their small talk or networking abilities as a bonus for going down the wrong path, or they may feel more bitter about the misplaced time and energy.
They pursued a social goal that was overkill for what they needed to accomplish
Someone may feel a bit awkward and lonely, and try to become incredibly popular and charismatic to get out of their rut. They really just need some basic tools in areas like conversation, making friends, and not coming across as a total jerk. There's nothing in their modest goals that requires them to have top 0.1% charisma. Many people set out to become ultra-magnetic and quickly learn they can meet all their needs when they're only part way there. Some are slower to learn the lesson, put a lot of effort into becoming more socially savvy than they practically need to be, and look back on all the hours they needlessly burned.
They pursued the wrong sub-goal and wasted time
Maybe their larger goal was well chosen, but they put effort into improving in the wrong sub-area. For example, they didn't have enough friends and thought it was because they had poor body language. They later realized their non-verbals were fine, and they needed to get better at taking the initiative to make plans with people, rather than waiting for everyone else to make the first move. Or maybe they worked at being funnier, when what they really needed was to learn some techniques to manage their nerves.
They learned and absorbed a harmful message during the process of trying to change
They didn't want to improve their social skills because they'd already bought into a false, harmful message about themselves. They had healthy motivations going in. However, while trying to make improvements they came across a concept that ended up doing some damage. For example, before they were friendly and trusting. Then they read some misguided advice that portrayed the social world as a cutthroat battle for status, where anyone who was nice was a sucker who'd get eaten alive. Not knowing any better, they believed what they read, and wasted a few years as a competitive, paranoid, passive-aggressive jackass. After coming back to their senses they cringe at the time they wasted and all the people they turned off.
Their social goal was to adapt to a toxic environment. They were made to believe they were the one who was flawed and needed to change. They later realized it was everyone else who was screwed up
For example, a guy has a long-time group of mean-spirited friends who have cruel, cutting senses of humor. He's their punching bag. He buys their reasoning that he's too weak and sensitive, doesn't know how to take a joke, has to toughen up, be a good sport, learn how to give as good as he gets, and so on.
He sincerely works to grow a thicker skin and get the hang of their style of no-holds-barred bantering. He does become better at holding his own in that dynamic, but still feels picked on, and deeply unsatisfied around his "friends". He eventually figures out that they're truly awful, toxic people, and their "joking" goes far beyond what most anyone would consider friendly ribbing. He wonders why he didn't wake up to that reality sooner, and regrets eating up all that time trying to keep up with a bunch of douchebags.
They simply failed to meet their social goals, for whatever reason, and now feel more broken and hopeless
Someone's goals could have been healthy and reasonable, or not. Either way, they didn't make much progress in accomplishing them. Maybe they were too nervous and gave up early. They could have made some early discouraging mistakes, or experienced a few really harsh rejections.
Now they feel like even more of a lost cause. Not only do they feel socially deficient, but they think there's no hope of that ever turning around. They regret even trying, and feel nostalgic for the time before they even attempted to improve, when they lived in a blissfully ignorant bubble.
This isn't to say they couldn't try again in the future and possibly even succeed this time. Just because someone has regrets about trying to improve socially doesn't always mean the attempt was a mistake. They may just need to approach the problem from a better angle. Sometimes there are multiple ways to tackle an issue, and the first few unfortunately don't pan out. It doesn't mean the whole thing is a wash.
This article gets at the same topic, from a different angle. It's focused on spotting less-healthy movitivations ahead of time: