For a freelance assignment this weekend, I screened the new He’s Just Not That Into You. Y’know the one with many stars but most people still know it as the new Drew Barrymore flick? A central theme to the movie and the book that it’s based on is about stopping the delusional from continuing on their path of obsession, from picking every single detail apart so as to desperately support even the smallest of possibilities that what you want is exactly what is happening.

No, I’m not thinking about any specific romantic stalking obsession. I’m thinking about the fine line of encouragement and cold hard wake-up-your- idea. I got really hurt and mad once when a friend told me, out of concern that I  was torturing myself for wanting to change an unchangeable situation called National Service, to give up trying to transfer from one department to another that I actually would enjoy. I eventually succeeded out of sheer tenacity and guts. What if I kept failing because I didn’t have what it took to be in the department and I remained unhappily depressed and fighting against the 2 years imposed upon me? 

Would I have regretted not listening? But what if I had listened, gave up and and served my two years with optimism? All the what ifs aside, what is the line to draw between encouragement and tough love?

Sometimes the line is very obvious. Like drugs or stuff that you have moral compasses for (selling backside, cheating, or self-destructive stuff). But what if the things they want is what you hope for them, but it’s just seems like a hopeless situation? I remember telling a friend to set his sights on a different industry because the job prospect for his dream industry was no longer favorable. He eventually did, but what if he didn’t listen and fought like I fought in NS? Such is the perennial curse of the millennial mantra: I can achieve anything as long as I work hard enough.

I’ve no amazing Sex in the City like plot conclusions from this indulgent meandering. Just one old reminder: what-ifs suck, but an occasional visit can’t be detrimental, as long as it helps to spur and inspire and is framed in a stock-taking appreciation of what you’ve been given. Right?

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