Your Nostalgic, Poignant Career Advice Is Useless To Me At 25 (or, The Career Advice I Wish I Had at 5)

“A career is a marathon, not a sprint.” “People regret spending time working.” “Don’t be afraid to fail.”

Thank you for sharing.

This advice is neither new; nor insightful; nor relevant. We can relegate it to the pile along with the other paradigms, buzzwords and hashtags, along with time-treasured greats like ‘think outside the box’ and ‘work smarter, not harder’. We can put aside discussions about recycling a hackneyed, cliched formulaic HBR-style article (oh, you’ve plugged your book at the end of the article; how unexpected!). But the greatest tragedy is this;

At 25, your nostalgic, poignant career advice is useless to me.

Your regrets are oriented towards family, towards open-mindedness, towards missed opportunities. These were some of the things you had to give up in order to progress, or the paths not taken that could’ve led to greater things. Still, I can’t help but feel that if you’ve written the article and have had the opportunity to write a book, you’re in quite a comfortable position. You’ve amassed some clout for your article to have spread to me, and you’ve had the education and opportunity and experiences to craft a good book — or had the money to self-publish.

Can I tell you what my fears are, at 25?

I’m afraid of being left behind. Some of my friends — there always will be a few — having careers that are taking off. Sometimes literally, flying around the world working on big, international projects, complaining about late nights spent in five-star hotels and rushing presentations while being jostled in a limo.

Sure, nobody wants endless work or sleepless nights, but what’s a few missed sleeps when you’re young? It’s career envy at its simplest. They may (to reach into the cliche pile) “work hard and play hard”, but even if they quit from the pressure they’d still be seen and hired as high-flyers, rocketing up the career ladder, rather than trudging along the treadmill like the rest of us. They’re already making twice what I make, right out of university; the gnawing question is not when, but if I will ever make what their starting pay was. We’ve just come out of the gates but people are already way ahead, never mind those with a head-start from parents or grandparents or dynasties. There’s no time to even think about anything other than sprinting to catch up — never mind the notion of overtaking; you just don’t want to be left behind.

I’m afraid of becoming obsolete. The life cycle in Singapore is peculiar; you never really retire. The aged in Singapore work, unless they can’t. Balding, white-haired old men and hobbling, hunched-over old women are out and about, clearing tables or washing toilets or collecting cardboard. Even the ministers and company directors work until their hair goes white. There’s a culture of being always at work, be it 10pm on a Friday night or while you’re on annual leave holidaying in Tunguska. Where there’s a wifi there’s a way to answer emails.

If you don’t your boss will yell at you. Or your clients will yell at you. Or your buddy will do it, and no prizes for guessing who gets the promotion. The squeeze comes from the top down, and those at the bottom squeeze themselves, and eventually the pressure gets to you. Do you want to adapt, or survive? Will you stay to answer that email at 7.01 pm or risk Stay-Late Nate looking more hardworking than you? Do you want to end up a white-haired Minister or a white-haired road-sweeper?

One of these two literally cannot afford to write a book.

I’m afraid of regrets. Maybe if I’d applied for better internships I’d be one of those high-flyers by now, or at least a middling helicopter. Maybe if I’d studied software engineering cum finance, I’d be funded by JFDI now. Maybe if I’d been hothoused and Tiger Mommed and Adam Khooed I’d be playing Carnegie Hall now. But what if I don’t get the promotion on time, or miss the boat on the transfer, or don’t get my feet under a desk before the next recession hits (again)? Can I really take the risk of stopping to smell the flowers, leaving early for a date or going for a holiday without the Blackberry?

They say hindsight is 20/20. Looking back, surely it all makes sense. Late nights, weekends, extra responsibilities and projects — it really didn’t mean much to your boss or your clients. If nothing else, it proved one thing: work doesn’t care about you. Work is a cruel and unfeeling monster that swallows up the energy you put into it and drains you dry, and cares only about bigger numbers and the next deal and more, more, more.

But you fed it anyway. And you’re probably feeding it now, too — are your juniors starting to drink coffee (or just drink)? It’s 6pm, where are your interns? How many people look like they’re sleep-deprived and it isn’t self-inflicted? But you’re in a position of some repute, and have the socio-economic status and free time to pen a book (presumably, doing extra work outside your working hours) in order to make more money and do more work.

Many of the above arguments are flawed. I’ve often argued against them myself. Many of the facts are slightly distorted — hell, I’m not even 25. But the lessons you’ve learned, the ones you’re sharing with a wistful look in your eye and a tinge of sadness at regrets and might-have-beens? Surrounded by my fears and insecurities, looking up the ladder and the endless toil ahead, they’re just not that relevant or useful.

And if overworking assures me I’ll get your job, your clout and your book deal, I’m happy to pay the price.

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