Why ‘hustling’ won’t fix your low-paying career

I spent last night diving deep into the r/askSingapore subreddit, reading stories from my fellow countrymen about their career struggles.

One post particularly struck me, a 30-year-old marketer trapped in a low-paying job, feeling overwhelmed and undervalued.

The comments were a mix of tough love and harsh realities.

But what caught my attention wasn’t the complaint, it was how familiar this story feels, regardless of where you live.

We’re all seeing these carefully curated success stories of people “going all in” and winning big, while the reality is much more nuanced.

I get that everyone wants to be a full-time internet entrepreneur. But there's absolutely no shame in doing it part-time while you hold down a job. Sometimes life doesn't let you go all in, and that's fine too.

Whether you’re in my country Singapore, San Francisco, or Sydney, the story remains the same.

Fresh graduates struggle to get a job.

Mid-career professionals feel stuck in dead-end roles.

Talented individuals watch their peers zoom past them on LinkedIn, posting about their latest wins while hiding their advantages and struggles.

We’ve all heard it.

“Go all in!”

“Quit your job!”

“Just hustle harder!”

“Take on more projects!”

“Work overtime to prove yourself!”

But here’s the uncomfortable truth: Simply working harder in a broken system won’t fix your career. It’s like trying to sprint your way out of quicksand, the harder you struggle, the faster you sink.

Remember that viral LinkedIn post about the 25-year-old who “quit their 9-5 to build a 7-figure business in 12 months”?

What they often don’t mention is the inheritance that funded their runway, the spouse with a stable corporate job covering their benefits, or the parents paying their rent while they “took the leap.”

The legends we admire have their hidden advantages too.

Jeff Bezos started Amazon with a $300,000 investment from his parents. Elon Musk came from a family that owned an emerald mine.

These aren’t rags-to-riches stories, they’re privilege-to-riches stories carefully repackaged as hustle porn.

But that’s not to take ANYTHING away from their hard work.

I’m just saying not everyone has equal opportunity.

The problem isn’t you, it’s the advice you’re following.

Most career guidance falls into two traps.

First, there’s the “Hustle Harder” trap, pushing you to work more hours in a system that’s already undervaluing you.

Then there’s the “Dream Bigger” delusion, telling you to quit your job and follow your passion without acknowledging real-world constraints.

But as I mentioned in my tweet, sometimes life situations don’t allow you to “go all in”, and that’s perfectly okay.

It often makes more sense to hedge your risk while gradually making calculated bets with your career.

Here’s why working harder isn’t the answer: There’s a natural ceiling to how many hours you can work.

More hours don’t equal more value in today’s economy. Busy work prevents actual skill development.

And perhaps most critically, overtime kills networking opportunities, the very connections that could help you level up.

Instead of following the usual “hustle harder” narrative, what actually works is creating a clear inventory of your current value.

Look at everything you’ve done in your current role, the projects you’ve led, the tools you’ve mastered, the problems you’ve solved.

You’re probably sitting on valuable experience you haven’t recognized.

Here’s what that actually looks like, no 90-day framework required.

Map your industry’s pay range and find the one skill gap that’s actually costing you money. Learn it. Build something small and real to prove it, a project, a mini portfolio, anything tangible. Then find someone willing to pay you for it, even a little.

You’re not trying to work 80-hour weeks or become an entrepreneur overnight. You’re making strategic moves that increase your market value. Forget becoming a millionaire by next quarter.

Just get from $0 to $1 outside of your job.

There’s absolutely no shame in building something part-time while keeping your day job. It’s often the smarter path.

You don’t need to become a different person. You don’t need to “crush it” or “kill it” or whatever other violent metaphor hustle culture is pushing this week.

You just need to be strategic about your next move.

And just try your best.

Talk soon,

Brendan