CEOs: We do not approve of side hustle or moonlight as it would be too distracting.

Also CEOs: With 3 directorships, managing 2 committee seats, and overseeing 5 properties as a landlord.

That contradiction should be everybody’s greatest lesson.

In a world where record profits and mass layoffs appear in the same news paragraph, betting everything on a single job isn’t prudent.

It’s dangerous.

Without a job guarantee, it would be foolish not to have something brewing on the side. The corporate landscape has shifted. Loyalty is no longer a two-way street. If companies won’t commit to your future, why would you commit entirely to theirs?

This is the reality of modern work: companies can announce record profits and mass layoffs in the same paragraph. It’s like they’re saying, “We’re doing great! By the way, you’re not.” The solution? Don’t put all your eggs in one basket that’s actively trying to crack.

And here’s the beautiful part: side hustles aren’t just insurance policies. They’re opportunity engines.

Think of Steve Jobs tinkering in a garage before Apple. Or J.K. Rowling writing on train commutes before Harry Potter changed everything. Sara Blakely was selling fax machines door-to-door when she invented Spanx. These weren’t distractions. They were the launching pads for something extraordinary.

Even if your side project never becomes the next billion-dollar company, it expands your skill set and widens your horizons. As the saying goes, opportunities come to those who are prepared, and that preparation must happen before opportunity finds you.

I started podcasting in 2015 for the simplest reason: I loved Tim Ferriss and wanted to be like him. The execution was rough. I was recording on my iPhone 5 with a tiny microphone that I’d pass back and forth between guests. Audio-only episodes. Post-production costs USD$50 per episode. And as far as I could tell, I was my only listener.

After 5 episodes, I quit.

But then COVID happened. I’d invested in a decent microphone for Zoom calls, so I rebooted the podcast. Over 200 episodes later, that decision to start again proved transformative.

The tangible benefits kept multiplying. I landed a paid gig co-hosting the first two seasons of Work It with Crispina Robert on CNA. The experience compounded as I moved into two other paid podcast hosting projects. Doing 200+ episodes taught me how to ask better questions (it’s almost impossible not to improve) and that led to moderation gigs at various events and conferences.

What started as a weekend hobby became a professional credential.

Writing was always my lowest barrier to entry. I started blogging when blogs were still novel, and I never really stopped. At different seasons, I wrote about recruitment, then career coaching, then entrepreneurship, even managing a parenting blog at one point.

Those scattered bylines attracted attention. Editors noticed. I went on to write for publications including The Middle Ground, Yahoo, and CNA.

Then came the book deal with Penguin. No More Bosses landed on Amazon’s Best Seller List.

The traffic generated from all this writing opened doors I hadn’t anticipated. I started doing brand partnerships, primarily on LinkedIn now. Each article, each byline, each piece of published writing became a small brick in a much larger structure.

Here’s something ironic: as a teenager, I desperately wanted to be an actor. Yet when it came time to embrace video, I resisted hard. It took me longer to conquer YouTube than any other channel.

I started with monologues. Basically reading commentaries I’d written for CNA on camera. As podcasting shifted toward video-first distribution, I leaned in and began publishing video episodes there too.

I then started a travel channel to experiment with vlogging, diving into a different style with projects like travel content from trips to Malacca.

Product review videos became sponsored opportunities. One recent video promoting the XCoffee robotic barista got amplified on LinkedIn.

Learning to produce video end-to-end—lighting, editing, pacing, storytelling—taught me lessons that directly enriched my day job.

As someone doing fractional marketing work for HR tech companies, those skills in visual storytelling and production value became invaluable assets.

Here’s my honest advice: start with what you’ll procrastinate on the least.

For me, that was writing. For you, it might be video, coding, design, or something entirely different. The best side hustle isn’t the one that’s theoretically perfect. It’s the one you’ll actually do.

And yes, I know you’re probably going to tell yourself you’ll start “next month.” Don’t be that person. The person reading this in 10 years wishing they’d started a side project is you.

Not every side hustle becomes a thriving business. Not every passion project turns into your next chapter. Some experiments fail quietly. Some give you just enough to make a difference. Some barely cover your coffee budget, which is still better than no budget.

But that’s not really the point.

The real win is that you’re building optionality. You’re expanding your capabilities. You’re creating multiple income streams and multiple paths forward. You’re ensuring that if one door closes, you’ve already built others. You’re also giving yourself the pleasure of telling your CEO “Actually, I have options” (internally, of course).

And sometimes, one of those side projects becomes the thing. The thing that changes everything.

CEOs were right about one thing (only one): side projects are distracting. They distract you from being fully dependent on a single organisation. They distract you from accepting “that’s just how it is” as an answer. They distract you from thinking your only superpower is showing up to meetings on time.

So start. Write that first blog post. Record that first episode. Upload that first video. Ask those trusted people what they see in you.

You don’t need to have it all figured out. You don’t need a perfect plan. You don’t even need your iPhone 5 to cooperate. Though honestly, if I managed it, you can too.

Because in a world without guarantees, building on the side isn’t a distraction.

It’s survival. It’s opportunity. And it’s the only honest response to a CEO who tells you to focus while they’re out juggling three directorships.

The best time to start was yesterday. The second-best time is right now.

Adrian Tan
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