So here you are, young and fresh and eager to get started with life. You have your relational commitments all sorted out, and now it’s time to take the ultimate step past the comforts of the Shire and into the world… It’s time to get a job.

You’re browsing WOBB for job openings. You haven’t even heard of half of these companies before, but they sure look cool! You apply to a bunch of them, and a couple shoot back an email asking you to come in for “a chat”.

So you dress up, polish up your CV, put on your best American accent (because Hollywood has taught you that all the cool kids have American accents. Only the bad guys have British accents), and off you go into the office where you’re greeted by none other than the founder of the company. She’s dressed down in a T-shirt over faded jeans in a smart-casual business look. To your surprise, she’s not putting on an American accent but an Australian one – and everyone knows that if there’s anything cooler than an American accent, it’s an Aussie accent.

She shakes your hand and leads you through the workspace, an open-concept office with computers concentrated in one area, beanbags piled in the corner by a hammock and some throw pillows; through a clear door you see a room where a sofa sits facing a 52” TV with a PS4 hooked up to it. In the next room, two smart-looking fellows are poring over some lines of code visible on a Macbook screen.

These sights disappear as you enter the founder’s office, where she invites you to have a seat. She asks you about your life. Your education. Your past experiences. She seems cool and laid back. Relatable, like someone you could grab a beer with. She also spends some time talking about the company, which she had started from scratch just some months ago with a couple of friends. She talks about her heroes, about what inspires her. At the end of it she shakes your hand again and thanks you for your time.

Some days later you receive another email – Congratulations! You have just received your very first proper job offer. You’re excited, but you remember what you read in the Adulting 101 article, and you know better than to grab the first job you see.

But how do you know if this is the job for you? How can you know?

Working in a start-up completes the trifecta of the hipster experience, trailing in right after insisting on artisan goods and having an unquenchable sense of wanderlust. It’s understandable, after all. You’re young and full of adrenaline in your blood. You don’t just want to survive, you want to live.

You want a job that inspires you. That stimulates your mind. You want to be in a new world where your contribution matters. Where you can prove that you’re worth more than anyone bargained for. You want a day-to-day existence that elevates beyond the everyday into something extraordinary, something exciting. And what better place to find all of that, on top of a basic salary, than a startup?

But not so fast.

Before you jump head-first into this decision, these are 3 questions you have to ask yourself before you start with a startup!


1. Is This Business Built On Strategy Or Charisma?

As a rule of survival, founders of start-ups have to be charismatic to some degree. All business is people business, after all, and when you’re a no-name, cashless company, charisma is all you have to bring the business in.

But just because someone is good around people, it doesn’t necessarily mean they have the necessary skills to build a business. As much as new-age management pseudoscience would have you think that “trust our employees; serve our customers” is a viable business strategy, it’s not. There are supply lines to manage. Investment decisions to be made. Growth plans to be charted out.

To draw an analogy, charisma is like that burst of inspiration-fueled motivation you get before you embark on an undertaking. It’s great for getting you off the launching pad. Strategy, on the other hand, is practically everything else: Your road map to the stars. Your determination to stick it out and see things to the end. Your daily habits and disciplines which, all in all, will prove much more valuable in pursuit of your goals.

To quote some dude on the internet, “Motivation is fleeting. Discipline is unyielding.”

While I can’t say for sure what constitutes a sound business strategy, I can share a couple of red flags when a business is built solely on its founder’s charisma: lots of promises with no delivery; an ADHD-like approach to projects, jumping from one to the next without any clear direction, or even before properly completing the previous.

adhd hyper winnie the pooh tigger


2. Am I Willing To Accept The Risks?

Whoa, hold on. Risk? What risk?

Surprise! Risk is not just a board game that ruins friendships or that nebulous thing investors are often found talking about. Like chemicals, it’s everywhere, even if some would like to pretend it isn’t.

There’s an old African proverb that goes, “If you want to go fast, go alone. If you want to go far, go together.” While many start-ups like to position themselves as a “lean, mean team”, that really only means that they have a low corporate inertia.

Think about the giants of the business world. The 3Ms and the Microsofts and the HSBCs. If I asked you to imagine if they will still be around 10, 15 years down the road, you would have no problem. If I asked you to imagine if the hipster café that just opened up nearby will still be around in that same time frame, you would probably have some reservations. That’s because these giants, over the course of their lives, have grown and developed sufficient corporate inertia. While it makes them oftentimes slow on the uptake and resistant to change, it allows them to barrel through most corporate-sized obstacles like economic depressions and financial setbacks.

If these big companies are the ‘tankers’ of the business world, the start-up resembles more like the ‘agility-based’ heroes. Quick, nimble, able to react at the snap of a finger, and if deployed correctly, can become a force to be reckoned with. But before it gains its own corporate inertia, even a moderately serious blow could severely threaten its very existence.

Depending on your luck, when you choose to work for a start-up, you could be either hitching your wagon to a star or strapped to a sinking rock.


3. Am I Willing To Be The Person This Place Needs?

When people mention the perks of working in a start-up, most imagine Valve’s or Google’s culture of openness and innovation, where almost everyone works on whatever they feel like working on at the moment. But understand that this is the way they are now, because they can afford it. This isn’t how they started out.

Working in a start-up pretty much means working in a place that has to fight for its very survival. Like a small boat in the big ocean, there’s no luxury of leaving the job to some other poor sod to worry about because it’s not within your job scope. This could mean doing things far beyond your comfort zone, like delivering last-minute presentations or figuring out how to do a cost-benefit analysis. It could mean working long hours with little to no overtime pay. It could mean getting your sense of self-worth trampled upon when someone else can do your work better than you.

Sure, it could mean growing your skill set exponentially and having a good-looking CV when you emerge victorious years down the road. But let’s be honest: It’s not for everyone.

Look, there’s nothing wrong with valuing security and predictability over peril and excitement. Some people are perfectly happy balancing accounts and sifting through financial reports if it means they never have to face a disgruntled client or if it means they get to go home while the sun is still in the sky. However, if you’ve decided that you’re going to work for a start-up, you’ve got to be sure you’re ready to become the person the place needs.


Bottom line is….

I want you to think of it this way: You’re not just some bloke looking for a job because you need to get your parents off your back. You’re a discerning investor, looking for the best place to grow your net worth. Hey, if time is money, and you’re going to sink 1/3 of your day every weekday into this place, wouldn’t you want to know your ROI?

Ask yourself: Would I invest money into this company? And if the answer is no – why would you invest your time into it?

At the end of the day, it’s a trade-off between benefits. The important thing, eternally, is to be honest with yourself about what you want, because that’s when you will know what’s right for you: In love. In life. And a job is both.




Posted by Joseph Ng