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Is the freelance life right for you? Or are you mentally built for your day job?

It may seem like a dream, not having to brave the daily commute and working in your pyjamas – but if you’re not built for the freelance life, it could spell disaster.

Is the freelance life right for you? Or are you mentally built for your day job?

(Photo: DESIGNECOLOGIST / Unsplash)

These days, it seems as if everyone is either a freelancer, or wants to become one. And while there are no official statistics in Singapore, according to the American blog Freetrain, 53 million people do freelance work in the US – which translates to a whopping one-third of the American workforce.

With so many people swapping out their office cubicles for a desk at home a la Carrie Bradshaw, you have to wonder if freelancing is something you should seriously consider. But I’m here to tell you that not everyone is cut out for a life untethered from a daily office job.

(Photo: Annie Spratt / Unsplash)


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The mistake many people make starts from the assumptions made in the last sentence: That as a freelancer, you can do what you want, whenever you want and live happily ever after having lunch with your tai tai friends and leisurely working on deadlines between your nail appointments and yoga sessions.


At the risk of simplifying things, freelancing is right for you if:


  1. You hate the inhuman crush of the daily commute, or the bladder-busting morning traffic jam on the CTE.
  2. You’ve missed a lot of milestones, say a birthday dinner, or your kid’s first steps and first words, because you were stuck in the office or on a work trip.
  3. You resent working so hard and making so much money for your boss in exchange for a comparatively low fixed salary.
  4. You have an obsessive-compulsive, Type A personality. In other words, you set a target and you do everything you can to achieve it.
  5. You have a supportive family. Nothing builds self-belief better.
  6. You’re not afraid to network and schmooze, whether it’s on LinkedIn or having coffee with a potential client. Because no one will know who you are or what you can offer if you sit at home all day and wonder why no one is calling you.
  7. You love a challenge. Every day will bring you new problems to solve and obstacles to overcome.


(Photo: rawpixel / Unsplash)


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On the flip side, freelancing is probably not right for you if:

  1. You don’t have savings of at least six months to a year. It will take you this long to ramp up your business to a level where you earn a halfway decent regular income. In the meantime, you need to eat. Which leads to the next point.
  2. You have a lot of financial responsibilities such as a mortgage, car loans, aged parents, children or a fondness for expensive designer items.
  3. You have no discipline. A successful freelancer will have a set daily routine and puts in the same, if not more, number of hours as a “full-timer”.
  4. You like company. For the most part, freelancing is a solitary experience. And in the beginning, at least, you won’t be able to afford a co-working office.
  5. You are the shy retiring type who is too embarrassed to chase your clients for payment. Many businesses will put off paying you for your services for as long as humanly possible.
  6. You have a thin skin and believe that “no” means you’re worthless.
  7. Your home environment is chaotic and filled with more distractions than Candy Crush. See point 4.

In other words, despite appearances, becoming a freelancer is no walk in the park. Besides coming to grips with simple spreadsheets to keep track of your accounts and expenses, and essentially running your own business, you’ll need to be patient and dogged.

(Photo: Chris Abney / Unsplash)

The jobs won’t come in immediately and there will be moments when you actually feel nostalgic about your mean boss. For the most part, you will work with lovely people, but there will also be nightmare clients who will make you want to swallow nails.

But here’s the point: If you’re unhappy in your job and you’ve been unhappy for a while, how else will you ever know if you were meant to do something else? Besides, where does it say that you have to be unhappy to make a decent living?

A few months ago, a friend of mine died suddenly from a heart attack. He was only 44. Most of us think he had been over-stressed by his high-pressure job. I remember him saying once that he’d love to buy an organic farm in Malaysia, settle down and raise chickens.

Since his death, I’ve often wondered if – at the beginning of the year – Tony had known he wouldn’t live to see Christmas, whether he’d have quit his job and followed that dream.

I guess we’ll never know now.

After practising law for eight years, Daven Wu saw the error of his ways and became a full time freelance writer and editor. He has never looked back.


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Source: CNA/pw