Understanding the downsides of flexi-work

I've enjoyed flexi-work for the last 15 years. Here's why I sometimes wish I'm back at a 9-to-5 job.

Understanding the downsides of flexi-work
Photo Credit: DALL-E 3

I've enjoyed flexi-work for the last 15 years. Here's why I sometimes wish I'm back at a 9-to-5 job.

There's been much debate about flexi-work since the unveiling of the flexi-work guidelines in Singapore last week.

We often marvel at how much greener the grass is on the other side. I've had the privilege of structuring my time as a solopreneur since 2008.

To balance the discussion, I outline some downsides of complete flexibility at work.

The benefits

But first, the benefits of full work autonomy.

For a start, you can be at key moments at home, focus on your mental and physical well-being, and be around to support your family.

  • Birth of my two children.
  • Attend to errands during the day.
  • Around during a challenging pregnancy.

And when my daughter was unenthusiastic about going kindergarten due to SM, I could send her to school every day.

The less spoken

It's worth pointing out that not everything's a bed of roses. Here's some lessons I learned.

  1. Measured by output, not the clock

Many have written about the shift to measuring by results instead of by "work hours" in a true flexi-work environment. But do you get what it truly means?

Not counted:

  • Replying emails, messages.
  • Sitting through hours of calls.
  • Helping out colleagues in another dept.


  • Number of sales closed.
  • Completion of assigned tasks.
  • Successful marketing campaign.

PS: 'Not counted' stuff still needs to be done.

  1. We work less than we think

It's actually next to impossible to work productively 8 hours a day - see Point 1. Invariable interruptions at home, managers asking for status updates, etc will only add to them.

So sure, you can accompany your spouse for a mid-morning medical check and start work at 3pm. With dinner and kids, you could well be working until midnight to make deadlines.

  1. Reduced 'fidelity' and connection

Working with editors and marketing leads remotely definitely saved a lot of time. But loads of nuances and subtleties are lost in digital-only communication.

And when it's time to trim the budget or scale things down, the tendency is to start with those where the connection is not as strong - which might well be those who flexi-work the most.

  1. It takes more discipline

Flexi-work may be a dream come true, but it demands a higher level of discipline and organisation. It's easy to fall into the trap of procrastination or distractions.

And when one is measured by output, even the perception of lower output can jeopardise one's career progression, if not the job itself.

👉 What's your experience with flexi-work?