What is the biggest challenge people have in their journey to financial wellbeing?

I feel that it is the external stimulus.

Afterall, there is only so much willpower available to handle the opposing factions.

Benchmarking against the wrong group of people? (who is the idol to mirror? A super saver, such as freegan, or investor. Even by investor, which form of investment and which idol?)

Afraid to go against society's norm?

A classic example can be something like "Payday is today. Let's treat ourselves well and Jiak Hor Liao/pamper ourselves or it's a norm to go overseas once a year by plane." Nothing wrong with travelling by plane or pamper ourselves, but is that what we really want, or what we are conditioned to think that is what we want? ​​​

Do not have the motivation or direction to the financial well-being.
For example, most of the ppl do not know how much they need to retire, hence they just work and spend without any goal in mind.
Once u know the amount, u will able to calculate backwards the amount u need to save or invest from now, then u will be motivated to execute it.

The biggest challenge i feel is inertia.

The inertia of starting a high-interest savings account, the inertia to find out about insurance needs, the inertia to research on what is needed for investment.

All these takes time, and by then you will probably waste some years in your life.

To start small, is a big step!

LOVE THIS QUESTION.

I would say the biggest challenge is no discipline, as it just underlies the first two factors you mention.

I liken achieving financial fitness goals to physical fitness goals, and here's why:

1. Both require time

Just as you don't get physically fit and limber in just a day (or even a month), it's the same with your finances. Good things take time (as with compound interest). ;)

2. Both require self-discipline

Just as how your abs don't just show up by sitting there, it also takes self-discipline to educate oneself, and also self-restraint to not be reckless with money.

3. Both require patience

It takes patience and sticking to the course. Just as how it's probably not wise to pop a pill that promises you a greek god physique, it's also wise not to go for get-rich-quick schemes.​​​