Transformation is easier said than done in Singapore.

As I inch closer and closer to my target retirement number, one challenge which I look forward to is the possibly of semi-retirement. In Singapore especially, this is not very easy because of two phenomenon which I observe.

a) Employed workers find it easier to get new jobs than unemployed workers.

I got this through third parties with close access to HR departments of MNCs and SMEs. One paradox which we need to contend with in Singapore is that while you have a job, it's easier to get another employer to talk to you. But if you are without a job, HR departments will wonder if you are the type of worker that can withstand a Singaporean workplace.

This makes it really hard to transition to semi-retirement. If you even need to stop work to perform a life audit, you make it harder to find a job which suits your personality more.

It also means that Gen-X workers as they hit their 40s will be more willing to tolerate obnoxious bosses to survive Singapore society.

b) The conundrum of real estate being affordable only to those with CPF.

One possibility for people who want semi-retirement is to start a "lifestyle start-up". This means I start a business that suits my life aspirations instead of a traditional start-up which is all about revenue growth, VC funding and burn-rate.

The problem with this approach is the problem of CPF. For folks with a 35+ year mortgage on a condominium, with a steady job being employed with a company, the monthly payments will hardly eat into your standard of living, but once you stop making CPF contributions and need to fund your mortgage using cash, a large chunk of your income gets eaten up from your home. For folks who have maxed out their Medisave, you may need to foot at least $1,400 extra every month to pay off your condominium loan.

This is consistent with the findings of Property Guru. HDB viciously attacked the study and used CPF as a defense but it's hard to refute the argument that our flats are expensive for folks who do not have CPF. This means the business owners and some free-lancers.

How this makes mid-life career shifts very challenging in Singapore. While I have some time before I need to address this, here are my suggestions:

a) Your passive income needs to cover your mortgage payments.

At my current passive income per month, I find that I have to keep on working in spite of being able to save a portion of my monthly dividends to make further investments every quarter. This is because I will need to address my upcoming Condo payments in 2014 which is largely coming in from my CPF payments if I stay employed. At 8% yields, it means another $200,000 savings which I need to accumulate over the years.

The good news of using passive income to cover Condo payments is that the amount is not expensed but goes into your equity section of your balance sheet.

b) Your time after office hours has to invested in self-reflection.

I think we Gen-X folks secretly envies the Strawberry generation. Without a family or debt commitments, Gen-Y is changing the workplace by being irresponsible and flippant, but I think in time Gen-X will be a beneficiary of this revolution.

Gen-X needs to spend their time after office hours to inventories their hobbies and ask themselves what kind of work they can engage in as a lifestyle choice. They need to push this agenda while holding full-time jobs and only transition after their passive income hits a reasonable level.

The challenge in Singapore is that you seldom can try a lifestyle before you buy it, some money needs to be spent on courses to simulate the new working environment.

While it is certainly tempting to "flip table" and quit, note that we have very close-minded employers and you are better off quietly interviewing instead.

A millionaire may not be able to afford to buy an executive condominium.

There are many scenarios painted where someone who makes $1,000 can afford a flat of his own. I'm going to paint a scenario that illustrates an opposing point of view.

Suppose you have $750,000 in cash assets and $250,000 in CPF making you a millionaire, your family expenses is $4,000 a month and you proceed to buy a condominium. The monthly payment for a condominium is about $2,500. ( $850,000 condo at 2% interest over 30 years )

If you can invest your $750,000 at 8% investment income a year, this means $60,000 a year or $5,000 a month in dividends.

What this means is that you have an monthly expense of $6,500 but an incoming dividend flow of only $5,000. You will need to work to make up the short-fall, otherwise you lose your millionaire status.

The illustrates the flip side of the wealth equation. While 20% of Singaporeans have a net asset base over a million dollars creating so much unhappiness over the rich-poor divide, I believe that in truth, many Singaporean millionaires have to wake up every morning and worry about how to make a living and actually do spend many years kowtowing to a boss because they bought into that Singaporean dream for condominium ownership. Of course, this can be made even worse if such a person has a car to pay off and tuition fees to pay.

So, next time someone talks about the $850 man who can afford to have a flat of his own, tell him the story of the millionaire who came to the conclusion that he actually can't afford an executive condominium from HDB.

Anyone can create any scenario to support his agenda.