I'm 50 and Quit my Job

Now I'm worried make a big mistake

About six months ago, I decided to resign from a steady, well paying job from a reputable company. At the time, it was an exciting - if not nerve wracking - experience. I even posted about it on LinkedIn and was really looking forward to the journey ahead: creating FoFty.

I thought, hey I’ve done this before… I quit my job at a top hedge fund and went to Silicon Valley to co-found a startup. I can do this again, I’m no rookie.

Well, I got that part right. I’m definitely not a rookie. Actually, I’m a “well-seasoned” (still can’t believe I see that phrase on CVs) veteran. And boy is that a game changer.

You see, when you’re 50, what you don’t have, is time. If you screw up, that’s it. Because ageism is a thing, and companies don’t like to hire old dogs who cost a lot of money and can’t learn new tricks. I’m old baggage - musty, slow, expensive and not appetizing at all. Ok, well I’m none of that but I know that’s what recruiters and hiring managers will think. How do I know this? I used to be on the other side of the equation hiring Directors, SVPs, etc. for large multibillion dollar organizations. In the US and in Asia. That’s how.

At the other end of the spectrum of what you don’t have, is what you do have and copious amounts of it at 50: responsibilities. I have two kids, a 6yr old boy, and a 2yr old girl. That’s right, I’m not only old, I’m an old dad which means, by the time I turn 66, I’ll have to cobble up enough money to pay for my daughter’s college tuition until I turn 70 before all is said and done.

There also was this, um, unfortunate divorce I went through earlier in life that not only postponed my fatherhood but also took a huge chunk out of whatever savings I had at the time, to the point where I basically had to start all over again to build my net worth back up.

Did I mention that I’m not a billionaire? Or even, a multi-millionaire?

I think you’re beginning to see where my worries stem from.

But wait, there’s more!

I don’t own a house and I’ve been renting ever since I graduated from college. In a strange way, I can completely empathize with the younger generation who have essentially given up hope because they feel locked out of the stratospheric housing prices and cost of raising children. It is no wonder that fewer and fewer people are having kids in the developed world.

The only problem is, unlike them, I don’t have time and already have children!

It gets better: my parents are still alive. My father is turning 90, and my mom 78. Thankfully, both of them are relatively healthy but I know they will not live forever and there will be pressure coming from that side of the equation at some point in the future.

And finally, I don’t have any pension or social security cushion to help out later in life. I gave up my American Green Card, and while I am now a Permanent Resident of Singapore, I just recently became one so there is not much in my CPF.

Man, that’s lot of crap stacked up against me. Which would make you think, why on earth would I quit my job then?

There are three main reasons:

1. I have a stash
   
   Remember how I said I never bought a house? That’s because I didn’t want to go into debt, which is basically what buying a house is. And because of that, I took that cash and invested in other assets that are a lot more liquid, and built up a small stash. It’s not huge and not something I can live off for the rest of my life, but it’s enough to at least supplant my endeavor and pay the bills for the time being - measured in years.
   

2. I must practice what I preach

   
   Here I am talking about FoFty principles and how they can guide you to make high quality decisions and execute on them. If I have this burning desire to help people through FoFty, obviously I need to follow through and apply the very same principles to myself! It’s the only way.
   

3. The 50s are your most productive years

   
   Life insurance people make living off this chart:

   

   I had a decision to make - do I spend the most productive years of my life and give it away to some corporation to exploit? Or do I invest in myself and build something on my own?
   
   I chose the latter. I decided to give myself the best years of my life.

So now, we’ve come to the meat of this post - and what I hope anyone reading this who may be in a similar situation can incorporate into their decision making:

Are you confident enough in your abilities that you think you can create a sustainable income generation engine at the peak of your life’s productivity?

If you truly believe so, and your life is configured in a way where you have a reasonable launchpad, then you should consider investing the most productive years of your life in yourself, and not into that retirement package dangling like a carrot in front of you.

I did.

But I’d be lying if I said that I’m not worried. I am. And I should be. The key is, despite the worry - which I recognize and acknowledge instead of papering over - I am still fully in control. Not the other way around.

Watch the full YouTube episode where I discuss this in detail over here: