I'm 32 and Need to Know When to Quit My Job and "Retire"

1 Reply

Before I give some context and background information on my situation I want to preface this with what retirement means to me. To me it is the freedom to what I want want and how. To wake up and my days are filled with working solely on my projects and goals. It doesn't mean I will stop working, I'll just stop working for somebody else.

I'm 32 years old and married with 1 child on the way and I live in Canada. My wife is employed full time and makes about $75k a year with pension and benefits. I work full time at a decent desk job making about $100k a year plus a small pension and benefits plan. 


I've been investing in real estate for about 7 years now and I have over 10 properties. Mostly a mix of single family and small multifamily (duplex type homes). They don't all cashflow as much as I would like as I have refinanced to purchase more or for other renovations. 


I have a side hustle that is real estate related that with more free time I could grow and build on to generate income, probably around $100k annually.

I know this question is often highly debated but my dilemma is do I sell off one of my properties to pay off my home mortgage. I get the whole use cash flow to pay off your monthly expenses and the equity in my home could be reinvested somewhere else etc. I feel selling off a property and paying it off (or at least a large portion of it) would give us some freedom, and a feeling of accomplishment. Our living expenses are low and we live within our means with no other debt obligations other that investment property mortgages and a personal mortgage.

I also have trouble selling a property knowing that it will very likely continue to appreciate, increase in rent and cash flow and lose on the continued principal recap.

Anybody else in a similar situation. Any advice or input would be appreciated. I don't have any friends or family that truly get this sort of thing so that is why I've come here.

Updated over 1 year ago

Also want to add that my net worth is approx. $1.5 million and growing. My portfolio generates about $2500/month in cash flow. I have some long term tenants and that number could be closer to $4000/month if they were rented at current market rents.

@Mike Honcho , without more specifics from you, it will be hard for us to offer specific advice. Without actual numbers, there's no way we properly assess whether any property should be held or sold. I think you need to start with a detailed analysis of your entire portfolio.

That being said, a few questions come to mind, which may help clarify your path forward:

  • Why are your rents at only ~60% of market? What's stopping you from pushing them to market?
  • What's your CoC ROI and IRR across your portfolio? What properties are trailing the average?
  • What kind of appreciation are you actually seeing?
  • Would your portfolio be more productive if you consolidated into 1 larger property instead of 10 smaller ones?

With a net worth of $1.5MM, you could be be seeing $12,500/month in cashflow with a 10% CoC ROI, which isn't outrageous. I'm sure not all of your money is in RE, but it's something to think about. Can you better re-deploy some of your capital to meet your cash flow goals.

Regarding selling off some properties to pay off your primary residence. This may be a good idea, if the properties are under performing or you've seen a lot of appreciation, but don't expect to see that same trajectory in the future.

Paying off your primary will provide emotional comfort and stability (money is emotional, don't ever let anyone tell you differently). Plus you can always tap into (most) of the equity through a HELOC.