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Monday, September 15, 2014

Diving In

Posted by Dave on September 3, 2014

I tend to over-think things and second-guess most decisions I make, especially when they’re money related. Most of the money-decisions my wife and I have made to-date about our plan to retire early were automatic – spend a lot less than we make and put all of the spare money we have against the outstanding mortgage.

Now, I actually have to do stuff – making lots and lots of investing decisions over the next (hopefully) 60 years. This month will mark the beginning of having funds available to start investing – which will be quite a change in my money-spending lifestyle.

I read a lot of stuff – a good chunk of it is money-related. Like most things on the Internet, a lot of the information available is contradictory. Some sources say that the market is at a peak right now and it would be ridiculous to buy anything. Other sources say that there’s never been a better time to invest in “Stock X”, or “REIT Y”. As an almost total rookie investor, and someone who is a constant second-guesser, this is the point where I get intimidated.

My whole investing plan centers around buying income-producing assets, which slowly (but hopefully surely) replace my wife’s and my salary, until we have enough money to be able to not work anymore. At a 5% return, every $1,000 we invest is going to increase our annual income by $50. I really try to keep these kind of numbers in mind when I go to spend money on something that is unreasonably dumb, because all of those decisions are doing nothing but adding to the time it will take us to achieve our goal.

In order to achieve my goal, I will probably start investing sooner rather than later, increasing our current annual income now. I will hopefully pick assets that will not result in me flushing money down the drain. I guess the good thing about having what could be called a somewhat stable job, is that if 100% of my decisions are wrong, I’ll still be able to eat. In some way of thinking, I think I’ll treat my retirement investing career the same way I’ve treated sports betting. With gambling, I assume that everything I put in is probably going to be gone. For someone who will hesitate to buy some random $5 item, explaining to my wife that this is within the realm of possibilities does give me a bit of a cushion when making these kind of decisions.

While I would prefer to not shovel money out the door, this pessimistic level of thinking does allow me to overcome my decision-making paralysis and continue down my path to financial independence.

How did you decide when to start investing? Do you try to time the market, or just find investments that fit your set criteria?

Long-term Insurance

Posted by Dave on August 26, 2014

One of the things that I enjoy when I write for Tim’s site is the feedback I get from readers on my financial plans. While I joke around, for the most part I’m a guy who kind of pretends to be a grown-up, who kind of has his stuff together enough to discuss my plans of early retirement. I enjoy the exchange of ideas that has happened between myself and everyone who takes the time to comment on some of the schemes I have put forth.

Leaving the workforce 20+ years before “normal” retirement age is something that not very many people have done in the past, or if they did, it wasn’t really written about widely. Not many people know if the plans they set out will work in the long-run, because the long-run takes so long to test for. I can run my average investment returns through prediction machines and compare the returns against all sorts of potential expenses. I can have a certain amount of assurance that the financial “plan” I have in place will work out okay in the long-term, but who knows? I may go broke and be scrambling for any type of job I can find 5 years after I quit work for the last time – this is the major risk of this kind of plan.

My wife and I both know the risks that may come from exiting the workforce early, and have discussed the possibility of insuring that we have enough money to make it through. One of the possibilities we’ve talked about is working at a subsistence level, in order to allow our investments to compound for another 5 to 10 years.

Given our low annual budget, it might be a good time to learn a new kind of trade – whether it’s an actual trade, or just something interesting to do. Given the fact that we won’t have debt or savings requirements, we could live a basic paycheque to paycheque lifestyle, while gaining a bunch of free time in a semi-retirement stage.

We just don’t know how any of our financial plans will turn out though. I have no idea how my current investment plan will work out over the next 10 years pre-retirement, or the 50 years after retirement. I can be pretty sure we’ll be okay with the goal we have, but a few extra years of compounding might be beneficial, for very little “pain” on our end, besides having to get to a job sometimes. The benefit from this type of arrangement is that we could spend with comparative “reckless abandon” compared to the savings rate we are employing these days.

Capital vs. Cash Flow

Posted by Dave on August 19, 2014

An early retirement plan is an inherently risky thing to take part in. The risk in following through with the plan is that money will run out before you are readily able to make more of it, but there are still bills remaining to be paid. On the other hand, there is the risk (although less detrimental) that I could be one of those guys that drop dead at 52, while walking up a steep hill, or shaking my fist at a bunch of punk kids to get off my lawn.

My wife and I live fairly cheaply – beyond my golf habit and my wife’s desire for warm vacations, we really don’t have expensive lifestyles. Beyond the possibility of health problems causing significantly increased monthly expenses, I wouldn’t expect much in the way of lifestyle inflation to take place.

I like measuring sticks to show progress. In the past, I have written about slowly knocking off individual bills through investment returns – slowly taking chunks out of monthly expenses until they’re all taken care of (with a buffer). From my standpoint, it will be difficult to tell myself to keep working (especially on a full-time basis) at the point when all of my annual expenses are taken care of. The risk at that point will be that my investment portfolio gets wiped out and I’ll end up sitting in a dark, cold house eating beans and rice.

I’m sure I’ve read this somewhere else, but I’m not sure who to attribute it to, but living off a portfolio of 20+ diversified stocks and bonds does seem to be a lot less risky than my current dependence on a paycheque. Even though this pay has been continually deposited for over a decade, and I don’t expect it to end, it is dependent on me continually showing up and working for the next 10 or so years.

If I have adequate cash flow to cover my lifestyle at age 45, with enough of a buffer built in to cover major expenses within a diversified portfolio how much risk exists? If, for example, I have $750,000, yielding annual returns of $25k, and my household expenses are only $20k – should I work until I get to $1 million?

How long would you stay working? How did you arrive at your comfortable “exit number” ? Did you err on the side of caution, or plan on exiting the workforce as quickly as possible?