Archive for the ‘Finance’ Category

Last September (2016), the wife and I paid off the last remaining piece of the mortgage of the condo I bought in 2008. Ever since then, I’ve been debt-free.

I hadn’t been debt-free since 1996 when I first got a student loan. After that, I got a car loan in 2007, and a mortgage in 2008. I paid off the student loans in… I forget. I paid off the car loan in 2010. And then, as I said, we paid off the mortgage in 2016.

And I love being debt-free! As it says in Proverbs 22:7, the borrower is servant to the lender. I don’t want to be anyone’s servant (when it comes to money), I’d rather be the debt-owner (via holding bonds), or the owner itself (via holding stock, or property, or loans).

I don’t want to be in debt so badly that an opportunity came up to be in debt and I refused to partake in it despite the fact it would have resulted in a big savings. I need to get a new iPhone, the one I have – despite being a year old – is only 16 GB. That was a major mistake, I should have gotten the model with the most disk space because I’m always running low. It keeps filling up due to podcasts.

Best Buy was running a deal wherein you could get a new iPhone and save $150 or $200 or something on it if you signed up for a plan where you pay it off via installments. I couldn’t figure out how to pay it off all at once, and documentation on the web suggested that you couldn’t do that. That would in effect be like being in debt, it would add the payments onto the cell phone bill.

I wouldn’t do it. Either I pay for it all at once, or I don’t pay for it at all. I do not want to have to finance any purchase. Been there, done that; now finished.

Potential debt: don’t let the door hit you on the way out.


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This week on the way home from work, I caught part of an interview with the Chairman of the House Ways and Means committee, Kevin Brady. He was talking about tax reform, and how the Republicans were planning a large tax cut. I heard something on the radio that I thought sounded ridiculous, so I went back and read the transcript.

Chairman Brady was proposing a tax cut and referred to it as paying for itself, that is, the lower revenues caused by reduced rates would be made up increased wages of 8%, and increased economic growth of 9%. If you increase the size of the economy, then a smaller rate on a larger share results in the same amount of tax revenue and that’s supposed to keep the deficit from getting out of control.

I thought that a GDP growth rate was completely ridiculous! The only countries in the world that have that high rates are developing economies – because their economies are in such a shambles, they overheat when they get an influx of new capital. Developed economies like the United States simply don’t see that type of growth anymore. If he meant 9% GDP growth per year, I threw up my hands in exasperation because he wasn’t serious.

I decided to read the Tax Foundation’s analysis of the Republican tax plan (Trump’s is similar).

Their analysis must be the one that Brady is referring to because their wage growth and GDP growth numbers are the same. They estimate the plan would lead to 0.7% after-tax income increases for the entire population (oh, gee, thanks) but would go up 5.3% for the top 1% (surprise, surprise). However, when accounting for the extra GDP growth, everyone’s income would go up by an extra 8%.

The economic impact is calculated at 9% by mostly capital investment, and some wage rate increases, and new employment.

Does this make sense?

The Tax Foundation’s estimate is based upon a super-crucial, critical factor. Everything in their analysis hinges around this one fact – that lower taxes can create economic growth by spurring investment, which increases production.

In other words, if a person pays $25,000 in taxes and gets a tax break of $3000, and now only pays $22,000, they will take that extra income and invest it or spend it in the economy. Businesses will take that extra revenue to grow their business, or take that extra investment to similarly grow their business. Our economy is built on capital allocation and consumer spending.

The assumption that people will spend money they get from a tax break is correct if it goes to the lower income people (the bottom 80%). The average person spends nearly all of their income on basic things like food, shelter, transportation, maintenance of their stuff, family, and so forth. Additional incomes goes to projects they were previously putting off.

For wealthier people, they don’t spend all the money from tax breaks. Instead, they spend some of it, or they invest it. Businesses that receive money expand – they can increase productivity or hire more workers.

But here’s the thing, tax cuts can increase economic growth if the money ends up in the economy. Yet wealthy people don’t spend or invest 100% of their rebates; instead, they save it. They don’t invest it, nor do they spend. They just save it.

There’s nothing wrong with people saving money. I save plenty of money. But the problem is that saving money doesn’t grow the economy as much as either spending or investing.

So, the assumption that tax breaks lead to capital investment is incorrect, it is an overstatement.

Capital needs to be absorbed by someone

A tax break makes the economy get bigger by capital investment if a business can expand and make more stuff if there is someone to buy it. Supply without demand doesn’t increase the economy.

If wealthy people are saving money, and businesses are producing more stuff but the people who are most likely to buy (the bottom 80%) aren’t seeing much additional income and therefore aren’t buying enough stuff, then there isn’t that much revenue growth based upon internal demand within the country.

This means that a corporation must export in order to make larger revenue based upon the capital investment. But most US companies sell locally, it’s only the large corporations that sell internationally. But those international customers need additional income, too.

The point I am making here is that capital investment needs to result in increased supply and demand. The reason why the US economy grew so much in the 1950’s and 1960’s is because of Baby Boomers; the large bulge in population resulted in increased consumers and increased demand. Business couldn’t keep up, and that led to inflation.

The US population isn’t increasing as much as it used to, so to say that economic growth can increase without a proportional increase in consumers doesn’t make sense.

That’s why developing economies can rapidly increase GDP – as their child mortality rates plummeted over the past 40 years, their populations increased. And with investment in technology, it led to more wealth for the population by turning poor people into consumers.

Tax cuts need to result in more consumers to achieve economic growth, but they mostly go to the upper classes who don’t spend or reinvest as much as the lower classes.

And the one final assumption is the last problem

The last assumption that is problematic is that the estimates go out for 10 years.

When I read that, I said “Well, this is useless as a prediction.” I recently read Nassim Taleb’s book Antifragile and he makes the case that making predictions more than 6 months to a year out is useless because there are so many variables that can change.

Basing an economic analysis 10 years out and assuming stable conditions is a recipe for disaster. Since I started working full time, I’ve lived through two recessions (2001, and 2008). I will probably experience two or three more in my working time. Every time, these recessions reduce government income and put strains on the economy.

These economic models never account for this, they are always on the happy path.

We’ve never had a happy path.

The conclusion

Ten years ago I was writing blog posts that reduced tax revenue can lead to increased economic activity. That’s somewhat true, but behavioral psychology proves that it isn’t as effective as what some economists believe, including myself (at the time).

I don’t have good answers either, as I am not an economist. But what I do know is that capital investment needs to result in increased production, or increased efficiency, and it needs to be combined with increased consumption.

That’s oversimplified, but I think it’s more accurate, too.

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Recently, the White House unveiled its tax plan which President Trump said would be the largest tax cut in history. Here’s a quick screenshot of the changes:


I’ve been quasi-doing my own taxes for two years, and each time I’ve almost hit exactly the refund that H&R Block comes up with. So, I did the math on my own taxes for 2016 to see how much more money I would end up with.

The White House’s current tax plan does not list the income brackets that the three rates (10%, 25%, and 35%) are applied at. Instead, I went with a previous document he released last year or the year before and assumed the 10% rate is up to 75,000%, and the 25% rate is all of my household income for the rest; the 35% rate is higher than I currently earn.

Based upon these new income and tax brackets, and adjusting for the higher standard deduction of $24,000 (for both me and the wife), and eliminating the personal exemption of $8000 (for both me and the wife), and adjusting for a new capital gains tax rate and assuming the dividend tax rate is also no higher than 15%, my tax refund would increase by $4200.

Doesn’t sound too shabby, eh?

The drawbacks

The White House has called this the largest tax cut in history.

Well, that’s kind of true… while all Americans would get a reduction in taxes, the biggest gains – by far! – go to the wealthiest Americans.

First, let’s look at how this helps wealthy Americans. The argument that this isn’t a tax cut for the rich is that it phases out all deductions except for charitable contributions, and mortgage interest; and in return, it greatly increases the standard deduction by about $12,000.

If you are in the (new) highest tax bracket of 35%, then reducing your taxable income by $12,000 is worth $4200. So there’s a freebie.

Next, by reducing the top tax bracket from 39.6% to 35%, then for every dollar you make over $300,000 (estimated top bracket for married filing jointly), your tax burden goes down by 4 cents.

That doesn’t sound like much. But if you’re making $750,000/year, then you would owe (750,000 – 450,000) x 39.6% = $118,800. Under the new Trump plan, you would owe (750,000 – 300,000) x 35% = $157,500. So here you owe more.

But let’s suppose you’re really rich and make $10 million per year. Under the old tax plan, you’d owe $3.7 million. Under the proposed plan, you’d owe $3.4 million. So here, you’d owe $400,000 less.

Under the proposed plan, the higher your income goes, the more you save under the new plan. But it seems weird that you’re better off if you’re already doing pretty well to make that much money.

(This analysis doesn’t account for the higher rates in the lower brackets leading up to the highest bracket)

Second, the wealthiest people don’t earn all their income from salaries which is taxed at the highest rate. Instead, they earn a big chunk from dividends and capital gains.

The average American – myself included – don’t make the much from dividends and capital gains. I do make some but I can’t live on it, not even close. And I have a lot of money invested.

Under the Trump tax plan, which mimics the Republican tax plan, capital gains are now taxed only 15% instead of as ordinary income if you hold for less than a year (in other words, the richest people would pay at 39.6% or even 35%). Let’s assume that dividends are taxed at the same rate, only 15% for both ordinary and qualified dividends.

Since wealthy people earn so much from dividends and capital gains, this drop of up to 24% on some of their earnings represents a huge benefit. If you bought and sold a property and flipped it for $100,000 and claimed it as personal income, whereas before you might be hit with a $39,600 tax bill you would now only have a $15,000 tax bill. That’s a big savings, and only wealthy people can actually do.

Of course, wealthy people only structure their income like this in corporations, but still.

Third, look at those eliminations. Eliminating the estate tax! Today, at the federal level, if you die and your heirs inherit money or property, it is tax free up to $5 million (states may have their own rates). Since almost none of us have almost $5 million to bequeath, this doesn’t matter.

Except to the super rich. Let’s be honest, this is a way to pass down inter-generational wealth without paying taxes on it. It’s a freebie for people who are already wealthy and probably don’t need the tax break.


Fourth, it eliminates the alternative minimum tax (AMT). I don’t even know what this is, all explanations of it online are like “This is complicated.”

What I do know is that in 2005, President Trump earned $150 million and paid $38 million in taxes. But, that was because of the AMT. Had he not had the AMT, he only would have paid $6 million (4%).

Under his plan, he’d have paid (10% x 75,000) + (25% x [300,000 – 75,000 + 1]) + (35% x [150,000,000 – 300,000 + 1 – 24,000]) = $52 million. I’m assuming he is not writing off mortgage interest nor charitable contributions.

So, Trump would end up paying $14 million more. I’m not sure he realizes this.

Fifth, President Trump isn’t going to pass a tax increase on himself. Another part of his plan is to lower the tax rate on corporations from 35% to 15%, and also make that apply to pass-through entities… like President Trump’s real estate partnerships.

If he’s smart enough to shelter all his income in that matter (and let’s face it, I’m sure he is), then he would owe 15% x $150,000,000 = $22,500,000. That’s about $16 million less than he would have paid in 2005.

So there you have it, that’s what’s in it for him.


I don’t see how this tax plan helps the average American. According to the analysis I’ve seen at those two links in this post, these tax cuts only add about 1-2% to 90% of the population’s after tax income, barely anything. The largest earners in the top 1%) see their income go up by 5%, and that’s 5% on a much larger amount (I think the cut-off is around $400,000; so $20,000 at a minimum on the low end of the wealthiest people and way more for the top of that bracket). For the average person, you’ll get a few hundred… maybe.

So yes, it’s the biggest tax cut in history but it basically goes to people who already are well off.

Doesn’t seem like it helps the people who need it the most.

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This is going to be a boring financial post. But I’m typing it up so I can refer back to it next year. This post does not construe tax advice, it’s a strategy that I think works as best I understand it.

It’s the end of 2016 and I’m currently doing some financial planning, specifically around taxes. In year’s past, I always used to estimate my taxes on Jan 1. But this past year, I’ve been doing it since October.

Over the past few years, tax refunds for myself and the wife have not been all that good, so I’ve been trying to come up with creative ways to increase it.

Charitable donations

One way to do it is through charitable donations which reduce your taxable income. The way I used to think it worked is that for every dollar you donate to charity, you get to subtract that dollar from your income and that goes against your taxes.

So, suppose you make $75,000 per year, and during the year you pay 20% of your income in federal income tax (this excludes Social Security and Medicare deductions). This means you would pay $75,000 x 20% = $15,000 in federal income tax.

Then, suppose you give away $7500 to registered charities. I always used to think the calculation worked like this:

Tax owed = (75,000 – 7500) x 0.2 = 13,500

15,000 – 13,500 = 1500 refund

That’s the way I used to think it worked, more or less. But it’s not. Taxes are more complicated than that.

For one thing, you get what’s called a Standard Deduction, and let’s assume it is $10,000 per year. The amount of taxes you pay throughout the year seems to account for this Standard Deduction.

Next, you add up all of your deductions which include charitable donations, deductible interest, sales tax paid, etc. If the sum of all of those is greater than the Standard Deduction, you get to use that against your total income. Thus, you have to give enough charitable donations such that the sum of all of them plus a few more other little deductions is greater than what you would normally for the Standard Deduction.

In this example, $7500 is less than $10,000, so I would not get to write off anything against my taxes even though I gave $7500 to charity. It wouldn’t be enough to reduce my tax liability. I’d have to give at least $10,000.

It’s good to give money to charity, but as a part of tax planning they are not that effective at reducing our taxes unless we give a huge amount [1].

Capital gains and losses

The one place that I have found to be effective is in capital gains and losses.

If you sell a stock or piece of property at a loss, you can use that against your income. So, suppose I have a stock I bought for $10,000 and sell for $5000, that’s a $5000 loss. I can reduce my income, not by the full amount, but a max of $3000 (and carry forward the other $2000 the next year). This is how Donald Trump could have conceivably avoided paying income tax for nearly two decades when he took a $1 billion personal loss in the mid-1990’s.

Many years ago, I bought a bunch of ETFs that track the general market. I’ve bought US stocks, foreign stocks, bonds, and Real Estate Investment Trusts (REITs). Some of these positions are up, and some are down. You would think that after five years they’d all be up, but no – some are still worth less than what I bought them for (roll-eyes.gif). Sometimes diversification doesn’t work that well.

But, what I can do is this – I can sell the stock (ETF) and then buy it back, and then use the “loss” against my income. For example:

a) In June 2014, buy an ETF at $50/share, 100 shares

b) At the end of the year, in December 2016, sell the ETF at $40/share, all 100 shares. I have lost (50 – 40) x 100 = –$1000. I then claim a $1000 loss on my taxes, reducing my taxable income by this amount. This is efficient because it goes right against the taxable income, no deduction magic involved.

c) I then buy the stock back right away at $40/share. Because I’ve only incurred trading costs, if the stock goes up (over time, cross my fingers) and I sell it down the road, I still can think of my starting point as $50/share.

The catch in this plan is that the IRS won’t let you do step (c). They aren’t stupid; you can’t just sell a stock, take the loss, then buy it back simply for the purpose of taking capital losses on your taxes. Instead, they have something called the wash sale rule. You can’t sell something and buy something similar within 30 days and claim the loss on your taxes. If you want to claim the loss, you have to wait at least 30 days before buying back something similar.

So that’s what I do – at the end of the year, I sell some stocks to take the loss, and then I wait 31 days to buy it back. I make no other trades during this period.

There is risk. I could sell it at $40, wait 30 days, and then have to buy it back at $45. That would suck.

Still, I take my chances. It worked out in 2015 because I was able to repurchase at the same price (or even a bit lower); hopefully in 2016 I can do the same in February.

The drawback here is that I am draining all my capital losses now instead of in the future. That is, if I have more income in the future, I have almost no more stocks to sell at losses. I am taking my chances here as well. But at the same time, now that Trump is in power, his proposed tax plan reduces this risk for us because of increases in the Standard Deduction. I’ve done the math on it, and his tax plan is friendly to the wife and I [2].

This works when it is well-executed

In 2015, I executed on this perfectly.

In 2016, I made a blunder. Instead of selling 200 shares (for example) to take a loss, I bought 200 shares. D’oh! I did this twice. Double d’oh! In order to fix this, I then had to sell 400 – the 200 I wanted to sell originally, and then the 200 I just purchased.

Tax-wise, this complicates things. Suppose my buy/sell over time looks like this:

– June 2012 – Buy 75 shares at $50

– Jan 2013 – Buy 80 shares at $55

– Sept 2013 – Buy 70 shares at $48

– June 2014 – Buy 60 shares at $45

It’s now Dec 2016 and the price is $47. What’s my net gain?

My stocks use a First-In, First-Out model. So, if today’s price is $47:

– June 2012 = ($47 – $50) x 75 = –$225

– Jan 2013 = ($47 – $55) x 80 = –$640

– Sept 2013 = ($47 – $48) x 45 = –$45

Total loss = $910

That leaves me with:

– Sept 2013 – 25 shares acquired at $48

– June 2014 – 60 shares acquired at $45

But of course, I wasn’t paying attention and first bought 200 shares instead of selling, which means I have to sell 400. This screwed up everything, so here’s what I think the situation is:

June 2012 = ($47 – $50) x 75 = –$225

– Jan 2013 = ($47 – $55) x 80 = –$640

– Sept 2013 = ($47 – $48) x 70 = –$70

– June 2014 = ($47 – $45) x 60 = $120

That’s a running total of 285 shares, so now we dip into what I just bought, the 200 shares at today’s price of $47:

– Dec 2016 – ($47 – $47) x 115 = $0

That brings me a net loss of $815 instead of $910. It also means that my future basis for all sales from this batch (85 shares) is now $47.

Not a good thing. I need to pay more attention in the future.

And then there’s dividends

One of the simplest ways to earn money without having to do anything is through dividend-paying stocks. Normally, you think about stock gains as buying low and selling high. But another way to do it is through buying a stock that is stable and paying dividends. There’s a debate over which method is better, but I do find that I like seeing my account have money deposited in it automatically, whereas buy/sell-at-a-gain requires me to do more work (should I sell now? Later? When!). Ideally you’d get growth + dividends, but that’s rare for a single stock. It’s more common through an ETF or mutual fund.

But whereas buying and selling stocks at a gain don’t generate taxes until you actually sell, dividends always make you pay taxes. My broker doesn’t withhold taxes, so all dividends that I get throughout the year add up into my total income and I have to pay taxes on it come the following April. I don’t have to pay taxes in my retirement accounts (401k and Traditional IRA) but I do in my regular brokerage account.

Dividends are interesting because they break down into two types:

  • Qualified dividends, which are taxed at a lower rate. In our tax bracket, they are taxed at 15%. These are usually US-based corporations and some foreign-based corporations, and you must have held them for a certain period of time (e.g., you can’t have bought the day before).
  • Non-qualified dividends, which are taxed as ordinary income (if you are in the 25% or 28% tax bracket, that’s what it is taxed at). Everything that’s not qualified counts as Non-qualified.

Thus, as you can see, if you want to earn income that is taxed most favorably, you should try to get Qualified Dividends.

The problem comes with diversification – you can’t just buy US stocks, you need to own some bonds, foreign stocks/ETFs, and REITs. Unfortunately, REITs’ dividends are classified as Non-qualified, so are bonds, and much of foreign ETFs are, too (at least I think so) [3].

So to optimize, you really should own your non-qualified dividend-paying securities in retirement accounts that are tax-deferred or tax-free; and qualified dividend-paying securities in accounts that are subject to paying taxes.

I did that a couple of years ago because I read the advice online in an article, but without really understanding why. Now I understand why. It turns out that my accounts are not fully optimized because I’ve instead chosen to reduce fees instead of taxes.

Still, the point is, dividends are a good way to earn income that is taxed less than regular income, plus it has no Social Security or Medicare tax.

On my previous years’ tax returns, it looks like all of it is being taxed as Ordinary (Non-qualified) dividends, but my current research suggests that about 2/3 of it should have been taxed as Qualified (15%) and 1/3 taxed as Non-qualified (28%). If I am right that I overpaid, that would reduce my tax liability even more. This is something I need to talk to the accountant about.

Getting rid of some other stocks

A long time ago, I bought shares in Apple. They split 7:1 a few years ago, and I had 98 shares. Apple was a great stock for a long time, increasing in value all the time. However, over the past two years the stock has lost its luster.

I’ve held onto it for three reasons:

1) I hope [4] it will keep going up, it’s Apple after all

2) I’m sitting on a big capital gain I will have to pay taxes on

3) It pays a decent dividend

Yet I’ve been thinking about selling it for a while and picking up some more REITs, there’s a particular stock I want to invest in.

I haven’t invested in it because I am afraid to – I almost bought in the summer when it was at $66, now it is at $55 – a loss of 16%! I think it’s currently on sale and is probably going to go up.

This new stock is a single stock, a REIT that currently pays a 4.26% dividend, far higher than Apple. But it’s only one stock, and that means it’s not diversified. A REIT ETF is VNQ (where I already have shares) and it pays a 4.1% dividend. Less, yes, but less risk.

But after doing the math above, it makes sense to buy a single stock that’s not a big part of my portfolio because it will be taxed as a Qualified Dividend (I think), whereas the more diversified REIT would be taxed as a Non-qualified dividend, and therefore 10-13% higher. That’s a big deal.

So, here’s what I did:

– I bought two more shares in Apple, bringing the total to 100

– I sold a covered call on Apple, expiring in February.

My hope is that the call option is exercised so it gives me spare capital to buy this other stock, otherwise I probably won’t sell Apple. The drawback of this approach is that it means my shares in Apple are hedged, and therefore any dividend Apple pays me count as Non-qualified (if the shares are exercised by then, it won’t matter).

* * * * * * * * * *

I know all of this is complicated. But taxes and investing are complicated.


[1] This is not accurate for other people, because other people get to deduct their mortgage interest and property taxes against their income. The wife and I cannot do this, we can only deduct it against our rental income.

[2] For the record, Hillary Clinton’s tax plan would make almost no difference other than costing us a couple extra hundred dollars. Bernie’s was extremely unfriendly, and would have cost us an extra 12-14 thousand dollars.

Donald Trump’s tax plan will increase the Standard Deduction from $12,600 for a married couple filing jointly to $30,000 for a married couple filing jointly. However, it will also get rid of Exemptions which are added on after you take Itemized Deductions or the Standard Deduction. Still, under the current tax code we can deduct 20,700 from our taxes whereas under Trump we would be able to deduct 30,000.

This means it would be even harder for charitable donations to reduce overall tax liability.

[3] It looks this way for me when I go back over my old statements.

[4] In investing, ‘hope’ is a four-letter word.

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The mortgage is now paid off

8 years ago, I made a huge purchase – I bought a condo for the purposes of using it as an investment.

The goal, for 8 years, never paid off. This was during the recession and I wasn’t able to get it rented quickly, nor get as much as I wanted in rent. As a result, I was taking a financial beating.

I refinanced once a year later, then refinanced again a couple years after that. Along the way the economy recovered so that turned my big monthly loss to a small monthly loss.

That ends now.

For your see, the wife and I successfully paid off her condo in 2013. We then started to pay down mine.

We paid a little bit extra in 2014.

We paid a lot more extra in 2015.

We paid a ton more extra in 2016!

And with that, the place is paid off. The wife recommended we just get rid of the balance once it got down to a certain amount. I agreed, and now the balance is zero.

That means that this month, for the first time ever, it will be a financial boon for me to own that condo. It’s now actually an asset (from the Rich Dad, Poor Dad point of view).


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I’ve always considered myself a reasonably savvy financial investor. I’ve read plenty of self-help books on the matter and for the most part, I’ve followed their advice.

I got into stock trading over 10 years ago and in the 5 years that I did it, I came to one important lesson – don’t try to trade stocks on your own; instead, focus on passive investing. I learned this because unless you’re doing it full time, it’s hard to do it better than simply passive investing.

I got into real estate investing also because of reading books on the subject. I made my first real estate investment in 2008 and it turned out to be a total disaster. However, now that the wife and I are married, we have a separate real estate investment that is profitable. In 4-6 months after my place is paid off, we will have a second one.

That means we will be completely debt free.

And leads me to uncertainty about what to invest in next. Because I don’t know. There’s a certain desire to simply spend the money on frivolous things, but we all know I am not going to be doing that, and I won’t sign off on the wife doing it either. I feel like I have a bunch of options:

  • I could just invest passively in the stock market. But, I don’t like the wild swings up and down. And, while it’s liquid, the fact is that I just buy-and-hold and I do like the monthly income that real estate has. There also are few tax advantages of owning stocks. But, I’ve read that stocks give you better returns than any other asset class.

  • We could buy more real estate. UGH! Neither the wife nor I are big fans of owning real estate, even though we’re starting to get pretty good at it.

  • I have thought about investing in HomeUnion. This is a real estate investment platform where you put up the money to buy a place, and they manage it all for you. That’s tempting, so very tempting. But not particularly liquid if things go bad.

  • I have thought about investing in FundRise which is a real estate crowdfunding site that sells eREITs. eREITs are like regular real estate investment trusts except with better returns and poorer liquidity (you can’t get out whenever you want but only at certain times, and I think you may sacrifice some returns if you do).

  • I have thought about investing in other real estate crowdfunding that specializes in commercial property. These are websites like RealtyShares, and apparently you get some of the tax advantages of owning real estate. But again, I’m not sure how to get out if things go wrong. And do I want to be that tied to real estate? The other downside is that I have to prove I am an accredited investor (which means we have a net worth of $1 million, or make $250,000 year as a couple).

  • I have thought about investing in a stock called Realty Income Corp, ticker symbol ‘O’. I’ve run across this multiple times, it has increased its dividend every year for 15 years and has consistently gone up in value. Plus, it’s 100% passive. But do I want to have that much money in real estate? And stocks have no tax advantages so I’d be getting a little bit of money each month which I’d just re-invest, but then get taxed on it each year.

So you see, I feel like I have this mental pressure to do something with extra money to invest otherwise I’m just wasting it. But I feel like these new crowdfunding platforms are so new that there’s way too much risk involved.

I am paralyzed with indecision.

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I recently read an article somewhere (I forget where) that if you want to look at someone’s future 10 years from now, look at what they are doing today.

If I look at myself and where I am now, would 10 years ago have predicted where I am currently at?

First, let’s look at where I came from. I grew up in a middle class household, but that’s not enough of a description. The province in Canada where we lived – Manitoba – is not one of the wealthier provinces but at the same time, we did not live in a poor community. If you map out people’s classes the following way (using this article as a basis, you should read the whole thing), starting from the bottom up:

  1. The lowest, poor class – chronically unemployed, generationally poor
  2. Labor class level 1 – unskilled labor, work at fast food restaurants
  3. Labor class level 2 – assembly line work
  4. Labor class level 3 – pilots, plumbers, and small business owners
  5. Gentry class level 1 – schoolteachers and starving artists
  6. Gentry class level 2 – professions like engineering and law
  7. Gentry class level 3 – scientists and entrepreneurs
  8. Elite class – Although you can get a job in finance and make a few million and kind of get into this class, you’re mostly born into it. These are families with “old” money. They don’t work unless they want to.

Don’t confuse social class with economic class; you can be a wealthy plumber yet still be labor class because social class is more than money. Instead, it’s about economic opportunity, the people around you, your political beliefs and attitudes, your social beliefs and attitudes, and so forth.

My family was either Labor class 2 or Labor class 3. We weren’t poor, but we did live on an acreage out in the countryside about five miles outside of the nearest town of about 2000 people, and 20 min outside the nearest big city (of about 600,000 people). I can tell we were Labor class 2 or 3 because the families that we were friends with, and made up most of the other families, were the same as us. My friends’ parents had similar jobs with some variation. Our cousins’ families were similar to us, too, again with some variation.What cements the fact that we were Labor class were the things we enjoyed – my brother and I liked watching professional wrestling. Those are Labor class leisures.

I, along with my two siblings, went to university. I got a degree in computer engineering. For all the talk about how university isn’t worth the cost, the one thing it does teach you that you can’t learn in online courses is how the gentry class thinks. That was a big part of what I learned, especially when I took a class in sociology (half of which was wrong, but at least I know how they think).

Fast-forward to today, and I am in Gentry class 2. I somehow got and kept a job at a large tech company for 12 years. I am paid well and many days (most?) I wonder how I manage to have landed a position where I am overpaid as much as I am; I do feel guilty sometimes when I look back at the friends with whom I grew up and I out-earn all of them, and even some of my smarter classmates in high school, too.

I sometimes map myself along the household income scales you can find by doing web searches, and the wife and I – combined – are in the top 10% in the country which isn’t unusual for people living in Seattle, especially when one of them works in the tech industry. I am not complaining about how fortunate we are, nor bragging. It just is, and it contrasts with where I came from.

By the way, the top 10% sounds impressive but it isn’t. The top of the economic scale doesn’t get exorbitant until you get to the top 1% and even then, not until the top 10% of that 1%, that is, the top 0.1% of the country. But we are still doing fine.

So returning to my question from the start of this post – could 10 years ago have predicted where I am now?

10 years ago was 2006 and I was working back in Winnipeg for the same company I work for now, and I wasn’t getting paid that much money. However, there were a few things I was doing right:

  1. I had started a few side businesses and failed at all of them. I failed in at least 3 network marketing businesses the five years prior to 2006.
  2. I practiced researching and trading stocks. I spent a ton of time doing this. I got good at outperforming the market in up-trends but losing most of it in down-trends, and that’s why I quit. I did better doing passive trading.
  3. I did some part-time gigs performing magic. These never paid a lot but I worked at it.
  4. I did a lot of programming in my spare time while I was unemployed, I developed my own stock market trading simulator.
  5. I read a lot of books on personal finance and got into Robert Kiyosaki’s Rich Dad, Poor Dad series of books, among others. So I was well aware of what it took.
  6. In 2001, I was working for a tech company in the UK when I was laid off but got a pretty good redundancy payout. I invested £3000 into an investment account for long term retirement. It lost about 25% in a year, though, so I withdrew half.
  7. I was cheap. I rarely spent money on frivolous things. In fact, after I moved back to Canada from the UK, I lived at home with my parents because it was cheaper.

So looking back on my habits from 10 years ago, it’s not that surprising that I am doing reasonably well now. I was good in school (but not university) and liked to read, was good at math and programming, and I was interested in finance. Today, I am in a stable position.

I look at some of my friends who are not in as good a position as I am. Some of them would spend money far too easily for my judgmental eyes and today, they struggle to financially get ahead or even to keep their heads above water.

I am fortunate to be in the position that I am in. It is a lot of luck that I was born in the family I was, that I was born in the country I was, in the time I was. But that is also augmented with some early habits I developed that have so far paid off such that I can do many of the things I want to do.

It is true that money does not buy happiness. However, what it does is allow you to do the things you like to do and pay to not have to do the things you don’t like to do.

The wife and I read a lot of books on personal finance. We are aggressively paying down the mortgage on the condo I bought in 2008, we put a lot into retirement savings, and I have a large chunk in regular savings. We have met with a financial adviser, we take financial planning classes, we have a will (!), and the strangest thing is that now we get invitations in the mail to attend free dinners put on by people trying to sell us things. So far, we’ve done one for solar panel installations, and then I went to another one for learning how to invested in Fixed Index Annuities. I think we’re going to one or two more in the next couple of weeks.

So, what will things look like 10 years from today? Will the things we’re doing now pay off then?

We’ll see.

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Another description of the social classes and labor classes can be found here:


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