7 Years of Early Retirement Tax Optimization

2019 was our 7th full year of this thing we do. It’s been an incredible ride – we’ve traveled, adventured, and procreated, with the best yet to come.

We’ve also done a fair amount of tax optimization, paying little tax each year while taking steps to minimize future taxes. How effective have we been with our tax optimization strategery?

Do these optimization efforts actually work, or is this just fantasy? (Caught in a landslide, no escape from reality…)

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The Go Curry Cracker 2019 Taxes

2019 was our 2nd tax year under the Tax Cuts and Jobs Act (TCJA), 3rd year using the Foreign Earned Income Exclusion (FEIE), and 7th year of paying ~$0 in income tax on dividends, interest income, and blog revenue.

But… this year I also realized a massive long-term capital gain which resulted in a massive tax bill.

Our 2019 tax return has some good examples of the FEIE, the long-term benefits of capital gain harvesting, and tax and travel hacking synergies.

Here are all the fun details.

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The 2020 GCC Asset Allocation

asset allocation and rebalance

We have been living off our portfolio since late 2012. Along the way I’ve made only minor adjustments – annual rebalancing, minimizing long-term taxes with capital gain harvests and Roth conversions, and adding the occasional small chunk of fresh capital as blog income allowed.

But after ~7 years of the stock market trending upward, and the conscious decision to spend more, in early 2019 we took some money off the table (sold stocks / bought bonds.)

When literally everything went to hell due to COVID-19, we sold some of those bonds to buy stock and increase our cash cushion..

After all of that… This is what our portfolio looks like in 2020.

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Award Travel Series: Alternative Redemptions for Miles & Points

The travel industry has experienced a gigantic upheaval since the onset of COVID-19. Stock markets are down 25-30%, jobless rates have reached unprecedented levels, and airlines have come to a screeching halt.

Since it is unclear when things might return to “normal”, and many can benefit from cash now vs travel later, here are three ways to cash out your points for immediate value.

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F.I.R.E. Damage

As poor an acronym as it is(*), F.I.R.E. (Financial Independence Retire Early) has become widely known, inspiring many to spend less and save more.

Not everybody thinks it is a good thing, however, and we are probably guilty of setting a bad example – indolent, hubristic, aggressive, patronizing, flippantly roaming the globe in luxurious fashion…

… so when the economy struggles and the stock market implodes, I am unsurprised that some headlines and individuals are excited for the opportunity to say, “I told you so” or to predict “the death of FIRE.”

Are early retirees at risk of serious F.I.R.E. Damage?

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