Investing has the reputation of being mysterious and intimidating. It’s something for older, more worldly, bebuttsticked captains of industry, not lowly millennials trying to make their way in a hostile economy. But like the president's reputation as a deal maker, this characterization is a complete myth.

Investing Deathmatch: Paying off Debt vs. Investing in the Stock Market

LET’S GET READY TO RUMBLLLLLLLLE!

It’s time for another thrilling episode of Investing Deathmatch, in which two forms of investing enter the ring, and only one leaves victorious. Or, more accurately, we decide that investing is a far more complicated affair than wrestling and the outcome of the fight depends on a number of nuanced factors.

But I digress.

TO THE BLOOD SPORT!

This fight has a long and sordid history. We’ll be uncovering old wounds, dredging up arguments long held in stalemate. We’ll be discussing a topic about which every damn personal finance blogger on the Internet has a very firm opinion. And we’ll be demystifying an age-old enigma of financial independence.

Brawlers, take your corners.

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I've tried making debt visualizations to help me stay on track. I'm going to share two with you today, including one that is fucked up and embarrassing.

Share My Horror: The World’s Worst Debt Visualization

Some days I wake up ready to crush my debts. I am filled with fire and vinegar. (No, the vinegar does not put out the fire.) I double down on everything I do on that day—I spend less, work harder, and plan more.

Other days, I wake up feeling like Idgaf, Queen of the I Don’t Give a Fuck Tribe of Greater New England. On those days, I find myself wasting time with stuff that distracts me rather than enriches me. I play old video games I’ve already beaten three times before, and mewl at my partner to take me to Five Guys. On those days, it can feel like the sacrifices aren’t getting me anywhere.

What can I learn from this? Besides the fact that I suffer from intermittent depression, because I already knew that.

I have a sprinter’s attention span and marathon financial goals. My current financial goal will take at least nine years to achieve. Maintaining momentum and motivation over such a long period of time is really hard.

I’ve tried making visualizations to help me stay on track, and I’m going to share two with you today. Including an old one that is weirdly fucked up and embarrassing.

Embarrassing!!!

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The proof is in the pudding. The cold, hard, numerical pudding.

The Debt-Killing Power of Rounding Up

If you haven’t noticed by now, I’m a big fan of incrementalism. Like an establishment politician, I believe in taking reasonable baby steps toward an idealized future (and unlike said politician, some day I’ll actually get there… at least where my personal finances are concerned). You can make really big progress on your debt and savings gradually, by degrees, and it feels so much more manageable and easy than committing yourself to meeting your financial goals in big chunks.

Take, for example, the debt-killing power of rounding up on all your bills.

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Why? Because fuck student loans.

I Paid off My Student Loans Ahead of Schedule. Here’s How.

I paid off my student loans almost five years ahead of schedule.

I dedicated every waking hour for a little over a year to stomping out these loans like the parasitic infestation that they were, and now that this monumental task has been accomplished it feels really, really good. I wiped out about the last $18k of loans in 14 months, and doing that required intense discipline and concentration. I channeled the mental fortitude of a Buddhist monk and the austerity of an Irish peasant circa the Potato Famine. Here’s why and how I did it.

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