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Paying Off Debt Is Never “Easy”

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One thing that I absolutely HATE is when someone tells me that paying off debt is easy if you’re making a good salary. Maybe I take it too personally, but it feels like a knock on my accomplishment. After all, I paid off $87,000 worth of student loans, but I also had a good salary that allowed me to do it. Was it easier to do than if I had been making less? Of course. But it definitely wasn’t easy.

A recent headline I saw reminded me that a lot of people think paying off debt is just a walk in the park so long as you make a high enough income. Take a look:

Earn Tax-Free Airbnb Income With The Masters Rule

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Most people that I talk to about Airbnb agree that it’s a cool concept. Now that Airbnb has become pretty mainstream, my guess is that most of you have used it before or at least know someone who has. At this point, I think it’s probably more surprising to find someone who doesn’t know what Airbnb is.

Even though there are a ton of people using Airbnb on the guest side, the majority of people I talk to are understandably hesitant about actually hosting guests on Airbnb. I definitely understand the concerns – they’re ones I still think about as an Airbnb host. My biggest fears are having someone steal from me or otherwise mess up my house. Luckily, nothing like that has happened to me yet.

Even though I know that most people won’t sign up to be an Airbnb host, I still always try to convince people to at least give Airbnb hosting a shot. My rationale is that you don’t need to do it all that time. Instead, you can just try it out a few times and see what it’s like. If it’s too weird for you, you can just deactivate your listing. At most, you lose a bit of your time. But I think even people who are weirded out by having a stranger in their house can handle hosting someone in their home for just a few days per year. Why not challenge yourself and see?

Independent Contractor vs. Employee: It Pays To Not Be An Employee In The Sharing Economy

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A huge point of controversy in the sharing/gig economy world has been how to classify those of us who work in it. Most people reading this have probably seen or read about lawsuits challenging Uber’s classification of its drivers as independent contractors, rather than as employees. The same lawsuits have been raging on with basically every app out there in this space, including delivery apps like Postmates, DoorDash, and Caviar.

I’ve sometimes wondered if the folks fighting to be classified as employees understand the huge benefits they could be giving up by going that route. Don’t get me wrong, I totally understand the problem with misclassifying workers. Most people need the benefits and protections that come with traditional employment.

But, I suspect that many people fighting to be classified as employees under these apps don’t really understand what they stand to lose.

What’s The Most You Could Save In Tax Advantaged Accounts?

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The government allows you to put a ton of money into tax-advantaged accounts – you just wouldn’t know it at first glance. Technically, a traditional or Roth IRA is the only tax-advantaged account that every working person in the US has access to. As of 2021, the max contribution per person to those accounts is […]

Why Does Anyone Invest In Expensive Funds?

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One of the things I’ve always wondered is why anyone would invest in expensive funds (I typically define an expensive fund as one with an expense ratio of around 1% or more). Since there are options – like Vanguard – with expense ratios of 0.1% or less, it’s never made much sense to me why anyone would invest in anything else. Why pay ten times more to invest your money in what amounts to basically the same thing?

One problem I have is that, as a dude who’s really into personal finance, I fall into a sort of personal finance bubble. I take a lot of the stuff I know for granted and assume that everyone just knows this stuff too. In reality, the vast majority of people have no idea what anything I said even means.

February 2017 Side Hustle Report – $800.33

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It’s a new month which means that I’ve got another side hustle report for you guys. Those of you who have been following along with these reports know that each month I document what I made doing various side hustles in the sharing economy. The great thing is that these side hustles allow me to earn income off of the resources I already own. These side hustles also don’t take up very much of my time and have minimal to no startup costs.

And the thing that doesn’t get mentioned enough. Unlike with starting up most businesses, side hustles like these allow me to start making money literally from day one! There aren’t very many side businesses you can start up where you can make money right away with almost no startup costs and very little risk.

We All Have To Start Somewhere

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I recently picked up a new book from my local library called The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World. As you can probably guess, the book is about the growth of Airbnb and Uber, and it starts at the very beginning of these companies, before they even existed. I’m still working my way through the book, but what I’ve read so far really hit home for me and reminded me of an important lesson that I thought was worth reminding ourselves of again – we all have to start somewhere.

It’s an important thing to remember that I too often forget. One of the frustrating things about getting into the personal finance space is feeling like you’re so far behind all the time. I’m pretty much at the beginning of my financial journey and it’s sometimes disheartening to see people the same age as me who are already nearing or at financial independence.

When Leaving Big Law, The Financial Struggle Shouldn’t Be Real

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One of the maddening things about working in big law was seeing so many of my colleagues squandering the golden opportunity that they had in front of them. There aren’t a ton of situations in which a 25-year old can make six-figures a year right out of school with basically no prior work experience. For the vast majority of new big law associates, that first-year salary might be more money than they’ve made in all of their other previous working years combined.

That’s why it always bothered me when I saw my colleagues renting expensive, luxury apartments and talking about the hip, new, foodie restaurant they hit up over the weekend. It wasn’t the money they spent that bugged me the most. What really bugged me was how normal a lot of them treated their big law salary. To me, earning six figures a year at 26-years old was a huge deal! I’d never even made more than $20,000 in a year. The way I saw it, this money was a blessing. And it wasn’t meant to be squandered.

Don’t Know What To Do With Your Life: Why Not Retire Early?

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One of my more financially interesting friends is my friend Jay (not his real name). While the rest of us are beginning or in the middle of our “real” careers, Jay still works as a bartender at the same restaurant he worked at while we were in college. He recently turned 30 years old, and if my calculations are correct, that means he’s been working as a bartender at the same place now for 8 years (longer if you count the summers that he worked there while in college).

Bartending always seemed like it was supposed to be a temporary stop. My friends and I all graduated college in 2009 – right in the midst of the financial crisis – and found ourselves unable to get any “real” jobs. I worked two minimum wage jobs and lived at home with my parents. My other friends did similar things. One friend worked at a sporting goods store. Another worked at a golf course. Some people worked at restaurants – typical post-college jobs that you’d expect a 22-year old to have to take after the worst financial meltdown in a generation.

Live Like A Student: Embrace Non-Traditional Ways Of Living

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If you had to ask me what the single most important thing you can do for yourself financially when you finish school, my answer would always be to live like a student. It seems so obvious, and yet, despite being so obvious, very few people actually follow this advice.

I live in a college neighborhood, so I see a lot of college kids when I’m out and about. Sometimes, I like to think about how weird their living situations are compared to your typical middle-class American. Most of these college kids live in rundown houses, usually packing four or more people into a house. It’s not uncommon for people to share rooms or live in tiny bedrooms no bigger than a closet. When I’m out doing deliveries, I’ll sometimes make a delivery to a dorm and am reminded that, for at least a year, most college kids live and sleep in a tiny dorm room with a person they’ve never met before!

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