The Complete Non-Boring Guide to Getting Started With Taxes

by Martin

“The hardest thing in the world to understand is the income tax.” — Albert Einstein

How much do I owe? That was my reaction while completing my taxes last year. I got spoiled when I was in college because I always looked forward to getting money back. While I know that technically getting money back isn’t such a good thing, it still sucks to have to owe money.

Ah taxes. A topic we think we know so much about, but really know so little. This year you’re not going listen to your crazy relatives or know-it-all friends. This is all you need to know about getting your taxes started. The rest is up to you to determine what the rules and regulations are in your jurisdiction.

I know that the deadline in the U.S is April 15th, 2014. Canadians have until April 30th, 2014. This is the best last-minute article (especially for Canadians) or how-to guide on taxes for all young folks. Actually, I wish that someone else had written this article so that I didn’t have to.

Oh and I’m not making this stuff up! I spoke with an actual tax professional for a long time. I asked questions that came from you guys. I wanted to help you with every single angle.

How do you get started with your taxes?

First, let’s look at the biggest issues with taxes and where most confusion comes from. We need to debunk a few tax myths too.

  • Parents have been doing taxes. It’s going to be a big culture shock if your parents have always done your taxes for you. You’re a grown up now. You do your own taxes and laundry (eating at home is still cool). You can’t rely on your parents to do your taxes, even if your parents pay for your school.
  • Nobody told me. Nobody has to tell you. You have to do your taxes. You can watch all the conspiracy theories that you want. Keep on watching them. Maybe you can ask the director for help when your wages are garnished off your check.
  • I don’t make enough money. Everyone has to file taxes. Just because you’re a 21-year-old broke joke, you’re not excused from taxes. It doesn’t matter how much money you make, you have to file your income tax return.

Now it’s time to ask a few common questions…

Do I get it all back? What you pay in taxes is what you get back, right? Why do you get a tax refund?

A tax refund is for overpaying taxes. If you don’t pay a lot of tax, you’re not getting much back. You may not even be taxable. This is why it’s important that you file your taxes so that you see where you stand here.

Martin’s helpful hints to getting started:

  • Print all of your forms out. If you’re a student, get your forms off the school’s site. Get your information. Don’t wait for it.
  • It helps to remember that there are new procedures since parents were in school. You can’t go 100% off what your parents suggest.
  • Get a professional to do it the first time. After a few years you can easily do your own taxes. It just makes sense to get a professional to file for you the first year.

That’s how you can get started with your taxes, regardless of your age. Now let’s move into the next stage of life.

Life after college. How do taxes work now?

At this point you have a job and a steady income coming in. Along with your new-found extra beer money, come taxes. Fortunately, taxes already come off your paycheck so that you don’t have to do them yourself. Your employer will also send you the proper tax documentation as well. You then use this to file your taxes. It’s pretty simple.

If you have tax write-offs and paid too much in taxes, you’ll get money back. If it’s the reverse, you’ll have to pay. You won’t find out until you sit down to file your taxes.

What about employee expenses? You generally can’t write off anything if you have your regular job that pays you. There’s only one condition and that’s when you get a form from employer that indicates that you’re responsible for your own expenses.

What are my helpful hints here?

  1. Try to pay more in taxes. A friend of mine works two jobs so he went to both employers and asked to pay extra in taxes. He does this so that he doesn’t have to stress about not paying enough taxes when it comes to tax season.
  2. Take advantage of retirement accounts. Look into retirement accounts on your own and through your own employer. Take advantage of these. Learn more.
  3. Consider donations and other things you can do to save money on taxes. There are many ways you can catch a tax break. Look into donations and other options.
  4. Don’t stress about not wanting money back. Some folks say that it sucks to get money back because it means that you overpaid in taxes during the year. Who cares? Nobody sees it that way. Everyone sees it as a nice chunk of change that comes your way in the spring.

Now let’s add a few twists to the simple tax scenarios. Let’s throw in some self-employment and rental properties.

How do taxes work when you’re self-employed (freelancing or anything else)?

With an employer it’s relatively easy. They do everything for you. Taxes come off every check. Now you’re on your own for taxes and everything else (literally!). You’re now self-employed.

You need to do record keeping.

You’re in charge of organizing everything now. You can’t rely on the accounting department (unless you create one). You have to track your income, expenses, and everything else. Nobody else will do it. The good news is that software has made this easier than ever before. I just went on Paypal and turned my income/expenses into a PDF file, printed it, and went through everything.

What are expenses that you can claim on taxes?

Anything that’s involved in you being able to earn that income.

I can only speak from experience, so I’ll get into blogging. You can claim hosting, Paypal fees, a home office if you have one, consulting, and a few other things depending on your tax laws.

What about conventions/trips?

It has to be realistic and there’s a limit on how many business-related trips that you can write-off per year. You can also only write off the business related portion. There might be issues with you writing off your bottle of vodka and red bulls.

Martin’s super helpful tips:

  1. Put 30-40% into a bank account, in case you have to pay taxes. You don’t want to get blind sided. You have to pay taxes. Don’t act surprised when you find out how much you owe.
  2. Create a separate bank account. This will make life much easier for you. Create a separate account where you just deal with business income/expenses. You don’t need anything fancy. You can just use a regular free checking account.
  3. Look into incorporation/creating a business structure. Can you create a business structure? Ask around and see what other people in your field have done.
  4. Get a spreadsheet. Keep your expenses in one place. Helps you personally. I have tried to do this for my online income. Sadly, I totally got lazy in 2012. I was stuck pulling an all-nighter trying to finish everything up.

What about a rental property?

Let’s say that you saved your money and have invested in a rental property. What do you have to do? Well, you likely guessed it. You have to claim this as well. You have to claim the rental property income. The good news is that you can also once again claim the expenses needed to maintain this property.

What expenses can you write off with your rental property?

It mainly depends on the deal that you setup with the tenant.

  • Maintenance fees.
  • Utilities.
  • Mortgage interest.
  • Property taxes.
  • Advertising.
  • Landscaping.
An important point for me was that I thought I could write off the full mortgage payments for my rental. I was wrong. The expert I spoke with, informed me that I could only write-off my mortgage interest.

Even more great insights…

Taxes are pretty damn confusing at times. We barely scratched the surface here. I just wanted to help you get started with taxes if you were lost. As always, make sure that you consult a professional and don’t yell at me for anything.

Make sure you understand what you can and can’t do. Ask first. Don’t listen to friends. Don’t take anything someone tells you as fact. Find out from your governing body or accountant. Get the real scoop.

Would you like some free money/help?

I can help you out! This is one of the main benefits of running a personal finance blog. I can help you have a better life than me.

I can help five of you file your taxes for free! I have been given coupon codes to give out to five readers that plan on or want to use TurboTax Canada. This is obviously for my Canadian readers only.

Since I only have five coupons, you must enter through email or through the comments to win. All you have to do is respond with what your favorite purchase with your tax refund has ever been.

File your taxes

I also want to share with you the best banking account that I use for storing my money. Saving my money with Capital One 360 makes it easy for me to keep things organized. I even created a seperate tab for “taxes” where I put extra money aside for taxes.

Help with filing taxes

Good luck with your taxes!

“In this world nothing can be said to be certain, except death and taxes.” — Benjamin Franklin

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{ 5 comments… read them below or add one }

1 Edward Antrobus

Starting about mid-January, I start checking all of my banks and loans daily for tax documents until they are available. It drives me crazy that my wife’s HSA information doesn’t arrive until mid February! I used to have my return by then back in the day when I could file the 1040EZ.

What drives me crazy are the people that are so lazy that they pay somebody else to take care of it for them when they are perfectly able to do it themselves. Last weekend my roommate paid me $7 to fill out his EZ. It took 5 minutes!

As far as business income, I haven’t bothered with a separate account. The number of transactions I have is pretty minimal, so I just put it in the savings account linked to my debt-paying checking account. That’s what I use my profits for anyway. That said, I have been separating out business taxes into a separate savings account on etrade. Since the money sits there for months at a time, it might as well earn nearly-nothing interest instead of next-to-nothing interest. :)


2 Martin

Hey Edward, it sounds like you can start filing taxes for your lazy friends!


3 steve

Hey Martin,

I am an SEO associate who just recently graduated college and all of your posts are super helpful for me moving forward. Just wanted to say that this post in particular was very informational.



4 Crystal @ Prairie Ecothrifter

Our taxes our complicated and my husband does them by himself by hand because we can’t trust anyone else to do it right. That said, records are the key to taxes. We keep great records of our business income, side hustle income, and all expenses. So taxes do take a full day or two since we have 6-7 forms to fill out, but they’re doable and correct…


5 Martin

Oh taxes are definitely a full day. I hope that this article clarifies taxes for folks in their 20s because the worst thing you could do is avoid them.


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