taxes : The Art of Non-Conformity

Life

Hate Paying Taxes? It Could Be a Lot Worse: You Might Not Have to Pay Them

I do wish it were simpler. I was surprised last year to learn that I agreed with Donald Rumsfeld on something.

Part of it is my own fault: I keep starting new businesses and entities. I have a tax return for my career as an author, another for my entrepreneurial work, another for WDS, another for the WDS Foundation (a separate organization), and now another for Pioneer Nation. Who knows what else I’ll have next year!

Why can’t Amazon or Zappos or Apple figure this out for the federal government? Imagine the possibilities.

Et Cetera

Earn Miles by Paying Your Taxes with a Credit Card

Link: Discover Card 3% Bonus

Speaking of paying taxes, for years people have asked me about earning Frequent Flyer miles or points by paying your taxes with a credit card. Wouldn’t it be great if you could receive a travel bonus for all that money you have to pay?

Generally speaking, this isn’t usually a great idea, because the companies that process tax payments are smart. They charge a fee, typically 1.87%, in exchange for passing along your money. At 1.87%, you’re paying $467 for every $25,000 in tax payments.

Fortunately, there's a new opportunity that greatly improves this calculation.

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Work

One Log Cabin and 800 Yoga Mats: Some Unconventional Tax Deductions from My Life in 2014

My tax return is complicated for a lot of reasons. First, I run several different businesses which all have their own set of accounting. WDS, our annual gathering, has its own legal structure, including a foundation that is completely separate from all my other projects. Last year we started an all-new event that also has its own legal structure.

So yeah, it’s complicated. It takes about 20 hours just to prepare all the info for my accountant, and as with most tax-prep tasks, it’s not usually a fun process. But I do enjoy seeing some of the charges on my statements from the previous year. They remind me of the crazy life I have, and the many fun experiences that I'm fortunate to participate in.