What does your response to Tax Day reveal about your character?

Today is Tax Day in the United States. Every year, you can see a big line (Not as big as the one for the latest Apple products) on this day outside the post office for people trying to get their returns out at the last minute. And yet there are some for whom this is just another day. Why is it that the same day that comes every year can evoke such a wide spectrum of responses from people? It has less to do with Tax Day and more to do with us. I believe that our response to Tax Day reveals our response to life.

I had recently read that one CEO has a unique way of interviewing candidates over lunch. He would call the restaurant in advance and he pays the restaurant in advance to deliberately mess up the candidate’s order during lunch. He feels that the candidate’s response to the waiter and the messed-up order can reveal whether the candidate can be a good fit for his company or not. I know that many first dates remained the only dates for many couples because of the companion’s response and treatment of the waiters.

I think that there are following five types of personalities when it comes to behaviors and responses towards taxes. Please let me know what your type is and if you think that there is a type that I have missed below:

1.      Cautious Charlie: This group of people consists of law-abiding individuals who are very cautious, worried about the remotest issues with the law, and hence they maximize their paycheck withholdings. They file their taxes in advance and they love to get a good refund. You will never find them worried on Tax Day, because they have worried throughout the previous year and during the months of January and February this year till the time their taxes are filed. As most of are scurrying to file our taxes, they have already received their refunds way in advance of the Tax Day. They are dependable people who are committed and would get things done. However, they might not be your go-to guys for late night wild parties.

2.      Adventurous Adam: These are the guys who are not necessarily the maximizers of deductions and minimizers of their tax liabilities. But they are willing to take risk. Most of the time they are sole proprietors or small business owners who have not maximized their withholdings or maintained separate funds to pay their tax liabilities. They get very surprised and shocked when they hear from their CPA about what they owe to the IRS. They file for extensions quite often.

3.      Ambitious Amber:  This group of people the top-end highly savvy entrepreneurs, tycoons and top leaders. They are powerful people and have the power to get legislation passed in their favor. They are the highest paid individuals but surprisingly they don’t have proportional tax liabilities. They have teams working for them who are proactive in identifying every possible option to minimize their taxes. Some of them pay zero taxes. I don’t know them because I never get invited to their parties, but reporters do a great job in pushing them to release their tax returns. I admire this group for their chutzpah, determination and ambition to maximize their achievements.

4.      Balanced Ben: This group of people consists of highly successful executives and leaders, who are well balanced in their life. They are neither over cautious nor highly adventurous, but they maximize their deductions, their retirement contributions and work with sophisticated CPAs. They are not as extreme as the Ambers, but they do whatever they can to minimize their tax liabilities. These individuals should be the role-model for highly successful executives.

5.      Fighter Fred:  This is a rare group of uncommon people who believe that they should not be taxed at all. It seems so bizarre, but it is true. Most of us are aware that we can’t escape death or taxes, but somehow this group never got this important memo. You might think that I am smoking weed for even thinking that such individuals exist. You might be surprised, just as I was when I heard about the Freds. The most famous example of a Fred is the movie actor Wesley Snipes. Wesley has been into multiple court cases with the IRS. Here is a story about him: https://www.forbes.com/sites/robertwood/2018/11/02/wesley-snipes-loses-23-5-million-tax-case-offers-irs-tiny-4-compromise/#5b9aaefb5632

What do you think about this list? Have I missed any type or am I completely off? Please share your thoughts. I’d love to hear your comments.