It’s been a heck of a tax season.
With what started out as a “simplified” tax law, with data already telling us that approximately 85-90% of American taxpayers paid LESS income taxes under the new tax law…. the reality is that the 10-15% of taxpayers who paid MORE federal income taxes under the new law are a somewhat unhappy – justifiably – group of Americans (as well as being you, my friends and clients).

So, here’s where the expression, “When pigs fly” applies. First, to define the expression:
- “When pigs fly” is a figure of speech insinuating a complete impossibility, or a way of saying that something will never happen. Says Wikipedia, “the phrase is often used for humorous effect, to scoff at over-ambition.”
So here we are, three days before “Tax Day” when nearly 100% of those reading this note have either filed their tax returns or for an extension. Either result was expensive, perhaps alarmingly so. Although I commonly refer to this state of affairs as “a quality problem”… there is little consolation.
…Except for dreaming of the possibility of a less expensive, more pleasant tax season to come someday. To that I say: WHEN PIGS FLY. Here are other near impossibilities, at least any time soon:
- Elected members of the US Congress coming together – from both sides of the aisle – to create a better, more balanced tax law. When pigs fly.
- US entitlement spending (social security and Medicare) being managed honestly and appropriately for today’s Americans, our kids and our grandkids. Note: the financial and societal solution is not Bernie Sanders’ “Medicare For All,” however significant changes need to be made on the private and governmental levels to entitlements and healthcare. Read this. When pigs fly.
- The top 1-5% of US earners and savers paying less taxes in the future. This “lucky,” hard-working group of people includes:
- business owners and founders
- senior managers at innovative American companies and manufacturers
- up and coming leaders and thinkers in business, education and industry
- those taking advice about prudent spending and wise saving (thus amassing $1 million- $5 million+ portfolios of savings
- kids who take their wise parents’ advice about prudent spending and wise saving… When pigs fly.
Might I add to this list:
- My ever getting Masters tickets through the yearly Masters.com lottery system (I am 0-7). When pigs fly.
- My ever playing Augusta National Golf Club. When pigs fly.
The point is that in 30 years’ experience of observing and advising in the financial services space I have yet to hear anyone overjoyed at tax time. Even those who receive back a modest or substantial refund (meaning they overpaid the US government in the form of a zero-interest savings scheme) are usually not overjoyed. They may be relieved, but not overjoyed. This year’s tax filing season has been confusing and frustrating. There must be a better way – a more fair process – of paying taxes in our great country. To which I say: I am hopeful.
And for Freddie Couples to win another Masters, although it would be awesome, the answer is most likely, When pigs fly.