The income tax has made more liars out of the American people than golf has.Will Rogers I have been doing tax returns a long time. The file cabinet says one of the first handwritten tax returns I compiled with my dad's help was 1991 which would place me in 8th and 9th grade. I had … Continue reading Tax Day

Turns out Mrs. Dress Pockets and I have 7 checking accounts. Seems a bit excessive doesn't it? One is a joint checking account between us where we have consolidated most of our monthly cash flow. One is a joint account I recently opened with eldest daughter. That still leaves 5 individual checking accounts: 2 for … Continue reading Spring Cleaning

Here's a brief summary of the last 2 years of Mr. Dress Pockets spending from Personal Capital. Mrs. Dress Pockets tracks her spending in Mint and thus this does not capture all of her spending. There are a few joint accounts that overlap. As I look to the future, 25k in annual day care and … Continue reading Pandemic Spending

Well the earth and I both completed another revolution around the sun. The Build Back Better Act got shelved with a big Joe Manchin thumbs down prior to Christmas. My alarm to stop my 401k after tax contributions and Roth conversions by 7pm on Dec 31 was ignored. By noon on Jan 1, I cued … Continue reading Happy New Year

The Build Back Better Act passed the U.S. House of Representatives last week and the legislation includes a ban on backdoor Roth IRA conversions and mega backdoor Roth 401k conversions of after tax money after December 31, 2021. The U.S. Senate plans to take up the Build Back Better Act after Thanksgiving and hopes to … Continue reading 2022 Savings Plan and Backup Plan

Eldest daughter landed a part-time after school job a few weeks back. With this sub 13.5 hour per week job, came a bunch of adult paperwork that I offered to help her with: I-9 immigration form, W-4s (federal and state), full-time student pension exclusion form, direct deposit form. Oh crap. She has no bank account. … Continue reading Money Training Wheels

It's almost annual health care benefit enrollment time and I've been mulling an HSA (Health Savings Account) post for just this occasion. I'll lead with my heavily reworked HSA spreadsheet and graph. Story follows. My first HSA experiment began in 2011 and lasted all of 2.33 years. This experiment was doomed from the start but … Continue reading A Tale of Two HSAs

Lately I've been mourning the loss of Locast - my favorite legally questionable TV streaming service. Locast wasn't even available in our DMA (Designated Market Area) but thanks to some stupid VPN tricks I was able to cherry pick which broadcast NFL games to watch. Location spoofing allowed us to root for Mrs. Dress Pockets' … Continue reading The Power of Small Wins

I was scrolling by cnbc.com earlier this week when the following article caught my eye: House Democrats propose new retirement plan rules for the rich, including contribution limits and a repeal of Roth conversions. An end to backdoor Roth IRA and mega backdoor Roth 401k conversions? Panic? Nah. Turn off the lights the party's over? … Continue reading Death and Taxes

[talking on the phone]  And I said, I don't care if they lay me off either, because I told, I told Bill that if they move my desk one more time, then, then I'm, I'm quitting, I'm going to quit. And, and I told Don too, because they've moved my desk four times already this … Continue reading Office Space