I just wrapped up our 2023 income tax returns after filing a last minute extension back in April. The extension was needed as we worked to wrap up the estate for Mrs. Dress Pockets's biological father. Final estate tax returns were filed in May and we received an estate K-1 to pass estate income through … Continue reading Taxes in July

I had two arbitrary early retirement number goals: 1) 401k balance of $1m and 2) HSA balance of $100k. I hit neither before cleaning out my office. But I understood with a hand wave market return of 10%, some time, and zero withdrawals that I would get there in a year or two. Turns out … Continue reading Coast FIRE

Happy Belated 529 Day! Another successful school year has come to a close. We had the juxtaposition of oldest daughter graduating high school and youngest daughter finishing kindergarten. One down, four to go! Turns out with a bit of dumb luck and years of $250 per month per child 529 contributions, we have enough education … Continue reading May the 29th be with you!

I noticed in January that my former employer stock was on a bit of a run. I decided to set a sell all limit order at a price of $199 per share. Why $199 and not $200? Because I thought a number of other shareholders would try to get out at $200 and I would … Continue reading Restricted Stock Units

Shortly after my last post on passive dividend income, I ran across an interesting idea from GoCurryCracker to tap dividends in IRAs before age 59.5 without penalty. If I sell $26,000 worth of stock, move that cash into Roth accounts, and then buy $26k worth of stock… I end up owning about the same number of … Continue reading Creative Cash Flow Thinking

I have been chipping away at our 2023 income tax return. I have most of the investment income done, leaving the rental income and expenses as my remaining hurdles. 1040 Schedule BTaxableInterest$1,311Dividends$6,995Total$8,306 $8k is nowhere near enough to live on but provides a month or two of family expenses. As I prepared to leave my … Continue reading Passive Income

Here is where we ended 2023 balance wise: Holding wise we continued our path towards simple: Mr Rollover IRA66% VTSAX34% VBTLX -- Now the only place bonds are held other than I bonds.Mrs 403b100% VITPX (institutional VTSAX)Mrs 457b100% VITPX (institutional VTSAX)Mr Roth IRA100% VTSAXMr HSA53% FSKAX -- I'll spend down FSKAX first as Mrs HSA … Continue reading 2023 Holdings

In the first few months of 2023 as my employment was winding down, I moved onto contemplating how to consolidate and simplify my employer based retirement accounts. Most of my net worth was tied up in my 401k plan in two different buckets. The first was a tax deferred bucket with $850k and the second … Continue reading To Rollover or Not to Rollover?

Star Wars Day was my last day of employment. In exchange for signing an electronic legal document waiving my right to sue for wrongful termination, I was given 3 months of salary in a lump sum. On my last day, I pedaled into work and returned a pair of laptops. I sat outside and drank … Continue reading May the 4th Be With You

Long time no post. There are plenty of financial coals in the fire lately, I just haven't found the time to sit down and document them. I will eventually get around to posting our 2022 top expense categories and a 2022 tax summary once I finish our income tax returns. Tick tock. I have remained … Continue reading The Internet Retirement Police