I am finishing up an exploratory/holiday trip in South America. I checked out a few countries and plan on returning to check out more but I had a death in the family and now have to return back to the U.S. for a funeral. One of the lessons learned however is to be vigilant of…
Category: Tax Strategy
Greetings From South America!
I’ve been in South America now for almost two weeks and having a great time. This is part vacation and part exploration for retiring overseas that I’ve talked about here, here and here. My wife and I are spending a month down here exploring two countries primarily. It is interesting to see how life happens…
My Genius Tax Plan Has Snared Me
Do you remember the old Wild E Coyote vs Road Runner cartoons? The series of cartoons featured a coyote intent on capturing the road runner with endlessly elaborate traps, tricks and tactics and sadly, he was never successful, the road runner always got the best of the coyote. I feel like that coyote. A few…
Short Term vs Long Term Capital Gains
One costly mistake you don’t ever want to make with an investment move is ending up with short term capital gains tax instead of long term capital gains. The difference of 1 day can cost you a great deal of money. Short Term Capital Gains Generally speaking, short term capital gains occur when you have…
Sent Uncle Sam $5000
As a follow up to my earlier post on my taxes, it turns out that $5k was the correct amount to send off to Uncle Sam. It’s always painful to see so much money leave my account but the only thing I can do is build tax strategies to reduce the amount. The $5000 is…
Retirement Planning: Lower Taxes & Return on Capital
As I continue to optimize my investment portfolio for retirement as well looking at tax optimization, I came across this great video on ETFs that focus on return on capital and lowering tax liability. I like the video because it covers that tax advantages and some potential pitfalls of the strategy. I’ve written about return…
I Owe Uncle Sam $5000 For 2024
After a disastrous 2023 tax year in which I ended up owing $15,000, I am happy to report that I’ve now reduced that tax bill down to $5000. At least that’s where I stand at the time of this post and I’ll wait till April to officially file my return. What Worked To Reduce My…
The Rule of 55 – Cashing Out A 401k
After approaching another round of burnout, I am very keen to “retire” so I have been exploring all my options. One of those options is the ‘Rule of 55’ and I’ve been doing research into this option. I spoke to my current 401k provider and they confirmed that I can pull my money out when…
A Whopping 7.254% Interest Rate On Municipal Bonds
I’m giddy with excitement. I got an email from Fidelity on some new municipal bonds offering a whopping tax equivalent yield of 7.254 percent. The real yield is 4.57 percent but keep in mind that the interest is free from state and federal income taxes so the adjusted yield is equivalent to about 7.25 percent….
My Tax Plan for 2025
It’s December and I finally made some decisions around tax planning for 2025. As your income grows higher and higher, tax planning becomes a core part of your long term strategy. W-2 Income I decided to defer about 1/4 of my income for 2025 in the company deferred compensation plan and I will also be…