Lessons Learned One Year Into Early Retirement

Resilience is accepting your new reality, even if it’s less good than the one you had before. You can fight it, you can do nothing but scream about what you’ve lost, or you can accept that and try to put together something that’s good.
–Elizabeth Edwards

12 1/2 months ago, my wife and I retired. I semi-retired, as I was (and still am) on several boards, but, otherwise, our lives went from the 8-5 grind (and way beyond the 8-5 as a co-founder of a startup private equity group) to the … Read the article

Should Early Retirees Who Will Depend on Social Security Buy Life Insurance?

People always live forever when there is an annuity to be paid them.
–Jane Austen

When I had clients who wanted to retire before they were eligible for Social Security, I would create models based on claiming Social Security at the appropriate time, giving them a secondary source of income beyond their investments.

In theory, Social Security should replace some amount of income that had been generated by investments, allowing retirees to accumulate less before retiring.

Even the fabled William Bengen 4% safe withdrawal rate study never mentions Social Security as … Read the article

Optimizing Your AGI to Maximize Obamacare Credits

When you aim for perfection, you discover it’s a moving target.
–Geoffrey Fisher

It’s coming upon the end of the year, and, if you are on the Affordable Care Act (ACA) healthcare plan, otherwise known as Obamacare, it’s time for you to start doing your end of year tax planning.

Why, you may ask me, must I do tax planning now if I don’t have to file my taxes until April 15?

The answer is that because there are a couple of tax planning moves that you need to make before the … Read the article

ACA Subsidy Thresholds, Using Rental Real Estate for FIRE, and Why You May Need a Traditional IRA

Creativity is great-but not in accounting.
–Charles Scott

2021 will be the first year that we are using the healthcare marketplace provided by healthcare.gov through the Affordable Care Act (ACA). Previously, we’d used my board work through the private equity fund I co-founded to pay for our healthcare, but given that I am dialing back my board work and I wanted to get the tax benefits, we decided to do it ourselves.

The first go-through in the application, I unknowingly entered an modified adjusted gross income number too low to qualify for … Read the article

The Sure Way to Put Out Your FIRE: Try to Hit Home Runs

“Eat your betting money but don’t bet your eating money.”

Even though we hit our FIRE (financial independence, retire early) target at the beginning of the year, my Apple News feed seems to think that I am still looking for quick ways to make a buck.

I mean…I am…it’s in my blood…

Joking aside, there are all sorts of click bait articles out there which seem designed to convince you that you can make truckloads of money overnight just by investing $1,000.

Such as this one. My feed is full … Read the article