TALKING TO A BROKER or insurance salesman? Here are 10 things you’ll likely never hear:

“Wow, your 401(k) has great low-cost institutional funds. There’s no way you should roll that money into an IRA.”
“Do you know that you could buy these funds outside a variable annuity and pay a fraction of the price?”
“Sure, you could make that trade—but probably the only person who will get richer is me.”
“My hunch is, this closed-end fund you’re buying will be at discount within a few months of the IPO.”
“Given the markup on that bond you just bought,

WANT TO BOOST YOUR after-tax wealth? Grab copies of your latest tax return and investment statements—and ask yourself these 10 questions:

What’s your marginal tax rate? That’s the tax rate on the last dollar of income you earn each year. It’s a crucial piece of information as you decide which retirement accounts to fund and how to invest your taxable account. You can get a quick estimate using Dinkytown’s calculator.
Do you expect your marginal tax rate to be higher or lower once you’re retired?

MANY SENIORS needlessly incur hefty penalties or overpay their taxes. The reason: They don’t understand the strict rules that govern removing money from their tax-deferred retirement accounts.
The IRS sets the year you turn age 70½ as the deadline to begin taking RMDs, short for required minimum distributions. (For 2020 and later years, the starting age is 72.) The feds allow some leeway for the first of your RMDs. But this is a tricky exception.

LIKE MOST PEOPLE, I don’t spend a lot of time thinking about my car insurance. And like most people, the only time I do think about insurance is when I need to use it. Four years ago, I was involved in a collision. My car was totaled and my insurance company processed my claim quickly. Because I was deemed to be not at fault by my insurance company, I didn’t have to pay my deductible or any other expense related to the collision.

IF WE HAVE DINNER with half-a-dozen others, we might all share the same meal and yet each of us will have a different experience—sometimes radically different. Even as we talk politics, crack jokes and swap gossip, we’ll each have our own thoughts whirling in the background: errands we can’t forget, work issues we need to resolve, incidents from the day we keep replaying, worries we can’t put behind us.
For me, those whirling background thoughts often concern financial notions I want to write about.

REVIEWING YOUR investment strategy? To get you started, here are 10 questions to wrestle with:

How much cash you will need from your portfolio over the next five years? That money should be out of stocks and riskier bonds—and invested in nothing more adventurous than short-term bonds.
What’s the total sum you expect to save between now and retirement? If you look at that future savings as a cash holding and count it as part of your portfolio’s conservative investments,

TOWARD THE END of high school, I landed in some predictably adolescent legal trouble: I purchased alcohol underage and had to shamefully explain what happened to my parents. As I dejectedly declared that I would pay the fine and admit guilt, my parents—concerned about potential career implications—instead insisted that I hire a lawyer with my own money. I had to work for more than a year as a busboy and caterer to reimburse my parents for the cost,

IT’S A COMMON PLOY among columnists: You start with the provocative statement—and then spend the rest of the article dancing like crazy, trying to defend it. Today’s provocative statement: Except in a few rare instances, I’m not sure why anybody would ever own municipal bonds.
At first blush, this sounds not just provocative, but downright stupid. If you’re in a high income-tax bracket and investing money through a regular taxable account, it would be foolish to buy taxable bonds and then pay income taxes on the interest you earn.

IF YOU DON’T SAVE diligently, you are highly unlikely to amass a decent-size nest egg. Time to make amends? Here are 10 questions to ponder:

Do you regularly spend more than planned? Try writing down every purchase you make. That’ll tell you where your dollars are going—and make you think twice before spending.
How much of your income goes toward fixed living costs? We’re talking about items such as mortgage or rent, car payments,

DON’T GIVE INVESTING advice to clients. That’s something I’ve repeatedly learned as a tax lawyer. Still, when financial markets gyrate, many clients want advice about taxes, especially the seemingly simple rules for capital gains—and I have a longstanding fondness for eating three times a day.
Let’s start with the basics. Take an individual who sells an investment that she has owned for more than 12 months. Any increase in its value from its cost basis is taxed at her long-term capital gains rate—15% for most individuals,

IT ALL BEGAN WITH an afternoon phone call between Andrew, my twin brother, and me. I made an off-the-cuff comment about starting our own company. For the previous eight years, both of us had worked at a large lawn care company and then, for a few brief months, at a medium-sized landscaper.
Neither of us doubted we would be successful. But we were taking a large financial risk: Starting our own company meant leaving the security of a regular paycheck,

VANGUARD GROUP is my favorite fund company—and the place where I now keep all my investment dollars. There’s no mystery why: Among mutual fund companies, Vanguard has long been not only the biggest champion of index funds, but also the firm with the lowest annual fund expenses.
Except that’s no longer the case.
Fidelity Investments, BlackRock’s iShares and Charles Schwab have all muscled onto Vanguard’s turf, offering index funds with lower annual expenses. This is obviously a marketing ploy: By offering cut-rate deals on select index funds,

COULD YOU SQUEEZE more happiness from your dollars? Here are 10 questions to ponder:

Which expenditures from the past year do you remember with a smile? Which prompt a shrug of the shoulders and maybe even a twinge of regret? Use those insights to guide your spending in the year ahead.
Could you commute less? Research tells us that commuting is terrible for happiness. You might move closer to the office or try to work at home a few days each week.

WHEN IT COMES TO your home, ignorance about taxes isn’t bliss—and it could be disastrous. I often field tax questions from homeowners. Most don’t understand how they’re affected by continuously changing tax rules. Even worse, they’re totally unaware that the rules have changed.
Want to save thousands of dollars? What follows are reminders of how to sidestep tax pitfalls and take maximum advantage of frequently missed—but perfectly legal—opportunities:
Mortgage points. Do you plan to purchase a new dwelling around year-end?

WORKING AT A COLLEGE is a bit like being in a time warp. Every year, I get older, but the students don’t. The 20-somethings I deal with make me realize just how much times have changed since I attended college.
Tuition. When I was a college student in the 1980s, 529 plans didn’t exist. Of course, tuition costs were also much lower, so there wasn’t as much need for a college savings plan.