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.

THIS BULL MARKET is more than eight years old, U.S. stocks are undoubtedly expensive and there’s even talk of war. Tempted to sell? Problem is, there was also ample reason to be worried three years ago and yet here we are, with shares both higher and more richly valued.
What to do? I fall back on my standard advice: Forget trying to forecast the market’s short-term direction and instead focus on taking the right amount of risk.

WANT TO MAKE SURE your family is adequately protected against financial disaster? Try grappling with these 10 questions:

What’s the minimum dollar amount you need each month to keep your household running? That’s a useful number to know if you’re forced to slash living costs because, say, you lost your job or you need to cover a large, unexpected medical bill.
How would you cope financially if you were out of work for six months?

WHEN I LOOK AT TODAY’S world, I often think of Charles Dickens’s famous line, “It was the best of times, it was the worst of times.” Technology, including the web and smartphones, has made life so much more convenient.
Still, one thing I really miss from the “old days” is the experience of the traditional bookstore. Shopping online is great, but sometimes it’s easier to choose from a curated set of 10 books on a shelf than to sift through an unwieldy list of a thousand choices online.

THE SOUND AND SMELL of the Pickle will be forever burned into my memory. As a wannabe cool teenager, getting rides to school and soccer practice from my parents in their inherited 1976 green Dodge Aspen coupe with whitewall tires—a.k.a. the Pickle—was beyond embarrassing.
Sometimes, my parents would honk pulling away, just to add insult to injury. Needless to say, it took a bit of humble pie to finally understand the lessons my parents were teaching me,

WE’RE ALL CONSTRAINED by the income we have and the wealth we’ve either amassed or had handed to us. Result: Those on low incomes struggle to cover daily expenses. The middle class pay for today, while also socking away money for their own future. What about the rich? They often use their wealth not only for themselves, but also to help future generations.
These are, of course, gross generalizations. Some folks on low incomes manage to save surprising sums for their own retirement.

GOT COLLEGE-BOUND kids? Make sure you and your children are on the right track financially—with these 10 questions:

Can you afford to help your kids with college costs? It’s important to talk to your teenagers early on about how much financial assistance you can offer—and that’s doubly true if they’ll need to shoulder much or all of the cost.
Will your family receive needs-based financial aid? Use the EFC calculator at CollegeBoard.org to figure out how much aid you might get.

I WAS LESS THAN 10 years old when I decided that I wanted to earn some extra cash over and above my weekly allowance. I took day-old sections from the Washington Post and went door-to-door in my neighborhood, selling each section for a dime. Not many fell for it, but there was a couple who were willing to hand over a dime to a young boy looking to supplement his allowance.
I doubt that I earned much from this endeavor.

“STOP PULLING MY leg, Grandpa. You’re kidding, right? Is it really true that people:

used to believe they could beat the market?
paid 2% of assets and 20% of profits to hedge fund managers?
got their stock picks from a guy screaming on the television?
thought cash-value life insurance was a good investment?
believed that brokers would act in their best interest?
studied stock price charts to figure out what would happen next?
bought and sold exchange-traded index funds like crazy?