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.

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 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,

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.

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.

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.

I DON’T THINK my parents ever had any sort of five-step plan to teach me about money. I was always parsimonious, so they weren’t very focused on how I spent. They did, however, teach me two powerful life lessons—which changed not just the way I thought about money, but who I am.
Everything has a cost. I attended private school from fourth to ninth grade, coasting by with B plusses and A minuses.

I RECENTLY RECEIVED an email from a friend asking, “What financial advice would you give to your younger self, now that you’re older?” I had to think for a while. But once I sat down to reply, I realized my attitudes about personal finance were already well-developed by the time I was in my 20s. I also realized my financial beliefs had been shaped, in part, by growing up in a family where money wasn’t exactly plentiful.

SETTING OUT INTO the business world, I was age 27 with a negative net worth. Among life lessons, there are many strong contenders, but nothing introduced me to “adulting” like debt. For that, I had undergraduate and graduate school expenses to thank.
Having secured a good job out of business school, I started to rebuild my finances. My grad loans had a relatively high principal amount and an interest rate of 6.8%, so I prioritized that debt over my undergrad loans,

SHORTLY BEFORE MY first child was born some two decades ago, I read a newspaper column urging parents to begin saving for college early in their children’s lives. Today, my son is not far from getting his bachelor’s degree in engineering, debt-free and (fingers crossed) with a bit in the bank for his master’s degree. My daughter starts college this fall and is on track for the same outcome.
I feel like we’ve been a real life middle-class experiment,

FOR MORE THAN 20 years, I was a homeowner. Like most people, I had a love-hate relationship with the houses I owned. I loved building home equity in the two fixer-uppers I lived in. I loved knowing my mortgage payment would stay relatively constant from year to year. But I never enjoyed yardwork and I hated dealing with unexpected repairs, including replacing an aging sewer line in one house—to the tune of $10,000.
After I got divorced,

IT WAS APRIL 29, 2009. My 12-hour workday had already begun when, at about 4:30 a.m., I received the call from Jonathan, my younger brother. He never calls at that hour. In fact, we never phone without first texting each other to determine the best time to talk. I sensed bad news and sure enough it was. Our father had been killed 36 hours earlier while riding his bicycle. In the months that followed,

AS I PREPARE TO MOVE from Philly to Boston this summer, I’ve struggled with how to handle my home. Do I sell the place and pocket the profit—or keep it as a rental property for future income and price appreciation? A quick Google search provides plenty of good reasons to choose either option. But when making a decision of this magnitude, what really matters is your personal situation—and that prompted me to sell. Here are my five reasons:

The financial benefits of renting out the place don’t outweigh the costs.