WHEN I ATTENDED Sunday school as a child, I was taught that God is always watching over me. It was a frightening notion, but one I grew accustomed to. My mother would often remind me to "watch your Ps and Qs," though I wasn't entirely sure what that meant. Nonetheless, I understood the importance of behaving properly. Today, it seems we have a different form of surveillance. As George Orwell so aptly depicted in his book 1984, Big Brother is watching. The idea of living in a society where every action and word are monitored by a controlling authority is unsettling. Yet, here we are, under the watchful eye of technology companies. During childhood, most of us had parents who kept a watchful eye on us. Ideally, they were loving and attentive, looking out for our best interests. But perfection is rare. Many parents are flawed, simply because they’re human. Successful children learn to navigate these imperfections, avoiding pitfalls that could arise from saying or doing the wrong thing at the wrong time. Survival and prosperity often depend on mastering this imperfect world. Our modern-day big brothers monitor our every action we take with our devices, whether it's our smartphones, electric cars, e-readers or laptops. We're constantly under observation, with the primary intention of selling us something. But do we want what they're selling? Often not. If we did, we'd buy it without the need for persuasion. Just like traditional salespeople, these electronic counterparts refuse to take "no" for an answer. They relentlessly push products based on our past behavior, assuming that's all we'll ever want. It's frustrating, akin to walking into a library and being confined to one section each time. So, what can we do? We must recognize the game that’s being played. It's a game where they claim to know our desires better than we do ourselves. But we still have the freedom to choose. Awareness is key. We must remember that we can resist these subtle nudges, and exercise our right to say "no." For some, especially spenders, this game is a boon, offering endless opportunities to acquire new possessions. But for others, like me, it's irrelevant. We only purchase what we truly need or desire, regardless of external influence. I worked with a guy who announced to me on Friday that he was going to look at Chevrolets over the weekend. I wished him luck. Come Monday, I asked him if he looked at those Chevy cars. He said, “Yes and I bought a Pontiac.” “I thought you wanted a Chevy,” I said. “I did, but the salesman showed me the Pontiac, so I bought it.” “When are you going to pick it up?” I asked. “I picked it up that day.” Talk about a good salesperson. Many people, who intend to buy one item, can be persuaded to buy something else by a good salesperson. That’s nothing new. But being nudged into buying something subliminally is all part of this new digital game. To win, you need to know the rules. Temptation has been with us from the get-go. Having the willpower to resist is a practiced skill. Knowing these forces are going to test our willpower requires awareness. Understanding what’s happening will help us say “no” when “no” is the right answer.

ANY BABY BOOMER WHO grew up around New York City is probably familiar with the name Robert Moses. He was the city planner who wielded enormous power over the development of New York from the 1920s to the 1960s. Having grown up on Long Island, I saw his work firsthand in two main highways, the Long Island Expressway and the Northern State Parkway. They were designed to appear park-like, with arched bridges, wide grass run-offs and trees alongside the entire route. Then there’s Jones Beach State Park, another Moses project. Alongside wide expanses of sandy beach, there are swimming pools, a two-mile-long boardwalk, refreshment stands and enormous parking lots. I’m among the estimated six million people who visit the park each year. My wedding reception was held at a Jones Beach restaurant. Moses couldn’t stop the Brooklyn Dodgers from moving to Los Angeles, or the New York Giants going to San Francisco. He did, however, build Shea Stadium on the World’s Fair grounds in Flushing, Queens, to house the New York Mets, a recent expansion team. Moses’s contributions to the New York region are sweeping—and controversial. He bulldozed neighborhoods to make way for great highways and towering bridges. Few had the power to stand up to his far-reaching plans. I remember the expression used to justify his decisions: “the greater good.” When you cross the George Washington Bridge into New York City, most of the traffic flows onto the Cross Bronx Expressway. You’ve probably been stuck on the Cross Bronx because its width is no match for the volume of traffic it now gets. As the name implies, the expressway cuts right through the Bronx. In building the road, Moses leveled many old neighborhoods, sending the South Bronx into steep decline. Before, neighbors talked and played along the avenues. After, they were cut off, and property values fell nearby because of the din and pollution of the expressway. The justification for this neighborhood’s destruction? It was “the greater good,” according to city planners like Moses. Neighborhoods were leveled so automobiles could pass through the city more rapidly. Drivers were the greater good, apparently, and the city’s residents—often poor and black—were not. This urban highway model was adopted by other cities, wrecking many older neighborhoods. These roads might have been built above the streets, like the elevated train tracks in Chicago. This wouldn’t have disrupted the lives of so many city residents. The powers that be, namely Robert Moses, decided differently, however. These overbearing policies still exist today in other forms. We all endured the COVID-19 pandemic. The powers that be decided that, for the greater good, we needed to stay home and shelter in place. I’m not arguing against the need for the lockdown. The public health measures saved many lives. But what about the individual? We have to live under whatever rules are imposed on us, figuring out how to make these difficult situations work for us. By doing so, each of us can also contribute to the greater good. Working within the rules and turning them to our advantage isn’t a selfish act—it’s a matter of survival. The more people take care of themselves, the better off we all are. If too many people rely on someone else to look after them, the whole community suffers. Self-reliance isn’t selfish. It’s a strength. Saving a portion of what you earn is a strength. Learning what benefits your employer provides, and using them to your advantage, is a strength. Understanding how to get a higher Social Security benefit is a strength. Making the right health insurance choice is a strength. No, we don’t get to decide everything in our lives. But it’s up to each of us to take responsibility for our own well-being, so we don’t become a burden to society. That’s helping the greater good.

THERE USED TO BE a TV show called Lifestyles of the Rich and Famous. I assume it was created to make viewers envy rich people and want what they had. The memorable catchphrase of the host, repeated at the end of every episode, was “champagne wishes and caviar dreams.” Envy is one of the seven deadly sins—for good reason. All it does is cause heartache and pain. When I was younger, I’d fall into the trap of seeing what others had and believing that, if only I had that thing or that way of living, I’d be happy. This went on for years. Don’t get me wrong: My upbringing wasn’t bad. We lived in a single-family home and we regularly took vacations. But while I didn’t live a life of pain and misery, I also wasn’t happy. Seeing what others had—a girlfriend, a group of buddies, family gatherings where everyone was laughing—made me want these things for myself. My wife, by contrast, had this sort of life growing up. She had boyfriends. She had a close-knit group of friends. There were family gatherings where everyone laughed and enjoyed themselves. As I grew older, I pursued these things, feeling they were missing from my life. The quest gave me direction and motivation, and—in some cases—securing these things did indeed bring me happiness. Still, when I was planning my retirement, I didn’t look to what others were doing, as I did when I was younger. Instead, my goal was a life that was simpler and less showy. I decided to pursue not happiness, but contentment. To that end, I took an inventory of the things and activities that I hated and those that I felt good about. After completing my list, I categorized the good things, and I discovered they fell into three groups: exploring, learning and achieving. All three give me a good feeling. These three pursuits might sound grandiose. Exploring could mean visiting Nepal. Learning might consist of getting a PhD. Achieving might mean writing the great American novel. My three look nothing like these. For me, driving down a local street I’ve never seen before counts as exploring. Learning can be finding out how Henry Heinz started the ketchup company that bears his name. Accomplishing can be a home improvement project, like successfully installing a low-voltage LED light. My advice is to find out what floats your boat. Make sure it’s what you want, not what society expects. Want contentment? Look inside yourself, and try to find a quiet place that you can go to in your mind and which makes you smile.

ONE OF MY MOST enjoyable jobs was in training and development. This involved creating lesson plans and conducting classes for the insurance company where I worked. One mantra in the training department was “define done.” When we ran a training program for another part of the company, our department manager would stress that we needed to find out the internal client’s definition of “done.” In other words, what would the client require or expect our department to deliver so that the client would be satisfied with our service? The client might be looking for us to, say, train 50 insurance underwriters across the country or to teach employees a method that reduces work errors. The concept of “define done” is also useful if you’re getting ready to retire or thinking of leaving one job for another. Knowing what you expected from a job will help you to know when it’s time to move on. If this criterion isn’t identified, workers might later regret leaving a job because they feel they left certain things undone. When I lost my job at age 64, I didn’t feel I was done with my career. I’d read how difficult it is for workers 60 or older to find work. This didn’t bother me much because I was used to hunting for a new job after losing my old one. These experiences were always difficult. But at age 64, my lack of fear gave me the courage to pursue my final job. I’d researched how my Social Security benefit would be calculated and what earnings are used in the formula. With this information, I could decide what salary would increase my lifetime Social Security earnings. If my new annual salary was greater than that in my lowest earnings year, that low year would drop out of the calculation. This information gave me the framework I needed to negotiate my final salary. The only benefit I needed was a 401(k). I already had health insurance coverage through my wife’s job. The upshot: My focus was getting a job offering an adequate salary, an acceptable commute and a good 401(k). One job met all three goals, but I was hesitant to accept the firm’s offer. I had applied for a different job at the same company 15 years earlier and didn’t get it, plus I didn’t like the reputation of the company’s CEO. Still, I took a chance and accepted the offer, and ended up staying until I was nearly 70, my desired retirement age. I consider 70 to be a good “done” age. The company let me go three months before I turned 70, but thanks to the negotiated severance package, vacation pay, a Christmas bonus and profit sharing, I was able to hold off on beginning my Social Security benefit until I turned 70. I had met my goal, so I felt comfortable calling it a career. My advice: Whatever you’re looking to do—perhaps volunteering, a full-time position or a part-time job—define what “done” means to you. If you don’t, there’s a risk you’ll overstay your welcome in your supervisor’s eyes or your own. Willie Mays was a great baseball player. But in my opinion, he didn’t define his “done” and continued to play well beyond his days of greatness. Had he defined when it was time to retire, he could have walked out on top and felt satisfied with his career. We all need to define our “done.” Otherwise, we could find ourselves giving up on a job too soon—or continuing to do something that no longer brings us the joy it once did.

IN MY ENGLISH CLASS in junior high school, we read a play called I Remember Mama. It was a story about a poor Norwegian immigrant family living in San Francisco in the early 1900s. The mother ran the household while her husband went to work and the children went to school. The mother was in charge of the family’s finances. Any time a family member needed extra money, he or she would have to ask Mama for it. She’d listen to the request and, if it was critical, she’d get the money from the petty cash fund. If there wasn’t enough petty cash, she’d ask the person if it was important enough to justify withdrawing money from the bank. Upon further review, the person would say it wasn’t. The big surprise: As we learn at the end of the play, there was no bank account. Instead of saying, “we can’t afford it,” Mama wanted family members to decide on their own that the item wasn’t important. This would allow them to save face and not feel poor. They squelched the desire themselves and moved on. My mother-in-law would tell me of her upbringing in New York City. Her parents were Chilean immigrants who didn’t have a lot of money. They raised their six kids on her father’s salary. They were poor, but so was everybody else in the neighborhood, so they never thought of themselves as poor. My mother-in-law’s life was just like the characters in the play. With money so tight, she constantly had to decide that some purchases just weren’t important. A digression: Two famous actors came from the neighborhood. When they were kids, Lauren Bacall and Burt Lancaster were friends with my mother-in-law’s siblings. What I found most interesting about I Remember Mama: Because family members believed the bank account was only to be used for the most important items, it made them reconsider what they wanted. I’ve inadvertently adopted the same mindset. Money that’s automatically deposited into my checking account is used for daily expenses. Once I move that money to a savings or investment account, I never use it. I could, of course. But in a classic example of mental accounting, I think of this money the way Mama’s family thought about the bank account. It’s never to be used except for the most important things. I’m not suggesting this approach is for everyone. I’m cheap. Moving money out of the checking account makes these dollars sacred and not to be used. The benefit of my mental lockdown is that my money grows at the expense of a luxurious lifestyle. By contrast, money burns a hole in my son’s pocket. When I give him money, he can’t wait to spend it. The problem is, he never decides what he wants to spend it on. He just wants to spend it. The result: Tip jars are filled and money is left on the restaurant table, even if we leave a tip using our credit card. My son would benefit from this “sacred dollar” mentality, but it’ll never happen. Still, for spendthrifts, adopting some mental trickery could allow them to reduce their debts and build up an emergency fund. They must believe the emergency fund is crucially important and the items they’re tempted to buy hold less value than maintaining that rainy-day fund. If not, the money will be spent—and they’ll never enjoy the peace of mind that comes from having a cash reserve.

I LIVE IN CENTRAL New Jersey. Within walking distance of my house are some McMansions—huge homes clustered together in new developments. I look at them and think, “Who cleans these things?” I live in a three-bedroom ranch-style house with an unfinished basement and a two-car garage. My garage is filled with two cars and my tools. The basement is filled with my wife’s stuff. We bought the house when my wife was pregnant. Thirty-three years later, there are three people living in the house. It was big enough 33 years ago and it’s still big enough today. Why would I want more? My neighborhood gets noisy during the week, especially in the summer months, because all my neighbors have a landscaping service to mow their lawns. Now, if they all hired the same service, the noise would be limited to a single day. But because all use different lawn services, the landscapers come on different days of the week. The result is that the roar of these high-powered grass-cutting hot rods fills my world five days a week. Meanwhile, I mow my lawn with my self-propelled Honda lawn mower. Every morning, I begin my day with a coffee mug filled with black coffee and no sugar, which I raise up and say, “This is the day the Lord has made, let us rejoice and be glad in it. Help me to be glad.” Then I list those things that occurred the day before that I’m grateful for. Basically, I count my blessings. This practice should not be new to anyone. “Count your blessings” is something we’ve all been told over the years. But how many of us do it? Money has always been important to me, and I saved diligently throughout my life. As a result, I have money “in the bank.” Is it enough? If I died tomorrow, yes. If I live to 100, I’m not sure. Now that I’m retired, I have embraced the concept of enough. I look at what I have and what I’ve done. I then compare that to what I wanted to have and to do, and I believe it’s enough. I don’t have a lot, but I do have stuff. Besides money, the one area of accumulation I’ve pursued since I was 18 years old was Craftsman hand tools. I’ve been working on cars since I was 16 years old. I have no business working on cars because I’m not very good. Still, I continued down this path. To make up for my lack of skill, I would buy the next “magical tool” for my tool box, thinking it would suddenly make me a master mechanic. It never did. The beauty of this focus is I have enough Craftsman tools. I don’t have every tool. But all in all, I seem to have the tools necessary to fix whatever needs fixing with the car or around the house. It’s a great feeling. I believe every one of us has our own “enough.” It doesn’t mean you can’t have more. But do you need more? Until you can identify what your enough is, how will you know when to stop accumulating and to stop pursuing? Arguably, money is something we can never have enough of. But until you decide that what you have is enough, how will you ever be satisfied? How would you define "enough"? Offer your thoughts in HumbleDollar's Voices section.