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How To Teach Teens Problem Solving with Composure and Resilience

As a political operative, I helped Members of Congress and Cabinet executives navigate through their daily political life by using my ability, learned over the years, to get an immediate feel for the dynamics of events, people, and places using a skill that I called “reading the crowd.”

My job wasn’t easy because it entailed keeping a principal firmly on schedule, which meant politely interrupting conversations, shuttling the individual through crowds of reporters and constituents, giving them a notecard with talking points a dozen times a day, and getting them back to their homes at night. I had to master being able to compose myself and problem-solve under pressure. But you know what was even harder? Getting through to my three tween sons so I could teach them these same resourceful skills.

Teaching Teens Life Skills

Why do they need these skills?

Because every day, our kids face surprises—classroom challenges, sudden blow-ups with friends, a chance encounter at a mall with a group of kids that could turn bad. My sons needed to learn how to handle people and the situations they created.  

Since my lectures alone weren’t cutting it, I made a game of placing my boys in real-world situations where they had to learn how to adjust to their circumstance quickly and find solutions to their problems

Creating problem solving games.

One Saturday we were at a big indoor mall. I took three $5 bills out of my wallet and handed one to each kid. “Here’s the deal. I want each of you to go into one store along here and get change for the fiver. This isn’t a race. You have to go alone and then come back and tell me about what you did.” I had their total attention. We were all excited to find out if they could complete their assignments alone.

Of course, I kept an eye on them. Each one took off, navigating through shoppers. I watched as two struck out at first, then went into other stores. When they returned, they joyfully shared their stories. “Dad, the woman at the cash register asked me where my parents were.” “The first guy said they don’t give change unless you’re buying something, so I had to go to the store next door.”

Learning to navigate more complex problems.

Aside from the change-the-five game, which we played often, there were other “games,” too. I sent my 11-year-old into a convenience store to purchase beef jerky and Doritos. I pulled into the parking lot of a carry-out restaurant and instructed the ten-year-old to memorize our order, then go in and get it. At the airport, I had my 11-year-old get boarding passes from a kiosk and had the 12-year-old deal with an agent, all while the rest of us stood by with encouragement and mostly to watch.

Playing these games with my tweens engaged their problem-solving skills. Each successful completion built their confidence. Each failure helped build their resilience so they could adjust their approach when they tried again. The game itself was thrilling, and they were eager to play and share their experiences, win or lose. To them, these were just games we played together; but of course, you and I know what I was really doing.

Building independence.

Fast forward to the time when my 15-year-old was at a train station in New Jersey. Even though he was confused about schedules and intimidated by the noise and surging people, my son managed to calm himself down. When he spotted a kid with an orange duffle bag reading “McDonogh School Athletics,” he remembered playing lacrosse against this school and felt comfortable introducing himself to the kid to ask for advice. It turned out the guy knew all about schedules and he was able to point my son to the right train. My son was able to compose himself and effectively problem-solve in what could have been a terrifying situation. The strategies he learned in our games paid off.

Asking my tweens to handle everyday encounters allowed them to experiment to find tools that worked for them in those situations. Working independently built their self-reliance and self-esteem. And having me and their brothers as a sounding board for working out challenges gave them the confidence to handle more complex situations later as they grew into young adults. 

Playing these games was one of the best things I did to help my boys gain independence. I hope now you’re inspired to give them a try in your family, too.

Jeff Nelligan works at the FDA and is the father of three sons; the two eldest are graduates of Williams College and the U.S. Naval Academy and the youngest attends West Point. He is the author of Four Lessons From My Three Sons: How You Can Raise A Resilient Kid and writes at

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