Why We Don’t Give Ourselves Permission

Meet Jack. He’s thirty-six years old, and his life revolves around working relentlessly to bring home a paycheck each month. Some days, he looks in the mirror and barely recognizes himself in the life he has created.

Let’s take a step back and see how Jack got here.

Not long after graduating from university, Jack landed a job at a good company and was on track for a promising career. He liked his work, put in effort during the week, but still made time for himself. A couple of nights a week, he went out with friends, played sports, and occasionally enjoyed a drink or two. Jack felt good about his choices and took pride in knowing his parents were proud of him, too. His hard work paid off—he was promoted, took on more managerial responsibilities, and steadily advanced in his career.

Along the way, he met his partner, fell in love, and got married. His salary grew, allowing him to buy a house and a car. Life was moving forward.

When Jack and his wife had children, they wanted to give them the best of everything, including a quality education. His wife decided to stay home to take care of them. Many of the kids at their school came from wealthy families, taking extravagant vacations—vacations Jack’s children soon began to expect as well. The pressure to keep up mounted. His job was still going well, but the weight of providing for his family never seemed to ease.

One day, Jack realized something unsettling: he was deeply unhappy.

He was still a competent manager and earning a solid income, so why did he feel so miserable? He felt like he was being pulled in all directions, yet he had lost control of his own life. Did he even enjoy his work anymore? He wasn’t sure. The stress of keeping up was wearing him down, and tension with his wife was growing. She always seemed to want him to be more—more present, more engaged, more something—but she was struggling in her own ways, too. Jack, meanwhile, was just trying to keep his head above water.

The truth was, he didn’t even know what he liked doing anymore.

He missed working with his hands. He used to spend afternoons tinkering with electronics in the shed with his dad, building things just for the joy of it. But now, there was no time. At home, his family wanted to socialize with the neighbors, but he resisted—he was exhausted after long days at the office. He felt guilty about it, knowing his family was frustrated and disappointed. The more disconnected he became, the more fed up he felt.

How could so many things be going well, yet he still felt so unhappy?

Rather than giving himself permission to really think about what he wanted from life, Jack had been riding a train instead of driving a car. He had boarded long ago, and now it felt like the train was moving too fast for him to step off. It sped past all sorts of interesting places, but never stopped long enough for him to explore. Worse, Jack wasn’t sure if he would ever get off.

At what point had he lost control? And more importantly—how could he take the wheel again?

If you’ve ever felt like a passenger on a train bound for a destination you didn’t choose, you’re not alone.