Learning to keep learning

Career advice for the younger generation as technology reshapes the world

Last year, I was in a small group of guys when, let’s call him Bob, shared that he wasn’t sure what career advice to give his son. I laughed and said that nowadays it’s almost impossible. And even in my day, advice from parents was often viewed with suspicion. Many of us, including me, are in careers that simply didn’t exist when we were in high school. If my dad had asked what I wanted to be and I answered, “I want to own an internet agency,” he probably would have replied, “What’s an internet?” That’s not a criticism of previous generations—it’s a reminder of just how fast the world has changed.

Technology, remote work, artificial intelligence, and global changes are reshaping what “a good job” even means, often faster than parents can keep up. Many of the careers today’s kids will hold don’t yet exist. Others are already being transformed or phased out. So how do we guide young people when the future feels blurry?

There’s an old joke that captures this perfectly. A mother is talking to her son on the phone. After she hangs up, she bursts into tears. Her friend asks, “What’s the matter?” The mother says, “My son says he’s going to become a doctor!” The friend replies, “Why are you crying?” She answers, “I wanted him to go into something with a future…I wanted him to become an electrician!”

Humour aside, there’s real truth in that joke. Jobs once seen as “safe” now face disruption. How many white-collar jobs will be replaced by artificial intelligence? Trades, once undervalued, are suddenly in demand. And entirely new career paths are appearing almost overnight. The focus needs to shift from choosing the right job to building the right skills and mindset.

I used to sell labour into the market and would ask business owners what they looked for in an employee. Without exception, the number one answer was always the same: “A good attitude—because I can train the rest.” I doubt that’s changed much.

So, in today’s economy, the most valued skills aren’t tied to any one profession. Communication, critical thinking, problem-solving, creativity, emotional intelligence, adaptability, and digital literacy now outlast any single job title. The real superpower isn’t picking the “right” job at 18—it’s learning how to keep learning.

Because today, careers are no longer ladders. They’re portfolios.

We’re also seeing a shift in how success is defined. While income still matters, many young people now place just as much value on flexibility, mental health, meaningful work, community impact, and control over their time. They want work that fits into a good life — not work that consumes it. That can sometimes look like a lack of ambition from the outside. It may be a more honest definition of success.

I remember going to a career coach when I was younger. His advice was to suppress who I really was, put on a mask, and learn to play the part because “that’s how the work world works.” I tried to follow that for a while, but it never fit. And honestly, until I built my own business, I never felt fully free to show up as myself.

One of the most challenging things for me in life has been to just “be me” while living in a world that’s trying to tell me to be something different.

Everywhere you look, someone is selling a formula for “success.” TV, magazines, social media—they all showcase polished stories of so-called successful people, usually defined by material wealth. The quiet implication is that if you don’t achieve that version of success, you somehow fall short.

Letting go of that garbage took years—but it changed everything.

I once had an entrepreneur friend confide that he wished he’d been more successful earlier so he could have helped his son sooner. I told him his child probably gained more from watching him struggle, adjust, and then succeed. Because in the end, the only thing we truly pass on to the next generation is values, and values are modelled.

Young people today feel intense pressure to have their whole future mapped out far too early. By Grade 10 or 11, they’re already being asked what they plan to “be.” That question can feel less like curiosity and more like a verdict.

There’s also an emotional side we don’t talk about enough. Anxiety among young people is rising. Climate change, economic uncertainty, housing affordability, global conflict, and rapid technological change all loom large in their awareness. Add career pressure on top of that, and it can feel crushing.

Athletes work on their skills, then take them to different locations against different opponents. Why not approach careers the same way? In tech, I’ve learned to see business like a video game: put a quarter in, play until you lose, then, armed with new knowledge, play again. It’s not about losing. It’s about learning.

And maybe that’s the best advice we can give kids in a changing world: don’t try to predict the future. Build the strength, curiosity, and confidence to meet it when it arrives.

Has it ever been different?

– Richard Gauder is the co-founder of CMS Web Solutions, a Canadian web development, hosting and education company, now specializing in digital accessibility. He is an occasional writer for the Advocate.