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Teenage Jobs in 2026: Why Entrepreneurship Prepares Your Child Better Than a Saturday Shift

Teenage Jobs in 2026: Why Entrepreneurship Prepares Your Child Better Than a Saturday Shift

September 14, 2026

Day 2194. Barefoot on the road. 16,830.77 kilometres into a 40,075-kilometre lap of the world. And today I want to talk about teenage jobs, and whether the traditional answer to that question is still the right one.

This came out of a conversation with my wife. Our eldest son is 15. He has had work experience before - he helped out in my cafe for a while, pot washing, customer service, the kind of work most people associate with a teenager's first job. When I closed the cafe, that opportunity went with it.

Rather than leave him without direction, I spotted something. My father had built up a collection of jewellery during his working years. Since retiring, it had sat untouched in a warehouse. I suggested to my son that he go to his granddad with a proposition: he would do the work to sell the jewellery online, they would share what came from it. His granddad agreed.

Six months on, my son is running a small but real e-commerce operation. He researches listings, manages the sales process, works out pricing in a gold market that has performed well, and takes home earnings close to minimum wage - from a few hours of work each week. He is 15.

My wife's position was clear. He needs something more traditional. Social interaction, colleagues his own age, the energy of a working environment with real people around him. I understood the instinct completely. My first reaction was to agree with her.

But the more I thought about it, the more I questioned whether that instinct is still correct.

I am 44. When I was 15, a paper round, a shoe shop, a cafe shift - those were exactly the right preparation for the world I was entering. They gave me reliability, an understanding of customer interaction, the discipline of showing up regardless of how I felt that day. I am not dismissing any of that.

The problem is, my son is not entering the world I entered.

Employment is being reshaped at a pace most parents have not fully absorbed yet. AI is changing entire sectors. Entry-level and service-sector roles are among the most exposed. The jobs that were available in volume when I was a teenager are either disappearing or being transformed into something different. Training your child for a version of work that looks quite different in ten years is worth questioning seriously.

What my son is doing instead is learning something more durable. He identified an opportunity - jewellery sitting unused in his granddad's warehouse. He negotiated a deal. He took ownership of an e-commerce process from listing to sale. And the next natural chapter, once the jewellery is sold, is learning to buy. Understanding how to source something at one price and move it at a higher price is a fundamental commercial skill. He will have worked both sides of a transaction before he is 17.

We call this agency. The willingness to look beyond the obvious and create something where nothing existed before. That is not what you typically develop from a Saturday cafe shift. Both forms of experience have value - they genuinely do - but the skill set is different. The one my son is building right now is the one I believe will serve him better in the world ahead.

I want to be clear about something. I helped him find this. I pointed him toward his granddad and toward the opportunity. But the work since has been his. The listings, the decisions, the relationship with his granddad, the results - all of that belongs to him. And the skills he is building are his to keep regardless of what any employer decides in the future.

That last point matters more than it sounds. The people most exposed in the next decade are those who built their entire working identity around being employed by someone else, and who never learned to create opportunity for themselves. The teenagers who will do well are those who learn early to look at a situation and ask: what do I do with this?

I run every day in barefoot-style shoes to raise one million pounds for children's causes. Today is day 2194. I have covered 16,830.77 kilometres of a 40,075-kilometre barefoot lap of the world. 23,244.23 kilometres still to go. Great Ormond Street and BBC Children in Need are the beneficiaries. I do this every day because consistency compounds. Showing up when it is inconvenient is where the real work happens.

The same principle applies to what I want my son to learn. Not from any specific job, but from any experience that teaches him that creating something beats waiting for something.

If you have teenagers approaching working age, think beyond the default options. Not to dismiss traditional jobs - there is still real value in them - but to ask whether there is a form of work worth your teenager taking on that prepares them for the world ahead, not just the one we grew up in.

The world is changing. The teenagers who will do well in it are those who learn early that opportunity is not always handed to you. Sometimes you have to see it, name it, and go after it yourself.

If this is useful, share it. Drop your thoughts in the comments - this is always a worthwhile debate.

Watch the full episode: https://youtu.be/Rs8xHbD5miQ

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I am on a mission to raise £1,000,000 for children's causes by daily run-vlogging barefoot-style, covering the total distance of a lap around the world—40,075 km.

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