The side hustle generation: preparing your child for a non-linear career future

For most parents, the idea of a “career” still conjures something familiar: choosing a field, earning a qualification, getting a job and climbing steadily upward. It’s the “job for life” story many adults lived – and the story they naturally expect their children to follow.

People in their 60s and 70s today, have held an average of 12.9 jobs in their working life. For Gen Z (born between 1997 and 2012), that number is expected to rise to up to 17 jobs across seven wholly distinct careers – not promotions or lateral moves, but fundamental shifts in skills, industry or profession.

Today’s labour market reflects that shift: US workers aged 20–24 remain in roles for just 1.4 years on average, compared with 9.8 years for workers aged 55 and over.

Today’s youth are growing up in a very different world – one where careers rarely follow straight lines, working lives are longer, and a weekend hobby can become a six-figure income stream. Stability now depends less on job titles and more on adaptability, creativity and personal brand.

This shift isn’t something to fear. It’s an opportunity to raise children who are entrepreneurial, resilient and equipped to thrive through continuous reinvention. For families navigating this change, understanding how the world of work is evolving – and how Gen Z and Gen Alpha are already reshaping it – is the first step towards helping children build careers that are dynamic, meaningful and uniquely their own.

In article three of this Invest-ED series, we provide practical examples of how parents can prepare their children for non-linear career paths.

Purpose over pay

What motivates young people to choose a career is also changing. According to Christopher Hosken, co-founder and CEO of The Startup School – an online learning platform backed by Investec to encourage South Africa’s entrepreneurial ecosystem – young people today are looking for careers that feel meaningful and flexible.

“They are not as interested in the idea of staying in one job for 20 years, as they want work that fits their lifestyle, aligns with their values and gives them freedom. This means they are comfortable exploring different paths instead of sticking to one traditional route.”

Hosken’s perspective reflects a broader shift already visible in the data. Randstad’s Workmonitor 2025 survey of more than 26,000 workers worldwide found that 83% now prioritise work-life balance over compensation – the first time in the report’s history that balance has outranked pay.

Diversifying income streams

As priorities shift, so too does the way young people earn a living. Rather than organising their working lives around a single employer or fixed career path, many are diversifying how, when and where they generate income. Here are some of the buzz words to familiarise yourself with as a parent:

The gig economy: Flexible work becomes the default

The gig economy is normal, not niche. It refers to a labour market built around short-term, contract or freelance work rather than permanent roles. Millions of young professionals now earn income through short-term assignments, freelance contracts or passion-driven micro-businesses. Flexibility, autonomy and project-based work are becoming the norm. In fact, by 2032, the gig economy is expected to more than triple to $1,847 billion. 

The rise of the side hustle

A side hustle refers to any income-generating activity pursued alongside a primary job or studies. More than 36% of US adults earn extra income through a side hustle, while in the UK it’s 19% of adults. In addition, almost half of Gen Z (48%) in the US has a side gig, followed by millennials (44%).

The creator economy: turning audiences into income

The creator economy is also booming. It refers to an ecosystem where individuals earn income by creating and distributing digital content directly to audiences, often via online platforms. From YouTube to TikTok to niche newsletters and online tutoring, millions of young people now monetise their creativity directly. They build audiences, cultivate personal brands and turn content into income, often before they’ve turned 18. 

In the USA, the creator economy has emerged as the fastest-growing segment of the digital economy, with full-time equivalent creator jobs increasing 7.5 times since 2020, according to the IAB Measuring the Digital Economy report.

For children growing up today, a “career” is less likely to mean a single job and more likely to resemble a portfolio – of skills, interests, income streams and experiences. For parents, the challenge is no longer steering children toward a safe, linear path, but helping them build adaptability, confidence and curiosity.

In a world where work keeps changing, the most future-proof advantage isn’t a job title – it’s the ability to learn, pivot and create value in many different ways.

The side hustle mindset

A generation ago, a side hustle was a hobby or a necessity. Today, it’s a lifestyle – and increasingly, a career foundation. For young people, side hustles function as learning labs, building real-world skills like budgeting, marketing, client management and problem-solving; confidence-builders, offering early independence, financial literacy and agency; and safe experimentation zones, where interests can be tested without long-term risk.

Many of the skills teens already have can translate into income. Editing videos, tutoring, designing graphics, baking, selling handmade products or building simple websites are practical, low-barrier ways to learn, earn and grow. These aren’t far-fetched ideas, they’re increasingly common starting points.

While South African labour law prohibits employing children under 15, it does not prevent them from earning independently through safe, voluntary and age-appropriate ventures that don’t interfere with school.

“For many young adults, starting a side hustle is how they enter the working world. It is often a dream that they would like to turn into a full-time focus,” adds Hosken.

“Unfortunately, though, given our tough economy, especially for entry levels in careers, it is difficult to break into the market. Therefore, it has become a norm to have a side hustle in order to sustain their lifestyles. They see entrepreneurship as a practical way to not only extra earn money but ultimately express themselves.”

The rise of the digital economy has also lowered the barrier to entry for well-paid careers. Self-taught developers, designers, video editors and social media strategists are building sustainable careers from skills and portfolio work rather than formal qualifications. These paths are no longer “alternative” – they are mainstream and in demand.

Even once young people enter full-time work, many won’t rely on a single income. Freelancing, digital products, online teaching and personal brands often sit alongside a primary job. This is the real shift: today’s youth aren’t waiting for opportunity, they’re creating multiple pathways to financial independence.

How to build a portfolio career mindset at home

The future of work does not require parents to be more controlling; it requires them to be more supportive, curious and open-minded. "Beyond what school traditionally teaches, young people today also need skills like research, creativity, problem-solving, communication, critical thinking, financial management and the ability to lead with empathy. Successful young entrepreneurs not only share traits of curiosity, resilience, openness to feedback, but a drive to turn something meaningful to them into a reality,” says Hosken.

Here’s how to actively prepare your teen for a dynamic, non-linear career

1. Encourage curiosity and multidisciplinary thinking:

The world no longer rewards narrow expertise. It rewards skill-stacks – combinations of complementary abilities that create unique value. For example:

• Coding + design = app creation
•  Storytelling + business strategy = content marketing
• Maths + gaming = game design or data analytics
• Science + drawing = medical illustration

Help children explore different fields, even unusual combinations. Let them solve small problems in creative ways and mix passions instead of choosing only one.

2. Normalise entrepreneurship early:

Entrepreneurship doesn’t have to be formal, it can be:

• Selling baked goods
• Designing graphics for classmates
• Offering tutoring
• Creating a small online store or selling second-hand goods on platforms like Yaga
• Starting a community project

The goal isn’t to build a big business, it’s to build a mindset: initiative, accountability, customer empathy and courage. Entrepreneurship is a muscle – the earlier it’s exercised, the stronger it becomes.

3. Teach financial basics:

Teens need more than savings ‘jars’. They need financial literacy for the gig era. Show them how to budget for inconsistent income, how to save and calculate profit vs. revenue. Give them small budgets to manage. Money isn’t just a resource, it’s a language. The sooner teens become fluent, the more empowered they are.

According to Hayley Parry, money coach and facilitator at 1Life’s Truth About Money: “Teaching teens the concept of personal profitability is a powerful place to start, because it builds financial capability no matter how they choose to earn – through a traditional salary, the gig economy or a side hustle. The core principle is simple: pay yourself first. Save, invest, then spend. It’s a lifelong habit that lays the foundation for true financial freedom."

4. Model adaptability:

Show them your own pivots. Parents have more influence than they realise. When young people see adults reinvent themselves – switching careers, learning new skills, starting side projects, taking online courses – they internalise a powerful truth: “It’s normal to evolve. It’s safe to try.” Share stories about your own career shifts, what you’ve learned from failure, skills you’re still developing. This makes adaptability feel natural, not intimidating.

5. Introduce role models with unconventional career paths:

Expose your child to people who monetise creativity, have blended careers (e.g., engineer + podcaster), freelance successfully or built careers without degrees. This expands a child’s definition of success beyond traditional titles.

Make use of podcasts, YouTube, networking events, career days and influencers to help tell these stories. Young people need to see a variety of futures before they can imagine their own.

“Today, we need to introduce young people to real world skills and role models and embolden them to learn from experience and teach them to see failure as part of learning to grow resilience. A great place to start is simply by encouraging them to lead school projects to build leadership, give them the chance to make decisions and own them to develop accountability and courage,” notes Hosken.

Why parents should feel excited, not overwhelmed

Your child’s future won’t look like yours – and that’s not a threat. It’s an opportunity. An opportunity to prepare them for a world where creativity, individuality and adaptability are real assets, and where passions can become viable careers.

Hosken stresses that parents don’t need all the answers. What matters most is creating a home where curiosity is safe, ideas are welcomed and failure is treated as part of learning. When teenagers are given room to explore – without pressure or judgement – they build resilience, confidence and a sense of ownership over their path.

The greatest gift parents can offer isn’t a perfect plan, but permission: to try, to fail, to learn and to start again. With AI, global platforms and entrepreneurship opening new doors, the next generation is already shaping careers around skills, interests and purpose – not job titles.

“We are raising the side hustle generation – innovators, creators, freelancers, problem-solvers and multi-career professionals who will shape the future in ways we can’t yet imagine. More and more teenagers are showing interest in entrepreneurship. They are hungry to learn and build something of their own and with the right mindset, and the right support, they won’t just survive the future; they’ll lead it.”