The rise of gap year demons

Editor’s note: This is Part 3 of a 3-part series on hustle culture, unpacking how Gen Z is redefining work, ambition, and success. You can read Part 2 here.

Highlight of the week: More nice messages!

If I were a linguistics professor running a seminar, deconstructing the term ‘side hustle’, I would title the session:

On identity, income diversification, and microcommunities: How side hustles took over the young mind.

(Did not use ChatGPT for that one – I can be high brow all on my own) 💅.

I would then kick off with an exercise. Can you identify what a ‘cool’ vs. ‘cringe’ side hustle is? Let’s try:

Example 1: You’re an econ student. At night, you stay up til 3am livestreaming Animal Crossing to a small but loyal following. None of your classmates know. 

Example 2: You work full time in consulting. On the weekends, you make tiny crochet hats for babies and puppies that you sell mainly to friends and coworkers. 

Example 3: You work part time at a café. On the side, you make social media ads to resell trending Amazon items. You get paid a commission of each sale.  

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How many do you think you got right?

Let’s break down the criteria according to our research group

👉 First, in order to have a side hustle, you need to have a main hustle.

To quote some of our Doomscrollers research participants: 

💬 Participant, 19: A side hustle is a luxury, but you have a real job. Not like these gap year demons who aren’t doing anything else. Get a degree bro. There’s no main bro. 🤡

💬 Participant, 25: I had this friend who always pretended to be an entrepreneur but actually just works in the deli section of a grocery store. If you’re trying to use your side work to be perceived as constantly busy or hustling, that’s cringe.  

💬 Participant, 18: I see a lot of content creators in college. It’s cool they’re putting themselves out there, but some of them want to make it their main (i.e. take time off school), which I think is short-sighted.  

TLDR side hustles should be complementary to other full time work or studies and not an attempt to inflate your sense of self.

👉 Second, it needs to make money.

Otherwise, it’s just a passion project. Like my close friend Hannah who bakes multiple batches of the most amazing cookies for her friends each week. 

💬 Me (mid-gobble): You know you could easily sell these right?

💬 Hannah: But that would take the fun out of it. Maybe if it was a non-profit. Like a non-industrial scale of cookies gifted to the public. I would love to do that full time.

💬 Me (dusting crumbs away): Aww, well here’s hoping your boyfriend gets his next promotion!

👉 Finally, it should relate to your identity.

This, I thought, was the most interesting point. 

What distinguished a cool vs. cringe side hustle boiled down to whether or not it tapped into a hidden talent, passion, or value you couldn’t otherwise express. 

💬 Participant, 23: It’s cringe if it lacks authentic personality, like if you’re just selling AI courses on the most effective ChatGPT prompts. Anything that’s an expression of your identity is admirable.  

💬 Participant, 18: [Side hustles] are admirable when your main job holds you back from being your whole self and pursuing your true identity.

💬 Participant, 26: If you’re into fashion, then it’s sick if you’re tailoring suits.

On balance, most respondents thought side hustles were commendable. Particularly because the internet has so many microcommunities, so even if you may find it weird or uninteresting, there’s going to be a segment of people who appreciate it. 🤝

Why this matters

Three quarters of Brits think running multiple side businesses alongside full time employment is the future of work. 

Why? In part, because traditional wage growth has been so stagnant, with the average side hustler earning 20% more each month than their static counterparts. 

This trend is mainly driven by millennials and Gen Z who are particularly enterprising. 

Yet, no matter how commercially viable the side hustle, the majority (63%) say they wouldn’t quit their main job. Similar to my friend Hannah, most view their side business as a counterweight to regular employment – something that brings them ‘joy and personal fulfilment’. 🎨

This is where the identity piece comes in. 

Gen Z workers are much less likely (61%) to say their job is a significant part of their identity, compared to their older bosses (86%), according to Deloitte. 💼

What the quiz reveals is that cool side hustles aren’t just about income – they’re a form of self-expression anchored in real-world constraints.

What’s next?

If you read this series, it should be pretty clear by now that young people want flexible work with opportunities to grow and the freedom to pursue side projects and passions along the way. 

Next up… TikTok-radicalized chrystal girls and other mystical pseudo-religious stuff 😇. 

So what?

💡 For strategists & researchers

• TLDR… Side hustles are no longer fringe. They’re a cultural and economic response to stagnation, identity expression, and algorithmic visibility.

• Ask yourself… What’s a part of your identity you’d rather not share through work?

• Check this out… A Gen Z explaining what I just wrote but in a 36 second TikTok.

💭 For self-reflective readers

• TLDR… Side hustles are generally cool, unless you’re dropshipping or selling AI courses.

• Ask yourself… What’s your great talent you’re hiding from the world? 

• Check this out…This Redditer’s side hustle to get free food.

– Liat