Why being an entrepreneur is harder to Gen Y than to millennials

Say hi to Julia,

Julia is part of Generation Y, and may or may not have read that brilliant Wait But Why article about why Generation Y yuppies are unhappy.

(It basically tells the story of “Lucy”, a GYPSY – Gen Y Protagonist & Special Yuppie – who is unhappy because her career expectations are way higher than her career path reality, as she feels entitled to success. And that I urge you to read. It’s amazing and the author, Tim Urban, is the best. But promise me you won’t let your attention span forget about what took you there in the 1st place, and PLEASE COME BACK HERE afterwards). 

Julia is kind of unhappy as well, just like Lucy.


but unlike her, Julia is not entitled and doesn’t feel like she was born special and is destined to bigger things just because she’s too awesome for this world. All the opposite.

She belongs to the group within Gen Y-ers who feel they’re probably less special than others, for 2 reasons:

1) They don’t fit in with the Gen Y-ers who simply finished college and kept working the daily grind of their careers like proper adults – the careers, by the way, they rightly chose when they were 17-19, applying for the correspondent university course. Let’s call them GYMBOs, the Gen Y Masters of the Being On-track.


2) They don’t feel as smart as people who are 10 years younger, the so-called millennials, who seem to be doing much better for themselves with their “sorry, not sorry” FOMO-inducing videos about being online entrepreneurs whilst travelling the world 1, or being CEOs of the coolest startups in the co-working space.



Let’s call this group GYNGAs – the Gen Y-ers Not Going Anywhere.

Julia has always felt smart, but she looks around and feels like somehow, so far, she’s underachieved.

We don’t need to dig as deep as Julia’s grandparents to get to the bottom of why, let’s only go as far as her childhood.

As a GYNGA kid, Julia remembers, among hula hoops, thunder cats and Van Halen songs, that the only way to success, according to her parents, teachers, and movies like Working Girl, was a commute powered by a train company called STUBEDOJO, as follows:

study hard in school > be accepted in a good university > do well in college > and finally get the maximum supreme reward: land a job in a blue chip multinational corporation (where the Working Girl script will unfold).

Anything different would be less.

Julia’s last year in college was filled with 5-stage interview processes to work in those corporations, and when her classmate Susan announced that she was going back to her small town to cook and sell pies with her mum, this is how her classmates reacted:




It was, for everyone around, the ultimate proof that Susan hadn’t made the cut, and had forever failed in life.

All because she didn’t get on the STUBEDOJO train. But the thing with STUBEDOJO trains and their single route was that its passengers not only learned to look down on people who wouldn’t buy the ticket, they also never learned any other possible path towards success.

Of course, they would still hear stuff like “be your own boss and you won’t have to put up with a boss who’s an idiot”, and “it doesn’t matter if you choose to be a garbageman, as long as you become the best garbageman of the world”, but it was all vague advice of hazy ideas that never had a space to actually flourish. There were never concrete, real-life next-door examples of people doing that around the GYNGAs. (As Marian Wright Edelman says, “You can’t be what you can’t see”). And prominent trailblazers were seen as highly gifted individuals who received a divine inspiration to create and build stuff on their own.
Fast forward 10-15 years after Julia’s college graduation, and while the GYMBOs are happily posting pictures of their 2nd kid on Facebook and moving forward with their careers, GYNGAs like Julia realized, at some point between the first month in college and today, that the mighty STUBEDOJO train wasn’t the only ultimate transportation to happiness and accomplishment after all.
It was only kinda hogging the market, with monopoly and propaganda (so typical of the 80’s as well).
But not anymore.
So she decided to find a different path, and adventurously jumped out of the train… just to roll into a strange futuristic land where 23 year olds are millionaires and run their businesses from their laptop in the afternoon, after having swum with the dolphins in Thailand in the morning. A land where CEOs of fancy revered companies are all in their 20’s, never finished college- or never even went to college, and are featured in “The Most Prominent Talents To Watch For”. Where everyone is faster and way more brilliant than she is. Or so say their FOMO-inducing videos, their social media, and Julia’s auntie and uncle who have a 1 year old grandson who can operate a smartphone.
 This, of course, can only lead to the 2 main facts about GYNGAs:

GYNGAs Are Anxious

Just like GYPSYs are taunted by all the social media image crafting they’re exposed to in a daily basis, GYNGAs feel overwhelmed with 90’s kids’ stories of instant success, genius app builders, and smartphone-operating powerbabies.

GYNGAs Feel Out of Place

They’re not the “proper adults” they feel like they should have been (and not only “it’s too late for them to go back”, but also, they’d be going back to a life they hate), neither they’re the wiz coder kid who created Flappy Bird in 3 days at the age of 19, and took it off because he felt guilty to make $50,000 a day off people’s addiction to the game…

… hence they can’t compete in today’s market and they are probably forever doomed.

And I realized this the day I was talking to my fellow 27-year old GYNGA friend and then-coworker in a terrible startup, and he was complaining exactly about how everyone there who was younger was more successful and/or rich than him.

If he was a true GYNGA and not a delusional GYPSY, he probably wanted to DO more, only didn’t know how. As we saw, STUBEDOJO is a very ruthless monopolist train company, that won’t provide maps for any other trains or road.

And how can you arrive at Successville if you:

1) Don’t have the roadmap, GPS, or even crayon-drawn pirate map to it?

2) Don’t quite know WHERE it is, even if you do have the resources to go?

Julia doesn’t even know where to start, whilst her millennial peers were practically born with internet, codecademy, fiverr – where you can have your logo designed for $5 (I know, the quality, but back when you were a fresh-out-of-college intern, the only way of having a logo or website done was to pay big-league amounts to advertising agencies, and now you can find freelancers online. You can BE a freelancer online) – YouTube where you can broadcast your product in an entertaining and engaging way (not just cat videos like Julia did for years like a social media grandma), Facebook groups and Instagram where you can actually find business leads, and so much more.

Julia was raised to believe that the only single possible way of being an expert in something is if she went to college to study this something. And she may even judge those who are making money from non-college businesses. Facebook Ad specialists? How would I become this, if when I left my university in 2002 Facebook hadn’t even been invented yet? Digital Nomad Retreat CEO? I was busy working while this girl was writing a blog. Mindset coaching? What does this even mean? Preposterous!, she says.

Julia can master all this and do very well, but just like she has to google what the word “bae” means, she may feel a bit out of this wave that is so natural to the cool kids.

But the biggest limitation is in Julia’s mind.  And as soon as she realizes that, she will soar. So here are some new train maps for Julia:

1)  You’re not less intelligent, less capable or less entrepreneurial than millennials. You simply are 10-15 years older, so you’re having access to the same technology they are, but at a stage when society suggests you should be all sorted out and firm in your path, whilst encourages them to start their first career. JUST. A. MATTER. OF. AGE.

2) So if you start whatever you want to do now, alongside millennials, they may come across as “geniuses who nailed it on the first try”, but that’s an illusion. They only got it “on the first try” because this is the train that has been advertised to them from the beginning, and that you just found out about after years of commuting with STUBEDOJO. Everyone can get a ticket for the new, modern, faster train. Just jump in and remember that age milestones are just a convention. And also this:


So who cares what other people say about your age and your expected age-appropriate milestones? (Again, pic credit to waitbutwhy)

3) Accept that you don’t need 3-5 more years of sat-on-the-grass academic discussion and 9-5 college classes to make your idea happen. You have life experience, professional experience, and thousands of books and quick online courses to support you.

3) You’re probably not seeing that whilst back in the day you secretly reproached Susan for undertaking an entrepreneurial project, you are now praising younger people for doing exactly the same thing. You are allowed to create your own business and do what you like, be it sell pastry, help people have healthier relationships, advise people on how to arrange their wardrobe, or whatever your brilliant brain keeps thinking of while you play Candy Crush. There’s a market for everything, especially if it helps others and you feel truly good and passionate about it (wow, maybe Julia and Lucy could hang out together and learn from each other!)

So go get them, and paraphrasing Tim’s advice to Lucy, the truth is that everyone else is just as indecisive, self-doubting, and frustrated as you are, and if you just do your thing, and keep putting your efforts in the right direction, it’s just impossible that you’ll never accomplish anything that is meaningful to you.

(Susan’s pie company may or may not have taken the market by storm, we’ll never know).



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