I just got through watching GirlBoss on Netflix. I’d read about it in a blog post and thought… given all the things I talk about on my blog and YouTube channel, maybe the show would provide some useful information, or at least inspiration. The show itself wasn’t everything I’d hoped and unfortunately, it’s been cancelled after only one season, but it got me thinking about the quiet revolution taking place in the workplace today.

In 2017, it seems that everyone is dreaming of starting their own business and very few members of the traditional workforce feel fulfilled in their roles. While the former is great, the latter really sucks. Not only does it suck for all my friends who hate their jobs, it sucks for entrepreneurs and startups, because at the end of the day, everyone needs employees.

So, what’s different about this Millennial work force? Why can’t they seem to do what so many generations before them have done without a problem? Why are they all so convinced that they are better off trying to make it on their own?

To understand the phenomenon, I think we need to go back a couple generations.

The Baby Boomers, born in the late 40s and 50s, grew up in a world with a high value for education. They grew up with a drive to see social change and the expectation of a decent paycheque, staff benefits and a cushy pension. They grew up optimistic… they went to concerts, danced their way into parenthood in the late 70s and managed to buy homes, cars and expensive toys with the income they made in the glorious seventies and eighties.

Their children had the best of everything; overpriced toys in the eighties, education in the nineties and cutting-edge technology in the naughties (btw, does anyone actually say ‘naughties’???).

So why is it that, a couple decades later, so many of these children are unemployed, depressed or living in shackles imposed by corporate overlords?

Why is it that so many of us feel absolute dread of the future and have zero confidence in the system?


I would posit (and don’t you just love the word ‘posit’?) that we’re overlooking an important factor here.

We all know about the lazy, entitled Millennials who know nothing about actual human interaction and were practically raised by Apple and Microsoft. As an early Millennial myself though (yes, if you were born in the 80s you’re a Millennial my friend!), I have enough recollection of the years before the digital boom to feel that we should take a close look at that OTHER generation. Not the Boomers… the ones who came after. The ones everyone was talking about before WE started making our mark on this world. You know who I’m referring to; the renowned Generation X.

Nobody talks about Generation X anymore, though they did when I was a child. It’s like the world has forgotten about them… but we shouldn’t. Oh no… we definitely shouldn’t. In fact, let’s talk about them.

You see, those cynical, sneaky, low-key GenXers are currently our BOSSES at work!

You reap what you sow, and the seeds that created our bosses are actually quite different from the ones from which we have sprung. Generation X was born in that awesome era of the sixties and early seventies; when our parents (for the most part) were teenagers. They were in their early teens when we were born.

They were NOT raised by optimistic flower children reaping rich post-war social benefits. They were raised at a time when birth control was becoming a ‘thing‘. They grew up in broken homes; when divorce was also becoming a ‘thing’. They were into MTV; the singers on it weren’t far from them in age. They were cynical about the world; being a latch-key kid will do that to you.

Because they hit the workforce at a time of relative economic downturn, what with all those Boomers clogging up all the good jobs, they had to get competitive. They didn’t dream of getting a nice job with a decent salary and settling down; they wanted to make a mark. Not surprising then, that Generation X gave usΒ Julian Assange, the WikiLeaks founder or Sergey Brin and Larry Page, the founders of Google.

Generation X got educated and they got active.

But, you see, they have no idea how to relate to Millennials. This often translates as total communication failure in the workplace, insanely lofty ideals or a general resistance to change. Shifting standards are perceived as a desire for ‘special treatment’. For a bunch of kids who had markedly less ‘special treatment’ than previous generations, who saw Millennials getting ‘special treatment’ GenXers never had… this just doesn’t go down well.

Generation X marked a massive decline in parental supervision of children… which made GenXers more independent… but it may have also made them terrible bosses.

Or I could be completely wrong. In any event, it’s only logical to surmise (which is a lot like ‘posit’ but nowhere near as fun to say) that part of the reason for the increasing millennial tendency to choose self-employment or entrepreneurship is because many of us feel unhappy, unfulfilled and unappreciated in conventional jobs. It’s also logical to theorise that this may be, in part, due to adverse environments created by management and senior staff.

To illustrate my point, let’s talk about Google. Maybe you weren’t aware, but Oprah is settling into retirement, and Google is now officially Ruler of the World. They are literally taking over everything. Email, Mobile Communications, Online Advertising, Social Networking, Maps, Web Browsing, Word Processing, Cloud Storage, Entertainment… I mean do you guys even remember the days when YouTube was just YouTube? Before it belonged to Google?

Google was created by GenXers, yes, but because it is a tech company, it employs (quite successfully) a disproportionate number of Millennials.

Everyone knows, though, that Google is no ordinary workplace.

Am I saying that Millennials need free gourmet cafeterias, massage rooms, on-site doctors, and nap pods at the workplace? That would only reinforce the negative stigma of the spoiled, entitled Millennial, right? After all, we’re the generation that expects everything easier, bigger, better, cheaper and NOW. But lets try to be fair; for those same reasons, a young professional today is expected to deliver better, flashier and faster results than ever before. And he wants to… and he will! But it would really help him to do so (and not look or feel like a homeless person) if he could also get a haircut, a shower and a nap right there at work.

Needless to say, Google has figured this out and is therefore an example of a massively successful business model. Management everywhere has got to listen.

Or… we could all continue to trickle out of the workforce and create our own startups. I’ve done it myself, so who am I to judge?











2 thoughts on “Generation Gap: Why Entrepreneurship Just Got Cool Again”

Join the discussion!

%d bloggers like this: