Generation Y, I Think We Have Problems

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Generation Y is known for its huge tech superstars, but its reputation isn't all good. Does this group deserve its increasingly bad rap? Brad Hines says yes.

Many people view the tech industry as almost synonymous with Generation Y. Picture baby-faced youth, cloaked in hoodies and running around computer servers, engaged in a Nerf battle. Exaggerated stereotypes aside, ever since I joined the full time workforce six years ago, I have noticed that disproportionately, the cohort of workers I enjoy working with least are my Gen Y peers.

I was born in 1984. That makes me among the oldest group of Generation Y, also known as "Millennials." On the whole, we’re a casual, social-media obsessed bunch. We’ve also frequently been called self-entitled, over confident attention seekers.

But I’m not pointing fingers. I speak from experience. And I’m not the only one who’s noticed. As far as workforce participation is concerned, Generation Y’s drawbacks have been getting a lot of attention. Dan Schawbel, founder of Millennial Branding and author of "Me 2.0: Build a Powerful Brand to Achieve Career Success," has spent his career studying Generation Y. He says managers of Millennials often find that they are "needy, self-entitled and lazy," despite what he believes to be the generation’s strong traits.

"They are good at multitasking, good at working both in groups and independently, are tech savvy and are eager to learn," Schawbel said.

Frankly I agree with Schawbel’s assessments. But it isn’t quite as simple as that; the weaknesses he identifies are part of a two-sided coin. That is, those same weaknesses can also represent strengths.

An Open Letter To Gen Y

So consider this an open letter to Gen Y: I think we have some problems, especially in the workforce. And I know you probably don’t want to hear this, but if you find these problems in yourself, they’re worth addressing.


Gen Y is often described as over-confident and self-entitled. I, for one, used to lament about a great job opportunity that was in the works for me at a Midwest technology company in the summer of 2006. I was being courted straight out of college to start as a manager there, including responsibility training employees in domain name valuation. The company seemed to like me a lot, but was not quite ready to make a job offer; they wanted to test me remotely from my native Boston first, for two months. After flying back home, I talked to the company’s headhunter over the phone. Then the issue of compensation for the two-month trial period came up.

"Six thousand per month I feel is good," I said coolly.

I heard a long silence.

"Really?" was the headhunter’s eventual response.

The job prospect mysteriously disappeared a few days after that phone call.

"Brad, we decided we don’t have the funds to hire for this position any longer," was the explanation.

The real explanation, most likely, was that my demand of an effective $72,000 annual salary for what was essentially an internship was a total disconnect from the expectations of the hiring company. I saw myself as a potential star; they were just trying to fill a role at a competitive market rate.

What I should have said is, "I’m not worried about that right now. For the trial period, pay me what you think is fair."

It was a hard lesson, and one that might have taken me many more years to learn if I’d gotten the job.

Some people would make the argument that the over-confidence I exercised is a general trait of all youth over the last century, not a trait unique to Gen Y. I disagree. In my experience, members of the Baby Boomer and older generations would have been more likely to offer to do the trial for free, for the sake of securing that kind of job right out of college.

Fearless Or Foolish: The Two Sides Of The Coin

My Gen Y friends share many of the same characteristics my generation is known for, no matter which Google Plus circle I choose from. Some might say we’re ruled by presumption and self-importance, but the enterprising fearlessness we were raised to embrace is more like audacity.

A few years ago, an associate of mine suggested that we start a hedge fund, with the notion that we’d be "an instant success" at it. Even I was shocked. Neither of us had any experience with that form of aggressive investing. There was little mention of hard work, or how long it would take to accomplish that goal; my friend just intrinsically believed we’d be successful at it. Perhaps he had taken the mantra we heard over and over again in kindergarten – "you are all special and can do anything you want to" – a little too literally.

But, as I mentioned above, strengths and weaknesses are two sides of the same coin. Our belief in ourselves has allowed us to make huge strides in the tech world, founding new companies, innovating, and sometimes making fortunes in the process. (Read about some tech company successes in 4 Top Tech Companies That Failed, Survived and Even Thrived.)

But while overconfidence (despite its problems) can take some pretty far, for many of us, it invariably leads to disillusionment. The things that would have made our parents happy disappoint us. We believe we are supposed to be perfect. Our expectations are aimed so high that they’re seldom met. And, as Schawbel explained to me, "Gen Y wants to make an impact on day one instead of waiting eight years to get on a big project. And they don’t understand why they have to work from nine to five …".

This could be why some people dismiss Gen Y as lazy. We are not. On the contrary, many of my peers seem to run themselves ragged, juggling the so-called work-life balance. And while snarky rants about employers – or anything for that matter – on Facebook are far from uncommon, no one seems to be amazed at how much we have or how far we’ve come. It brings to mind comedian Louis CK’s now acclaimed Conan O’Brien appearance, where he aptly noted that "everything is amazing and no one’s happy."

My generation’s expectations are part of what has helped many of us achieve great things. Unfortunately, having ultra-high expectation means we’re unlikely to be satisfied with anything. Ever.

Who Are We?

So let’s get introspective about who we are as a generation, and why. We are the generation in which everyone got an award, just for participating. We were bombarded with cultural and media obsession over a handful of overnight startup success stories. We’re tethered to cellphones, social media and the constant praise many of us grew up with. We were taught that everyone is unique and special.

But hold up. Let’s be realistic here. Special implies that you have something extraordinary relative to the norm. Merely being born after 1980 doesn’t exactly qualify. Contrast that with our Gen X and Boomer counterparts who, I think, had lower expectations about their own careers, and less pressure to succeed from their parents. It’s easy to see why Gen Y is always agitating for something more.

How the challenges Gen Y faces will play out – and whether the problems they face can be solved – is not something I know. According to Schawbel, part of the answer is in preparation and education.

"Colleges need to do a better job of preparing Gen Y for the workforce transition. Companies should embrace entrepreneurship because Gen Y is very entrepreneurial and they want their ideas heard," Schawbel said.

That sounds like a start. But personally, I believe that holding a mirror up to bad behavior is often a powerful way to expose a flaw. Perhaps with time, my generation (myself included) will learn to weed out some of their quirks, having watched them play out in those younger than themselves. Most of all, I feel Gen Y should be less quick to defend its reputation, and instead ask if such criticisms are justified.

So let me kick it off. I’ll start by saying that I did some very Gen Y things while writing this piece: I tweeted about it, I procrastinated, I checked Facebook more than I meant to, I told my parents about it, I pestered my editor for feedback, I used the word "I" dozens of times, and, well, I may or may not have hummed the "Fresh Prince of Bel Air" theme song while typing.

But then, I did get the job done, and the word out. Your move, Gen Y.

(Millennials’ attitudes, beliefs and background make them well-suited for the tech industry. Read more in Millennials and Tech Jobs: A Match Made In Heaven?)


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Brad Hines
Brad Hines

Brad Hines is a digital marketing strategist and freelance writer at, and founder of, a nonprofit that is partnered with the United Nations World Food Program to raise world hunger awareness and for other humanitarian issues. Brad is a lover of art, travel, cooking, and design.