Forget About Generation Y: We're All to Blame for Workplace Woes

I've been blogging about generational differences for over a year now. But with all the back and forth, constant banter, and little resolution, it feels more like ten years.

It feels like everyone is saying the same stuff over and over. Boomers and X'ers complain about Generation Y, and then Generation Y complains about everybody else. But really, we should all just be complaining about ourselves together.

We all have a lot of similar traits that make the workplace really suck sometimes. But for some reason we're so distracted by the minor differences between us that we forget how we're all a pain in the ass sometimes.

Generations aside, here are three things that will always remain the same:

We all have unrealistic expectations of each other.

Does Generation Y have unrealistic expectations when it comes to our first jobs? Absolutely, but who can blame us?

When it comes to education, I can't remember one professor who taught me the ins and outs of entry-level living. And parents, well, let's face it. It was a much different world when then got out of school than it is today.

So while Gen Y needs to get a grip on what it means to be at the bottom of the food chain, managers need to re-evaluate what they expect their young workers to be in tune with. It seems pretty logical to me that we won't know everything.

We're all a little stubborn at first.

My first real project was facilitating groups of senior management on a new operating model being released to the company. Nobody wanted to change and there was a lot of resistance.

"Why do we need to change now?" they'd ask.

Everyone left grumbling about all the work they'd now have to do, explaining this system to their employees. I didn't hear from any of them for weeks.

Then a couple weeks later people starting calling for materials to hand out to their employees. It started to make sense that no matter how much they fought, the company was still making a change.

I think the same is going to happen with the rift between Generation Y and the rest of the workforce. Only it will happen a lot slower. Change is a dirtier process when it occurs from the bottom up.

But just wait until you catch your boss texting and loving it. They're already sending emails via Blackberry, which is really not that different.

We're all whiners.

The older I get, the more I realize that we are all just a bunch of whiners. And by we I don't mean Generation Y. I mean we as in everybody.

For over a year now I've listened to older generations hate on Generation Y, then Generation Y hate back. Even I threw my own two cents into the blogosphere, adding some fuel to the on-going fire of generational conflict.

The sooner we come to terms with the fact that we all have something worth complaining about, the sooner we can cooperate using the only method that's ever kept the majority happy—give and take.

I'm hoping as more Gen Ys mature and become accustomed to the realities of the workplace, it'll be easier for us all to grasp that we all have problems, regardless of our generation.

But even then, Gen Next will enter the working world, bringing more grief for the rest of us who are corporately over the hill. So let the cycle continue, I guess. Just don't let me become the guy who calls all those young employees selfish and entitled. Let me be the cool boss, please.

It's Not 1968: Why You Should Trust Everyone Over 30

In the 1960s Baby Boomers famously popularized the phrase, "don't trust anyone over 30." In general, the Boomers were anti-establishment, and did not want to conform to society's norms. Trusting anyone over 30 was seen as conforming.

I was recently asked, "If the boomers motto was don't trust anyone over 30, then what is Generation Y's motto?"

Without much thought I blurted out, "Get as many people over 30 in your corner as you can. Learn from them. And do it better."

Gen Y may not be driving around with bumper stickers or wearing pins with this slogan, but if you take a quick tour of the blogosphere you'll find thousands of Gen Yers discussing things like how to negotiate a salary, how to be productive, how to find a mentor, and how to make work better in general.

We give each other advice and we learn from our peers, but everyone in their twenties is well aware that with age and experience comes wisdom. And if you want that wisdom now, you better embrace the "old folks."

I genuinely trust people over 30. I trust that they've already been through the things that I'm going through. I trust that they've hated entry level jobs, they've backpacked across Europe, they've started companies, and they've dealt with the confusion of dating in your twenties. They've learned from their failures and successes. I trust that they have all that experience to share and I'm open to learning from them.

This does not mean they did everything the right way. Everyone makes mistakes. But it's a lot easier to make mistakes if you refuse to listen to anyone who's been in your shoes. My plan is to listen to everyone and to trust everyone over 30, until they show why they shouldn't be trusted.

Over the past year I've learned valuable life and career lessons from mentors and experienced co-workers, friends and acquaintances. In the past few weeks I've learned things like:

1. Patience is a virtue

2. A good manager never stops managing

3. Be yourself 24 hours a day

4. It's OK if everyone doesn't like you

5. Business to Business sales can all boil down to 2 things – solving a problem or creating an opportunity

I couldn't have learned any of these things if my motto was don't trust anyone over 30. Experience is invaluable. It's something you just can't get overnight. But you can learn from those who have it.

Don't close the door before it's open. Talk to older people with open ears. After you spend a few minutes talking, you'll quickly know who to trust and who not to trust. If you start with the thought that you can trust everyone over 30, you can learn some pretty cool stuff in your 20's.

Learn to Become Equals With Your Boss

I have a problem with authority. I have since I was a kid. It's probably the reason I wasn't cut out for life in a large organization and it's why I eventually became an entrepreneur. But as much as I don't like to admit I'm working for anyone else, Penelope Trunk is our CEO and, well, she's the boss. So over the past 8 months I've learned how to work with her so that I put myself on equal footing, most of the time. Here's how I've done it.

Know what's important to get approval for in advance, and keep the rest for yourself

If your boss is any good, he is busier than you are. That's just how work works. As you move up the chain, you're responsible for more things and you have less time for details. I've seen this first hand as Brazen Careerist has moved from a 3 person start-up to a larger team with six full time employees and a whole handful of part timers.

Penelope does not have the time to check off on everything. It's been a big switch for me, but I've learned to be selective about what I present to her. In the past, I would call her to give me the green light to draft a proposal to send to our lawyer or the investors. Now I make the call on what is important enough to get the final go ahead. What I've found is there aren't too many things that are truly necessary for her to give the go ahead on before I get started.

Going around the boss is a little risky, you need to know what things must absolutely be approved before going through with, but in the end, getting the right things done, even without permission in advance will make you and your boss look good. And it will begin to turn the boss-employee relationship into a peer-to-peer relationship.

Save the details

Tiny details do not need to be shared with your boss. When you're explaining a new product, service or opportunity, talk about the big picture. If your boss is high up on the food chain the chances are that she is always thinking five steps down the road. As an entry level employee or new manager, it's your job to do the day to day work to keep the company moving in the right direction and it's your boss's job to be thinking 3 months down the line. Sharing too many details will open a big can of worms that should be avoided.

Tell your boss about the presentation, talk about the benefits and the potential risks, but don't bother going through the PowerPoint slide by slide and don't tell him how nervous you are. Then follow through, and things will work out great. You may think you're holding back information that your boss wants to know, but in reality not discussing the minutia will save time and allow your boss to concentrate on the important things.

Notice the little things that help you make good choices about communication

It's important that you learn how your boss operates in different situations. Penelope often quickly says no when I bring up a new idea, without giving it much thought. I've realized that when she is thinking about something else, she often makes snap decisions. I used to argue. We would scream at each other for a few minutes, I would be pissed the rest of the day and nothing would get done. Now, I just say OK and I walk away.

I've realized over the past few months that often she doesn't shoot my ideas down because they're bad, she's just busy with something else. So I'll approach her the next day, usually in the middle of a conversation that's going well, and I present the idea in a new way. I explain the benefits and possible risks, and almost without fail, we go ahead and give the new idea a shot.

If you want to gain some authority in your company, no matter what size, it's important that you take ownership of your role, and sometimes, do things without asking. When you're the boss, there won't be anyone to ask, so you may as well get some experience doing it now.

Thinking Inside the Box: Not Goodbye, More Like See You Around

I've never been one for long goodbyes, so I'd best go ahead and put this out there right up front… this is going to be my last post for Employee Evolution.

Before you shed any tears (I know, no one is crying but let me have my moment), just know that I'm not leaving entirely, just migrating over to Brazen Careerist. You see, the focus of EE is changing, and us guest bloggers are being shuttled over to BC so we can add our thoughts to the rising chorus of young professionals who demand a difference. So think of this more as me heading to a new house in the neighborhood rather than moving to another country.

I'm not entirely sure what my new role over at BC is going to be as of yet, but I know I will be offering more than just stories and humor, and can hopefully couple what I've been doing here with some helpful tips in ways to get ahead despite our youth. You might see me pop up from time to time in the journalism or politics section of the community, and I hope that if you aren't already checking out BC now that you'll start doing so, there's really a great community of bloggers over there who appreciate the readers.

So as I go I first want to say thanks to all of you who have read and commented on my posts week in and week out. When I was suffering through my old job, it was such a release to be able to come and write about my experiences in such a way that I could get all the frustration out while finding a way to make things at least remotely interesting to you all. Your encouragement, advice, and well-wishes were always welcome, and while I may not have responded to every comment, I read each of them. Your thoughtfulness continued as I moved halfway across the country and started the search for my true meaning, and my only regret is that I will no longer be able to bring you along on my journey as I seek that "dream job" we're all constantly chasing.

I also have to thank Healy and Paugh, who took a chance on me as just some random guy who wanted to write a weekly column. Jackie's Millenial Muse works made me really want to be a part of EE, and I'm glad the guys were willing to give me that opportunity. I'm looking forward to continuing in partnership with them (and Penelope as well) over in the BC community.

So now I'll wrap things up before I start getting choked up thinking of the good times we've shared. You have all been so good to me, and I thank you for letting me come into your life for a few minutes each week and share the joys, sorrows, dreams, and failures of the life of one simple twentysomething longing to be more than just another anonymous paper-pusher.

And now, since I'm told to always leave them laughing, and since I am an avid Indianapolis Colts football fan, a joke.

A Bears fan, a Colts fan, an Eagles fan, and a Patriots fan are all climbing a mountain. Seeing as it is the nature of sports enthusiasts, they all begin arguing about who is the most devoted fan of them all.

Suddenly, the Eagles fan says, "Oh yeah? Watch this! This is for the Eagles!" he shouts, and then proceeds to throw himself off the side of the cliff.

As the remaining three continue climbing, the Bears fans says, "That was nothing, this is for the Bears!" and casts himself off from an even higher altitude.

As the Colts fan and Patriots fan sally onward, still arguing, the Colts fan suddenly proclaims, "This is for everyone!" and promptly pushes the Patriots fan off the cliff.

Thanks again everyone, I'll see you around.

Standing at a Crossroad: Am I Still a Millennial?

Because of blogging, my life took a complete one-eighty in less than a year. One day I was working in a cubicle, the next I was part of a startup. And as much as that whole scenario blew my freaking mind, I didn't change via startup alone. The biggest changes actually occurred from within.

Events in our lives have a way of shifting our attitudes about certain things. Sometimes that's bad, but then sometimes that's really good. In my case, let's just say that I'm a more seasoned millennial than I used to be.

And I think that's a good thing. Because while I inherently see the world through the eyes of my generation, I'm starting to understand what Gen-Xers and Boomers are talking about.

No, I don't think we're a bunch of narcissistic brats all of a sudden. But I do understand why we're sometimes misunderstood. Because as life takes its toll and we all grow up, I think we all find that our virtues mature.

Here are a few things that have matured with me during the past year.

I'm not as idealistic.

When I first read the cover of Strauss and Howe's Millennials Rising: The Next Great Generation, I think I tricked myself into believing that we're already just as stellar as my grandfather's generation who kicked butt for all of us during World War II. But let's face it, we haven't proven anything yet.

I do still believe our generation has the potential to be great. But I'm pretty sure now that it's going to take a lot more work than I originally thought.

A year ago I would've said that Generation Y is going to change the world and social media is going to be the vessel. Today, while I still believe that social media is a powerful ally, I'm not as naïve.

It's going to take a lot more than tech savvy for Gen Y to make change the way we talk about changing things. We need hands-on action. And while a few critics pointed me to some great examples of millennial leadership, I still haven't seen enough.

But maybe I'm demanding too much. Maybe we're on the right track and just too young to take the reigns of leadership. That would be just fine with me. But in the meantime, I'd rather demand more than be satisfied with less.

I'm more skeptical.

When I first heard Barack Obama speak, I said to myself, "Wow, there's the guy who's going to save this country." I was completely blown away. And looking back on it all, I kind of get mad at myself. I want to be smarter than that.

I no longer believe in the hype, I believe in results. Words like hope and change, used to give me goose bumps. Now when someone tells me they're going to do something all I can say is "We'll see."

And that may sound like I'm lacking in hope, but I'm not. I'm very hopeful. In fact, I voted for Obama in the primaries, and probably will vote for him in November too. But I realize that actions speak louder than words, and I'll definitely give the guy a hard time if he makes it into the Oval Office but doesn't live up to all he promised.

The problem I've seen in myself and in my generation thus far is that we're a lot of talk. And sometimes we believe in things without asking for proof.

But maybe that's all we can do until we gain more momentum. I'm sure anxious to see how we turn out, but until then, we'll see…

I'm not as bold.

When I started blogging, I used to run my mouth too much. I'd take something preposterous that someone said about my generation and respond with something equally, if not more preposterous. While shock and awe is typically a lot of fun, it's better to be taken seriously.

Today I think things through. When I get a nasty comment from someone who calls me an amateur, sometimes I don't say anything at all. It's not always worth it to stoop to their level.

Why does this matter?

It matters because I refuse to give Gen-Y dissenters exactly what they want — proof that I'm a hack. Some people feed on their ability to fire people up. And as soon as we lose our cool, they get exactly what they want.

My new motto: Stay cool. Backlash is always going to suck, but as soon as I give into the hate I lose my leverage as a reputable voice.

I'm more myself than I've ever been.

For about a year after graduating college, I was depressed. Between leaving long-time friend behind and searching for a new meaning for my life, it was a rough spot in my life. Then things started to fall into place.

Over the past year I've experienced the ups and downs of a first job, endured startup stress, and learned a lot about myself. And I don't want to toot my horn too much, but it feels awesome.

And at the same time, while all this awesomeness surrounds me, I wonder if I'm staying aligned with the values of my generation. Do I need a reality check? I'm really not sure.

Maybe I'm just opening up a new chapter. Maybe other members of my generation are starting to feel this way too. With all the garbage channeled our way via media campaigns, politicians and marketers there's no doubt that we're all getting a little nauseous.

So maybe I'm not alone. Are others breaking the stereotypes too? I'd really love to know, because either I'm losing touch or just headed down a different track.