Generation Y: Here Are the Real Dues We Need to Pay

When I hear older generations talk about Generation Y having to pay their dues, I get a little sick to my stomach. Not because I'm trying so hard to avoid the whole thing (I am), but because I have more important things to develop before worrying about a fat paycheck and a corner office with a view.

Due paying gets a bad rap because it's consistently associated with cubicles, meaningless work and low-paying jobs with little benefit. But I believe that there are other inevitable obstacles—more important ones—that we need to conquer before deciding where we stand within the working world.

Here are three due-paying opportunities that we all need to think about before fussing over the traditional connotation of "paying your dues."

Discover who your true friends are.

If you're more than a year out of college you've likely figured it out—everyone you considered friends at school is not going to be there forever. In fact, it's quite possible that you'll encounter some mild betrayal before long. It comes with the territory.

I consider myself pretty lucky. But there are times when I'm utterly let down. And because everyone has their own goals, though sometimes fairly hazy goals, you shouldn't dwell on the people in your life that didn't end up being as loyal as you thought they would be.

What I've learned to do is this: whenever somebody lets you down, put your energy into someone who consistently picks you up. Those are the people you want to center your life around. And it's those people who will continue to add meaning in your life as you pay your dues as a twentysomething.

Discover what it's like to be alone.

While I continue to realize that I still have some true friends, there are still days when I can't help but feel lost and alone. And I think that most people feel this way at some point.

Whether you're single, dating or married, we all have to figure out for ourselves where we fit in the world. Sure, you can count on your loved ones for support, but it's you alone who makes the decision about where you fit and what makes you happy.

One thing I've learned since moving to Madison and starting Brazen Careerist is that life can't be measured by your social life alone, and it's certainly not measured by a paycheck or by where you stand in the hierarchy of the working world. The most important measure in life is how you feel about yourself. And some of the biggest revelations will hit you not when you're out partying with friends or working towards a higher salary, but when you're by yourself, alone and kind of unsettled by the things that are still missing in your life.

Sound depressing? Sure. It's seldom a fairy tale experience for any of us. But what you learn through these experiences is what you need to move forward and be more of the person you want to be someday.

Feeling alone is a big part of paying your dues. Don't fear it; try to embrace it and get comfortable.

Discover your fear, and conquer it.

Lately I've been reading Christine Hassler's 20 Something Manifesto. I learn best from listening to other people's experiences and this book is jammed-pack with twenty-something life.

Today I read about fear and I can't stop thinking about what Christine says:

If you have a skill, dream, or desire that you are passionate about pursuing, perhaps the biggest obstacle you will face is your own fear…Fear can keep us in bad situations, and also from pursuing our passions. Fear can often be a stronger motivator than the desire for success, stopping us in our tracks before we even find out what we want.

Lately I've been talking to a few people who seem to have something in mind that they want to do, but aren't sure how to really do it. But I'm starting to believe it's less about the actual drawing out a plan and more about drawing up the courage to make it happen.

Whether it's leaving a new job, starting a new one, moving away from family and friends, or any other daunting scenario I've ever faced, the most difficult part of the transition was mustering up the courage to do it. But once I sucked things up and overcame the fear of failure, everything else was gravy in comparison.

And sure, I still encounter little failures along the way. But they only make me better. A few scars are worth the irritation because you'll look at them later and remember what you did wrong that put them there in the first place.

So before you fret about office politics or the way the working world views Generation Y, think about developing yourself. People are always going to whine about how lazy and self-absorbed young people are, so let's just spend these years paying real dues first–ones that will actually pay off for the rest of our lives.

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.

What to Do When You Hit a Juncture: Don't Put Life on Hold

One of the most important things I've learned over the past year is that you should aim to live in a place that mirrors your own personality. Unfortunately, most of us won't find ourselves in that perfect place from the get-go. So it's important to not let it get you down, or keep you from achieving your goals.

I have no intention of staying in Madison for more than a couple years. Just enough time to get our business going and hopefully move somewhere that suits my personality. But a couple years is a long time. If I just put things off because I'm waiting for the perfect place to take action, I'll miss out on a lot I've looked forward to for years. Timing isn't always everything. The other half is putting your dreams into action.

What I realized through my lack of action over the past year is that great things can happen in a juncture. We're really just procrastinating when we deceive ourselves into thinking we should wait.

Have you ever told yourself these things in a juncture?

If I'm just patient, good things will happen to me.

Image Credit: jenvanw
The first time I probably told myself this was in high school. And it was probably over a girl. Because I was probably awkward and goofy.

But with confidence and a few more years under the belt, we should all learn that patience is only half a virtue. The second half is a willingness to put yourself out there, even if it might crush your ego.

If you're in a new city and you're social life sucks, it's probably because you're not taking enough risks. Being quiet and reserved can seem like the right move because it's safe, but in fact, it's killing your chances of meeting the right people.

Weekend homework assignment: Go to the bar and put yourself in a situation that runs the risk of making an ass out of you in front of the opposite of sex. Sound like an all-time backfire? Maybe.

But maybe not. Great relationships usually begin during awkward moments. Test the theory out for yourself. If you fail, miserably, I'll owe you a drink.

I should just put in more hours working. I'll enjoy myself later.

When we first came to Madison we lived via late-night meetings, skipping out on happy hours – it was a first-class ticket to depression.

And I really hate that I used to live like that. There's a risk of having only weak relationships when you choose to live this way. Fall into this trap now, and who's to say you'll escape from it later?

My new approach: go out whenever you can reasonably afford to. As long as it doesn't seriously affect your work, it's as an important element on your path to success as climbing that ladder every day.

Everything I create here won't matter once I leave. Why waste my time?

I once met a girl from Mexico who convinced me to study Spanish. I went home and bought Rosetta Stone. Granted, I'm susceptible to foreign girls, but it's proof enough to me that short-term friendships can affect our lives.

Now that I'm finally settled in Madison, I'm embracing every new friendship I possibly can because I've learned to be okay with "temporary." Change is going to happen and nothing is permanent.

People who can adapt quickly to change can find happiness almost anywhere. So learn to embrace where you are all the time, even if deep down you wonder if you will ever think anything but "this sucks."

It's doubtful that anyone in their twenties is completely in tune with their environment. And even if you are, that will probably change as you grow older. What's important to realize is, as long as you're willing to embrace where you are today, you're probably going to end up in the right place tomorrow.

How I Try to Cope with My Own Anxiety

I have anxiety. And not the kind you get when employee reviews come around either. I'm talking about clinically-diagnosed, heart-palpitating, mind-numbing anxiety. It sucks. But I've learned to live with it.

The reason I'm sharing this is because the transition into adulthood is hard enough without having to deal with a mental defect. And considering that one out of every ten Americans suffer from some sort of depression, there are bound to be a few readers out there snagged by the mental funk I've dealt with for awhile now.

When I first started working on Brazen Careerist, I had a serious relapse of anxiety attacks. One thing that's really difficult about startup culture is that it lacks the structure that most corporate jobs embrace and many people who deal with anxiety need. So to get a grip, I had to make some changes in my life.

But it really doesn't matter what type of work environment you're in. It's easy to become paralyzed in any setting. And there's nothing we can do to prevent it reflecting on us. Anxiety and depression are not visible handicaps, so we don't get a reprieve.

The simple truth is I never wanted a reprieve. So I tailored my life to my condition and became a better man for it. Think you're like me? Then check out what I do to keep myself level. Maybe it'll change your life.

Don't put yourself in a box.

Easier said than done when you're sitting in a cubicle, but when I was in a corporate setting, I took every opportunity I could to get up and walk around. If I didn't, I started to get nervous.

Today, I take a break from the office at midday and walk my dog. If you have an opportunity to get outside during the day, it's the best medicine for an anxiety-inflicted brain. Between the fresh air, the openness, and the change of focus, it's a great way to put your head back on straight.

If you choose to stay at your desk and fight the urge to get up, you're just fighting your anxiety. And you don't fight anxiety, you suppress it.

Find structure.

Like I mentioned, depressed people sometimes need structure to make things work, especially the anxious ones.

We're a lot like dogs (seriously). Regularity keeps us happy. Variability means we're probably going to annoy you. And we're generally really fun to be around as long as you deal with us in the right way.

So create a life for yourself that's organized. It won't always work, but people who make the effort do much better than those who don't.

Give yourself things to look forward to.

While you're searching for structure, make sure you give yourself little gifts here and there. It doesn't have to be an everyday thing, and it probably shouldn't. There's such a thing as too much structure in everyone's life, so to compensate you have to throw in some random fun to keep yourself sane.

I personally like doing a Tuesday-night happy hour. And who doesn't? But alcohol isn't always the answer, especially for mental conditions. So find some other activities you can turn into a gift and plant them randomly throughout your weeks.

I like to play darts with my neighbors and unwind. I don't do it every day. But when I do, it's like free therapy. Even when I lose.

Have a good friend on speed dial.

If you've never experienced anxiety, depression, or any other form of mental illness, you might not think it's even legit. And that's okay. I've run into a lot of people like this. I used to be one of them.

The problem is that such thinking makes it really difficult for those who do suffer from anxiety to cope with it. Because nobody really gets what the hell is going on.

What I do is rely on someone like me – a friend who deals with the same crap I do – to talk me through any temporary lapses I may have. Because having an anxiety disorder is a lot like being an alcoholic. Unless you suffer from the disease yourself, it's really going to be hard to talk someone down from an attack when you don't know what terrible feelings they're stuck with.

This person could be family, a friend, or anyone, but whoever it is, make sure they're reliable. There's nothing more frustrating than putting your faith in someone who can't deliver.

Rules Make Me Tired, and Other Things Penelope's Boys Taught Me

Last night, Penelope had a dinner date, but nobody to watch her children. So being the great co-workers that we are, Ryan and I put Cinco de Mayo on hold and spent an evening getting to know her two sons. They're both very smart kids, and I learned a lot from them—a lot about leadership, surprisingly enough.

Eye contact can make or break your message.

Like all older brothers, Penelope's older boy would not stop picking on the younger one. As often as I would say "Stop," sure enough, two seconds later they were back to wrestling on the floor.

Why wasn't this working? My approach sucked. I was on the other side of the room, eating a buffalo chicken salad. I might as well have sent him an email saying, "Stop picking on your little brother."

So I decided to get up and look him in the eye. "Hey, I need you to calm down, and leave your brother alone."

"Okay," he said. And he did.

Think about the last time your supervisor criticized you from a distance. Was it effective? Probably not.

The best way for a leader to make an impression and affect some change is through face-to-face interaction. Otherwise, all you're saying is that you really don't care that much, at least not enough to cowboy up and put your foot down like you mean it.

Reverse psychology works…sometimes.

We spent some of the night outside playing with my puppy. The kids loved it. And I figured I was both keeping the kids occupied and tiring out the dog before I put him to bed. Great productivity, right?

Eventually it was time to go in. Luring kids back inside was about as hard as the puppy. So I figured I'd do what I usually do for the puppy, lure with food.

I told the kids that maybe there's ice cream in the freezer and that we could have some if we went in. Instant success.

It turns out there was no ice cream, which sucked because now I had kids on my hands who wanted sweets. Back to wrestling–but you get the point.

Okay, calling reverse psychology "leadership" sounds a little twisted, so think of it as offering rewards for doing something you know your employees don't want to do.

Maybe let them go home early if they meet a tight deadline, or you can buy them lunch. Get creative. Just make sure you can deliver. Because like a kid who doesn't get his ice cream your employees' disappointment will not be good for you in the long run.

Know when (and when not) to check in.

We finally got the kids to calm down by putting on an episode of Scooby-Doo. And Ryan and I took that opportunity to go in the other room to relax.

Five minutes went by and I felt the urge to check on the kids. Things sounded pretty quiet, but when you're 24 and you have no idea how to deal with kids, you check in a lot.

The moment I walked in the room, the puppy followed. And with the puppy comes playtime, again.

If you're a manager, it's good to check in on your employees. It shows that you care, and it keeps them focused on what you want them to focus on. But don't overdo it. Too much distraction will pull anyone off focus. Know when to back off and let things be.

Rules are good, but not too many rules.

Penelope's younger son wanted to climb up on the counter and get a cup. I said he wasn't allowed on the counter. When he asked why I said, "It's against the rules."

He said, "Rules make me tired."

And you know what? That's true: rules make us all tired. So one key to being a good leader is knowing when to bend or break the rules. If you're cringing right now, just hear me out.

A manager's best workers already know when to bend or break a rule. They know that to get the job done the way you want it, protocols sometime have to be modified.

You should know when it's okay too. If the employee is doing something dangerous (like getting up on the counter) stop them. But if they're doing something harmless and it's going to help deliver something great, maybe you can make an exception.

I'm no expert on management. I'm no expert on babysitting kids either. But I know that good leadership requires a manager to understand the behaviors of others, even if they don't make sense to you at all.