It’s hard not to be inspired by someone like Shane because he has a new idea to share with me every time we chat. I really liked his idea for Ask Summit and was happy that he asked me to be a part of it. I’ll let Shane and his partner in crime, Andrew Swenson, explain what Ask Summit actually is, but I wanted to share my interview for the project. I answered the question: What do you say to people who tell you that they hate their job.

What really bugs me about people who say that they hate their job is that they take no accountability for making their situation any better. You gotta take charge of your own destiny to make things happen. I talk about this below with Shane …

What do you say when people tell you that they hate their jobs? Any sympathy for their strife? Let me know what you think …

Over time I realized that I didn’t really hate Penelope. What I really hated was my lack of confidence when becoming self employed. Once I figured that out, we became friends.

A friend. Not a mentor. I have learned plenty about myself just from being around her, but I don’t want to be like her. I have a lot of people like this in my life.

Trial and error is my mantra. I’ve always learned things the hard way. It makes sense that I would ally myself with people I don’t typically agree with. Things are more interesting that way, and you learn more too.

When is the last time that you learned anything about yourself without conflict? The biggest lesson that I learned in 2009 was to push back when people are expecting too much out of me. I learned to set expectations for people, and if they didn’t like it, tough luck. I didn’t learn how to do this through someone I wanted to be like, I learned it through people who are nothing like me at all.

In essence, the big epiphany moments, the light bulbs, every “a-ha” was something that I came to when I stepped closer towards people I didn’t want to be like and further from people who made me feel comfortable. Chaos has been my muse, and so far she’s treated me quite well.

Life would be boring without the people that make us tick. They force us to think in different ways because we want to debate their ideas. Some days we win, others we lose. In the end, we all learn something.

I’ve never had a mentor in the traditional sense, and I think that maybe I don’t need one. I’m not the type of person who needs people to hold in high regard. I just need people who push me. And usually the best person to do that is someone who is not very much like me at all.

I’m telling you this because you might spend a lot of time beating around the bush, too. Sometimes we end up hurting ourselves when we indulge in such tomfoolery.

I spent two days in Tulum, Mexico convinced that I was going deaf. I went diving through a bunch of reefs and caves. I was convinced that all the pressure changes knocked something loose. It’s stupid, but these are the kinds of neurotic thoughts I’ll do back flips over on a daily basis.

It took me two days of blue funk to pony up and go to a Mexican doctor. I barely understood his broken English, but he squirted a syringe of what looked like club soda into my ear, then ten minutes later pulled out a ball of wax. He showed me the dime-sized wad before tossing it down the drain and writing me a bill for 1,299 pesos.

The money didn’t matter. The time I spent worrying about the outcome cost me two days of vacation, and that did matter. I could have been sipping tequila on the Riviera Maya—not a care in the world—but I spent two days comatose from my own angst instead.

I want to learn to be better at confronting things early. I want to axe out the stage of fear where I let hours decay while I think about ungodly outcomes. I think if we all learned to do that a little better, we’d be a lot happier with our lives.

Sure, it’s quite possible that you’re the ass-kicking lord of confrontation—by god you better be blogging and sharing some of that wealth—but I’m not. And if you’re anything like me, please raise your glasses, then go schedule some time to reflect on the things you’ve been brooding over for way too long.

Like maybe there’s tension at work and you’ve been avoiding butting heads because it’s unnerving. Confront that.

Or maybe you just haven’t been blogging because you’re afraid that what you say will suck. Confront that, too.

Whatever it is that’s holding you back from living life, unabridged, confront that shit and move on. Once you’re done, you’ll feel stupid for not doing it sooner, but relieved that you finally did.

When Brazen Careerist moved out of my apartment and into a real office things changed, but we were able to adapt. When the business started getting more demanding, we were able to adapt too. Even when we moved into a 900 square foot apartment with my girlfriend, who initially didn’t like dogs, we adapted.

The change that pushed me over the edge was that I felt stuck. Even worse, I felt as if the dog was stuck too. He showed me that he felt stuck by pulling used coffee filters out of the garbage, tossing the grinds all over the carpet or by opening the refrigerator and eating multiple sticks of butter and then vomiting.

Meanwhile, I showed him I was stuck by spending money. Three-hundred dollars a month on average to be exact. That’s chump change compared to what parents spend on daycare for their kids, but for a twenty-something making startup money, doggie daycare is a bitch.

Pun, definitely intended.

When Charlie first came into my life I wrote a post where I said, “you couldn’t take my dog away from me with an army behind you.” I really believed that, and I can honestly say that I tried everything to make it work.

Giving Charlie up was easily one of the hardest things I’ve ever had to do. There are days when I regret the decision. There are even days where I look down by my fireplace and wonder why he’s not there. But I really have to believe that letting him get unstuck was the right thing to do. Hopefully, it will help me get unstuck too.

One of the most important things I’ve learned from being in a startup is to not let yourself get stuck. When people get stuck, businesses fail. Give it the proverbial “college try” of course, but if it doesn’t work, move on.

Such is the same in other aspects of our life.

I was thinking that at the end of the post I might tell you to not get a dog if your life is unstable, like mine. But I don’t really think that’s right. In fact, a dog might be exactly what you need.

When I got Charlie, I was lost in a lot of different ways. I was in a new city. I had been struggling to find meaningful relationships with people. I wasn’t even sure if Brazen Careerist was going to work. Then I adopted a 2-month-old chocolate lab puppy. He didn’t fix any of my problems, but he reminded me to take joy in the more simple pleasures of life—something that I had forgotten.

So who am I to say that having a dog isn’t right for you? During the two years that I spent with my own dog, I’ve experienced so much joy. And even though after two years of fetching, chasing and cleaning up poop our relationship no longer made sense, I wouldn’t trade the time I had with Charlie for anything.

In 2010, I’m going to write more. I wrote a lot in 2009 actually, but most of it was marketing copy for Brazen Careerist. In 2010 I’m going to take things back to a more personal place.

I’ve gone through a lot of changes in the past year, and there’s a lot that you don’t know. For instance, I spent the last year trying to train a dog who knows how to open a refrigerator door. I failed miserably, and a week ago I had to give him away.

I also moved in with my girlfriend, who I’m incredibly in love with. The only problem is that we live in Wisconsin, in a 900 square foot apartment with 1,500 books (mine and hers).

Oh yeah. I spent two days in Mexico convinced that I was going deaf. I went to a Mexican doctor and he pulled a dime-sized ball of wax from my ear. I was fine, and it reminded me to stop being so neurotic.

Those are just a few things that I’m likely to write about.

I thought it would complement all these changes quite nicely if I changed my blog design too (thanks Zerflin). Even though blogging isn’t anything new to me, I hope that the experience I have this time around is as fresh and as fun as the great new look my buddy Benjamin has given to the site.

My goal is to keep writing and keep posting, even when I suck. And hopefully some of it will make you laugh. That’s one of my goals, too.

So here it goes. I’m back in the Blog-O-Sphere.

“Bigger and better things,” is the first phrase that come to mind, though I don’t think that bigger is the word I should use to describe it.

I’m certainly not living in a bigger place. Compared to the dump I lived in last year, it’s actually a lot smaller. And sometimes smaller is what we want.

We just launched the new-and-improved Brazen Careerist—a career management tool for next-generation professionals. It will help change the way people control their professional identity. We’re going to get bigger. That’s scary when bigger doesn’t always mean better.

What I learned from the transition into my new, cozy apartment is that living in a big place might mean living in a dump. It’s hard to maintain and it doesn’t always feel like a home. One of my chief concerns with the new Brazen Careerist was that the same principal would hold true.

But I’m not scared about that anymore.

I spent the last month and a half reaching out to bloggers in our community to ask for help promoting the Community when we finally go live. It’s something we had never done before because we never felt this passionately about a product launch. I figured it would be a challenge, but after sending over 100 requests, I didn’t receive a single “No.”

I’ve always felt humbled being able to say that Brazen Careerist would be nothing without its community. And after experiences such overwhelming support pre-launch, I don’t even care how cliché it sounds when I say it.

And through that I realized why I had been so scared in the first place. Not because the Community was going to get big and clunky—Ryan Healy has been way too anal for that to happen—but because I am going to have to change the way I work as a Community Manager.

I pulled Penelope aside a couple weeks ago to talk to her about this.

“How exactly does a Community Manager scale?” I asked.

“Where does his/her career path lead?”

“Ryan, you’re doing a great job,” she reminded me.

And I realized that I know exactly how to scale my job. Well, not exactly. The Community Manager role in business is still a little young to know the exact path, but I know that it involves growing along with the Community and continuing to be a voice to as many as possible even when that number rockets through the thousands, to the tens of thousands, hundreds of thousands and millions.

Long story short, I know that you’re all going to love the new Brazen Careerist. It’s cleaner. It’s more fun. It’s social media. And the focus is finally right where it should be—on you.

And even though you may be a little shell-shocked at first—like my girlfriend feels about her shoes being housed in the same apartment as my 90lb Labrador—the bigger-and-better Brazen Careerist is going to be everything we promise that it’s going to be. And I’m still going to do everything I can to be your voice and bug our development team to make the changes you all want to see.

If you haven’t already checked out the new Brazen Careerist, please go take a look. And if you’ve never joined, now is the perfect time to go become a member.

Our Community Feedback group is open and for business. Let us know what you think!

The room was a can of sardines, but more optimistic. Tangled in a motley web of businessmen, congressmen and college students, we parked it next to a middle-aged bald guy. Pulling out a shot glass from his jacket pocket and slamming it on the table, he asked the barkeep to pour some whiskey.

“Hey,” he said. “Would you guys like to take a shot with me?”

Dan and I looked at one another, then back at the guy. “Sure,” we decided.

“It means a lot that you both are doing this with me,” he said. “I’ll tell you why after Obama takes his oath.”

We sat there, quietly sipped on beers, listened to Biden take his oath, then Obama. Looking over at our friend, I saw tears.

“Cheers,” he said. We took our shots. I forgot what whiskey tasted like midday on a Tuesday. Closing my eyes for a moment, I regained my composure. When opened them, the man was pointing to a pin he was wearing on his chest, a young man in uniform holding a puppy.

“This is my son,” he said. “He died in Iraq four years ago.”

He told us how passionate his son was to go into the Middle East—keen on making the world a better place—only to find himself appalled by how everything was being done. He couldn’t wait to come home and dedicate his life to changing America’s foreign policies.

He never got to do that, but his fortitude lived on through his father. Obama’s Inauguration—in his eyes—was the catalyst for change that his son had dreamed about.

“On Memorial Day,” he said, “do me a favor.”

“Tell my son’s story to someone … anyone.” He just wanted his son’s story to be told. And today, I’m doing the best I can to live up to my promise.

During the month of May, two amazing bloggers, Sam Davidson and Matt Chevy, teamed up to get young bloggers talking about change. I couldn’t think of what to write about. Then I remember the promise I kept to that stranger on Inauguration Day and the lesson that I learned.

It has nothing to do with politics, or foreign policy, or Republicans versus Democrats. It’s about the power each of us has to make a difference today, right now, if we’re devoted enough and perseverant enough to make things happen. It’s a fragile gift, because we never know when that chance might be taken from us.

I’ve been thinking a lot today about the people I know whose dreams of cultivating change were cut too short. Like my friend Kaity, who might have lived on to help save the rainforests if she didn’t die of an over dose two years ago. Or my friend Chris, who would have made one kick-ass electrical engineer if he didn’t die tragically in a fire before he even graduated college. And of course, Sgt. Mark Allen Maida … a total stranger to me if it wasn’t for his father.

As another Memorial Day drifts past, and we all go back to work, school or whatever else we do with our time, let’s try not to forget how easy it is to fall back into idle behaviors. Let’s try to remain focused on the things in our lives that we want to and need to change.

Change isn’t enclosed in bubble wrap. It’s not going to wait until we’re ready to commit. And when the chance has gone, we rarely get a chance like it again.

The coolest thing about being a community manager is that I get to socialize all day. It’s a big part of my job to create genuine conversation. And it reminds me a lot of starting good conversations at the bar.

Social media is a lot like being out in the bar scene. And being an effective social media user is a lot like being an effective bar crawler. It takes enthusiasm and it takes endurance—and all of us have a off-putting experience that we wish we could forget.

Don’t call me alcoholic. I’m not. I’m just being allegorical. And what better to turn into a metaphor than two of my favorite things?

Here’s why effectively navigating the bar scene and effectively navigating social media have so much in common (add your own metaphors via comment).

Know what you want before you try to order a drink.

People who don’t know what they want when they get to the bartender don’t get served. Or get served slowly. Social media users who don’t know what they want before they commit to using social media don’t do any better.

When a new blogger asks me for advice, I ask: “What is your goal for blogging?” A lot of people don’t have a great answer. And a month or two later, 75 percent of the people I talk to have moved on to something else.

Don’t confuse the need for a goal with the need for an end goal. You’re goal will change routinely over the course of your social media use. But just like going out for some drinks, it’s good to set a few expectations before the night begins.

Know your limits.

The good thing about social media is that nobody’s egging you on with shots that you didn’t ask for. The ball’s in your court. Stick to what you’re good at.

You should stick to what you’re good at—at first. There’s an overwhelming conception that if you’re not using every hot, new social media tool you’re falling behind. Erroneous! Starting right now is still considered ahead of the curve.

Take your time. Know what’s going to be difficult to stomach. If you’re not good at drinking Tequila, don’t drink Tequila.

Understand what makes a good cocktail.

My roommate showed me his LinkedIn profile the other day. Under experience he listed “pimp with the most.” So I said to him, “Dude. This isn’t Facebook.”

If you’re going to blend social media with a particular piece of your life, make sure that it’s going to enhance your life, not hinder it. You might as well be drinking a Long-Island Ice Tea in that case. They taste terrible, and they only make you look and feel ridiculous.

A little flair goes a long way.

Ask my favorite blogging bartender, Chris Myers, and he’ll tell you the same. If you want to be remembered, be memorable.

But you don’t need to learn to balance bottles of Ketel One on your chin or tell really amazing dirty jokes— like Chris—to be memorable. Figure out what makes you a fun person to kick it with offline, and translate it into something you can do online.

Know when it’s time to go home.

Oke Atatah isn’t going to use the Internet for the next two weeks. That’s a little extreme for me, but kudos on his part. I put a lot of value in the time that I spend away from social media. Everybody should.

People who spend too much time at the bar are typically called alcoholics. I don’t know what people who spend too much time on social media are called.

Losers? Perhaps, but the point is simple. Social media is a tool for complimenting your life, not supplementing your life.

And don’t forget to have some fun.

We’re all learning that social media is a valuable tool for our careers and our personal lives. Regardless of what you’re using it for, have fun doing it.

If I wasn’t getting a thrill out of blogging, I wouldn’t blog. If Twitter wasn’t such a fun way to connect, I wouldn’t Tweet.

Always be conscious of how much fun that you’re having when you’re using social media. If you’re not having fun, you’re probably not doing it right.

Speaking of bars … Who’s going to a Twestival tonight? And if you’re not going, why?! Click here to check out a list of Twestivals going on in 175+ cites around the world.

If you’re at the Chicago Twestival, keep an eye out for me. I’m looking forward to meeting some cool people from the Brazen World.

A new chapter of NBC’s Heroes started last night. And while most people were cringing to see what offbeat plot twists the writers could possibly err on this year, I was still sitting on the edge of my seat.

Heroes is my guilty pleasure. Even though the ratings suck and critics are cutting the show zero slack, I’m a sucker for good character development. That’s what keeps me watching week after week.

Consider it my inner Gen-Y enthusiast talking, but Heroes has Generation Y written all over it.

Okay, we don’t have superpowers. But it’s easy to see that Heroes isn’t really about superpowers at all. It’s about emerging into adulthood, discovering uncanny abilities and figuring out where we fit in an ever-changing world.

Here are a few elements of Heroes that keep me thinking about the Gen-Y community …

Emerging from the shadow of our parents—following our own path.

From over-protective parenting to attempting to blow up Manhattan, the young heroes on Heroes have some serious mommy/daddy issues. And that’s not to say that Gen-Y parents are bent on world domination, but we’ve taken a ton of heat for how our parent’s have influenced our lives.

Take Noah Bennet—Claire’s Dad—the epitome of a helicopter parent. Or Angela and Arthur Petrelli—so remarkably consumed with their children’s future that they’ve been priming them since birth.

Even Sylar—the uber-villian on Heroes who suddenly became good, then bad again—is constantly reminded by his elders that he’s “special.” If that doesn’t scream Gen-Y woe, I’m not sure what does.

Discovering our true strengths and using them for good (or evil).

We all have the capacity to use our strengths for good or for evil. Yet sometimes doing the right thing is harder than it looks.

Take Nathan Petrelli. He can fly. But his real power is on the political scene. He’s a mover and a shaker, inspired to change the world, but even gets his judgment clouded from time to time …

This season begins with Nathan selling out his friends to the U.S. government as they’re rounded up Guantanamo style. Still, it’s hard to consider Nathan a villain. He’s just lost.

One thing I love about Heroes is that it reminds us how hard it is to flawlessly develop our strengths. We all walk down the wrong path at some point. It’s all just a matter of how far we tread before we realize we need to turn around and walk somewhere else.

We are more powerful together than we could ever be apart.

The biggest flaw of all of the characters on Heroes is that they’re stubborn. Everyone wants to be the hero. And it ultimately makes saving the world a lot more complicated.

As seasons one and two will point out, things get climactic when our heroes finally start working together. This chapter seems to be no different, only it’s their own asses that they have to try and save.

I’m excited to see what happens to these characters as they face adversity together. Maybe Hiro will finally get the reality check he deserves. Because whenever he tries to “save the world” on his own, he screws something up.

Lesson learned: We all want to be heroes. But sometimes we’re stronger as a group than we could ever be apart.

Learning to embrace each other’s strengths to make a difference will be one of the greatest accomplishments we can make as a young, emerging community. And as anxious as I am to see how it all turns out on Heroes, I’m more interested to see how things turn out as Gen-Y matures as a community in the really world.

I guess we’ll just have to stay tuned and see …

I’m impressed by how many ways people can use 140 characters of text. Nothing in social media is as captivating to me as the Twitter phenomenon.

My most recent Twitter obsession? The Tweet Up.

Two weeks ago Brazen Dan put together a killer Tweet Up for Team Brazen and other local Twitterers in the Madison area. The turnout was amazing.

With Twitter’s high-speed approach to consuming information, it’s only a matter of time before Tweet Ups start sprouting up in every major city around the country.

Mainstream? Maybe … it’s hard to ignore the potential.

I’ve read a mountain of posts about how Tweet Ups are a valuable way to network. I don’t need to retell that story. But I do think it’s important to start thinking about how you can make a Tweet Up in your city a success.

The fundamentals.

Propose a Tweet Up in your city. If you don’t have followers in your city, find some first. Make your Tweet sound something like this …

“Who’s down for a #MadtownTweetUp this Friday? Brocach on the Square. RT Please!”

Make your Tweet Up name (Ex: #MadtownTweetUp) memorable so people include it when they re-tweet (aka “RT”). You’ll be able to keep track of how successful the Tweet Up is going to be by doing a Twitter search for your Tweet-Up name.

Take a rough headcount so you know roughly how many people are going to show.

Find a good venue.

Atmosphere is crucial when you’re hanging out with people you’ve never met or rarely hang out with. Make your meet-up spot a neutral environment—something that everyone can enjoy.

The first Tweet Up I attended in Madison was at a piano bar. Low key. Dark. No good.

The last Tweet Up we had was at an Irish pub. Lots of energy. Irish music. Killer!

You don’t want to go to a place that kills the mood to socialize. You don’t want to psyche people out either. Wherever you pick, keep in mind that not all social media heads are known for their offline social skills.

Make things comfortable. Beer helps too.

Call ahead.

How much does it suck when you get to a bar and there’s nowhere to sit? Multiply that woe by the number of people in your Tweet Up and you get a pretty great reason to call ahead.

Name tags, pens, paper.

Name tags are lame. I get it. But at Tweet Ups they’re essential. Fun too.

The best part is putting a face to the name. I finally got to meet @antrover ,creator of the bacon bot (a bot that Tweets you when you talk about bacon). Kind of looked like Jim from The Office (I digress). But I never would’ve known it was him unless he wore a nametag that said “@baconbaconbacon”.

Want to go Twitter crazy? Order a T-shirt with your Twitter ID on it.

Be memorable.

At our last Tweet Up, someone brought stickers and keychains from their company. I thought that was pretty cool. And it was a good reminder of who she was when I followed her the next day.

Even better than company schwag …

Just be candid.

The best way to be memorable is to be as outgoing and as candid as possible.

We have this guy in our Tweet Up group who works for the cable company. I started ranting to him—I mean really ranting—about my bootleg DVR. He told me to Tweet him next time something goes wrong. I know he’ll remember me when I finally take him up on the offer.

Alert the presses!

Andy Drish came into town last week and I was surprised when he told me that his Iowa Tweet Ups were getting media attention. I shouldn’t have underestimated how intriguing Twitter culture can be.

Alert your local papers, new outlets, etc. before any local Tweet Up. Many sources are already in the Tweet-O-Sphere. See if you can find yours.

Sponsorships?

Sure. Why not? In fact, companies and organizations should be leaping at an opportunity to sponsor such a hyper-connected group of people.

Sponsorships pop up in places you’d never expect. Just remember one of the most important rules of social media: Don’t be afraid to ask.

Beyond the Twitter …

Some cool sites are popping up to facilitate Tweet Ups even further. I’m pretty stoked to see what they develop over at Tweetup.com. In the meantime, check out what these sites are doing to strengthen their local Twitter scene.

• Tweetup.org
• AustinTweetup.com
• ChicagoTweetups.com

Who’s going to be the IT hero in Madison who puts together MadtownTweetup.com (it’s available)?

It’s always good to be gracious.

Send some thank-you Tweets after the event. It’s a small gesture that goes a long way.

They’ll remember it. Then they’ll tell two friends, and they’ll tell two friends and … you get the idea.

Before you know it, you’ve got a local social media community that any good social media boy or girl can take advantage of.

And that’s a beautiful thing.