Working with Penelope Trunk — Tales from a Startup Soap Opera

People ask me all the time, "What's it like working with Penelope Trunk."

I questioned whether or not I should answer that question in a blog post. But what the hell! I gave her some huge leeway with her post about Ryan Healy and me. So here's the other side of the reality-show startup saga that's consumed our lives.

P is a raw, business-driven machine. I'm pretty sure she's a robot. She literally doesn't sleep. I'm not even sure if she owns a bed.

You'd think she would eventually collapse, have a meltdown or something. Well, Healy and I have been here over a month and she's still going strong.

Eight-thirty in the morning – it's time to get to work. Healy and I meet P at Thieves, the infamous coffee shop that headquartered her blogging operation before we came along. And yes, people really do want to murder her there. I find it amusing. Still, it's not exactly prime locale for doing business.

P has already been there for hours, probably eaten about three bagels (it's all she eats) and she's already pissed off anyone looking for a few hours of peace and quiet. We get our morning cup of joe or tea, whatever the lack of sleep the night before calls for, and sit down.

The owners are replacing the art display in the shop and I'm a little irritated. I had been admiring the previous display for a week. It was sort of a dark fantasy world on canvas. And yes. It was predominantly sexual.

"You don't know what great art is," P says.

The walls are now covered with spectrums of neon.

"Now this is great art!" she says.

She explains to me how great art forces me to see the world in a new and interesting way. I watch my favorite piece get packed into the back of a van…

It only took a week before our workdays started to creep from the coffee shop locale to a new site – our apartment. Naturally, that didn't add any normalcy to our lives.

If you know P at all, you know about the time she spent as a professional volleyball player. It's the icing on the cake for any bio she's ever given.

What she doesn't explain in her bio, however, is that she still harnesses her athletic gifts on a daily basis. Only she's not playing volleyball, she's leaping around my apartment like a 5-year-old kid.

If you ever get P on the phone, ask her what the hell she's doing while you're on the line. Chances are its ballerina spins, shoeless skating across a wood floor or handstands in the hallway.

Occasionally P stops by our apartment for an evening meeting. Usually around the time I'm making dinner. She can't get over the fact that I'm a guy who cooks. She calls me gay. I tell her to shut her mouth or she's not getting any stir-fry.

Cooking to P is ordering Chipotle burritos for dinner guests or nuking Lean Cuisines so she doesn't waste away during her all-night work binge.

I tell her about Parent's Weekend at our college fraternity; a 2-day bash that's actually one of the best times all year. She can't get past the fact that we drink with the parents. She's flabbergasted. I wonder what shocks her more, the drinking or the fact that we actually want to hang out with our parents.

If it's the drinking, I totally get it. She can't handle a glass of chardonnay without getting all loopy. How can she even fathom the idea of college-level inebriation?

The parent thing is another story. At the risk of making generational speculations, I wonder if people in her age realm just don't get the bond between millennials and their family. Is rocking out with your kids considered helicopter parenting?

P's college years were far from what I would consider normal. She didn't go to parties and rarely had a sip of alcohol. Her idea of a good time was, as she puts it, "people watching." Which I totally get, but honestly, what's more fun than watching drunk people?

What I really admire about P is her consistent ability to bring out the best in people. The past few weeks have been especially tough for me. I really miss the east coast. So P and I took a walk and discussed my separation anxiety.

We sat in an old Willow tree that arched over the water's edge on Lake Mendota. It was a completely ridiculous location, but sort of standard for our working relationship.

She recognized right away that I felt trapped, that I needed something I could use an escape from the day-to-day startup hustle. So she recommended I do some volunteer work.

I loved the idea.

I almost couldn't believe how easily my angst was laid to rest. It's rare for someone so foreign to influence your life like this. And that's possibly the best part about our working relationship.

A Millennial's Muse – Part 5: Getting a Grip

Here read the true tales of a young twenty-something cubicle dweller by day – dreamer of "there's got to be more than this" by night – trying to find the moral of her everyday story. Walk with Jackie down cubicle lane every Wednesday as she humorously shares the pitfalls and high points of moving to a new city for her first job, building a life post 5 o'clock, and searching for meaning in every crevice of her stu-stu studio.

Dear Fellow Millenials,

Two months into my first job and with a perfect attendance record, I guess I lived up to Allen's definition for success. The remaining 20 percent slice of the success pie (it's always food with me) depended on the most challenging part of my day. Around 5:02 p.m. (not one to linger), I'd wait for the elevator to take me out of cubicle headquarters. There were four elevators, two on each side of the 8th floor lobby. When the bell dinged to signal the arrival of the elevator, I would attempt to turn toward the just-dinged elevator. This was basically a hearing test that I failed four out of five days each week.

I continued to explore my co-worker relationships (good way to pass idle time) and set out to fill the unpaid hours of my life with activities that spoke to the student and hip-hop dancer in me.

Blessed Neighbor

Neighbor sneezed two to three times everyday, without fail, so I began saying "bless you" to break the ice (pacify my superstitious soul) and promote cross-cube dialogue. Each "bless you" made Neighbor laugh. Neighbor said that I was like the voice of God blessing her. Yeah, that's me.

As the sneezing persisted, Neighbor and I got more comfortable with each other. And by comfortable, I mean that Neighbor started tossing Jolly Rancher candies (favorite flavor watermelon) over our shared partition. She became my conscience in a way, where I just vocalized random thoughts that popped into my head.

"I could use some dark chocolate."
"I think I need a haircut."
"I'm especially cold today."

On occasion, she'd briefly respond or grunt. Some people actually had work to do.

Wake up, Little Bossy, Wake up

On the metro heading to work, I hooked my arm around a pole so as not to somersault into the lap of a business-suit clad man (it's happened before) and spotted Magnum sound asleep. I leaned toward her, as far as my grip on the pole would allow, and whispered, "Boss…wakey, wakey." She jumped, blinked repeatedly, and then looked up to see who had stirred her sleep. I couldn't tell if she was smiling or baring her teeth at me like a wolf prepared to attack.

The first sign of Magnum taking a liking to me was an occasion when she called me into her office. I was so nervous that before entering, I (Jewish) crossed myself the way I had seen people do it on TV by way of the Father, the Son, and the Holy Spirit. Desperate times call for desperate measures.

Turns out she wanted to show me a purse she bought on her lunch hour. I thought it was tacky, so I told her she had a really unique sense of style. Magnum smiled to herself and seemed pleased. This began a pattern that would lead to the most critical lesson I'd learn at my first job – do not allow yourself to be befriended (beyond reason) by your boss.

Bros

Throughout the day, Dark-humored Dan and I "shot the shit" as he referred to our exchanges. We addressed each other with masculine nicknames like Champ, Chief, Buddy, Man, Dude, and my personal favorite nickname for the Darth Vader of the office, "oh captain, my captain" (remember Dead Poet's Society?). Dark-humored Dan said that if he was the captain of the ship, then I should have been prepared to drown.

Play Time

Looking back on the things that sustained me during 20 months at a job I largely loathed, it was the structured activities I did after 5:00 p.m. that connected me with interesting people and saved my brain from spoilage. For starters:

-I joined a book club that met once a month at a Mediterranean restaurant. Hummus and prose – fabulous.

-I took a knitting class (jumped on that trendy bandwagon) and eventually finished a scarf during a season that was too warm for neck coverage.

-I did a continuing education class at Georgetown University, learned what a Hoya was, and became the teacher's pet. Story of my life.

-For exercise and family bonding, I took a hip-hop dance class with my sister. The instructor – a choreographer on a reality TV show involving competitive dancing – asked for my number. He called only between 2:00 – 4:00 am. I never answered, but I suspect that he didn't want to take me out to dinner.

When I told Magnum about my extracurricular discoveries, she kept saying that these were things she "always wanted to do." Her unwavering interest unnerved me, so I thought about testing her with something obscure like, "I just found out about this weekly online chat group for people who are into girl-on-girl Tibetan porn…you in?" And if she was game, I'd grab my desk organizer and run.

Happy Wednesday,
Jackie

Enough with the praise already, and start working smarter

According to Sunday's 60 Minutes segment, Millennials are nothing but a bunch of narcissistic, praise hounds who want nothing to do with hard work. Judging by the dialogue we've created on Employee Evolution and the insight of our Millennial peers, CBS needs to do a little more research.

This whole deal about constant praise is getting on my nerves. Who really wants to hear they did a great job on an Excel spreadsheet that took all of 20 minutes to create? Who wants confetti thrown at them by little clowns running down the hall? Do you really want to hear, "Great job today!" before you go home every night? I certainly don't.

Managers, please check the empty praise at the door. Instead, bring your young employees some honest guidance and feedback, and bring lots of it. We're in our early to mid-twenties. We spent the past four years navigating a college life that doesn't even come close to preparing us for the real world. How can we possibly know how to handle new and difficult situations at work? And how can we possibly know if we are doing things correctly without a little help?

Constructive criticism goes a long way. Sure, it's not always fun to hear that I did a poor job of preparing a PowerPoint presentation, but if nobody tells me, how can I ever improve? Managers who are too worried about offering some constructive criticism are not only doing a disservice to their company, but are doing a disservice to their employee's futures. Deserved praise, helpful guidance and constructive criticism all go a long way, as long as you're honest, your employees will respect you. And genuine respect is the only thing that will truly breed loyalty.

Now that we have the praise issue taken care of, let's talk about our lack of work ethic.

It's probably true that kids aren't taking jobs as early as they used to. And yes, this can probably be blamed on the pressures of needing a ridiculously impressive resume littered with extra-curricular activities to get into college these days. But all those team sports, volunteering experiences, business clubs and world travels are breeding a new kind of work ethic. It's called smart-hard work.

If employers took a look around the blogosphere they would find a huge number of 18 to 25 year olds discussing the intricacies of Lifehacking, the art of productivity and the best ways to minimize their times spent checking email. Results are what really matter, and Millennials innately understand this. Being a hard worker is a great trait to have, and it will certainly take you far. But being a smart-hard worker will take you much farther.

A hard worker will work his tail off for eight hours a day, and no doubt stay late to do extra work whenever asked. A smart-hard worker will take advantage of technology and figure out how to get eight hours of work done in six hours, convince his boss to let him work remotely and spend the next two hours updating his blog, making business connections online and going to the gym to keep in shape.

And a smart-hard worker is smart, mind you. So he will work 'til all hours of the night when it is absolutely mandatory to get the job done – not just to impress the boss and get to the corner office.

I admit, Millennials are in the midst of adapting to the real world, and it's no easy transition. So give us feedback, give us guidance and please tell us when we did a bad job. We want to learn from the people who have been in our shoes.

But don't forget to notice our knack for efficiency, productivity and ability to work for results rather than hours. It's all about getting the job done and having a life. People have been trying to figure out how to do this for years; I think we're finally on the right track.

Welcome, 60 Minutes viewers

If you're visiting after viewing the "Here come the Millennials" segment on 60 Minutes tonight, welcome.

Employee Evolution was founded in March 2007 as a work-related blog, by young people, for young people.

This blog is part of the Brazen Careerist community. Brazen Careerist elevates the voice of Millennials to highlight our vision of the new workplace; we match top young talent with the people trying to reach them.

We also help companies successfully recruit and retain young people. Brazen Careerist has a track record for helping companies shift their way of thinking to make themselves more appealing to the workers they're trying to reach.

BrazenCareerist.com will be launching in the next few weeks. To get in touch with us, please contact me at ryanhealy@employeeevolution.com.

If you're interested in reading more from Employee Evolution, here is a quick overview.

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Boomers are reinventing retirement, I'm going to bartending school

Millennial praise; less confetti, more counseling

How Gen-Y is decentralizing corporate America

The safe route is overrated

Reject mediocrity, embrace productivity

Be responsible, go back home after college

Searching for a reason to be loyal

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5 Things You Can Do to Finally Grow Up

I never thought I'd see the day when I told myself it was time to grow up. After graduation, I tried so hard to cling to my college mentality, visiting friends and doing "college things" again, but ultimately I needed a reality check.

"You can't live this way forever." I told myself. "It's time to start acting like an adult."

So I did…sort of. It's more of an ongoing project of mine. Each day I try to do something to improve myself, but it's no easy feat. Especially if you loved college as much as I did.

So whenever you're ready to take the plunge, here are a few things I've been doing to forget about college living and move onto adulthood:

Get up in the morning

Mornings weren't my thing in college. Truthfully, they still aren't.

Unfortunately, the adult world could care less. It doesn't operate on the out-all-night, sleep-all-day mantra of my college years.

So I'm training myself to be an early riser. I fell off the horse today, as slept in until 10. But I seldom wake up any later than 8:30 anymore.

After awhile it just happens naturally.

Take care of your body

The closest thing I knew to a healthy snack in college was the celery sticks I got with my buffalo wings. And that ain't good.

Now that I'm out of college, I'm extremely conscious of my diet. And I also exercise regularly.

Not only do I feel better health-wise, but the boost in energy makes me more productive and more engaged when it comes to work.

Go on a date

Put a flock of horny college kids in a crowded place, add music and booze; and what do you get? The closest thing to dating there ever was before graduation.

Real dating is somewhat of a challenge when you're used to the sleazy nature of college life. But I think I've figured it out.

Meet people outside of the realm of bars, clubs and parties. When there's no drinking involved, you hold a better chance of making a real connection. And that's what real dating is all about.

Make new friends

You're best friends can be your worst nightmare when you're trying to transition into adulthood. Not that I mind, but I still get roped into the ridiculous antics I thought I retired from after college.

I learned quickly that a big part of growing up is branching out. Meeting new people is an opportunity to act like an adult without having to live up to the childish expectations of the people who have known you forever.

Of course, you're best friends will always be your best friends. And that's good, because you can't be mature always.

Well, you can…but you're not much fun if you do.

Know how to have a good time

Alcoholic, workaholic, what's the difference? Either way, you're managing your life terribly.

Maturity means knowing when and how to flip the switch between work and life. And it's a big challenge, don't get me wrong.

Make enjoyment one of your top priorities while still remaining conscious of your other responsibilities. If you don't, good times will always take the backseat to the mind-numbing day-to-day grind of adulthood.