How to start a company from your cubicle

Since freshman year of college I knew I wanted to be an entrepreneur. I created my own major called entrepreneurship and I swore off working for "the man" forever. Turns out, it's not as easy as it sounds.

After college, I got a job with IBM Consulting. My plan was to get some real world experience for three to five years and then start a business with the connections I made and the knowledge I gained.

Things didn't go as planned. I wasn't learning all that much and I had plenty of extra time in my cube at the Pentagon. So I started a blog…I mean a business…I mean a blog.

Anyway, here are five important tips to consider if you are trying to start a company from your cubicle.

Be patient

Far too often I talk to people who have an awesome idea for a great new website, product or service. They are always excited and sometimes, the idea makes a lot of sense. But for one reason or another, they seem to give up on that awesome idea in a couple of days and tell me about their new awesome idea the next week.

No matter how amazing an idea you have, it takes time to grow a business, or to grow a blog for that matter. The only idea Ryan and I had was to write about entry-level jobs and to occasionally chime in on the "Gen-Y" discussion. It wasn't much of an idea, but we stuck with it. One thing led to another and we started a company based on that stupid little idea.

So be patient, remember it's not the idea that matters, it's the execution.

Be Realistic

Starting a company is not easy, especially when you're in your twenties. Be realistic about how much time and effort you can put into whatever you are trying to start. Working 40 hours a week at a job and 50 hours a week on the side is probably not good for your health and it's certainly not good for your social life.

If you have a decent idea and a good team of people, don't worry about getting everything done in a month or two. And whatever you do, don't quit your day job until you know it's time. I can't tell you exactly when you will know because it depends on your tolerance for risk. But when the time comes, you'll know.

Be a "B-player"

If you want to climb the ladder or even job hop in a particular industry then you need to be an "A-player." But if you know, deep down, that your job is not for you and you WILL start your own company, you have to learn to be a "B-player."

Do the work you are assigned and do it well. If you're trying to start a company there is no need to go above and beyond at work. Asking for more assignments or staying late on the job will only take away from the time you have to get your business off the ground.

But beware, this is a tricky way to play the corporate game. You need to be sure your social skills are sharp. Make sure everyone likes you, especially the boss. Go to all the social events, eat lunch with your team and be yourself. People perceive you as a great worker if they think you are a great person. And perception is often more important then reality.

So sharpen up your social skills and do what you're asked. Remember, a "B-player" is still above average.

Don't be afraid to work on the job

If you're an entry-level worker, and you take my advice about being a "B-player," you will inevitably have down time on the job. I'm sure older workers are shaking their heads at this, but it's true. Nearly everyone I know who's not on Wall Street is bored to death in their cubicle at one point or another.

If possible, make use of that down time and do something to get your business off the ground. When I was negotiating with Penelope about the equity structure of Brazen Careerist, we had some pretty heated discussions. For a couple of weeks you could find me in the courtyard of the Pentagon, in 90 degree heat, in a full suit, pleading my case and discussing the future company.

It's funny to look back on, but I got my job done and I did it well, even if I spent a few minutes on my "other" job.

Get Lucky

You can have the best idea and the best team. You can be patient and you can follow all of this advice. And there is still a damn good chance that you will never start a company while you're working in a cubicle. It's hard and it takes a huge amount of luck.

I totally lucked out by emailing Penelope at the exact time she was looking for someone to write a twentysomething column. We lucked out that a Wall Street Journal reporter wanted to cover our blog after two months. I'm not naïve, we have been really lucky thus far.

But you know what they say, luck happens when preparation meets opportunity. So know what you want to do and prepare for it, because you never know when the right opportunity will arise.

Going home for the holidays, where everything stays the same

There's only one thing scarier than change. And that's no change at all. A lesson learned as I visited my hometown in New Jersey this past Thanksgiving.

I couldn't have been more happy to visit home. I spent the majority of my time catching up on the past two months I've been away, and I shared my chaotic life story with my curious family and friends.

I spent a good amount of time with my friend Kevin. He's always been the kind of guy who knows what he wants in life.

Kevin has lived in our hometown for the entire ten years that we've known each other. It's possible that he'll never leave. He likes simplicity and comfort. Part of me has always admired that about him.

On the eve of Thanksgiving the bars were jam-packed with familiar faces. High school friends, now emerging adults, returned home with new lives and new stories.

Some of those people are married, some are in grad school, others haven't even left town at all. But no matter what their tale, I can't help feeling that they're still the same old person I knew back in the day. When you're back in your home town, it doesn't really matter what you do somewhere else.

I made a point to have lunch with my old co-worker, Janet. She was awesome to me when I was in the corporate world – one of my first real-world mentors after graduation.

Over a great Italian meal (something I still can't find in Madison), she filled me in on the office politics. It still amazes me how quickly people come and go. Firings, transfers, promotions – I often wonder how anyone could make a legitimate personal connection in that world.

Still, part of me misses the structure of it all. Nine-to-five isn't all that bad when you consider the ambiguity of time when you're an entrepreneur. But entrepreneurship also has its benefits…

One of the highlights of my trip back was visiting my friendly neighborhood coffee shop, CitiSpot. I've yet to find a place that knows how to make a cup of joe like CitiSpot.

It was my home away from home before I headed to the Midwest. Every afternoon I headed to the small, side-street shop, grabbed my fix and sat down for a session of productivity I've yet to find anywhere else.

I'm lucky enough to score my "money" seat all week. It's right in the center of the room, which is usually not my style. But at CitiSpot, it's exactly where I want to be. I'm a different person there.

Around three-thirty in the afternoon, the teenage crowd rolls in. Schools out and they're standing outside drinking coffee and smoking cigarettes – typical "cool kid" stuff. I laugh. I used to do that too.

And maybe that's why I'm so comfortable there. Nothing ever changes. There's something unusually reassuring about that.

And yet, I recognize that I can't always live in this state of ease. Ultimately, the well always runs dry.

So I spent my last night in Jersey doing what's typical for me and my friends – a couple beers and a good movie. It may sound like a waste to some people, but to me, it's perfect.

I know that the next day I'll get on a plane to Madison and go back to startup life, which is less ordinary and far more complicated than anything I have ever experienced before. A little bit of normalcy is okay for one night.

A Millennial's Muse – Part 7: The Corporate Tornado of My Life

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 Millennials,

"Burrrr," said the Jackie

You can take the girl out of Florida, but you can't take the "I get chills from ice cream" out of the girl. Immersed in the viscous territory of winter, I attracted attention at work as the girl who wore her coat all day. People would walk by my cubicle and do a double-take, offering a "Yeah, that's a nice coat and all, but why are you still wearing it?"? look.

I read their silent judgments – those warm blooded bullies – and countered their stares with, "Ok, I'm from Florida, and I'm having a hard time adjusting to the weather…alright?!"

I self-diagnosed myself with Seasonal Affective Disorder. Snow flurries can be agents for sadness. I also harbored cheetah envy since I could no longer run through the National Zoo in the mornings due to frigid temperatures.

Corporate America – On the Rocks

Not enough that I had to work on President's Day (in the nation's capital – talk about sacrilegious), but the heat hadn't been turned on during the weekend, which produced the coldest temperatures DC had seen that winter.

On Monday morning, the office was an icebox. People were wearing their coats and scarves as they went about their work, and the security guard in the main lobby manned her desk in one of those fashionable hats with ear muffs attached. My sentiments to the rest of the company – welcome to my world. Who's making fun of the Florida girl now?

People were complaining and I thought it a prime opportunity to realize one of my many goals: fighting in the name of a good cause/inciting a riot so we could go home. I've always wanted to be chained to something, chanting, "Heck no we won't go!" on the premise of some moral principle (I'm 100 percent serious).

I was about to start rallying the troops, but then I heard that there was a sponsored breakfast and all were invited. I'm a sucker for a bran muffin, I'll admit it.

A Loaded Gun

After an all-day client meeting, Magnum and I took the out-of-town visitors (thorns in my bum) for dinner. Magnum and a martini were a dangerous combination (and I thought I was a lightweight).

She became loquacious, loud and was calling me "Boo-Boo" by the end of the night. After dinner, we dropped the group off at the hotel, and Magnum suggested that she and I continue drinking. Hail to the chief I did.

Secrets were shared, many laughs had and by the end of the night we were crying to each other about not being able to find guys that could compare to our fathers. I tried to pick up the tab but Magnum said, "Honey, come on, we're expensing this sh@! to the client." So much to learn.

Pistol Smoke

Magnum finally did it; she shot someone. Dark-humored Dan was unexpectedly fired while I was picking up office supplies at Staples – story of my life.

When I got back to work – 3-ring binders and alphabetical dividers in tow – his computer monitor was blank except for a flashing cursor. I thought it was strange, but I was eager to assemble the new organizational object of my affection so I didn't give it much thought. Toward the end of the day, Magnum called me into her office and broke the news.

I took it pretty hard. Speechless sounds about right. I felt like the last remaining person held captive in a stand-off. How could he leave me alone with an armed boss? How could this happen when just the day before he asked me:

"Hey, want to go jump in front of a bus with me?"

"Public or charter?" I questioned.

"Which ever one is bigger," he said.

He was my "boy" and the levity of my day, so I worried that my job would become completely dull and void of laughter. Naïve me didn't realize that upon his departure, I'd be assuming all of Dark-humored Dan's tasks in addition to my own. I soon became real tight with a phenomenon known as overtime – coming in early, working through lunch and growing bitter quickly.

Looking back, I learned more about the association industry, the competencies of my position and my work ethic (huge) in that intensely tumultuous time. I literally had to comb through Dark-humored Dan's desk and return countless phone messages he ignored, rectify invoices he buried under file folders (un-alphabetized…) and try to make sense of rampant post-it notes.

Work Makes Me W(h)ine

You know you've had a bad day at work when you're walking home, pass a wine store with a sign outside boasting a free tasting at 5:30 p.m. and you wish with every fiber of your being that it is still viable at the current time of 6:30 p.m.

I walked inside toward the tasting table where the server says she can offer me a Sauvignon Blanc, a Pinot Noir or a cocktail slushy. "And which would you like to try?" she asks.

"All of them."

On the defensive,
Jackie

What's on your Holiday wishlist?

'Tis the season where family and friends start asking the dreaded question: what do you want for Christmas? I was actually talking to my girlfriend about this and she made a very excellent point:

At this stage in my life I don't need more "things." I'm at a point where I value experiences over things.

Brilliant. As a student of the uber-successful Tim Ferriss I agree entirely that I'd much rather a few bucks towards a ski-trip in Canada over a few bucks towards a new suit. Sure, it's not as fun for parents but its more meaningful to me.

The way I see it, in twenty years I'm not going to think about how nice that jacket looked. Instead, I'll stop and remember the great time I had.

Besides, we have too much stuff anyway. This year I'm going to ask someone to donate to a cause in my name or sponsor my upcoming adventure. That sounds like a pretty good wishlist to me.

What's on yours?

In the midst of selling out, learn to stay true

When Ryan Paugh wrote me a Facebook note asking me to provide tips on "How to stay true to yourself while chasing the dream," I closed my browser and didn't revisit his request for two weeks.

After all, how could I, the king of perpetually selling my soul to "the Man," write anything about staying true to oneself?

In 2004, I was on top of the world. I had just chartered a chapter of a fraternity in record time at Johns Hopkins University, finished a stellar internship at Bloomberg Financial where I rubbed shoulders with the CEO and won the stock market competition, I had a beautiful girlfriend, a job offer and I hadn't even started my senior year.

Yet, there were things I forgot along the way. As I tried to be "Mr. Perfect," I started to call my family less. I became more concerned with myself and my needs than those of others. I lived to add titles to my resume and to win every opportunity possible. And for what? I don't know.

It took selling my soul to a man who wouldn't take it: Bill George, before I started realizing the importance of being truly authentic. In working with him I was able to begin applying his tools and bring meaning to my life again.

Get to know yourself:

Where is your favorite spot in the world? Wherever it may be, mentally place yourself there and ask what it is you are connected with in that moment. Then, do your best to align yourself with those things in life.

Get Feedback:

Ask others for direct feedback on how they think you're doing as a person, a friend, a colleague, etc. If you don't know anyone who will give you direct feedback, you may need to rethink the criteria you use to keep friends.

Take Risks:

Tell people how you feel and take action. It might be awkward to tell your boss how you really feel about your job, but opportunities will open up when you're willing to step out of your comfort zone.

Have Fun:

Be honest about what you like to do. Do you like eating corn dogs at the beach? Then do it – and enjoy it wholeheartedly. Having fun helps remind us how to keep all the other things in perspective.

Life, as they say, is definitely full of twists and turns. If we are able to stay true to ourselves during this journey we'll certainly have more surprises and opportunities to live for. What's more is that we'll influence more people around us and leave a legacy that cannot be duplicated.

As for me, I have no idea where I'll end up next, but I know that by staying true to what's important in my life, I'll have little problem getting there.