Why Carrying a Briefcase Isn’t Necessarily a Sign of Success


Kids, times have changed.

No longer can you tell a successful businessman or woman based solely on what they wear or where they sit in the office. Especially here in San Francisco, that grungy looking guy with ripped jeans and dreadlocks could be the CEO of a multi-million dollar business.

It used to be that the prototype for a successful business was one where everyone arrived at 9, lunched at 12, and left at 5. Today however, that explosive new tech firm may be operated out of someone’s bedroom at any hour of the night or the local coffee shop. Such is the new face of company culture.

These new expressions of the professional workplace can be surprising for people whose formal relationship with “the office” has mostly been informed by television and movies. For a long time, I thought that “the office” was dominated by jammed copiers, stale coffee, and the miserable average Joes working in a very tall, very glass building.

Turns out that my office is just full of weird people who enjoy doing group planks on the hour every hour.

And I love it.

Like many first-generation college students, my parents were none the wiser on what life was like at a white collar job. For them, wearing formal attire to work and driving a nice car were signs of an important person. At my job, there isn’t too much of that going on. But, with these things being the expected signs of success, it goes without saying that my current employment situation is a little… confusing for my family.

Let me break it down for you.

In high school, I was in the top ten of my graduating class. I took over a dozen AP classes and logged more volunteer hours than I can remember. I moved across the country for four years in order to study at a top-notch private liberal arts college where the total tuition cost is enough to buy a nice-sized house for a family in my hometown. I worked all throughout the summer at a number of different internships, meaning that I didn’t make it home too often. I then went abroad for a semester and studied things that I couldn’t study anywhere else in the world. I majored in economics and took classes in statistics, industrial organization, and psychology…

…all so that I could wear Vans and a hoodie to work every day?

Where did they go wrong with me?!?

Well, nowhere. I have a position at a great company on the fifth floor in an office building in downtown San Francisco where people get paid regularly and have health benefits and everything!

I understand my family’s confusion. All of that time and money invested and they’re not seeing any tangible, visible evidence that any of it was worth it. I don’t blame them for being confused. I was confused too the first time that someone told me that I didn’t have to wear a power suit in order to be happy.

First-generation students (or anyone, really) can feel all out of sorts when they walk into a space that they imagined all their lives only to find that it doesn’t look anything like they thought it would.

So what is a sign of success nowadays?

The truth is that in some places, traditional markers of success have been thrown out the window. When the families of first-generation workers don’t see these hallmarks at the end of that long journey to the land of Better Opportunities, it’s easy to think that the system has somehow failed their child.

I’m here to say don’t fret, fellow first-geners! The system hasn’t necessarily let you down. Success is all about context. There’s a huge difference between real office places and ones that you see on the screen. All of the stereotypical accessories that you may associate with success may not be all that they appear to be. These include, but are not limited to:

  • The Briefcase.

I remember my first big internship. I spent hours shopping online for the perfect bag that was within my price range that showed that I was a competent, capable, and prepared worker. I was panicked when my first day arrived and I hadn’t found a bag. I was so distraught that I didn’t take one at all, not even to hold my lunch in. I literally showed up that day with nothing—no notepad, pens, jacket, paperwork. Nothing.

Imagine how silly I felt when I walked into my boss’s office and saw that her professional gear for the workplace was an old gym bag that she carried all of her files and folders in.

When I get on the train every morning, there are a good number of well-dressed men in ties and women in pantyhose who are rocking the traditional leather purse or briefcase. More power to them. However, there are just as many CEO-looking dudes rockin’ a well-worn Jansport and casually dressed professional women carrying canvas totes.

The Lesson: Professional people aren’t necessarily playing by the rules anymore. Don’t be taken too off guard if you and your boss carry the same beat up old messenger bag into work every morning. It’s not the accessories that make the (wo)man.

Also, I have a friend who carries around a really expensive leather briefcase. Full of comic books. Anyone can carry around a fancy bag, or not.

  • The Suits and Ties.

Once, I was at Dave & Buster’s and the guy who cashed in the tickets at the check-out booth was wearing a three-piece suit and a silk tie. Another time I interviewed at a big-time software company and my interviewer was wearing a T-shirt, skinny jeans, and neon Nikes.

No, these two hadn’t switched places for the day, and this isn’t a scene from a weird dream where everything was backwards. This is the reality of the city that I work in. Depending on your industry and the culture of your city, it may be the senior staff that’s in cut-off shorts and your barista in the button-down and sweater.

The Lesson: You may have to shift your views of what successful people look like in order to get the full experience of working at a company. Try not to judge an individual based on what they wear to work.

  • The Corner Office With a View.

Some of the coolest companies that I’ve worked for didn’t have “prime real estate” offices for anyone at the company, no matter how high up they were. A lot of the time, the office was one giant open floor plan with dividers that gave different teams and individual workers their own space. One office that I worked in was actually a repurposed three-story Victorian house that The Grateful Dead used to live in. True story!

Both types of work spaces handled millions of dollars a year and were super productive places where I learned a lot about my industry. These were a far cry from the skyscrapers that some of my friends worked in, but they were just as legit.

The Lesson: Movin’ on up ≠ Deluxe office in the sky.

  • The Ominous President or CEO.

Remember that grungy dude from the train? Who ended up being an employee at your office? Who sits in the cubicle next to you? Who offered you a beer on the first day?


Yep. That’s him.

In the media, the head of the company is portrayed as the workplace equivalent of a high school principal. Just the thought of being sent into his or her office struck dread into the hearts of students everywhere.

I don’t know about you all, but I’d take a personable CEO over a fear-figure any day.

The coolest thing that I’ve noticed about shifting office cultures is that at some companies, the CEO is right there working the floor with everyone else, offering high fives and sharing funny videos. The saying “we’re all in this together” is so much more believable when you can actually see, hear, and talk to the faces behind the brand.

If you have your eye on this prestigious position, don’t think that you have to be the aloof and all powerful god-like man on the top floor. You can work side by side with the people that power your machine and still be respected.

Bonus points if you bring donuts.

The Lesson: Success is measured not in what your position is, but what you do with it.

  • The Arrival Time.

If you’re not one of those bright and early people, then you’re in luck. With changing workplace tides comes a later start time for companies that don’t believe that the early bird necessarily catches the worm (Did you really think that there was only one worm?).

I once interviewed at a company that apologized profusely for scheduling me at such an early time. It was 10am.

These days, I get to work around 8am. Some days I even show up at 7, while others arrive at 9. My roommate goes to work any time between 6am and NOON. Really. She is no more or less important than her coworker who gets there at 5am or their boss who strolls in around 10am.

Something that we all have in common is that we try our best to produce quality work that’s on time. I’ve learned that it doesn’t really matter what time you get to work, as long as you get your work done.

The Lesson: Your arrival time is not correlated to your rung on the corporate ladder.

As the first person in your family to enter the professional office world, you may be surprised by some things in your workplace. Explain to your family that you may not wear a starched white shirt or shiny dress shoes to work. Help them adjust their assessment of success to fit your achievements into their ideals. Definitions of words like “success” are not set in stone. Put your own spin on it and achieve all that you set out to without the restrictions of expectation.

Homework time! Keep in mind that every company is different. Offices range from traditional to casual to everything in between. It’s okay to rock that 9 to 5 life or test out the crazy hours of a caffeine-fueled start-up.

Your new office may be exactly what you expected or not at all. To find out what the status quo is in your workplace, be sure to reference sites such as Glassdoor. Here you can find posts from past and current employees regarding company culture. You can also search for YouTube videos or Instagram accounts managed by your company that will give a glimpse into a day in the life at your new office (and an idea of how to dress/what type of bag to carry).

Don’t be afraid to ask questions. Seek opportunities to better understand your particular office, what is expected from your personal appearance and behavior, and what ways your personal growth will be measured. It may not be a personal parking spot or company credit card that shows you what you’re worth, but the respect of your coworkers, supervisors, and interns that could make your time at a company worthwhile.


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