You mustn’t be afraid to dream a little bigger, darling.
— Tom Hardy

Tuesday morning, 11:10 a.m. I’m five minutes early to the World Trade Center, handing over my license and having my picture taken on a card that reads “Conde Nast.” A simple coffee date with a friend of a friend, but on so many levels a highly significant moment. My heart races as the elevator opens and I see the masthead for the publication empire displayed on the wall in front of me. I’m 12 oz of coffee in, but I swear my jitters come only from nervous excitement. I immediately flash back to when I was fifteen, tearing out pages of Teen Vogue for my visual journal in the days before Pinterest (yeah, I actually kept a REAL journal full of collaged pictures of things I found inspiring!)

This is the company that is responsible for Architectural Digest, W, Vogue, Bon Appetite, Traveler, The New Yorker, Glamour, Brides, GQ, SELF, Allure, Vanity Fair, and Wired, among others. The company that has, in many ways, held together the publication industry when many claimed it was failing. Instead, they bootstrapped their efforts to keep it alive and pivoted with the market. Today, they inspire more than 100 million consumers and their portfolio contains some of the most “iconic titles in media.” Even if you don’t read their magazines, you’ve been impacted by the work of this powerhouse, as Meryl Streep so eloquently reminds us in The Devil Wears Prada.


“This… stuff? Ok, I see. You think this has nothing to do with you… because you’re trying to tell the world that you take yourself too seriously to care about what you put on your back… and it’s sort of comical that you think you’ve made a choice that exempts you from the fashion industry… When in fact, you’re wearing a sweater that was selected for you by the people in this room from a pile of… stuff.”


In stark contrast to the high-brow condescension that I remember from the movie, Meredith greets me as I enter the lobby with a giant smile. She walks me through the offices and shows me the closets that contain all of the coveted samples. She points to the putting green in Golf Digest, and rows of wedding cakes in the Brides stockroom. We go up the elevator and enter the window-lined Conde Nast cafe 40 floors up from the ground. I get a spectacular view of lower Manhattan, and Lady Liberty holds her torch in solute to the glossy conglomerate. Sitting down with Meredith, who is the digital editor for Traveler, we watch as a group of fifteen shuffles past. As it turns out, this morning is orientation for a new wave of Conde Nast hires. Coffee and tea in hand, we begin to chat. As she recounts her budding career in journalism, I caught glimpses of a few themes that I absolutely had to share!

Rule of One Degree

"You're usually about one degree of separation away from your idols." These were the famous last words of my friend Kelly who moved to New York in February. I had just finished telling her about my experience so far in the city and my disappointment that you couldn’t just “go to the Conde Nast lobby.” I meant it as a joke, but Kelly goes - “Do you really want to do that?”

She told me that living in New York City has taught her that you’re usually about one degree of separation from most people you want to meet. I think this is also true in small business, and especially with social media. These days, you often have a direct line of communication to some of the most hard-to-reach celebrities in the world.

Before you go and DM George Clooney the love letter you wrote when you first saw him in Ocean’s Eleven (which BY THE WAY, I was actually seated next to his attorney on the flight to New York, so ya’ll, this one degree away is REAL), take a minute to scale it back and think about what else is possible. What about the entrepreneur who inspired you to start your own business? What about the girl in town who you think you could totally be friends with? What about the author of the book you’ve essentially turned into artwork with all of your highlights and underlines? What would you say if you actually could chat with them?

As amazing as it is to connect one-on-one with some of these people, I think the mentality of decided what you would ask is a great practice in perspective. As cool as it was to be in the Conde Nast building, the hours leading up to that meeting were some of the most reflective I’ve had in a long time. Knowing I only had a moment to learn as much as I could, I became selective with where I wanted the conversation to go and what I was trying to get out of it.

We're All Hustling

This was probably one of the best insights I got out of the conversation. Initially, I was curious about how they select content that’s online-exclusive or print-exclusive, but as I heard more, I realized that we’re all trying to figure out what makes people consume digital information. It’s easy to think that the big brands have figured it out, and it’s smart to assume that they’ve captured the best talent to attempt to do it well, but at the end of the day we’re all faced with the exact same problem.

How do I create online content that is both disruptive and relatable?

We’re all trying to figure it out, which includes trying new things. Even though large companies tend to have large budgets, they also have a process of approval that makes it difficult to keep up with constantly changing trends on the internet. When reaching out to companies and proposing partnerships, consider how your unique circumstance as a solopreneur might actually solve a need with a larger company. For instance….

If you notice that their competitors have a podcast but they haven’t jumped on the bandwagon yet, reach out to ask why and see if you can jump in and help get it off the ground. If a new social media platform hits the market tomorrow, ask if they need a guest poster while they prepare new content. It can even be as simple as being engaged with the new ventures of large companies that you love. If they just started a new video series on youtube, consider sharing it on your own channel, leaving a thoughtful comment, and sending an email congratulating them on what may have taken them months to produce and approve. Be creative in the way you pitch partnerships and affiliations with larger companies.

We’re all trying to beat the same algorithms and elicit the same engagement. By contributing in a beneficial way to the goals of a larger company, you show that you understand their end goal.

You may hold more cards than you think.

Preparation = Flattery

When it comes to interviews and meetings, being prepared is sign of respect to the person who is giving you their time. When you are meeting a potential new client or contact at a large company, do your homework. Find out what they do at the company and how long they’ve been there. See if you can figure out where they went to college and if they grew up in the area. Then, create a mental list of questions from there.

Because Meredith and I shared a mutual friend, I had a bit of an advantage going into the meeting. When it comes to an experience you may not have again, don’t forget the importance of your first impression. “Um, so like, do you have a lot of friends here?” isn’t going to feel interesting or relevant, and may cause the other person to mentally check out.

It’s easy in situations like this one to jump right to the point, but if you’re able to first find some common ground outside of business, it’ll feel more natural to speak with transparency when it comes to the questions you really want to ask.

Present Yourself

So to be honest, it wasn’t my first time trying to see the Conde Nast lobby. Before getting to New York, I assumed seeing those kinds of places was as easy as showing up.


Turns out in New York, big businesses enjoy the view from the top, and you can’t get anywhere close without elevator access. Wednesday morning, outfitted in my nike running shoes and black athleisure, I was ushered out of the lobby before I could even ask if I’d found the right building. However, less than a week later, I walked into the lobby with purpose and was treated in a completely different manner.

As someone who deals with visual communication on a daily basis, I should have known. We make assumptions based on what we see.

Brush your hair, pull out your good skirt, and show up. Not that it benefits the other person to see your pulled together wardrobe, but it does something to your self-confidence to put your best self forward and it helps other people take you seriously.

As small business owners, things happen when people take you seriously.

Intentionally Dream

And my parting lesson is this - be intentional with your dreams. Ruthlessly intentional. Own your story and the things that inspire you.

No, I’m not an avid fan of the fashion industry. I couldn’t tell you what stood out this season during Fashion Week. But I know when Jessica Chastain was featured on the cover of W in January 2013, we spent an entire class in design school talking about it, and I decided this industry mattered.

I know that even though I couldn’t get Louis Fili, my typography idol, to answer my email, I got her senior designer to and turns out his work is remarkable. And one day he may be my one degree of separation.

I know that when I took a part-time job as a coffee barista when I was just starting freelance because I really loved making cappuccinos and wanted to get to know people, I met the handsome guy who’s sitting next to me two years later as I write this post.

The most insanely magical things can happen when you do something about your dreams. Just try, and change your course later if it doesn’t work. Put yourself out there, and see if it’s what you thought it would be. When you decide that nothing is permanent and people are people, you open yourself up to a world of possibility.

start here

You may be thinking, “Cool. I’m so glad you know what you want, but what if I don’t feel interesting? What if I don’t know what my dreams are, just that it’s something other than my current situation?”

I’ve also been there. Sometimes our circumstances command so much of our attention that we are temporarily blinded from our imagination. If that’s the case, it’s time for some creative brainstorming. I’ve created a worksheet that will hopefully help you to identify just a few new dreams to add to your long-term goals. Commit them to your memory and begin taking small actions to get closer to realizing them.

Then comment below and let me know your own big dream that makes you most excited!

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