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Why I Cried in Front of My Interns: My Courtship with Ryan

Last summer, my friend introduced me to a potential client (whom I’ll refer to as “Ryan”). Ryan was a highly-respected entrepreneur who had built multiple million-dollar businesses. He was funny, quirky, and visionary. I thought we were a match made in business heaven.

Ryan and I would talk on the phone and on Skype. I sent him five pages of my ideas, and in our next conversation, he hired me on the spot. I was on cloud nine and excited to get started, and then the next day he broke up with me. Ryan told me that things were moving too quickly. “You don’t just marry the first person you date,” he explained.

Ryan said that he would be talking to several other PR and marketing firms. He wanted to make an objective, informed decision. I told him I understood. I thanked him for his honesty.

When he visited New York a few weeks later, we met up for coffee at the Ace Hotel. Then we walked over to Madison Square Park. We sat next to the fountain, talked about our Myers-Briggs personality types, and then he proceeded to break my heart. “I think you’re great,” he explained, “but these are my reservations about hiring you…”

Essentially, he felt that I did not have enough experience. I had just started my company. He wanted someone more established. It was painful to hear, but I’m glad he was so honest with me. I didn’t have to wonder why it didn’t work.

I went back to my office and explained to my interns what had happened. As I went into the details, my voice started to shake. And then I burst into tears.

Why Crying Is Good

People always say, “Never cry in the office! Suck it up! Cry alone or in the bathroom.” But I don’t care. Crying is good.

Crying is an honest expression of our emotions.

Most importantly, our emotions are our power. For me, the intense power behind my emotions is what drives my ambition and success.

Unfortunately, in our culture, crying is considered taboo. In traditional work environments, we are expected to stifle our emotions rather than express and address them. We falsely perceive those who are tough and emotionally shut down as somehow more competent in business.

Now, I’m not suggesting that we cry in the office all the time. But what I am saying is that your emotions are okay. When you’re doing work you love, and especially when you’re running your own business, it’s only natural to be emotionally attached.

Why Do We Cry?

It’s because we feel so deeply. It’s because we care so much. It’s because that one thing we want means everything to us. I feel blessed to have experiences that move me to tears. Because if I didn’t, what kind of life would I be living?

I’ve always had big dreams. Dreams that were much bigger than my current reality. And that is what ambition really is: pursuing a goal or desire outside of your immediate reach. Whenever this happens, failure and disappointment is always a very real possibility. But that’s okay. Actually, it’s good.

I once heard Cheryl Dorsey, president of social venture fund Echoing Green, say, “If all our investments work out, we know we have failed.” What a wise woman, and what a powerful statement.

What Cheryl meant is that if Echoing Green only pursued investment opportunities where success was guaranteed, her organization wouldn’t have taken any risks. As we know, the greater the risk, the greater the reward. So without taking risks, Echoing Green would have been missing out on the biggest opportunities.

The same goes with your life.

As one of my favorite sayings goes, “If your dreams don’t scare you, they’re not big enough.”

It’s completely true. If you want to reach your full potential, start getting uncomfortable. Start taking risks. Expect rejection, pain, and disappointment. Allow the fear and emotions to run through your entire body, even if it feels paralyzing. It’s part of what it means to be truly alive. In fact, your deepest discomfort signals your greatest area for growth. When you recognize this, your emotions become your most powerful source of wisdom.

Everything Always Works Out

The beautiful thing about life is that everything always works out. While Ryan and I did not end up working together, I’m so glad I had that experience. I learned a lot from my interactions with him. I learned a lot from my pain.

Pain is actually our greatest teacher. As human beings, we tend to learn more through pain than we do through pleasure. From that perspective, the pain of this loss was its gift to me. Not only that, it was Ryan’s gift to me, and I’m grateful for that.

I learned not to put all my eggs in one basket, and I learned that what you think you want might not actually be what’s best for you. For the month of July, I did not pursue any other clients because I was convinced that things would work out with Ryan.

Once I turned my attention away from him, other people started approaching me about helping them with their businesses. As I started talking to these potential clients, I realized that what I was looking for was in front of me all along, and I didn’t even see it.

This is why I love Jack Canfield’s  quote, “Everything you want also wants you.” If something is truly meant to be, it will happen. If you’re truly the best person for the job, others will see it.

Yes, you still have to work hard and show them everything you’ve got, but there is no need to force your desired outcome. Have faith that everything will work out beautifully. Trust that whatever happens is always the best possible outcome, and know that what you are looking for is always within your reach.

Have you ever lost something you wanted so badly that it moved you to tears? Did you later realize that this loss was actually a blessing in disguise? Please share in the comments below!


Selena Soo (founder of S2 Groupe) is a business strategist for personal brands, focusing on marketing and publicity. Through her signature course Elevate Your Brand, Selena loves helping visionary entrepreneurs, experts, and coaches reach more people and change the world. Join Selena’s newsletter for weekly inspiration and tips to improve your business and life.