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When Your Business Makes You Cry


There may be no crying in baseball, but there's definitely crying in business. That’s been my personal experience anyway, and that of every woman entrepreneur I’ve ever worked with.

Starting—and running—a business is often scary, hard work. The big fears—

Will I fail?

Will I ever have enough time?

Am I missing too much of my kid’s life?

— and the big challenges (finding clients, making money, getting everything done) are real, and you're human.

Your emotions will come out. And if you’re a crier, you'll cry. Also, even if you’re not a crier, you'll probably cry.

And this is okay and normal, so let it out— and try to find a compassionate shoulder to cry on—preferably one belonging to someone who has her own business, so that instead of telling you that maybe it’s time to let your business go, she'll share her own stories from the trenches, which will make you feel better, and then help you brainstorm solutions, which will help you get back up so you can keep on going.

The Pepperlane community provides a particularly convenient and robust shoulder to lean on, so definitely feel free to let your feelings fly here. And for those moments when you’re far from a friend or too weepy to operate a keyboard, try one or more of these techniques:

Remember that you are 1,000,000% not alone.

Every day, at any given moment, people are having panic attacks, breakdowns, meltdowns, fits of vapors, all-out tantrums and secret crying jags about their businesses.

They’re worried about everything from typos to looming bankruptcy. They’re scared because their businesses hold so much—of their money, their futures, their sweat, their dreams—that they feel massive pressure to keep everything safe.

A threat to the security of the things they hold dear will trigger an emotional response, and there will be crying. Totally normal.

Fantasize about giving up.

Sometimes it helps to give yourself permission to just throw it all out the window.

It may not be remotely realistic to actually follow through, but letting yourself think it is can let your body relax because it sees a way out.

The night before my first live event, which was an elaborate affair that had taken months to plan and involved a capella singers and glittery gift bags, my anxiety level had ratcheted up so high that I burst into tears at 11:30 P.M. because I couldn’t get the name tags to print perfectly.

I was on the floor sobbing when I finally called my mom and told her I wasn’t going to the event. She gently reminded me that I was leading the event and that a lot of people were going to be sitting there waiting for me to show up, but I was adamant: if I couldn’t get the name tags right, I wasn’t going.

When I finally calmed down, I accepted the fact that, while I was exhausted and nervous and a perfectionist (and should have made the name tags earlier in the week), I would rather go to the event, even with imperfect name tags, than not.

By opening up my options, however nuts they sounded, I was able to choose the one I really wanted, and move forward.

Go to the worst case scenario.

This may seem counterintuitive, but typically when I walk a client through the scary places all the way to the worst case scenario it ends here:

“And then I’ll die.”

Whether they’re starting with,

“I offered to discount my prices… again!”


“I just lost my biggest client,”

— we move through how one disaster will lead to another until they’re homeless, alone and dead.

Here’s the deal:

You probably won’t die because of whatever feels really hard today.

I am not minimizing the pain and fear of these moments—trust me, I have had plenty of them.

But I’ve found that if you’re willing to face the truth of the situation, to lay out what might happen and be honest about what you’re afraid of, it is MUCH easier to be rational and realistic about it and to decide what to do next.

This is not always easy to do by yourself. That’s why I called my mom. That’s why I work with my own coaches, and why my clients work with me. We’re not supposed to know how to handle everything, and we can’t possibly expect ourselves to see clearly all the time.

Having an objective person by your side, a rational voice that's outside of your own head, who gets what running a business is like and will take a stand for you even when you can’t remember why you started your business in the first place, is invaluable.

Having someone safe to cry to is also invaluable, especially when that someone can help you get beyond the tears and back on track.

Surround yourself with the kind of support that will shore you up when you’re feeling weak and lift you up when you’re ready to reach for the stars again. And keep a box of tissues on hand so you’re ready when you need them.

Jennifer Zwiebel helps visionaries make their dreams real.

The founder of A Place of Joy™, Jennifer works with extraordinary entrepreneurs and thought leaders whose visions can help heal the world, who can SEE what’s possible, and who know they create best with a thought-partner, creative collaborator, strategic planner, and deep-belief-evolution guide. 






Written by Guest Post

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