Doing Failure Fearlessly: An Honest Letter on Facing Reality with Confidence

I have now written this article on the subject of confidence ten times in my head. Each version is more positive, more upbeat and, ultimately, less unrealistic than the next. All in the hopes of inspiring others and creating a cheery spin on the subject. So, in the spirit of being confident, I decided to scrap it all and be real with you all.

Enough is enough.

In a time of mass amounts of social change on the daily in politics, human rights, and responsibility, we are finding that transparency is what we’re craving as a society. So let’s just be real and honest with each other, cutting the fluff and speaking from the heart. As humans, the blinders and rose-colored spectacles that we’ve grown accustomed to wearing are now being replaced with precision x-ray goggles. They’re showing us the world, ourselves included, crystal clearly. As entrepreneurs, we always try put out best foot forward, don’t we? We strive for the ideal and reach for project perfection at all times. Weakness isn’t an option, or so we think. We show the best sides of ourselves constantly, the versions that are most desirable, most interesting, most entertaining… the “most” everything.

It is utter B.S.

Conveniently, we leave out the parts that aren’t sexy, attractive, stimulating and people-pleasing. You know, the unflattering truths that truly make us all human. Those extra hours staying up late editing in front of a computer, chipping time away from family and friends for work projects. We stress that our social media feeds aren’t curated enough, running our health into the ground along the way. We worry our brands aren’t growing enough or, on the flip side, growing too fast. It’s become entirely too easy to forget that, at the end of the day, we’re only human. There’s only so much of us to go around.

We, “confidently” paint a curated picture for the world to see, forgetting that we’re killing our truth in the midst. Why? Because we aren’t confident enough to show the unifying reality that is our imperfection. Personally, I look in the mirror, eight years into owning my business and I find myself struggling. I am a bubbly, colorful, extrovert but this year in particular has been a challenging one professionally, personally, mentally, physically and emotionally. It’s been full of huge highs, deep lows and lots of in-betweens. I say this because I know I’m not alone. I’m confident enough to say the following phrase because I think we all need to hear it. Brace yourselves…

It’s OK to not be OK!

Have the confidence in yourself to know that you’re enough, that candy-coating your existence isn’t helping but rather hindering you. As entrepreneurs, we’re all doing our very best, day after day. I know that to be true. No one is perfect and if anyone says they are, they’re lying through their teeth and should shipped off to space! Have the self-confidence to forgive yourself and move forward. No one has all the answers. Not one person has it all figured out. No one is perfect.

At a time when we all are so concerned with what other people think of us, it’s time to look inward instead of outward and know we have had the tools all along. It takes confidence to be honest with yourself but you can do it – I believe in you! It takes confidence to shake off the self-doubt, shame, judgement and all those monkeys living on our shoulders. Have the confidence to fail. Tomorrow is a new day. Take your failures and your missed marks, and turn them into launch pads for feature-worthy work and professional milestones. It’s your future and I know you can rock it!

Anything But Gray Events

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About the Author

Holly Gray
Holly Gray

Holly Gray is the CEO of Anything But Gray Events. The Los Angeles based company specializes in planning and designing colorful corporate, wedding, and social events for creative clients. As a second generation event planner, Holly strives to be an all-around expert in the events field and continues to push the envelope whenever possible. With a dash of sass, a hearty laugh and a splash of bright pink lipstick there you have it! ANYTHING but Gray.

3 thoughts on “Doing Failure Fearlessly: An Honest Letter on Facing Reality with Confidence”

  1. Gloria Mesa says:

    Yes! I often time find myself working extra hours chasing social media and leaving my husband and my dog to watch TV. So sad! I stop myself from doing this. I want to be present for them and for me.

  2. Tracy Bowles says:

    I love your “Honest Letter” article! Thank you for your transparency. I truly relate to this and feel most if not all entrepreneurs feel the same. Thank you for your encouragement and your words of wisdom. It’s ok to not be ok! I needed to hear this.

    1. Holly Gray Holly Gray says:


      You are so welcome! As much as I love to hear uplifting stories, I think it’s also important to remember that struggle is just as much apart of what we do as entrepenuers. The more real we get, there more walls come down and we help each other succeed!

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