Holly Gray, Events by Holly Gray

Tell us a little about yourself and the road that led you to starting your business. Where does your creative fire come from and how do you feed it?

My creative fire came from the spark of always standing out. As a younger person, it meant being the loudest in the room, coordinating when everyone else matched and raising my hand first. As an older person, my desire to stand out comes without effort. In my business, Events by Holly Gray, this translates to choosing rainbow over white, skipping instead of walking and cake instead of salad. The road that led my to who I am today was not a straight one, but it was well-traveled and so worth the wait.

What was the biggest obstacle to starting your business? What challenges have you faced and how did you conquer them?


DaybreakandDuskThe biggest obstacle for me was continuing to be positive through the ups and downs. I was lucky in that I found clients right off that bat. But, like life,  business comes with highs and lows. In the times when works is scarce, the right clients aren’t coming your way or you feel defeated by self-doubt I always find turning to those around you who bring you up, have faith in you and make you laugh till milk comes out your nose is always key!

What have you loved most about this adventure in being a GirlBoss? What have you loved least Despite the hard parts, how do you keep such a sunny + sweet outlook? Or, on a difficult day, how do you push yourself to keep going?

Well, as someone who, for most of their adult career worked in a room with a desk, an unforgiving boss and a lack of creative freedom, I love that I make my own life. In that I mean, it is all up to me. I make all the rules, do things that way I want to do them and answer only to myself. It is not always easy though. Juggling all aspects of your life and business is not a walk in the park. It’s long hours, many sacrifices and the occasional (depending on the time of the month) crying breakdown fit with a pint of ice cream. The hardest part of being a GirlBoss for me is the lack of security. I am a single women. There is no one else in my life to fall back on financially. I have to make it all work. That is a lot of pressure. BUT, that pressure keeps me motived and very proud of myself at the end of the day when I finally get to hit the pillow at night.

DaybreakandDuskWhat do you see in the future for your business, and how will you get there?

I see growth and moving toward taking on more specific clients and events that fit truly my business model, mentality and aline with my creative vision. Basically, I want to work only with clients who have big personalities, creative minds, a keen sense of humor and who “get it.” I want to know that every client/couple I work with is half human/half unicorn. They are out there, and I will find them.

What the best piece of advice for women who are interested in starting a business? 

Don’t try and do it all for the love of beans! Outsource. outsource, outsource. For me, I am not great with web design and the back end of my website. I have tried and failed. SO, I pay a wonderful women who is great at it (shout out to Parisa of Web Couture) to do it for me. It pays for me to pay someone who is better at it.  I spend less time being frantic about my website which means I can focus on other projects that suite me more. You don’t have to be Super Woman to be a great GirlBoss, you just have to think like one!


What do you wish you had known when you started?

How to be better at math. I know that sounds funny, but it’s true. Math and budgeting is such a helpful skill to have when you own your own business. Of course, I’ve gotten better with it over the years but I still have to take off both shoes to count sometimes…HA!

Holly Gray Vitals

Website: eventsbyhollygray.com

Instagram: eventsbyhollygray

Facebook: Events by Holly Gray

Pinterest: EBHollyGray

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