Sharon Fain is a Boss. She runs Right Brain PR and Academy of Handmade. We met on Twitter and shortly after I became the co-leader of Academy of Handmade's San Francisco Chapter. The main reason I love working with Sharon is that she is all business. The first time I got off the phone with her I told my husband, "Damn. Sharon has her s--t together." Whenever I need a sounding board for whether or not I am jumping to ridiculous conclusions, Sharon is there get me back on track. She is most active on Instagram (follow her here), but you can find here all over the place as @academyofhandmade. XO, Caitlin
I've always been a pretty anal planner and my personality is one that tends to believe that if you do the right things and plan well enough, then everything magically just falls into place. WRONG! A chronic pain condition I developed in grad school was my first lesson in You Can't Plan For Everything. Good thing, because when I started my own business (to allow me the flexibility to deal with said pain condition) things not going as planned is just routine. When you are running your own business and carving your own path, your strategies and plans are largely guesses. Educated guesses, hopefully, but still guesses.
In the beginning I would get frustrated when things wouldn't work. I would follow the plan that experts give you (and my own training) and would try to prepare as much as possible. I have lots of experience and education in marketing and PR so I would get annoyed when things wouldn't work in starting a business the way it will often work when a business is already established.
I quickly learned that running your own business, especially one that is much more entrepreneurial, you have to just be okay with things not going the way you plan in the short term, but that doesn't mean you need to give up on the long-term goal. When you are working on a project or something that needs to be done to reach your goal, that's when you power through and zig and zag when things get rough.
For instance, when we had our past awards show it seemed like just about everything that could go wrong did. Our MC backed out last minute, I had an apartment that flooded and I needed to completely move less than two weeks before the show, the awards we made got ruined through no fault of our own, the wifi didn't work the night of the event so taking payments through our sponsor Square became difficult, a sponsor who had promised us VIP bags bailed, the people who volunteered to play music at the event backed out that evening and you get the idea. All of this was stuff I couldn't just be "oh, whatever" about. It was all stuff I had to basically will workarounds into existence.
While these were all "little things" figuring out new ways to go to get to the big picture of an awards show was crucial. Each of these circumstances wanted to make me go into the fetal position in a corner with a baby bottle full of wine and a box of chocolate. Even though all of this was incredibly discouraging and I had to scrap some short-term things, I never gave up on the overarching goal of the show because I knew that this is at the core of my business.
I think that when you get into this, you've got to have incredible discernment over which things are the "small" things that you have to just be okay with falling apart or not working that you just can't force to make right and the things that are the big goals that you can't let die no matter what. Both are discouraging to have go wrong, but only one will kill your business and the other is just a pothole (uh, maybe sometimes a sinkhole!) in the road.