September 27th, 2011 | 9 comments | 3Ring Media, Skydiving

In an attempt to reflect on where I am as of right now versus where I thought I’d be when I started on this journey at the beginning of the year, I thought I’d highlight some of the highs and some of the lows I’ve experienced this year. First up, the lows.

As the skydiving season here at CSC comes to a close, the fun jumpers start to dwindle down because of the weather, the weekday business seems to slow down a bit once the college kids go back to school, and, as I have for two years now, I start to panic a little bit.

Last year I was freaking out because all of my new friends were going to New Zealand or Florida or Texas or Arizona or somewhere else that’s bright and sunny and warm. Including the boy. He was slated to go to Skydive Spaceland for the winter, and I didn’t really know what that meant for our relationship. So as season started to wind down, I got a bit worried about what my future will hold. As the story goes last year, I had been talking to an agency in Austin, but I wasn’t sure if this feeling of total fear in the pit of my stomach was a sign to not do it or a sign that I definitely needed to make that leap.

But, I did it. I moved to Austin, dabbled around in the agency world down there, then decided that it wasn’t just my job in Chicago that I didn’t like, but just the way my career was panning out overall. It wasn’t like I hadn’t just worked at two of the most badass firms on the planet (hey Weber and WCG peeps! Love you!) but it was more about what I wanted my life to be about. I had multiple people tell me I was throwing my career away when I quit. That I was on a fast track to success and doing big things in this industry. When I decided I wanted to move on from the agency world as I knew it, I was working 300+ hours a month. 300. That’s insane. Granted it was a very busy time in a growing company, but holy shit it wasn’t what I signed up for. And “throwing away my career?” Really? Life is too short to spend 300+ hours working on something that doesn’t light a fire under your ass, that doesn’t make you want to jump out of bed in the morning, that doesn’t totally make you want to shout from the rooftops about how amazing life is every day.

Then 3Ring Media was born in January. It was legally a company, but I had no idea what it would actually grow to be. It was a first step. Maybe a little backwards from how most people get started, in that they probably have a solid idea, a business plan, and THEN do the whole “I’ll pay to make my company legit now” thing. I just knew that if I wanted to quit my job and move back to Illinois for the skydiving season at CSC, I needed an LLC because I was going to be an independent contractor. That’s how I got on this train of being an entrepreneur.

My post Corporate-America plan was pretty simple: Quit my job before SXSW. Go to SXSW as a “free agent” of sorts, with no company name attached to my badge. Just me. On my own. Doing my thing. Then I’d move back to Illinois (which really could have waited until later in the season because the weather was so yucky but I digress), work with CSC, get their social media stuff set up for success, manage that, put their event calendar together, rock those events, and then head out to wherever we were going for the winter and do it all again. During the course of the season, I’d continue networking and making shit happen so that once winter rolled around, if I wasn’t able to continue working with CSC during the down time, I’d have a big fat pool of potential clients to choose from and I wouldn’t miss a beat on having money coming in.

What actually happened? I did everything up until the “continue networking and making shit happen for 3Ring” until, well, July, when I realized I was about seven months behind where I wanted to be at that point. I hadn’t really done much for 3Ring. I was squatting on a Twitter account, sure, but I didn’t even have a logo, let alone anything remotely close to a product or lineup of services I could offer, or a website to sell said products or services.

Cue panic attack.

From July to present day, I’ve had many a day in the Giraffe (our RV on the dropzone) where I would break down into hysterical sobbing. The dog would be there, sitting in my lap, wondering “okay, what the fuck is wrong with Mommy?” The boy would sit down with me, listen to my hysterical sobbing and ridiculous wails du jour: how I’m going to fail as an entrepreneur and a businesswoman and a skydiver and a person, and then tell me that “we’ll figure it out” and that “good things happen to good people, and baby, you’re a good person. You’re good at what you do and you just need to show that to the world.”

Seriously, peeps. I would land from a skydive, freak out about my performance, set my gear down, then hustle over to the Giraffe and cry. And really, I’m not crying about the skydiving. I’m new in this sport, I’ve come to grow to love the learning curve. But everything else, the fear of failing as an entrepreneur, a businesswoman, a skydiver and a person would just literally choke me. I’m talking hysterical sobbing to the point of not being able to breathe. One sly comment from another jumper, one weird glance after a jump, and I’d totally lose it. The place that was supposed to be my happy place would quickly turn into this really small dark room that I had to escape so I could breathe. But then I’d cry so hard I couldn’t breathe. It grew to be quite ridiculous.

We were doing laundry a few weeks ago and when the boy started putting the folded clothes into the bag, out of order, I had a panic attack. We were in the car on the way back to the dropzone and I couldn’t breathe and I started crying hysterically and when he asked what was wrong, I didn’t know. It was ridiculous.

And it had absolutely nothing to do with the jumping or the laundry. It had everything to do with my own fear as I realized that I wasn’t even close to being where I wanted to be at this point in time. That if CSC ceased to exist tomorrow, I wouldn’t have any other means of getting paid. I didn’t have other clients lined up. I wasn’t good enough in the sky to be an instructor yet. And, being the planner that I am, that terrified me.

But, fortunately, this whole entrepreneur thing isn’t all about soggy Kleenex or the splotchy “I just had a really ugly cry” face after a healthy sobbing session. Really. The highs are high, too. And I’ll cover that part next week when I get back from what may go down as the most amazing week in Sydney’s life as it stands right now. Tomorrow we leave for Colorado to fly with our friends at SkyVenture Colorado, taste as many of 3,000 beers as we can at the Great American Beer Festival, and then, I head out for my first solo skydiving trip, to the Chicks Rock boogie at Skydive Elsinore. All the boogies I’ve been to are the ones I’ve hosted or something that the boy and I went to over the winter. Actually, come to think of it, I’ve never been to a dropzone without the boy. He’s always seen it before I’ve jumped there.

The Chicks Rock trip came up suddenly, which was a difficult decision to make in that I’d be gone on the day of my first 5k. So, while I won’t be running through Bucktown, I promise to get in at least one good run while I’m in California. Maybe I’ll see how far it is to run around Lake Elsinore.

Are you an entrepreneur? Are you starting your own business? What are your lows like? What are your highs like? Why do you keep going?

Tags: Starting my company