It’s safe to say that Misfit Conf was the best conference I’ve ever been to (and I’ve been to quite a few). Not only were my fellow speakers amazing and inspiring people, but so were the attendees, and the folks behind the conference. AJ and Melissa Leon put together an outstanding event, in Fargo, ND no less (no offense Greg), and their attention to detail was mind blowing. If you want a great recap of Misfit Conf read Srini’s post on Facebook. I don’t want to recap the conference, I want to explain why I feel lost after such an amazing weekend.

You see, I’m at a bit of a crossroads in my life right now. I run a business that’s currently in a state of ambiguity, but it’s also a business that was previously very successful. IWearYourShirt has been my life-blood for the past 4 1/2 years, it’s changed me as a person, it’s brought about awesome opportunities, helped me meet tons of great friends, let me build a fantastic community, but after this past weekend, I’m lost.

Let’s back up for a minute. In 2007 I left the 9-5 world to start my first entrepreneurial venture. I took a big risk leaving my secure job that I didn’t really enjoy, to do something else, something I thought I was truly passionate about (co-owning a web design company). As it turned out, I wasn’t really passionate about web design, websites, finding great clients, or any of that, I just liked doing it a lot more for my own company than someone else’s. Then, I conjured up the idea of IWearYourShirt and took another risk. Except this risk had a much more profound affect on my life. Since 2008 I’ve been doing something I really enjoy, but am I actually passionate about it? After listening to my new friend Joshua Fields Millburn challenge me to ask new people I meet “What are you passionate about?” (instead of “What do you do?”), I realized I couldn’t answer that question myself. This isn’t the first time I’ve had this feeling, in fact, just a few months ago I was talking with my girlfriend Caroline and confessed that I didn’t know what I was passionate about. I do know that I’m excited by a bunch of things: food, shoes, IWearYourShirt, cars, design, building stuff, traveling, helping companies, my family, cool t-shirts, the city of Jacksonville, etc. But, I’m not sure I’m actually PASSIONATE about any one of those things in particular. And the majority of my fellow Misfit Conf speakers have found their passion and are extremely happy. (jerks! jk…)

So what the heck do I do from here? Well, I’ve had plans in place for the next phase of IWearYourShirt, and I’m going forward with those because I strongly believe in those plans and I love the company/brand I’ve built. But the direction I’m going in with IWearYourShirt, might take a detour here or there. I want to really think about creating value for both Shirt Wearer and Sponsors, and as my other new friend Greg Hartle told me at Misfit Conf, I want to feel like I’m actually contributing something to the world. Maybe that happens with IWearYourShirt, maybe IWearYourShirt is simply a conduite to get me there.

I do know this: I want to write more, I want to ask for help from my peers (I’m looking at you Pam Slim), and I want to share more personal videos that bring you guys along with me on this journey. In the past I would have thought about structuring this in some way, and thinking about optimizing it, but I think that’s part of what’s been holding me back from finding my passion. I just want to share my thoughts, hear your thoughts, and hopefully find my way. I’m guessing there are many of you reading this who might feel the same way, and maybe even some of my fellow Misfit Conf attendees.

Let’s not do this alone, let’s find our passions together.