Running with the group of friends and collaborators that I do, it’s easy to feel competitive and inadequate quite often. I surround myself with people producing massive amounts of original and creative output every day. Really smart people with really big ideas. But I guess I’ve always surrounded myself with people like that.

In high school, when I got my first guitar, I didn’t bother starting a band with my classmates, no, I, at 15 years old, asked our 27-year-old neighbor if he would be in my band. He was an adult. He had a job and some money and access to better equipment for recording, and he would be more likely to be taken seriously so we could break into the music business. Or so that was my thought process. We wrote and recorded over 70 original songs together (including “Can’t” and “Forgiven”, which I later rerecorded with Tom Milsom and Luke Conard). We planned and partially wrote a musical stage show, and even inquired about renting the main stage at the Chicago Museum of Science and Industry to perform it. But my bandmate moved to California before we could finish the piece.

In college I wanted to start an independent publishing company. So I hooked up with two veteran writers from Chicago and we proceeded to attack the world with words. We opened up an online shop, started publishing original content daily, a weekly webcomic, podcasts, printed quarterlies and distro catalogs. Buttons and plans for posters and shirts. I learned a lot from that process which eventually all came in handy when DFTBA Records was formed a few years later. The publishing company fell apart as profits were close to zero, we under-charged for everything, as we failed to put an appropriate value on our work, hoping the lower prices would lead to more sales.

And now I’m the president of DFTBA Records, a company with well over a million dollars in revenue each calendar year. A company co-owned by myself and two of the smartest and hardest working people I know, Hank and John Green. Yet I still find myself volunteering to take on more work. Usually for less than fair market value for my time and talents. Or for free. I still find myself developing new projects (some successes, some utter failures), and feeling that competitive and inadequate insecurity pop up probably more often then I care to admit.

It’s not enough that John asked me to design all the packaging and most of the collectable memorabilia items in the Fault in Our Stars audiobook box set this month, because Oh! Alex Day released a new holiday single - I wanna do that too! Or, the Project For Awesome is coming, let me volunteer to manage the raffles and the shipping of all the prizes. It feels good to be included and, of course, to volunteer to help out. Or, hey, Lauren Maggiacomo-Fairweather needs a new website design, I’ll volunteer to do that - I make awesome websites!

While I was growing up, my step-dad worked two full time jobs. He did it so one paycheck would pay the bills, and the other was his to blow on whatever he wanted. So not only did we have food on the table and a roof over our heads, but we also had a step-dad who knew how to spend money and have a good time. I guess I always admired that. Sure it was selfish in some ways. Working 16 hours most weekdays, and then spending the weekend having a ton of fun (mostly at the horse track), he wasn’t around much. But it was also very unselfish, in that he made sure to provide for us first, and then work an extra 8 hours a day for his fun money.

I probably take after him more than I’d care to usually admit. I work my ass off most days, even when that cuts into my time with Kristen, or other family and friends. Because not only do I want to (unselfishly) provide a fantastic life for her, but I also want to (selfishly) retire early. Or at least have the option to (over 60% of my annual income gets saved and invested for an early retirement).

But I think it’s starting to borderline on unhealthy. Some days I face an insurmountable To Do list, and occasionally deal with people who are really pissed that I didn’t get something done by the time I said I’d do it. And even when I do decide to do something fun… play Risk, watch a movie, go for a jog, work on new The Caulden Road material… I can’t enjoy it, really, because I know there are other things I should could be doing.

I always have the best intentions when agreeing to take on a project, or do a favor, or whatever. But there are only so many days in a week, and there is always some emergency with DFTBA that needs to be dealt with first. I should remind myself that most people with this kind of workload have full-time assistants to handle all the less-creative work, including all those famous friends I try to keep pace with project-wise. So I should start consciously taking on less. Or hire some eager assistant.

This isn’t a cry for literal help or anything. Sometimes it’s just fun to type into tumblr while waiting for iTunes to finish uploading Matt Maggiacomo’s new album for processing.