Taking the Captain’s Chair

It’s been a little over a month since I’ve left my full time job.  I’m slowly discovering how to live a life that is sustainable both financially and for my well-being.  For the record, I am still not where I want to be yet, there are days when I get overwhelmed with how much I need to do, and there are days when it’s just not fun at all.  There are not, however, days in which I regret leaving my job.  More about that later.

Capdan Picard

Capdan Picard makes it so… frightening.

One of the interesting shifts in my life has been the new role of leadership I’ve taken on.  I no longer have the “luxury” of sitting back and letting someone else choose the direction I should be going.  I now have to choose my own path and make it so, or else nothing gets accomplished.

Back in 1999 I was working over the summer at Sesame Place.  The previous two summers, I had played in the park band, the Sesame Brass, and this year I was hired back as the band captain.  This was mostly more of the same stuff I had done the last two years, with a few new responsibilities thrown in.  Without going into too much detail, it was one of the most traumatic summers of my life.  I was unable to balance my role in what was essentially middle management with the relationships I had with my coworkers from the previous summer.  Add to it teenagers, drama, and clashing egos, and I vowed never again to work in a place where people above me told me how to treat people below me.

From that point forward, I avoided leadership roles in the jobs I took, instead choosing jobs in which I had a specialized skill-set that often translated to a moderate level of autonomy.  Looking back… wow, that was almost 15 years.  Thanks Sesame Place!

I even avoided leadership roles in music.  I played in a series of different groups in which someone else wrote the music (for the most part) and someone else booked the shows.  Certainly I added my own flair and intuition to whatever I played, but I was a far cry from directing any of the ensembles or bands I was playing with.  Whoever happened to book the show determined the time, location, and pay.

When I started performing my own music about 5 years ago, it’s true I was leading the band… but it was a band of one.  And man was I a taskmaster to that one lazy band member!

In more recent times, though, that has had to change.  While I was still taking orders at my old job, I began doing a lot more booking for the different groups I played in.  As I was playing mostly as a side project to my full-time employment, I wasn’t so worried about money; rather, I wanted to just get out and play with as many different groups as possible.  So for my songwriting project Neon and Shy, I would call the venues, book the shows, and (often) become intimate with the cold gaze of rejection.  I began to make connections to book events for  Four Lads Insane (Bowie tribute), Three Men and Three Women in Black (Johnny Cash tribute), and Late Night Double Feature (Rocky Horror meets Rocky Balboa tribute).

PolkadelphiaProbably the biggest change for me came when I formed the modern polka band Polkadelphia back in March.  For the first time, I was leading a band that involved other full-time musicians. Just like my time at Sesame Place, I found being squeezed between two groups of people: this time it was between the musicians in the band and the venues that want us to play.  The squeeze comes when I have to choose between pushing a venue to pay us what we’re worth, or turning around and asking my colleagues to play a show for a wage that is an insult to their talents.

The big difference for me is how much control I have in this situation as opposed to as a 21 year-old at Sesame Place.  I get to choose the venues to play at, I get to choose what we should earn, and I get to decide whether to stand my ground or find some leeway.  Half of it is dizzyingly scary.  I can’t tell you how many times I have paused before emailing a quote for the band, steeled myself, held my breath, and tapped the send button.  However, I am equally elated when the client or venue comes back to me with respect for the number that I believe we should earn.  Because not only does it tell me that I’m on the right track, but it gives me the opportunity to tell these people that I play with how much I respect what they’re doing.

Around the time I left my job, I also started getting more freelance computer gigs.  A client would ask me the process for going about distributing video online, and with this kind of stuff there isn’t a manual or a standardized best practice to reference.  I’d have to decide the best plan of action to accomplish what they wanted to do, then help the client to follow that plan of action.  Once again, it was scary to have to put it all on the line, but ultimately rewarding when it worked the way I anticipated.

This became especially magnified when working with my first web design client.  This time it wasn’t just a singular component I had to plan.  I had to solicit my client’s vision for what he wanted his site to be, and temper it with my own design sensibilities and the limitations of the medium.  There was a lot of back and forth about certain web components that I was convinced would look better one way versus another.  I was able to present my image of how his website could look its best, and we found common ground in the few places we disagreed.  There were scary moments in which I didn’t know if I would ever finish the project or even overcome a simple obstacle like lining up all the text in one area.  However, my previously acquired computer skills, my eye for the aesthetically pleasing, and my understanding of organizing content all came together to make our vision a reality.  In fact, today we just launched the new site over here.

So back to why I don’t regret leaving my job.  There are plenty of reasons I feel this way, but probably the biggest has to do with how I’ve revisited the role of leadership in my life.  I’ve taken everything I’ve learned since 1999 and beyond, and crafted it into a way to direct the projects in my life.  This time around I’m making sure that I have both control over the types of projects I lead and mutual respect within the projects I’m leading.  The most exciting part is finding that I don’t have to just be in charge.  I can also, dare I say, enjoy it.


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