Reflecting on the first 15 seasons of Olde Towne Carolers!

Caroling season 2019 is finally at an end.  (My last gig of the holiday season was January 7th.)  I still can’t quite believe that we’re wrapping up our 15th season of OTC!  

When I created Olde Towne Carolers, I was still a young soprano in my late 20’s.  Now I’m solidly into my 40’s, and I’ve learned so much along the way of what it means to run a business, how to manage people, and how not to let the stress of a busy season get the best of me. (Well, I do my best with that last one…)

I’ve been doing a lot of reflecting on the life of this business I started all those years ago.  (And imagining what the future holds for it as well!)  Even though some things are always the same year after year (“Jingle Bells” always elicits enthusiastic applause!), there are so many things that have changed.  I thought I’d wax poetic a bit on some of those changes, AND the many things OTC has been through…

– Number One: MapQuest vs. using map apps on our smart phones. Holy cow is this a biggie!  In the beginning, we had to print out directions off of MapQuest before going to a gig.  You had to REALLY pay attention to the names of streets, how many miles until the next turn, etc.  And if you hit traffic?  You had NO IDEA how long it would take you to get to the gig.  You even had to pull out your old-fashioned map once in awhile if you needed to try another route.  And you always had to listen to the traffic reports on the radio.  I do NOT miss those days!  Thank heavens for Google maps!

– We are EVERYWHERE!  (Well, almost!)  I started out with gigs near home, and now we cover the entire Northeast USA (Maryland to Maine) and the greater Chicago area!  When it was time to expand outside the mid-Atlantic region, it made sense to head to my former grad school stomping grounds: Boston!  (Those singers cover new England.)  And after a few members of Olde Towne Carolers moved to Chicago over the years, it made perfect sense to expand to that city, too.  I’m so proud of all of our carolers, and how they are spreading holiday cheer far and wide!  I also must admit that I’m incredibly proud to have such a successful business – it’s very gratifying!

– I used to have a part-time job AND teach voice lessons during December – hahaha!  (Gotta laugh some more; hahahahahaha!)  Let’s just say that Olde Towne Carolers has grown so much that it’s pretty much a double full-time job during the holiday season.   Emails, contracts, invoicing, payroll, singer assignments, AND SINGING ACTUAL GIGS!  I’ll admit that sometimes the stress of it all gets to me, but stress is different when it’s your own company.  Each season, my goal is to manage stress in a more healthy way.

– Unfortunately, in the business world some things have changed for the worse.  There are way more incidences of clients saying they want to book, and then ghosting on us.  (Meaning, they just stop responding to all communications.)  In the early days, a person’s word was still their bond.  But we’re having to watch out for our singers and ourselves more and more because that is not always the case anymore.  (However, I’m glad to report that this kind of occurrence is still in the minority, and we have AMAZINGLY wonderful clients to make up for the bad seeds out there.)

– We have a LOT of singers who sing for Olde Towne Carolers!  We started our first season with just six singers and a few gigs, and now we have over 100 talented musicians performing for OTC!  We need so many singers because the season is short and so consolidated.  This past year, our busiest date was December 14th – we had 20 gigs that day alone!

– We’ve had some fantastic performance highlights throughout the years.  I think back to ten years ago when we performed as part of Disney’s Christmas Carol Train Tour.  (I’m a huge Disney fanatic, so that was quite a big deal for me!)   Then in 2010 and 2011, we were on national television on the Rachael Ray Show.  That was quite exciting!  In 2011, we performed at the Fallsview Casino in Niagara Falls, and opened for headliner Olivia Newton John.  Around the same time, we started an annual tradition of appearing on our local tv news (WFMZ) each holiday season as part of their Music Monday segment.  For the past three years, our Boston troupe has been the opening act for all the Pentatonix shows in that city.  Last year, we sang at the Christmas party for the network television show, Blue Bloods.  And this year, we performed at the holiday party of major fashion house, Carolina Herrera.  We are also thrilled to return every year to regular engagements for some of our favorite clients; Longwood Gardens, Skytop Lodge, Promenade Shops, as well as area malls, country clubs, tree lightings, and retirement homes.

Honestly, I can’t wait to see what the next 15 years have in store for us.  One thing’s for sure: this company of mine is my baby.  I’ll continue to work as hard as I can to make it even bigger and better, with quality always reigning supreme.  We’ll keep doing the best for our existing regulars, while continuing to win over the hearts of new clients each year.  After all, we bring the very best of what the holidays have to offer: the music!

See you next Christmas, everyone!

-Jennifer

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