Five things I Learned from Desk Job to Freelance Life – Caitlin Featherstone

This week we are very excited to present Caitlin Featherstone for Five Things Friday. Enjoy!


Caitlin Featherstone is a Southern California Native currently residing in Brooklyn where she is working as a full time freelance musician and teacher. Since moving to New York City three years ago, Caitlin has been playing consistently with a number of orchestras, churches, theater companies and opera companies. She has also recently joined The Brooklyn Conservatory working as a music teacher in several of their Public School music outreach programs. In addition to freelancing, Caitlin is the fifth and newest member of the “Deliciously Creepy Cabaret Sensation”, Orphan Jane. A locally famous music ensemble. In 2016, Orphan Jane released their second album, “The Traveling Everything Show”, on which Caitlin is featured. When she isn’t playing trumpet, Caitlin is a professional Dog Sitter in the NYC area as well as an aspiring Sommelier. Caitlin is a graduate of the Oberlin Conservatory where she studied under Roy Poper and received her Bachelor’s in Trumpet Performance and a Minor in Ethnomusicology.

This past March, I decided to make a crazy and seemingly stupid life change. I decided to quit my cushy day job of two years and dedicate myself to my trumpet career full time. This meant losing the stability of a weekly paycheck and my own personal office where I called the shots, and buckling down to finally take action and move my career in the right direction. However, it also meant finally having the freedom to take chances, having the time to take care of my mental and physical wellbeing, and actually feel like I was being proactive about something that gave me a purpose for being in New York!

Since getting back to the city in September after a long difficult summer upstate (story for another time) I have faced challenges and surprises around every corner. In such a short time, I have felt my outlook on this profession and my lifestyle change drastically. I have learned things about myself and the people I surround myself with that I never could have imagined. On that note, I would like to share 5 things that I have learned over the past few months as a (rookie) full time freelance musician in New York City.

1) Making your own schedule is hard!

When I was locked into my 10-6 work schedule, I pretty much knew what my days would look like. Work all day, hit the gym if there was time, and then head to my evening trumpet obligation. Upon attempting this new freelance musician lifestyle, I realized that I had a lot of free time, and it was glorious!! Sleeping in, staying in my pajamas for most of the day, catching up on all of the Netflix, and of course, having the time to practice trumpet. It wasn’t too long that I realized that I was being incredibly unproductive and not making the best use of my blessed free time. I knew I had to change my mindset and create a schedule that would allow me to make progress in my goals and feel good about everything that I had accomplished that day. It was not easy. Waking up at 8am knowing that I didn’t have to be anywhere until 7pm that evening was tough. Starting my daily practice routine by 9am was even harder. Getting my lazy butt to the gym every day was the hardest! It all seems fruitless and a waste of energy and focus. However over time, I realized that now that I was my own boss, my life was my business and I needed to make sure that everything was in check and things were getting done! Several months in, I’m still struggling with this daily schedule but now I know and understand why it’s necessary and is all the motivation I need.

2) It’s the little things that make the big difference.

Admittedly, this realization was brought into clarity by one of my new favorite books, The Slight Edge. The book focuses on explaining how the seemingly insignificant and mundane things that we do on a daily basis are what shape our success in the future. This may seem like an obvious concept but keeping it in mind and applying it to everything you do is truly enlightening. I have seen the effects of this concept in such a short amount of time and I look forward to continuing to apply this mindset to every aspect of my life.

3) Sleep and Exercise are blessings!!

Working a full time job and freelancing (mostly) full time doesn’t allow too much time for personal care. I.e. sleep and exercise. Two things that allow us to be the most alert and productive! Seems a bit ironic…. Since revamping my life, I have made sleep and exercise a priority, and let me tell you, worth it!!! Getting enough sleep and pumping out those 30 minutes on the elliptical every day have completely changed my mentality and outlook. I’m no longer in that sleep deprived fog, I no longer hold onto anger and frustration, I am able to look at situations with a more open mind and make clear confident decisions. Not to mention I’m dropping all those sad stressed out pounds!!! Lovely side effect!

4) Being ready for anything is so important!

When life is moving slowly and there isn’t much going on, it’s easy to get behind and slack off. I have learned this lesson the hard way over and over again. Not being constantly on my toes has caused me a ridiculous amount of stress and anxiety and I’ve realized that I am always on call. I need to have my ducks in a row and be ready to play my best at any given moment. This is still something I struggle with but at least I’m figuring it out!

5) Every day is an adventure

The absolute best part of my new life is the ever changing excitement that I get to experience on a daily basis. I never expected each day to be so drastically different and surprising. Having a desk job, I knew exactly what to expect every single day and how it would make me feel. Now, even when repeating an activity such as playing the same show night after night, I can always expect the unexpected. As someone who is easily bored with mundane and repetitive things, this aspect keeps me alert and always guessing. I’m loving it!!!

Some (or even all) of these points may seem like obvious realizations, but honestly, they all caught me completely by surprise. Obviously exercise and sleep are important. Obviously you should always be prepared. But it’s not all obvious. Not until it becomes your reality. Looking forward to continuing to improve myself and learning many more “obvious” lessons!!

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