Our next post features Jessica Trainor - opera singer, teacher, and now Career and Life Coach based in Boston, Massachusetts! Jessica is a former client of Rowan Coaching, and when she decided to pursue coaching herself, I knew I wanted to bring her on as a Guest Coach. Jessica ditched her day job almost a year ago to focus on the careers that mattered to her, and just got back from five weeks of working remotely. Check out some of her observations and insights from her travel! 

“Don’t give up the golden ring!”

“Things will get better. Just tough it out – you need this job while you work toward your goals!”

Those were the two big pieces of advice given to me while I wrestled with giving up my supremely cushy and consistent 9-to-5 job. But, really…it felt AWFUL to be there, and was draining my energy for the things I truly valued in my life.


I wanted to quit so bad. I wanted to really invest in my creative pursuits, and work toward finding a job where I was my own boss, and my office was anywhere with wifi. I knew the job I had was toxic, but I kept digging my heels into the sand. Why? Fear.

Fear is not all about the scary, horror movie, run-away-from-Michael-Myers-Halloween stuff. Fear is that voice in your head that comes up with reasons why you shouldn’t do something. Since we don’t have lions chasing after us on the regular, our fight-or-flight response turns on when we are dealing with things like money, health insurance, social morays, thinking about the expectations of others, projecting our emotions and feelings on others, etc.

A few questions though – what would it be like to forget all of those things for a second, and craft the life you want? What would it be like to step out on the other side of your fear? While considering the leap, what is the vision for your remote life or non-traditional career?

If you’re considering taking the plunge and ditching your day job to create a life where you can work from anywhere, here are a few helpful insights I’ve learned in my first 5 weeks of remote work.  

Find Your Tribe

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Not only does this mean find the people you click with in terms of friendship/relationship– it means find the people who will support AND work with you. Remote opportunities only work when expectations are clear for you, your employer, and your clients. Being transparent with your needs actually benefits you in this situation, especially if you are in a creative field! Finding a job, coworker, or teammate that values and invests in your creative career is so important. Finding the right tribe can also foster opportunities back in your home base.

List Your Good

This is something that Rowan Coaching Founder and Principal, Colleen Star Koch, talks about a lot in her work. What are you good at? What do you celebrate about your personality? What hobbies are you super into? What secret ninja skill do you have that maybe you haven’t told anyone?

Maybe you are really good at creating tours and trip itineraries. Maybe you’re good at painting. Maybe you’re an organizing goddess. Whatever it is – write it on a list. When we observe what we are good at, and what we have to offer in our skill set, we can more easily find opportunities for work and growth. How many times has “I suck at…” produced an opportunity? None? That’s what I thought! Listing your good can broaden the scope of remote work opportunities, and perhaps lead you to opportunities you would never have thought of or seen. Plus, people often succeed and have the most fun when they like and are good at what they do.

Clear The Space

If you get to the point where you are able to travel and work remotely, it can be super exciting once you arrive to your new destination. Distractions abound when soaking up the sights and sounds of a brand new “office.” Maybe you’re wired on the excitement of being somewhere new. Or, maybe you’re exhausted, and need a break (face it: long flights and logistics can suck sometimes!).

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No matter what, taking a moment to be fully present is essential. Check in with yourself, and see what you need (and what your clients and work might need of you). This might look like finding your spot for work at a quiet café, having a slow day with no activities and low hanging projects, or just getting out all your energy in one big day of touring so you can focus on your work days afterwards.  Find what works for you so you can maximize your growth through experience, and be a responsible coworker and collaborator while you’re traveling.

Determine Your Needs

Pulling the plug on your regular schedule can be intimidating. But, running yourself like your own business can help mitigate scheduling mishaps and burnouts. When do you feel most productive? Can you work on your more intense projects at that time? Perhaps low energy parts of the day can be invested in self-care, be it a workout, a museum pit stop, or a walk in your destination. Happiness drives our energy upward, and is proven to make us more productive. If fear is whispering about finances, ask yourself, “What do I need to feel happy?” Making an expense list, and breaking it down by work days per month can give a measureable goal to keep us on track (and, when remote, can motivate us to get shit HANDLED).


Giving up the “golden ring” of my 9-to-5 has given me something way more precious – the ability to grow and challenge myself, and create a life that is flexible, fun, engaging, and lucrative across all sectors of my life (performing artist, coach, and teacher).  I’ve hit my goals, made new ones, and discovered some that I didn’t realize were important! There’s still a lot to learn, and I am so excited to see where my next year in this path will take me.

Jessica Trainor on The Swing at the End of the World - Baños, Ecuador

Jessica Trainor on The Swing at the End of the World - Baños, Ecuador