by Annie 

Published: October 28, 2020

Updated:  October 14, 2021
reflections in Iceland

Every year as my birthday nears, I’m drawn inward for reflection time. It’s an intentional time set aside to look back on what the previous twelve months have given me. To say the last year has been a bumpy ride would be an understatement, and I know I’m not alone in that sentiment! 

Last October, I’d recently taken the leap into full-time entrepreneurship. Trusting myself and Life to work together and stay afloat was one of the most challenging things I’ve ever done. Then along comes COVID-19 in March and upends everything I’d been building, forcing me to get creative and come up with new ways to continue to serve my mission of empowering women. While there have been moments where it felt I was about to tumble into disaster, the last year has also stretched and expanded my creativity in the most awesome ways! 

As I was thinking about the last year as a journey, it totally reminded me of driving on, what I call, the Sky Roads in the West Fjords of Iceland. Yes, most everything in life can be turned into a travel metaphor, in my mind.

Into the Wilds

sky reflections

In 2016, my cousin’s wife and I went traveling together for a month, two weeks of which we spent in Iceland. We rented a little red car that immediately let us know this wasn’t her first trip around the island. Her steering pulled to one side and the windshield wipers were off-kilter too, but she was our steady companion for the duration. 

For the last four or five of the trip, we set out into the wilds of the West Fjords. You know you’ve really gotten off the beaten path when someone hears your American accent in a campground and asks how you found out about the place. The trek to get there was anything but a smooth ride, much like the last twelve months. 

Pavement wasn’t really a thing in the majority of places we drove. We spent many hours bumping along the dirt roads which tightly hugged the edges of the fjords. Sometimes we would have to go up and over these massive formations rather than winding around the edges. These excursions are what became known to us as the Sky Roads. 

Our little car would climb the dirt roads and, as we reached the top, we couldn’t see how the road continued on the other side of the ridge. The only thing visible through the windshield was sky. I’d keep my foot on the gas and we’d hang on tight, hoping the rest of the road would become visible before we flew off into the clouds or plunged into the sea.

view on the sky road

The road always reappeared, but not before we had a harrowing moment of uncertainty. We learned to trust. Plus, the views from the top were always unbelievable. The last year has felt very much the same, I’ve realized during my reflection time -- hanging on, hoping the path will appear, and learning to trust.

Twists, Turns & Trust

winding roads

The sky roads seem to be a perfect comparison for my 38th trip around the sun. The road never felt smooth. I spent a lot of time and energy trying to find the sweet spot where the rocks had been cleared and the biggest bumps were a little more worn down. 

It started with sifting through the noise of what the “gurus” have to say about building a business to find MY way or creating a business that’s totally aligned with me as a person and my mission.  When covid hit In March, it felt like I really had flown off the cliff and was headed for the sea below. Somehow I managed to stay above water, thanks to my resiliency, creativity and amazing support system. I definitely couldn’t have done it alone. 

It’s impossible to count the times where it felt like I was heading into nothingness, only the sky visible in my view. There were countless moments where I had no where I was going or if the road would even reappear. It always did. This is how I learned to trust. 

Every time, just like the sky roads, I’d crest the ridge and suddenly see where I was going next. The next part of the path would be revealed and, once my heart stopped racing from the anticipation, the views did not disappoint. I’d find my inspiration, hit the gas and go boldly toward the next stretch of road.

A New Road


This year, I’m hoping for a slightly smoother ride. While the sky roads are fun, once you get used to them, I’m hoping for some pavement this year. Something like Romania would be great -- asphalt and smooth, narrow two lane roads full of surprises, some potholes, a few detours, but relatively easy to navigate and beautiful scenery along the way. 

For this year, I’ve chosen “Possibilities” as my theme. My intention is to dream bigger, play more, experiment and explore. Creating intentional reflection time helps me integrate the lessons from the road I’ve been traveling and visualize where I’d like to go for the next season of this journey.

Your Thoughts

How do you start a new season, year, etc.? What kinds of rituals or reflections help you find your path forward?

Keep Reading...

About the author 


Fun Lover. Food Eater. Bold Explorer. Big Dreamer.

Annie is a fiercely independent traveler who loves to create unique and interesting experiences. She thrives on finding the magical moments and hidden gems waiting around every corner. Her passion for helping others make their travel dreams come true fuels her work as a travel planner, consultant, educator, and community builder.

{"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}
how to be bold

Ready to see the world on your terms?

Get travel inspiration, resources and everything you need to

create your next adventure delivered right to your inbox.