We’re excited to introduce you to the always interesting and insightful Lori Konkler. We hope you’ll enjoy our conversation with Lori below.
Lori, appreciate you joining us today. Before we talk about all of your success, let’s start with a story of failure. Can you open up about a time when you’ve failed?
Not only did I leave my 9-5 but at the same time I decided to move to the Caribbean at the same time…and before I had ANY income in my businesses let alone consistent income! Obviously….I FAILED hard. After 6 months reality hit…I was living in paradise but I had no money and was not growing like I had thought. So, even though on the outside we had it all, on the inside, it was falling apart.
We were struggling financially, our landlord was a slumlord at best
We were faced once again with a tough decision….go back to the states for work while we travel back and forth for our businesses or stay and likely fail completely.
So, back to Wisconsin we went, braving the winter with a few trips back and forth to the islands as we needed for the businesses. Frankly, it sucked and we knew we couldn’t sustain it. It made me sick to think about giving up but it made me equally as sick to think about financial ruin that could happen if it didn’t work.
Then ….a miracle, I found the perfect gig back in the islands, based in paradise, travel and ability to work remotely….I was killing it, getting constant praise, loving the freedom and travel….until one day it all came to a halt when I was told my position was being eliminated….and just like that….back came the fear.
I was faced with the decision….accept the fear of the unknown and make my businesses work….or accept the life I despised and go back into a regular 9-5 with 2 weeks of vacation and leave the island…..it was terrifying but ultimately decided it was now or never….this HAD to work….that was 3 years ago and I have never looked back, multiple businesses later, making more than I ever did in a 9-5, I have no regrets but LOTs of stories and lots of education to share!

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
Lori Konkler is an Intuitive Business Success Coach & Strategist for remote based coaches, consultants and strategists redefine and simplify their sales and beliefs in themselves in order to build success in their business and have a powerful personal brand.
As the Founder of Xennial Traveler, she has helped business owners around the world to enroll clients, find their voice and become credible authorities in their space. Back in 2016, she ditched her 9-5 corporate as a Director of Sales & Marketing for a Fortune 500 company to seek out a new life of freedom working on her time, at her pace, on her terms from anywhere in the world and is passionate about helping other freedom focused travel lovers to do the same.
Specializing in social media and marketing, sales, business operations and leadership, Lori is a bit of a business “unicorn”. She helps entrepreneurs and business leaders to not only tap into their own power but through this power, helps them elevate their offers. Through her unique guidance of empowering and building confidence in those in business already, she helps them get the outcomes for their bank accounts booming and clients giving them praises. “Teaching how to create offers or to write content is one thing but owning, displaying and demonstrating your unique zone of genius is another.” Lori helps those in business already position their offers in a way that has their dream clients lining up to pay them.
Lori’s straightforward approach to business in the online space proves to be a huge asset for entrepreneurs looking to master their marketing, sell with confidence and convert like crazy.

Let’s talk about resilience next – do you have a story you can share with us?
Watching breath-taking sunsets in New Zealand, exploring the beaches in St. Croix – this was the life my husband and I imagined for ourselves back in 2016. After a month long vacation and returning to the cold of winter and the depressing realization that it would be a year before we had any vacation time to do it again, not to mention the monotony of our 9-5’s we took a leap of faith, started planning our move, started selling almost everything we owned, gave notice to our jobs and made the decision to change life for good. We made the decision to move to the Caribbean to start the first of 4 remote based businesses and to begin our lives as expats and digital nomads. However, the road to making this a reality was much longer than we thought it would be. It was a long, hard grind for a while there but we kept our goal ahead of us at all times. After over a year of on-and-off jobs, tears, traveling back and forth to the states, and re-re-re-drafting our business plans, the light bulb went off. We found a model that began to work for us…and I mean really work! Our bills no longer overshadowed our earnings and began to gain that freedom of mobility we were looking for in the first place.
Fast-forward to today: Four successful businesses and a couple of coaches later, we are not just financial success stories. We are also free to be successful anywhere in the world!
I’m here to tell your listeners that if I can do this, so can you! Just because it didn’t work for you the first time (or first couple of times) that doesn’t mean it is out of reach. Take me for example: From my own experience I have been able to help hundreds of aspiring entrepreneurs and business owners learn how to create a thriving business model that can support their lifestyle from anywhere in the world! A model that works ! Their results have been amazing, and have allowed them to build profitable businesses, gain freedom to travel, and of course fire their 9-5 jobs.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
As a director, I always made it my mission to train my teams to the level that not only could they elevate their career but that they could walk into my job with little effort. Many leaders are scared that if they train others to do what they do that they are putting themselves in jeopardy but I knew from early on that there is room for everyone and by empowering and teaching others, I would also continue to grow. Teaching, mentoring and helping others to achieve their goals lights me up in a way I struggle to put into words. Even though I now have the freedom to work less than ever before, even with multiple businesses, I find myself drawn back in not because I need to but because I LOVE what I do and the people I serve. I have always felt called to help others and specifically to help others realize that they CAN have everything they want, in business and in life. I lived in a world where entrepreneurship, digital nomadism and ultimately the life I wanted for myself were a foreign concept. Society in the past has led us to believe that we SHOULD live a certain way and for many years I fell victim to this but when I didn’t feel fulfilled I broke away from the mold. My friends and family judged me for the choices I made, they projected their own fears onto me and tried to hold me back but instead of once again succumbing to their desires and expectations, I made a conscious choice to fight back, and to continue to pursue my dreams and live life on MY TERMS. It was a hard fucking road but eventually, I made it and I want others to know they too can make it – whatever your ideal life looks like, you can have it, don’t let anyone tell you otherwise.

Contact Info:
- Website: https://thexennialtraveler.com/
- Instagram: https://www.instagram.com/xennialtraveler/
- Facebook: https://www.facebook.com/lori.konkler
- Linkedin: https://www.linkedin.com/in/lorikonkler/
- Other: Facebook Group called The Success Zone: https://www.facebook.com/groups/thesuccesszone/
Image Credits
Facebook: Misty Winter Instagram: 📸@mistywinterphotography

