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“What’s luck got to do, got to do with it?!”

Yes- I am actually bopping to my personal remake of Tina Turner’s famous love ballad. But real talk, I hear it all the time- “you are so lucky to travel so much.” Lucky. Ya know, that one word really frosts my cupcakes. Fortunate? Abso-freakin-lutely. But lucky…I can’t fully get on-board with that.

First instagram picture!

First instagram picture!

I know that the actual person saying this has no ill intent, but for any hard working individual, this can be a bit of a trigger. Luck is defined as “success or failure apparently brought by chance rather than through one’s own actions.” I’m throwing up virtual high fives to all those that may have happened upon success without any actual effort, but I have a feeling that my hands may be whiffing and coming up empty.

Travel, by nature, requires effort. If you have ever coordinated a family vacation, LAWD…you know it requires the patience of Job and organization that could rival Marie Kondo.

A travel agent comes into your travel plans as an outsider, not knowing your style or financial situation. We inquire candidly about personal preferences, while chatting about budgets (all while trying to make such a hot topic as comfortable as possible- let’s be real, people are funny about money). Then we translate all these hypothetical concepts into life changing realities. We do our best to salvage flight plans derailed by weather, to sort out hotel bookings before clients even know there was a blunder, rearrange transportation to perfectly align with updated schedules, and deliver it to our clients in (metaphorical, and sometimes literal) shiny package. We are like the Mysti Copelands of travel. It’s hella hard…but we do our best to cover the broken toenails with beautiful pointe shoes and twirl our way through pirouettes with smiles on our faces. Y’all…the show must go on!

All this to say that it is HEAVY to bear the burden of someone else’s hard earned vacation days and checks that have been saved for months (maybe years) to make this magical experience come to fruition. BUT we do it. Not because we have to (do you know any travel agent that hates their job and truly feels trapped? I actually don’t), but because WE LOVE IT.


Yes. We get to travel. We travel during off-seasons, when client traffic is low (and weather can be a bit iffy). We travel for on-site visits where we walk 10 miles a day to check out properties for future clients (and make it look damn glamorous on Insta-stories). We will fly across the world to look at hotels, because we GEEK out on it. Lest – my friends, none of that is a vacation.  Our vacations turn into work REAL fast. I have found myself trying to find ways that I can have drinks at hotel bars on my own honeymoon (sorry, JR), as to camouflage my intention to scout the next hot spot for future travelers. I do realize that I’m seriously ill.

Where I do feel confident that luck comes into play, is that I was born to a family that has supported my endeavors and taught me hard work. I quit a lucrative and very stable job to live with strangers in Italy, in hopes of creating content and a travel blog. I went through a divorce, where I had to charge the court fees on my credit card (I didn’t even have $400, because I had quit said lucrative job). I moved in with my parents for 6 months. My parents provided groceries, housing and support through something that many could never afford to get through without having to go back to a traditional job. SO many people would be trapped by circumstance- and I am not naïve to this.

What many don’t know, is that I did all of this while working for my family’s business. YEP. I built a million dollar business while working another job for my dad, so that I could get on my feet while learning about our family’s 96 year old air conditioning company. I picked up condenser units from warehouses, sold filters, ran permits, and scheduled client meetings during lunches, evenings, and weekends. Working 100 hours a week was a norm. Take-out was the standard meal, my house was a disaster, and my appearance matched (still sorting that one out). I am truly lucky to have a dad that built a small business that supports my entrepreneurial spirit, and allows me to pursue my dreams to grace the cover of Forbes. That part- I will give you- complete luck that I am not worthy of.

Our group for Eating Italy

Our group for Eating Italy

I began my travel business with no clue. Truly NO ever-loving clue about the business of travel- I just knew I loved it. A word to those searching for the secret sauce- passion and resilience can take you places that luck never could. I have failed. And failed. And failed again. I have booked flights on the wrong dates and paid out of pocket to correct an error. I have paid 12k on a credit card in hopes of earning it back through booking a group trip. I have been yelled at by customers because their seat assignment was changed on a plane (note: agents are not in control of this), and they threatened to sue. I was audited by the IRS where I had to prove that I have sold each location that I have ever written off as an expense (and won). I was told that my concept wouldn’t work- that maintaining a business with such in depth detail to personal itineraries was not sustainable. I listened. I tweaked a bit- and held strong on the points that mattered to me. I bent, but didn’t break. I found the most amazing humans that I could, and asked them to join my dream. They accepted and adopted it as their own. Robin has been by my side through the beginning, and held steadfast as I fell off the face of the earth during what I call my “survive not thrive” phase. I joke (but am very much not joking) that she kept my business alive when I couldn’t see the light at the end of the tunnel.

If you’re still reading, YOUR vision doesn’t have to make sense to anyone else but you. YOU WILL FAIL….but I am a firm believer that the surest path to failure is the one that you take when you are trying to please everyone.

Thomas Jefferson said it best – “I’m a great believer in luck, and I find the harder I work, the more I have of it.” That, my friends, is one hell of a “declaration” (see what I did there?)!

Follow the adventure!