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HOW I WORK: An inside look at how Travelmation’s Lynnlee Stanford turned a side hustle into a decade-long travel career from her living room

Lynnlee Stanford, a Travel Advisor and leadership team member at Travelmation, has spent 10 years building her business from soccer practices, coffee shop corners and dance center parking lots while helping families plan everything from Disney vacations to destination weddings.

Lynnlee Stanford has been part of this community since she was 10 months old, when her family moved here for her father to coach football at Choctaw in 1990.

  • Today, she works from home as a Travel Advisor and Independent Contractor for Travelmation, where she also serves on the agency’s internal leadership team overseeing a team of agents and working in the finance department.

What started as a fun side hustle a decade ago has grown into her sole source of income, and the agency itself has expanded to more than 2,500 agents across the country. Between securing 5 a.m. Disney dining reservations, filtering hotels in Hawaii for client quotes and chauffeuring her two daughters to activities, Stanford’s days are a constant balancing act powered by a laptop, a portable monitor and an afternoon coffee.

Are you a lifelong local? If not, where are you from originally and how did you end up in the area?

My family moved to the area for my dad to coach football at Choctaw when I was 10 months old in 1990 — besides college, I’ve been here ever since!

What’s your current job title and where do you work?

Travel Advisor — I work from home as an Independent Contractor for Travelmation as well as work on the internal leadership team for the agency, both overseeing a team of agents and working in the finance department.

What’s your morning routine?

My morning routine consists of trying to always beat the kids up for a little quiet time and coffee. I love to read in “my chair” and take a few minutes to get ready for the day. Some mornings start earlier than others if I am helping clients secure Disney dining reservations for their upcoming trip, which go live at 5 a.m. CST!

Describe what a typical workday looks like for you.

A typical workday involves that morning shuffle of breakfast making and lunch packing and getting my two daughters off to school. Then, I open my computer … which as a remote worker, is my best friend! In the travel industry every day can be different because no two trips are the same.

But that morning and midday work time is normally filled with email responses, client phone calls and calls to a supplier to make payments, confirm requests or modify trip information. Though I am an Independent Contractor, I also work in a dual role on our agency’s leadership team. So we easily squeeze in a Zoom meeting or scheduled phone calls to discuss internal needs, or I meet with agents on my team to help them solve a problem or brainstorm ideas about their book of business.

After lunchtime, it’s time to wrap up those loose ends from the inbox and then get ready for school pickup! Once my girls are home, my first step before carrying on work tasks is always that afternoon coffee. And then it’s back to the computer. Maybe I am trying to help a family find the perfect connecting cabins on a cruise for a family of five, or I am filtering hotels in Hawaii to add to a quote, or I am talking with a bride about her preferences for the perfect destination wedding.

Then with kids ages 8 and 11, we start that evening shuffle of activities and — let’s be honest — chauffeuring to various activities. But while not every day, the evenings can also involve work … because my clients might be working all day and talking about their trips in the evenings.

This job can keep me on my toes, as it very rarely looks the same day to day, but you can always guarantee that I will have my computer by my side and can work from any soccer practice, dance center parking lot or favorite coffee shop!

What’s the first thing you do when you get to work (or start your workday)?

I open my inbox. I use my email inbox and my client management system as my constant to-do list. A clean inbox means a happy inbox and pressing needs have been taken care of.

What tools, apps, or gadgets can’t you live without?

My laptop, wireless mouse and portable monitor — and then software-wise, a client management system where I can continually set reminders, keep client notes, files and things like your Delta SkyMiles number or Hilton Honors number so that when my repeat clients need something, I have everything stored right there!

Apple or Android?

Android — I know, I know. But I love my Microsoft Surface and Google Pixel phone!

What’s your go-to coffee (or tea) order?

Double shot over ice, splash of almond milk!

What’s your go-to lunch spot or work snack?

Chick-fil-A — there’s always a space to sit, Wi-Fi available and food of all sorts!

What’s one local business you love supporting?

Pink Coyote Dessert Co. — a family favorite. We might visit there an embarrassingly high number of times in a week.

What’s the best piece of career advice you’ve ever received?

No one is going to market you but you. Ten years ago I started this as a fun side hustle, and very early on our founder (at that time just about 25 of us agents) said on a Zoom call, no one was going to market you but you. You have to put yourself in the conversations. That has lived in my head for 10 years when I ask myself, “Oh, should I do that?”

If you could give your 20-year-old self a piece of advice, what would it be?

Follow your instincts and do not hesitate to jump through the open doors that might come your way and do something that is fun, that you love.

How do you unwind after a long day?

My non-work gadget that I cannot live without is my Kindle — reading at the end of the day is how I shut my brain off. This is a habit I picked up probably about five years ago because it actually was hard to stop working. When you work for yourself, no one is telling you when to work, but also … no one tells you to stop! I had to implement some boundaries, and that culminates in whatever fictional world I step into with my Kindle!

What’s one thing most people don’t know about you?

I try to watch the Oscar-nominated best picture movies each year!

What’s your favorite local event or tradition?

I love the downtown area — concerts, seasonal events, farmers markets. It would be hard to pick just one, but I love the way our little area thrives in those spaces!

What’s inspiring you right now (book, podcast, person, hobby)?

“Joyful, Anyway” by Kate Bowler: this is more of the self-help category of reading, but I find it based in realness.

Early bird or night owl?

Early bird!

Most used emoji?

🤣

Music while working — yes or no? (and if yes, what’s on your playlist?)

Yes — well, Taylor Swift. Or I am a podcast junkie and love Armchair Expert.

Favorite motivational quote?

“A good process produces good results.” — Nick Saban

Standing desk or sitting? Mix?

Sitting desk — or table or wherever I end up working that day!

If you could give any advice for someone getting into the same field as you, what advice would you give?

Never hesitate to insert yourself into the conversation — people are busy in their lives; they may or may not read social media posts, etc. I circle back to the quote that impacted me … no one is going to sell my strengths like me! So that can be you too. Also, there is a very broad realm of travel agencies out there, and I would do your research and find the best fit for you and the business you want to run.

Are you a member of the FWB Chamber of Commerce?

Yes! I believe being present in the local community is so important, and I know that my agency at large is not located “here,” but that is sort of the cool part — I get to run and manage my own book of business and allow it to have a presence in our area.

Anything we missed that you want to add?

I signed my first contract 10 years ago this month. At the time, my sister-in-law was battling a terminal diagnosis, and honestly I signed that contract as like, “Why not do something I love?” But also, I had traveled with my family, and our last family trips before Erin passed were some of the most special memories. It was easily the catapult to push me to take a risk. I am so thankful for that push she gave me, and here I am 10 years later where it’s my sole source of income, and our agency itself has grown to 2,500-plus agents all across the country. But I love, more than anything, that I get to play a role in the milestones of people’s lives. Yes, I love Disney — always have; it was my gateway in. But now my business is so much more than that, and I love helping people prioritize special moments, time away — business trips too (I’ll do it all!) — and celebrations in their life because I do truly believe those moments matter!

I also believe that longevity and tenure matter, and the knowledge and relationships I have built in this industry are worthwhile. But at the end of the day, this community has been the reason for my success, and I honestly can’t wait to see what the next 10 years hold!

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