Would You Buy a Trip From This Person?
Is it possible to still do what you love for a living?
No, really … I’m being serious!
I’ve reached the stage of unemployment where I’m entertaining entirely new career paths. And I think I might be onto something.
In all the stuff I’ve done in the seven months since I was laid off, being able to devote so much time to writing has been my favorite. I’m just a few chapters shy of finishing the rewrite of my Woody Guthrie manuscript. It’s in the hands of an agent right now. Another agent passed on it last week, but assured me it was her, not my work. Really, her email was probably the highest praise I’ve gotten for what I’ve done on this book project.
Today I turned in a first draft of an essay for a new food culture zine in Los Angeles that goes to print in January. I’m excited to return to food writing, and extremely excited that it’s in L.A. And I’ve loved getting published on Another Jane Pratt Thing. I have some goodies to pitch to her this week.
And I truly love what I’m doing here. The audience might be small and quiet, but I appreciate all of you who are taking the time to read these posts about events and places that have meant a lot to me.
So much so that it has me examining travel’s place in my life. Having to postpone trips during my unemployment has been crushing. Right now, I should be in New Orleans for my birthday, but here I am.
Anyway, I truly thrive on being elsewhere, and I love processing my travel experiences, realizing what I learned from each trip, and then crafting it all into something someone might find interesting enough to spend 10 minutes reading.
I’ve written about my feelings regarding flying while fat and traveling while disabled, both experiences that I openly share to make life better for other travelers. Something that gives me more satisfaction than just about anything: A few years ago, a fellow fat friend asked me how I travel since airline policies regarding fat passengers are so financially limiting. I was more than happy to give her the details and help her prep for her first flights in several years. She went to a huge Pókemon event in Chicago, visited her family in Florida … I can’t remember what else. It made her so happy.
Unfortunately, she died far too soon, within a year of that conversation. After recovering from the shock of losing her, it occurred to me how important those trips were. How happy it made her to once again be able to go where she wanted, do what she wanted, hug who she wanted.
I can think of a lot of ways that I could have been a better friend to her, but knowing that I helped her take those trips gave me a little bit of peace.
Of course, I didn’t expect anything in return for sharing what I’ve learned in my travels. But … what if I did?
Last week, I reached out to my friend Jenni, owner and operator of Three Seas Travel in Key West. That’s right—she’s a travel agent on the side while working in IT. She’s been in the travel business since 2017, and I had some questions. She had lots of answers.
So, I’m doing something I can’t say I ever planned to do: I’m waiting for a phone call that will get me started on getting certified to be a travel advisor.
I don’t know why I didn’t think of this sooner.
Would you trust me to plan and book your trip?
At this point, I want to focus on the kind of travel I know and love: domestic travel. I’ve never been on a cruise or stayed at a resort. It’s just not my thing. While I’ll gladly help people book those trips, I really want to focus on travelers who want to travel the way I do. I think the combination of travel agent tools and my know-how in finding interesting places and things might be somewhat in demand.
What trips do I want to book?
Flights and lodging for you and 20 of your far-flung friends to attend a music festival
Dream trips for people who think they can’t travel because of physical limitations
Culinary tours
Art tours
Mapping your epic road trip with lodging, restaurants, and activities
Immersive travel that lets you experience a place like a local
New Orleans beyond Bourbon Street
Los Angeles beyond Hollywood
Chicago beyond the Miracle Mile
Your centrally-located family reunion or conference in St. Louis, Tulsa, or Kansas City (or anywhere, really, but I love these places)
Following your favorite band on tour
Spending 6 days on the road …
I’m seriously looking for feedback. Is this a service you or someone you know would pay for? I promise I won’t hold you to it if you say yes. We’re still talking hypotheticals.
Bonus: income means I travel more, which means I write more.
So, would you buy a trip (or a flight or a hotel booking) from this person?



I would totally buy a trip from you. I love guidance about traveling alone and not getting in over my head on a trip that's too active (where I will likely hurt myself) or scary. I'm so intrigued by the backroads adventures and tiny river cruises but it all seems like a lot and way too social. I feel like you will be really good at listening to your clients' needs.
You travel the way I like to travel. I plan my own trips because finding the places is part of the fun and anticipation for me. However there are a lot of people who don’t enjoy the pre-trip leg work and want to have a curated journey, from hotel to restaurants and activities and tours. I think you could build a business with this model!