By Fritz Gilbert, TheRetirementManifesto.com
Special to the Financial Independence Hub
Have you ever thought about seasonal work in retirement? My friend, Kirk, recently leveraged seasonal work to experience something for the first time in his life. He became a cowboy, through a seasonal job at a Dude Ranch.
At Age 58!
You may remember Kirk, he’s visited with us before (including his thru-hike on the Appalachian Trail, his broken foot on the Pacific Crest Trail and the story of breaking his ribs when he Lived Life At The Limits on a mountain bike ride with yours truly). This Fall, he’s heading to Nepal to do some trekking around Mt. Everest. Interesting guy, my friend Kirk, and we can all learn something from the way he lives his life in retirement.
Today, he tells us the story of doing seasonal work in retirement at a Dude Ranch, which he did in the Spring of 2018.
The old military and corporate guy became a cowboy. Well, that may be a bit of an exaggeration, but he did “wrangle horses” for 6 weeks at a Dude Ranch. How cool is that?
Here’s his story…
Working On A Dude Ranch

I promised myself I would write three “potential” blog posts for my friend this year covering what could possibly be my most adventurous year since my retirement began 2 ½ years ago. Caution: I am not the spectacular writer that Fritz is; however, here is my latest adventure …
(Note from Fritz: I don’t know about my writing skills, but I do know that Kirk lives life more “on the edge” than anyone I personally know. Nepal, really? That Kirk guy is nuts!)
When I retired roughly 2 ½ years ago I decided to do away with my “LinkedIn” account. I was cleaning up some old things from my work years and didn’t think I would need a resume in my retirement life. As I started checking off things in my Dump Truck List (Buckets are no longer big enough) I started realizing that I had some skill gaps. Ultimately, I wanted to be a wrangler for a cattle drive in Montana but realized that wasn’t going to happen if I didn’t have some experience handling a horse.
I researched some possible jobs through www.coolworks.com and drafted a list of the qualifications for some of the wrangling jobs which interested me. Much to my surprise, I met them all with one exception:
I had no experience in riding a horse.
Having grown up on a farm really prepared me well for many aspects of the job, but we never had horses. How could I learn to ride a horse, handle the tack, teach the ranch’s customers, etc. if I didn’t know how to handle horses myself? While I suppose I could have paid for the experience — I am FI [Financially Independent], after all — there was something in me that kept gnawing in the deep recesses of my mind.
Thoughts which whispered, and thoughts that led to my decision to pursue seasonal work in retirement:
You have been so frugal all your life to get to FI, is this really how you want to spend your money?
Would you really be able to buy this experience or is this something you have to spend time acquiring skill, talent, and familiarity?
What other experiences do you need now in order to pursue the future adventures of your dreams?
(Note from Fritz: I like how Kirk thinks several moves ahead. Dream for your tomorrow, and identify what you should be doing Today in order to achieve your dreams. Move your life from Good To Great).
After much thought, I decided to venture out to an unknown area for me and listen to the younger crowd who said many of their wonderful experiences were as “Workaway” people. Workaway is simply a web service that connects people who are looking for experience with people that are looking for help. The Workaway people generally work 4 – 5 hours per day, 5 days per week in exchange for room/board and experience. Given that I have plans to travel through Asia in the coming years, this approach could help with some international options as well. I looked into the site http://www.workaway.info and decided to give it a try.
It was somewhat difficult to determine where I would go to gain this experience. I wasn’t sure how it would all work out, so I decided to minimize my risk by choosing a location that:
- had good/great reviews by those who participated
- was close so if it was horrible I could bail
- had more than just myself as a workaway so I could learn from the experience of others
I ended up selecting a Bed and Breakfast Dude Ranch in upstate NY, only an hour away from where I grew up and where my mother still lives. If it was a horrible experience I had a solid Plan B. I would simply bail out and stay with my mom, working around her house to complete some things on her “To Do” list. It would also afford me the opportunity to spend time with some aunts, uncles, and cousins which I had not seen in far too long. Continue Reading…