Seasonal Work In Retirement: A True Story

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!

Kirk Became A Cowboy At Age 58 by working a seasonal job on a Dude Ranch. Today, his story. Click To Tweet
Kirk. A “FIRE Guy In His Prime”

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  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, after all), there was something in me that kept gnawing in the deep recesses of my mind.

Thoughts which whispered, and thoughts which 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 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.

The Experience

Kirk’s Wife (“Flat Mona”) Goes Along On All His Adventures

When I arrive at the ranch, there was a check-in period where I placed my pack on my new bed andwas shown around a bit.  Informal check-in completed,  I headed to the barn, where a birthday party for fifteen 12-year-olds about to take place. I didn’t want to miss the party!   There were 2 other workaway people there, a lady from France and a gentlemen from Germany (both under 21 years of age) and a few other helpers. I approached them, and introduced myself as the new seasonal worker.

When I introduced myself they about fell down. How Old ARE You, They Asked? Click To Tweet

I smiled and told them “58”.  They were shocked (probably not in a good way), but eventually they realized I would not play the role of their father or grandfather.  I was just another guy who knew a lot, was willing to share what I knew, and eager to learn the things I needed to know to work at the ranch.  (Note From Fritz:  Like, um, how to ride a horse?  I’m sure they loved having an old guy at a dude ranch who didn’t know how to ride!  You’ve got Grit, Kirk, I’ll give you that!).

After learning that weekends were the busiest time and they needed everyone on hand, I set my schedule to leave Tuesday evening and return Thursday evening.  This allowed me to spend my 2 days off each week with my mom and relatives.

The work itself was easy enough and there was so much that needed to be done that I could do whatever I wanted, depending on which task best fit my age and experience.  A typical day would look like:

  • Waking each morning around 7:00 AM, late for a ranch hand but the norm for the farm
  • Begin feeding the horses, then have breakfast with the crew.
  • Over breakfast, we would discuss what needed to be accomplished for the day, then get to it.

On occasion, I would mend a fence, build gates, fix plumbing issues, shingle sections of roof, clean horse stalls etc. On many days I was able to do my favorite task at the ranch:  take one of the horses and clear a section of trail.  One of my best accomplishments for the ranch was getting their Allis Chalmers D-14 tractor to run after sitting idle for more than 7 years:

Video of Kirk getting that old tractor to purr! (click to view video)

Learnings From My First Seasonal Work In Retirement:

All in all, it was a good experience and I am considering doing something similar in Asia next year. However, I’m unlikely to something like this again in the US.  Why?  The reality is that a 6-week minimum required time for this adventure was, in my humble opinion, far too long.

I really enjoyed meeting some of the clients and their families. The stories of some of their adventures were amazing, and I’ve added a few of the ideas I received into my new “Dump Truck List”.  The other Workaway people added a nice balance for me, giving me some good folks to hang out with and creating some good memories together, like trout fishing in a nearby river:

I really enjoyed the young man from Germany as he let me use what limited German I remembered from my time in Germany during my younger years in the military.  He really appeared to enjoy many of the things I did, which was a nice encouragement during my Workaway adventure.  He has been on a few of these Workaway adventures internationally and I learned a good deal from him as well.   Finally, because I was close to my childhood home I was able to visit some relatives and see some old friends I had not connected with for many years,  which was a really special blessing.

Financial Impact Of Seasonal Work In Retirement:

For those of you wondering what something like this would cost to do, I spent roughly $400 on this total experience which included transportation.  From a price perspective,  you can’t beat it.  However, just like when looking for a new job in the business world, be very selective and know in advance what you are looking for.  It’s invaluable to put some time into thinking what you really want to experience before you choose your seasonal work in retirement opportunity.

Next Adventure:

I’ll be headed back to complete the Pacific Crest Trail the end of June.  I have half of Washington and all of Oregon as well as about 200 miles in the Sierra Nevada Mountains to complete, roughly a little more than 800 miles. (Note from Fritz:  Kirk’s also got a trip planned to Nepal in the Fall, and if all goes according to plan, Kirk will soon be trekking in the Himalayas.  Is this guy amazing, or what?)


Seasonal work in retirement is a viable option for folks, like Kirk, who are looking to learn new skills.  It can also be a great way to travel at a minimal cost, make new friends, and experience a life that’s different from your everyday routine.  It does require a commitment, though.  As Kirk notes, his 6-week commitment was a major consideration, and many seasonal jobs expect you to work a minimum of 3 months.

My wife and I are considering seasonal work in retirement, most likely in a National Park somewhere in the Western USA.  We’re also thinking about becoming campground hosts.  We’re going to wait a few years before we get serious about the possibility, but seasonal work in retirement is on our Bucket Dump Truck List.

What about you?  Have you ever done seasonal work in retirement, or are you considering it in the future?  Let’s chat in the comments…


  1. Very cool! I mean, what young boy didn’t fantasize about being a cowboy at one point? I know I did, especially since I grew up in a big city and cowboys only seemed like aliens from another planet to me.

    Plus, after 27 years of white-collar work and strengthening up my mouse-finger, doing some good ole-fashioned manual labor is probably refreshing, and of course good for the body.

    1. Good point, AF. Too bad our Momma’s listened to Willie Nelson as he sang “Don’t Let Your Babies Grow Up To Be Cowboys….”. Ah well, a real advantage of FIRE is the ability to pursue our dreams. I like the idea of seasonal work, and the flexibility it provides (location, job, skills, etc), and appreciate Kirk sharing his story with us today.

  2. Great story Fritz – Kirk has that kind of spirit to make a life amazing and rich. My father did the same thing when retired at 55 and then flew floatplanes for logging camps. Doing what he loved, getting paid, and adding even more to their wealth.

    1. Thanks B – that’s another thing to add to the “Dump Truck of ideas” – flying a float plane sounds so incredible. When an individual retires early they have so many years to do really interesting things.

  3. Wow this article made my day! I am 56 and have been looking at the Work Away site for the past few months. The plan is when I turn 60 to retire and do a year long world tour with my wife using the Work Away program now and then to help with the cost and also for the cool experience. Thanks for sharing! PS. Love the “Dump Truc”k idea as well!

    1. Thanks Ben, Workaway was a great experience and the people I have spoken with really LOVE the international aspect. I’ll let you know what Asia is like after my run through there next fall.

  4. Fritz are you sure you and Kirk are not twins? Love hearing about all the adventures. Keep them coming.

    1. Thanks David, for sure we could be as with so many readers of this blog, we enjoy living life to the fullest.

  5. Fritz and Kirk, WOW, thanks for a great read and lots of awesome ideas today! Very well done. I definitely need a bigger bucket… Hold on—I hear a dump truck backing onto the driveway now!

  6. Thank you CYNHUZ – Fritz is a remarkable writer and we have a very adventurous friendship. Glad you thought the “Dump Truck” idea was fun, there are so many things we can do when we retire early why limit ourselves to a bucket – Ha Ha

  7. Kirk sounds like a real interesting guy! Hope to get an update after his Nepal trip. I’ve heard of people doing seasonal work and it definitely sounds like something fun to do once living the FIRE life.

    1. Thank you Mrs. Wow – Kirk is a moderately interesting guy however far less so than many of the readers of Fritz’s blog. For sure he promises an update after completing the PCT / after Nepal and maybe one to end year 3 of retirement with complete financials (maybe). FIRE most assuredly does open a world of possibilities.

  8. This is a great story and I love how he shares the importance of understanding what you are getting in to while explaining all of the benefits too. Even six weeks can be a long time if you aren’t super clear on why you are doing it and what you hope to get out of it. We are doing this same thing right now – but the school calendar dictates our “seasons”. We hope to do some substitute teaching from mid-April through mid-June (to help me keep accruing retirement system credit so I can retire with my max pension at 55). After I can “officially” retire in 4 years, we’ll see about seasonal work though… Great story!

    1. Thank you Vicki – there are certainly many avenues to reach a desired outcome, looks like you may have found one that is going to work well for you too. The 4 years will pass quickly and you’ll be loaded with opportunities.

  9. That’s amazing. I think it’s great that Kirk is getting out there and having the time of his life. Workaway sounds really good. I would try it once our son goes to college. It sounds like a great way to see the world and meet people.

    1. Thanks Joe – It really is a great way to meet new people and see the world from a very different perspective. Learning new ways to accomplish the dreams of your heart is always exciting …

  10. Kirk, that sounds like a fabulous adventure! Clayton and I would love to manage a campground for a bit…what fun! Miss you and your wife tons! 🙂 Fritz, I don’t always comment, but I really appreciate learning through your blog…THANKS!

    1. Thanks Sharon, it was a grand adventure. I almost always learn something from Fritz’s posts and others who comment, its such a great experience to have so many interesting people sharing insight and ideas.

  11. I love the idea that he takes “flat Mona” with him wherever he goes. That warms my heart. Especially because that backpack for the PCT must get every ounce scrutinized! Thanks for sharing this excellent adventure. I admire how Kirk is living and he’s technically my age. Somehow he seems younger!

    1. Thanks Susan – everyday my body tells me I am not 30 anymore but I don’t believe it until I spend that 15 seconds looking in the mirror. Flat Mona is truly a God Send, made by my grandchildren for me when I travel as I miss the family so much, and your correct – every ounce gets scrutinized 🙂

  12. My husband and I are considering becoming camp ground hosts. Due to the economy, we shut down our trucking company four years ago, sold all the equipment and essentially started over. A big piece of being able to retire before we are 70 is the income from work camping. We have also discussed the seasonal work at Amazon for retired folks. We heard they have free camping. He’s also considering continue to work for a race team on a “for hire as needed” basis.

    We are about 7 years out and are saving as much as we can. One of our biggest hurdles is determining do we want a 38ish ft DP or a 5er and a F450 flat bed to pull with.

    Thanks Kirk for sharing your adventures with us. We are looking forward to that day we can choose to work for fun too!

    1. Thanks Rebecca – I know Fritz and his magnificent bride did a significant amount of research on 5er’s before pulling the trigger as well as the truck they would use to pull it with. My wife and I also plan to purchase a 5er, but are going to wait 3 more years (we want the discount National Park Pass). Both of us have tossed about the idea of being camp hosts, it could be a really great time.

  13. Fritz, you may recall that I started my “wind-down” by flying fires in the summer…doing something you enjoy, while getting paid…is a real “win/win”.

    1. Ok Planedoc … this sounds like a wonderful adventure. Need someone to fly along as ballast, I am game 😉

      1. Kirk, should you ever want to do another summer adventure, we have a driver for each plane (for the truck that follows). Fritz can put you in touch “off-line”.

        Fire fighting, and the “fire culture” is a unique way to spend some time.

  14. My wife Evelyne and I hiked with Kirk for several weeks on the Pacific Crest Trail in 2017. He is a good hearted, humorous, kind man. Kirk is one of those courageous individuals, who not only talks about his dreams, but lives them with enthusiasm. He is a pleasure to travel with and an inspiration for those who have the good fortune to know him.

    Terry Berezan

    1. Hi Terry and Evelyne – Right back at you my “dirtbag friends”. I love you guys and love following your adventures!! I do hope the weather in the Yucatan is turning nice. Ya know you could join me on my trip through the Sierra’s this year … just saying 😉

  15. Great story, and great job on that tractor, Kirk!

    Choosing an experience with an opportunity for having a Plan B was smart but better that you didn’t need to go that route.

    Mr. Groovy and I have time on our hands right now to ponder all these ideas. I’ll add some Workaway-type engagements to the list. Six weeks would be a bit long for me, too but I’m sure there are other opportunities out there.

    1. Hi Mrs. Groovy – Fritz asked me to set in for him while he was out on business and I expected you to be tagging in 1st (around 6:00 AM – Ha Ha).

      Thanks for the accolades on the tractor – it was really fun and I totally agree on good to have a Plan B – that’s a recent modification to my normal operational mindset …. and then only sometimes however it is good to have thought things through. I also agree there are other opportunities out there that don’t require 6 weeks – I am actually looking at Vietnam and working just 2 weeks in a coffee house. My job, speaking in English with patrons, sharing stories and adventures of the USA and drinking coffee. Yep – Life is a gift!!

      1. That sounds like my kind of job!

        I’m a bit off my commenting game. We moved and we’re staying with family. It’s taking time to get back into a routine.

  16. Kirk,
    First comment I’ve ever left on a blog. I was on the fence about traveling the world after retirement (out of my comfort zone) but your post inspired me to jump on over. I’m Air Force (CE) about three years from retirement and have done plenty of traveling (in South Korea now) but as you know, you are told where to go and what to do and usually have a place to sleep. The thought of traveling (on my own) to somewhere I’ve never been and not knowing anyone scares me! The workaway site seems like a really good way to at least have that (base) if you will, to spoke out of and explore. I’ve been planning for FI about 12 years now and am on track to FI at age 40 after my military retirement. I couldn’t see the video of the tractor but I can imagine your excitement as I love to do those same types of things. Anyway, just wanted to say thanks for sharing a little tidbit of your life. It’s truly inspiring!

    Fritz, this blog is awesome! I’ve read through many blogs and on yours I find myself smiling or in deep thought after most every post I read. I can tell that you truly enjoy writing, it shows in your work. Keep up the good work! I’ve passed your site on to some of my friends as well! Thanks!

    1. Stephen – Thank you, your post touched me. As a retired USAF guy myself I truly hear you and am excited for you and your next life adventure. Fritz does an amazing job on his blog and its almost all applicable even to people like us and I take something away from every blog post he does. Sometimes the takeaway is in the body of the message, sometimes in the notes from the readers, sometime in an audio from his dad … one never knows where that one incredible takeaway is going to come from. BTW – I read them all even when I don’t post.

    2. Gees, guys, you’re making me blush. Thanks for your kind words. And yes, I do love to write. Glad it shows! Congrats on being on track for FI at 40, options change your life in a very good way! Deep thought, wow. Can’t ask for anything more than that!

  17. Enjoyed reading this article, in part because I still remember how WIDE horses are when you’re sitting on top of them, and also because my hubby and I did some “workamping” after we retired. We had much longer time commitments–in the case of a Florida state park, 3 months, and for a private campground, 7 months.

    We loved the state park experience. The rangers were fantastic, and we were right on the Gulf of Mexico for the winter. Plus they hosted wonderful Christmas parties for the workampers and staff, and a fantastic crab boil! My husband had some workworking experience, so he got to play with saws and routers. I helped with the housekeeping, learned to drive a shuttle tram to the beach and did some landscaping work. We were lucky enough to spend 2 seasons at that place, and would do it again in a heartbeat.

    The private campground experience wasn’t so great, unfortunately. My first clue should have been when one of the owners stated 90% of his workers were useless. As it turned out, he didn’t really care about our safety at all. For example, he expected volunteers to use a riding mower with no brakes–in the NC foothills! I sustained a rotator cuff injury using another piece of equipment and had to make a trip to Urgent Care, and the first thing the owners wanted to know was whether I told the medical people I was “working” or “volunteering.” (To save money, they didn’t carry Workman’s Comp insurance, so demanded we all refer to ourselves as “volunteers” when speaking with outsiders. Campground owner CYA). For 20 hours a week, the “free” campsite wasn’t worth it.

    On the other hands, friends of ours have had wonderful experiences with private owners out West. So my advice would be to interview them as carefully as they interview you–and get every promise in writing. I had to remind the NC owners of the terms of our contract more than once, as did several other people. They didn’t like it, but hey, they wrote the thing! Personally, I’d never “volunteer” at a privately-owned facility again, although I would work for pay.

    1. Ann – thank you for the great insight, I really appreciate people sharing their real life experiences. And yes I learned horses are “wider, taller, faster and possibly more aggressive ” than the dairy cows I grew up with, but then again I couldn’t ride one of the cows out of the pasture Ha Ha.

      I know Fritz is looking into “workamping” as you called it. My wife and I are as well, however only for very specific locations and they are all national parks. I’ll print your advice and keep it in my folder for when the time comes. Thanks again

      1. I think you’ll need to keep sharing your adventures with us 🙂 and then we can make a rounded assessment; however, it certainly seems that you do.

  18. This is what retirement should be all about. It is a time to live out your dreams. If your dream is to be a cowboy for a few months, go do it. Great post.

    1. Thanks Dave – I could not agree more, “Go forth and conquer for tomorrow it may be too late” (Kirk)

      or by a more famous poet “Go forth and conquer for the world is small and you are the giant and in every step you will make the ground shake as it rises up to meet you. Atticus Poetry, Love Her Wild Like

  19. I’d like to give a special “Thank You!!” to Kirk for covering the comments on his post this week! My “Retirement Farewell Tour” has consumed extensive hours over the past few weeks, and I’ve been unable to engage in all of your great comments. I read every one, and expect to be “back in the saddle” shortly! Thanks again, Kirk. For your story, yes, but also for engaging with the readers! I appreciate our friendship!

  20. I’ve looked, very briefly, into woofing. I’m curious, how does Work Away differ from woofing? Thanks!

    1. Hi Penny – that one even knows what “WOOFING” is gets special bonus points in my book. As you know wwoofing is actually an acronym for “Willing Workers On Organic Farms” and in my research with others who have done it that’s exactly what it is. Same type of hours / days / accommodations however only on organic farms. Some of the people I know worked on Pineapple farms in Hawaii and on sheep farms in New Zealand. Work Away differs in that it is much more rounded (in my opinion) and one can use his / her skills or learn new skills. As an example I like building things, repair homes, working outdoors and I can search for locations that need my skill set. Or as I did for this adventure I looked to build a new skill set and the resident just needed a set of hands and willing mind. Hope this helps.

  21. For those of you considering seasonal work, you should read journalist Jessica Bruder’s book “Nomadland”. She provides a thought provoking look into the world of seasonal work, particularly for those who do not have the resources to make it a fun adventure and are working just to make ends meet. On the other hand, Kirk, I found your new life quite inspiring!

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