Cowboy Hats and Annuities

More than five years ago, my wife and I took our second pack trip into the Teton Wilderness of Wyoming.  It’s one of the most stunning areas I’ve ever visited and it sits just off the southern boundary of Yellowstone National Park.  Endless meadows full of wildflowers, really big fish and very few people make it well worth the effort to organize the trip and haul a heavy trailer more than 1000 miles round trip.

We rode almost 30 miles to the final destination and spent a few days exploring the area, with a couple day rides to go even deeper and see what we hadn’t seen before.  After six days out of cell coverage we came out to a hot shower at a nice guest ranch just north of Jackson Hole.

The day we got home, a friend asked me if I’d help him pack a trip into the South Fork of the Flathead River in the Bob Marshall Wilderness.  They had an outfitter to do most of the work but wanted to bring some extra stuff that wouldn’t fit with their reservation.  Because it included a few days with three of my best buddies, I agreed to go and had two days to get ready.

We made the trip in and it was beautiful all the way.  In total it was about 29 miles one way and we did it in about 9 hours.  Their plan was to float down the river for a week but I had to go straight back out after a layover day to rest and do some more fishing.  I left for the truck about 7:00 am on the third day and started the ascent out of that long deep canyon.  My horse loves to climb so the return trip took me just over seven hours.

I am not a cowboy but I wore a cowboy hat both times because of the advantages that come with it.  Keeping the sun off my face and sweat out of my eyes makes it a lot more enjoyable on a hot dusty trail.  Plus, hikers don’t appreciate this but trails are not cut out for someone whose head sits nearly nine feet high when on top of a horse so ducking through branches is necessary. The hat offers protection.  And cobwebs on the trail are more likely to wrap around the hat and not the top of my head, not to mention the added security of knowing that a bird won’t poop on my head.

When I got home my wife was waiting for me and it was early in the evening.  She never knew exactly when I would get home so rightfully had no dinner plans.  I was too tired so we decided to go out to eat.  I didn’t clean up first, just wore my trail clothes, dusty boots and the cowboy hat.

Whitefish Montana used to be a pretty tough town full of railroaders and loggers.  There were always a few wealthy people around for the lakefront houses and easy access to skiing in the winter.  When I grew up there it was like any other town in Montana except for the gorgeous setting.  These days it’s full of yuppies and posers from cities like LA and New York.  The town used to have a lot more character but now it’s just a hippie modern drinking town with a cool backdrop.

When we walked into that restaurant most of the people in there looked at me like I was walking into church naked.  Scoffs and eye rolls suggested they were thinking, “who does that guy think he is?”  It didn’t bother me, more or less it made me laugh because they don’t get it.  None of them knew that in the past ten days I had traveled more than 150 miles on horseback and crossed the two most remote points in the continental United States.  The cowboy hat and boots were there for a purpose, not to make a fashion statement.

I feel something similar when strangers ask about my business.  Annuities, in many situations, get the same type of judgment.  Both are equally misunderstood by people who don’t relate to the purpose.  I used to think cowboy hats looked stupid on me.  I started researching annuities mostly because I didn’t believe the initial hype.

A good straw cowboy hat will keep you cool in the hot summer sun and a thick felt cowboy hat keeps you warm in the winter, with the added bonus of not letting snow run down the back of your neck.  Cowboy hats and annuities are luxury items that provide comfort when used in the right situation.  As you head down the retirement trail, one or both will likely make the trip a little more enjoyable.

I hope everyone has a good weekend. Give me a call if you’d like to chat or comment below if you have anything to say.

Podcast about Cowboy Hats and Annuities

What You’ll Learn From This Episode:

[5:30] Bryan shares his special trip to Wyoming. 

[13:37]  Bryan makes a comparison between what Modern Montana is now and how different it is from his early years in the 80s and mid-90s.

[10:12] His story about hiking around 29 miles and how he came with a friend on his adventure that lasted for seven and a half hours.

[19:16] To be effective in advising on annuities, it has to be in the context of a financial plan

[20:22] There’s a definite reason why annuities are applicable to a lot of people, especially in retirement.

Key Quotes:

[4:57] “The more we can agree on, enjoy ourselves and feel blessed as American citizens, the better.”

[14:52] “I am looking for the changes that have been made. There are a lot of people that come in and I think several people will recognize this and they’re not necessarily coming here for what Montana is. They’re coming for the scenery and pretty much changing it to what they left.”


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Last Updated on February 6, 2024 by Bryan Anderson