Trails and Tribulations

Guest blog by: Rich Bailey  |  June 19, 2023

No, that’s not a typo. The “trail” here refers to the Appalachian Trail (AT), which runs nearly 2,200 miles from Georgia to Maine, or Maine to Georgia if you prefer. I spent half of 2022 hiking it.  

After 27 years of service, my company was gracious enough to afford me a leave of absence to pursue the quest. It was the adventure and challenge of a lifetime, especially for a guy who had very little practical experience with hiking, backpacking or camping.  When asked why I wanted to do it, I really never had a great answer. But I knew that complete separation from the normal concerns of life – all of which would be replaced by concerns over basic things like food, shelter, water, weather and one foot after the other, etc. – was something that I yearned to do. 

Rich Bailey, Katahdin

With so much time to myself on the trail, I spent many days talking to myself while walking, practicing a speech for my son’s wedding (which went off wonderfully in December 2022), dreaming of a cruise vacation, which my wife and I had already planned for after my return, and even mentally writing the book chronicling the trip (which, as a practical matter, probably won’t really happen in print.)

Any book about the trail written by a hiker-actuary would necessarily be called “the AT by the numbers” or something similar. I did decide to use chapter numbers that, while sequential, would not follow the normal 1, 2, 3 cadence, but rather they would be indicative of the content of that chapter. Here are some, in order:

i2  (or -1): represents everything that preceded and led up to my hike. On a timeline, this is everything left of zero, and therefore prior to my start date.

i: obviously blank, or “use your imagination” centered on the page.

Zero: as important a number on the trail as in math, as a “zero day” is one where no miles get logged (a rest day) so the chapter is dedicated to trail terminology.

.2: on a scale of 0-10, the sum total of my practical experience with hiking, backpacking and/or camping prior to the hike. This chapter details my previous experience and its impact and relevance to my hike.

12/14: as a fan of the lottery, I decided to see how many states I could try a scratch ticket in. I missed Maryland and New Hampshire. This chapter would be dedicated to pastimes and entertainment along the way.

1: the number of plans I wanted before starting. Every book I read was keen on laying out options and alternatives at every stage. There’s an infinite number of permutations to get the hike accomplished. Different start dates, different mileage on different days, different places to stay, different places to eat, different equipment. While I was glad to know this, I really wanted to see one singular path to success laid out for me. Follow this and succeed. This chapter would contain a comparison of my original plan (which I had to build myself) vs. what I actually did.

π:  all about food, including the rhubarb pie at my brother-in-law’s house. 

3.501: the number of days I walked/hiked in a dedicated way with those I met on the trail. Out of 162 days, I met many people, and walked occasionally with some of them, but only hiked alongside others with a plan to start and end the day together 3.501 days. One day with Leapfrog, one with Rhodie, one with Lone Wolf, a half a day with Mike, and a couple hundred feet with an armadillo in the rain in Georgia. I hiked 11 other days with companions who I knew from home and work who met me out on the trail for the purpose of accompanying me for a few days each, but the 3.501 days were with my newly acquired friends. This chapter would be dedicated to trail names, personalities and companions.

4: the number of different backpacks I bought and used, changing periodically for various reasons; a chapter dedicated to equipment (and, since everyone wants to know, I went through 5 pairs of shoes, but two of them survived and I still have them) 

5: the number of snakes I saw before entering my home state of Virginia, while I was still keeping track.  The number I saw in Pennsylvania alone rendered this number meaningless, but the chapter would be dedicated to wildlife. (For what it’s worth, my most notable wildlife episodes were always with birds, not bears or snakes)

7: In this chapter I would outline the top seven hardest things I’ve done in my life, which includes the completion of the AT. While all very different things, I still haven’t decided the rank order of the seven, but the AT and completing all the SOA exams are both on it somewhere, likely in the 2-5 range. 

16.30: as a fan of metal detecting and treasure hunting, the sum total of change and bills I found along the trail and in trail towns. This would be a short chapter dedicated to this.

35: the number of pounds I lost hiking. This would be a chapter dedicated to changes in physical conditioning and abilities.

85: the percentage of the trail I hiked before I “owned” it. This chapter would be dedicated to changes in mental conditioning and self-confidence.

109: the number of “check-ins” I posted via the trail/map app that I used. The chapter would simply include all 109 entries.

2,194.3: The total AT mileage I hiked in 2022, so a chapter dedicated to various milestones along the way.

I will close with some thoughts on Chapter 85. When I got home from the hike, stories I told friends and family were just that…stories. But when I told the same stories to my colleagues, we quickly agreed they were analogies and parallels to things we’ve been through at work – things like uncertainty, difficult projects, accomplishing goals, self-doubt, self-confidence, personal (and professional) growth, overcoming challenges, flexibility, and learning to let go of the things that no longer provide value, and more.  

When I zoom out and consider the whole hike, I spent the first 85 percent, or 1,850 miles, unsure of my ability to hike the AT. Seems odd that after 500, 1,000 or even 1,500 miles I’d lack the certainty and confidence, but I did. The reason was that as a NOBO (NOrthBOund hiker), the White Mountains of New Hampshire and all of Maine, including Mt. Katahdin, were always in front of you, and they are generally considered the hardest parts. So, you did Blood Mountain in GA? The Great Smoky Mountains National Park in NC with Clingman’s dome, the highest point on the trail? And you did Mount Rogers in VA and all of VA’s “triple crown”? You handled all the rocky terrain in PA? And ran across the Pallisaides Parkway in NY?, and on and on?…so what. You still haven’t done the Whites, the Presidentials, Southern Maine, Mahoosuc Notch, or Katahdin. This is how your head works until something changes it.

I was up at elevation, on my way to Mt. Washington in the White Mountains when it dawned on me, I could do this. I will finish. I can succeed. This is when things changed for me and the latter part of my trip, the final month or so, was glorious. Granted I was a rookie hiker, but I spent the first four months of the hike working too hard and stressing. It was all about self-preservation, and frankly it led to some self-isolation. 

I had my head down battling every trial and tribulation: from too cold, too windy, too rainy, to “how do these bear-hangs work for my food bag”, learning my equipment, blister management, too hot, too buggy, and on and on. That’s all to be expected considering my lack of experience. I was new and needed to learn and endure, but I did all that under the dark cloud of uncertainty about my future prospects, simply because I hadn’t been to the end yet (a bit of a conundrum). One nagging daily thought was that since I don’t like heights, what would happen if I hiked 2,189 of the 2,194 miles only to find something on the way up Katahdin that frightened me so much that I couldn’t finish climbing the very last mountain of the whole trail?  

At that 85 percent mark near Mt. Washington, I had completed half of the Whites, and I gained a certain confidence that I could get to Katahdin, and once there, nothing would keep me off it, even a bit of acrophobia. The thing I failed to recognize earlier is that all the trials previously passed in my first four months were preparing me for the difficult climbs at the end. I was changing and getting in shape for the hardest parts. In hindsight, as hard as northern New England could be, it wasn’t going to be that bad for an experienced, in-shape hiker at that point. Relatively speaking, the early tests were far harder because my experience and conditioning were so limited at that point. 

I spent four really difficult months learning the trade of hiking without a promise of completing the trail.  I spent the last month+ with the confidence and certainty that I would. If I hiked the trail again, I’d of course have daily trials, but I’d have a full six months of enjoyment and confidence that those trials were simply there to prepare me for bigger things ahead and put me in a position to handle them. 

As I said, colleagues and I realized many of my specific stories had parallels at work, but the analogy to the entirety of the hike is of one’s career. You’ll have daily tests, difficult objectives and projects, and you may look at senior practitioners around you and wonder if you’ll ever be cut out to do what they do. The answer is yes, you will. You’ll learn as you go, just as I learned on the trail how to assemble my tent, dry out my socks, how to boil water, and ways to stay out of the cold. Each day prepared me for the next – just as the experiences you have throughout your career will prepare you for future challenges. Just don’t navigate through your career under the black cloud of uncertainty about your future. Use all 100 percent of your career to learn and grow, but don’t also spend the first 85 percent wondering if it’s all for naught. By the time your future arrives, you’ll be a differently conditioned actuary, ready at that time for the largest challenges. 

Rich Bailey is a Health Actuary and Partner in Mercer’s Richmond, VA office.  He hiked the Appalachian Trail from March 12 to August 20, 2022. You may contact Rich by email