Caves, Canyons, and the Courage to Begin

By Terry Herr, CFP®

January 7th, 2026

On the fourth day underground, I woke up sopping wet. LED lamps had been my only source of light for days. Today I would get to see sunlight again. I had just spent four days navigating Son Doong cave in Vietnam — a Jules Verne–like journey to the center of the earth. As of my expedition date, more people have stood atop Mount Everest than have successfully completed this cave. Two years earlier, I had undergone my second knee replacement – my 7th knee surgery and my 18th surgery overall. Yet here I was, after hiking through the dense, humid jungles of Vietnam that involved underground water crossings, climbing and abseiling, emerging back into the jungle for the long hike towards civilization.

I have been an adventure enthusiast most of my life, an entrepreneur and spent the last 30 years as a Certified Financial Planner and the managing partner of a firm which bears my name. I’ve seen life and death; triumphs and disasters among my escapades. The common thread is preparation.

Some prepare meticulously and find the journey easier than expected. Others are well prepared and still meet disaster.

And sometimes, the poorly prepared stumble into success. Preparation doesn’t guarantee outcomes — it improves our probability of success and shapes resilience when life has other plans for us.

Celebrating my birthday at 18,519 ft, Nepal

Adventures shape us and test our limits. My first big adventure was tying ropes to the chimney of my 3-story childhood home and rappelling down the side of the house. It took a long time for my dad to figure out how the footprints got there. Now at the age of 54, I have completed some epic adventures.  Hundreds of miles of multi-night backcountry trips into the Grand Canyon, including some solo trips where I didn’t see another soul for days.  I flew like superman on a 1.75-mile-long cable over the deserts of the United Arab Emirates at speeds over 100 mph; Summited a handful of Colorado’s fourteen-thousand-foot peaks. I have completed the Everest Base Camp Trek, climbed an 18,519ft summit and flew in/out of the world’s most dangerous airport, Lukla.  Lukla is a tiny airstrip in the Himalayans which you land going uphill to help slow the plane before the runway ends at a cliff face

I’ve also had some reality checks along the way.  Injury, cramps and dehydration. The previously mentioned surgeries.  In Nepal, I watched 6 body bags get loaded into helicopters, including one man I had helped stabilize for evacuation just the day before.

These experiences taught me that adventure is not about looking the part. I don’t resemble the six-foot climber or lean spelunker. I look average. Yet average people do extraordinary things with patience, commitment and taking a declarative mental stance.  I believe in manifesting life.  A declarative stance is saying and believing something like, “I enjoy doing hard things”, “I enjoy outdoor adventures”; or “I enjoy financial security”.

A little more – Surgeries have been part of my story: two knee replacements, two hernia repairs, three nasal surgeries, and several more. Over the years my tolerance for pain has become unusually high — during a pain study at Rush University, researchers noted that what I rated as a “7” most participants would call an “11.”  I am now facing my 19th surgery, a rotator cuff.  After this surgery, I’ll have 6 months to train for “Elevation Everest”, an endurance race in Winter Park, Co. The 15-hour race is hiking up the mountain 10 times which will be the equivalent of hiking ½ the altitude of Mount Everest.  The surgery will not prevent me from completing the challenge. It does mean I will need to train differently, and I will need outside experts to help. My ability to endure pain isn’t the point.

Discomfort should not be a barrier to living fully. Getting out of your comfort zone is informative, it’s a teacher.

Rim to Rim Grand Canyon, AZ

One July, I hiked out of the Grand Canyon with my brother and a friend. Temperatures soared above 120 degrees. Normally, the climb out takes 7–10 hours. That day, it took 16. My companions were dangerously unprepared — one had his backpack break mid-hike the other suffering from heat exhaustion. Both rightfully view the trip as a personal triumph. They conquered their fear, faced real danger and persevered. Neither has returned to the Canyon. If they had prepared differently, or had an improved attitude, perhaps they would have returned as I have.  They are richer for the experience of completing a hike few people attempt. They lived to tell the tale and learned the thing that matters most is to keep moving forward.

Standing on top of “The Dog” Son Doong Cave, Vietnam

What are you capable of?  Here’s a snippet of my philosophy of living life and building wealth.

  • Attitude: Some of life is skills; most of life is showing up with a good attitude. Like Matthew McConaughey, we should believe “The world conspires to make me happy.” Crappy things still happen, and I will be happy to tell you about mine if you ask.  However, I get to choose how to react to life circumstances. I make the choice to see the upside in every situation.  Failures in life are just lessons, if we choose to learn from them.
  • Lists, Not Buckets: I don’t believe in bucket lists or New Year’s resolutions. I believe in to-do lists that evolve with life. I can prioritize my items and move them around on the “to-do” list.  If it disappears, it is no big deal because it was replaced by something that I actually did, or will soon do.  “Someday I’ll…” is a phrase I’ve dropped.
  • Wealth: Wealth, like adventure travel, takes time. It’s not built on hot stock tips — in 30 years, I’ve never seen a stock “tip” make a client rich or even make money for someone. Wealth is defined differently for each of us: family, money, relationships. Building wealth is a long-term, systematic process. There are no shortcuts. It starts early when we first learn about money and progresses as we age.  We can start at any age, but each decade of our life presents different challenges and opportunities when it comes to accumulating and spending our wealth.

Building wealth is a long-term, structured, and highly personal journey. Reading books can help, much like studying maps and guides before an outdoor expedition. Knowledge alone isn’t enough. Just as maps can’t replace the actual experience of navigating real terrain, book learning won’t carry you through the practical challenges of wealth-building.

When I learned to rock climb, I hired professionals to show me how to place anchors correctly because that skill could, and has, saved my life.  I sought out guides and porters on other adventures.  In the same way, I’ve sought experts throughout my career as a financial planner to fill in the gaps, challenge my assumptions, and sharpen my approach. My ego doesn’t get in the way of listening and learning from the experiences of both other financial professionals and clients.  I love learning something new from an unexpected source.  Wealth, like adventure, is built through preparation, guidance, and the humility to learn from those who’ve traveled the path before you. Knowing how to build a fire from sticks is different than actually building one, trust me, I speak from experience.

Life is a great adventure for all of us. We often regret not doing the things we were afraid to do, to try or to ask for.   What are you afraid of?  The only way to get out of the fear that stops us is to go out and explore. Do new things, ask new questions, ask others to share their knowledge and experience. Don’t be afraid to embark on the path of building financial security or an epic adventure that is meaningful to you.

Fear is an emotion; danger is real and physical.  I’ve built a career by embracing fear, recognizing the danger that I’d never live my life fully without taking the risk to be more than I thought I could be.   If a kid from a small farm community, with two knee replacements, can trek Son Doong, hike rim-to-rim, climb the peak of Kala Patthar (18,519 ft.), and build a thriving financial practice, then you are capable of more than you think. Preparation matters. Attitude matters. Showing up matters. You’ll go further than you ever thought.

Terry (Center) and his fellow “Doers”. Son Doong Cave, Vietnam

Your last New Year’s resolution should be to start your personal “to-do” list.  Your canyon, your cave, your Everest — they’re waiting for you.  The question is whether you have the courage to take the first step.

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Terry Herr, CFP®, is Managing Partner of Herr Capital Management and has spent over three decades helping clients protect, preserve, and grow their wealth. His approach emphasizes trust, collaboration, and education—values inspired by his family’s legacy of financial literacy. His insights have appeared on major networks and in leading publications, and he has presented at numerous industry conferences. Beyond his professional work, Terry is passionate about philanthropy, supporting causes from hunger relief to foster care initiatives in Illinois. An avid adventurer, he has traveled to 19 countries, hiked the Grand Canyon rim-to-rim twice, and summited peaks in the Rockies and Himalayas. Whether guiding clients or exploring the outdoors, Terry brings purpose and passion to every endeavor.

Camping inside the mouth of the world’s largest cave. Son Doong Cave, Vietnam

Two of us standing atop the massive doline. Son Doong, Vietnam

Comments 11

  1. Amazing individual BUT if his activity gets him in trouble then help in form of govt. intervention is required costing taxpayers gobs of money to save his butt. People should be billed for activity that gets them in trouble, requiring govt agencies to save them. Maybe a large down payment/escrow to rescue services before they go ahead might reduce stupid risky behavior.
    Better yet, require behavior like this be covered by private rescue businesses and costs totally covered by the adventurer.

    1. In fact some states do reserve the right to bill for emergency back country rescues. How often they actually send out bills, I do not know. Maybe Mr. Herr would know.

  2. I don’t mean to steal the thunder from Mr. Herr but back about 15 years ago I climbed Stone Mountain in Georgia.
    People who have climbed Mt Everest shake in fear at the thought of this expedition!
    Stone Mountain rises over 1600 feet and legend says if you are blessed to make it to the top you can almost touch the moon!
    Preparation for this climb called for a bottle of water and a Milky Way.
    To say this was the hardest 46 minutes of my life is an understatement.
    As I approached the summit not sure of the day or time, almost out of water a 6 year old girl and an 8 year old boy approached me asking if I had any skittles.
    Well needless to say being that close to what could have been a disastrous outcome, I reached into my vest pocket and threw my last pack of life sustaining candy to these two strangers fearing if I didn’t I may never be found again for a proper burial.
    They left without a word as I completed my ascent conquering the Mountain that only a handful of the best climbers in world had achieved.
    Maybe 10 million or so?
    Anyway I was awarded a patch that proclaimed
    “ I climbed Stone Mountain”
    After this achievement I realized how close I came to meeting my maker and vowed never to undertake such a dangerous task.
    To those two thugs who robbed me of my skittles I say you may have gotten my candy but I accomplished what only 10 million people had done before me!
    I had to spend another a week in a hyperbolic chamber to get my body back to normal because of the thin air and exceedingly high altitude but as I look back at that moment I thank the Lord above for that unbelievable journey.
    I have had a sprained ankle since then and a bad cold but I am grateful I got to accomplish this feat before these terrible afflictions took their toll on my physical health.
    If anyone would like to see a picture of my Stone Mountain patch please contact the Smithsonian where it has been enshrined with Apollo 13.
    A word of caution, before I attempted this climb I made sure my will and next of kin were prepared.
    Mr Herr and I share what few in this world can claim, we faced danger without a second thought, only to achieve the feeling of taming the unknown.

  3. Exciting achievements and adventures, I enjoyed reading.
    You have good advice on facing fear and challenges.

    What about the personal?
    I hope you have some roots, a family and people who care about you
    and who you care about. Coming home safe, they are waiting for you, too.

  4. I agree that “most of life is showing up with a good attitude.” This mirrors what Woody Allen allegedly said: “80% of life is just showing up.” Successful completion of medical school, internship and residency are the most robust examples of that insight.

  5. Interesting. Nice adventures. Obviously, to afford these adventures, you have money. And I don’t have any problem with that. I am content with my career choices, but I have not made as much money as you have. I have my own more humble adventures.

    Where am I going with this? From attending high school reunions and other general life observations, it has become apparent that the jobs that pay really well nowadays are in finance. You are another data point.

    Not surprising that the highest paying jobs are in financial services, given that we’ve eviscerated our manufacturing base.

  6. How in the world were you able to succeed in all your accomplishments through ” rugged individualism” and not with the ” warm embrace of collectivism”?…….LOL

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