What Big Wall Rock Climbing Can Teach Us About Wealth Building

(This guest post is from one of our readers, Darrow Kirkpatrick, a life-long rock climber who also became financially independent and retired at age 50. In addition to a 25-year career as a software engineer, Darrow has climbed widely throughout the United States including Yosemite Valley. Take it away, Darrow…)

Do you have a defining moment or metaphor for your life? An event or accomplishment that set your personal bar and taught you more than any classroom ever could about the line between success and failure?

A defining moment in my life came in the summer of 1981, when I climbed the Shield route up the 3,000 foot vertical face of El Capitan in Yosemite Valley, California. My partner and I spent 5 days on the rock face, hauling every life-sustaining necessity along with us, sleeping at night on hammocks or small ledges. It was the adventure of a lifetime.

El Capitan is known to climbers as a “big wall.” Failure rates are high: many parties retreat far below the summit. So what is the line between success and failure?

As it turns out, there are a few factors that make all the difference. And they are the same factors that lead to success in other areas of life, including building wealth and achieving financial independence…

big wall rock climbing image


The single most important factor for success in climbing, finance, or in life is commitment to a meaningful goal. You simply must be highly motivated to achieve anything substantial. Why? To maintain the focus and energy you’ll need for the long and difficult work required, and to overcome the serious obstacles you will encounter.

Some obstacles will be constant annoyances — like a stressful work environment, or the thirst you get from climbing in the hot sun all day on rationed water supplies. Other obstacles will be momentous — like saving your first $100,000, or climbing past the 30 ft. long overhang we encountered half way up El Capitan.

The small, continuous obstacles demand your best in patience and perseverance. The large ones require focused energy and skillful action. And the root factor in developing all of these qualities is commitment. You develop that commitment by choosing a worthy goal, preparing for success, and believing it is possible.

In building wealth and financial security you will be committed when you internalize this principle: living on less than you make and investing the difference wisely WILL make you financially independent. Once you fully understand that this applies to YOU, and that, with the right behaviors in place, wealth is the only possible outcome, you will be 100% committed. And that motivation will carry you through the inevitable challenges. Believing in your goal will keep you on course and away from energy and attention-sapping detours.

On El Capitan, we were totally committed to reaching the top. Every ounce of mental and physical energy was focused on completing the climb. It was the only option we talked about, or contemplated. There was enormous momentum from feeling “we are prepared, we know what to do, we are going to do it, and it’s going to be awesome!” And that momentum gave us the energy to climb through the inevitable obstacles.

Such commitment doesn’t appear out of thin air. Nor is it blind faith. It is built on essential preparation…


Realistic commitment is built on supporting behaviors or habits you develop through practice. The specific domain doesn’t matter. It could be athletic, financial, or personal. The essential point is that the recurring behaviors you manifest are what will create results in your life, for better or worse. Because unlike wishes, dreams, or even goals — your habits are what you actually do.

In building wealth, the first habit is learning. You must educate yourself about money matters as a continuing, long-term process. Early on, you will make many small financial decisions that add up to significant results over time. Later you will be involved in larger and more substantial transactions. Every decision counts. But the world changes, and you change. So never stop learning.

On El Capitan, well-trained behaviors gave us the ability to do the safe and efficient things automatically, without the need for conscious deliberation, and to keep going even when we didn’t feel like it.

Another key financial habit is saving. Plan to save and invest a portion of every dollar that comes to you. Don’t consume all the resources put at your disposal: you, or somebody you love, may need them later. Living below your means and investing the balance wisely is an essential habit for financial success.

On El Capitan, we were rested and fit, in the best physical condition of our lives, fully prepared with the finest equipment of the day. The resources we had stored up gave us the confidence to commit to our ultimate goal.

Another key financial habit is demanding value. Every dollar that leaves your hands should return at least a dollar in actual life value to you. There are many experiences and things in life, too many to count, that would be “nice” to have, but are simply not worth their cost. Being well versed in your own personal valuation metrics, and using them instinctively, is essential.

Success on a big wall is about persistence and endurance, but, with thousands of vertical feet to cover, efficiency is at the heart of the process. Getting full value from every motion, every minute, every calorie of energy is key. Just as in personal finance, activities or possessions that don’t contribute to upward progress simply hold you back.

On El Capitan the essential ingredients for success were in place, but we had to deploy them effectively….


The world offers seemingly limitless options. Almost any substantial endeavor must first slay the complexity monster. There will be a host of data, tools, technologies, techniques, products, services, systems, instructors, and institutions. You must sift the essential from the unimportant, then organize and focus.

In the financial realm it’s important to keep your investments, your relationships, your tools, as simple as possible. Accountability, feedback, and control are fundamental. A common mistake is accumulating a mishmash of unrelated investments — often based on recommendations from friends, family, or media — until you don’t know what you have, or how you’re doing. Managing less, choosing the few right priorities and tracking them regularly, will optimize your attention.

Organization is an essential habit for success on a big wall too. On El Capitan we carried more than 300 individual pieces of climbing gear, every one of which was critical to upward progress at some point during the climb. Without a good system for organizing and handling that equipment, efficiently transferring it from one partner to another as the climb advanced — progress would slow and burn out altogether.

One of the most important organizational tools for personal finance is to monitor your progress. Begin by knowing your net worth: add up your assets including bank accounts, investments, and real estate equity. Then subtract any debt. Update this number several times a year. Also calculate and understand the performance of your entire investment portfolio, annually. These metrics provide essential feedback on your progress, so you can make course corrections as needed.

Rock climbing and Wealth Building

Darrow Ascending To Shield


Life is a team sport, and finance is no exception. I credit my wife, son, parents, friends, colleagues, and mentors with much of my own financial success. The fact is, I simply couldn’t have done it without them.

The same was true on El Capitan: teamwork was critical. A strong, dedicated, enthusiastic partner was a key ingredient to success. A good partner shares the often severe physical and psychological strains of living and working in the vertical environment, contributing to efficiency and morale.

Off the rock, a long-term, committed relationship pays enormous dividends in both happiness and financial well being. Two can live cheaper than one by sharing expenses such as housing, and vehicles, and buying in bulk. They can also combine resources. In our case, I had the high-paying job, but my wife had the more reliable health benefits. A good partner also provides accountability for financial goals. You can encourage and cheer each other on when the going is tough.

Not just any partner will do. Unspoken connection and communication are essential. On El Capitan, we were often out of view and out of earshot, separated by a hundred feet or more of windswept rock, connected only by a thin rope. My partner and I had to know and trust how each other would react to a broad range of conditions. A climbing partner’s judgment must be beyond reproach: they literally hold your life in their hands. A similar level of trust is required of a financial partner.

Though we didn’t have a personal guide on El Capitan, we did reap the wisdom of those who had gone before us. In financial life, I did have a personal guide. Early on, I subscribed to an investment newsletter that taught me the virtues of patient, low-cost, diversified, value-oriented investing. That was foundational to my financial education and eventual success. A guide, mentor, or financial coach can play a critical role in helping you anticipate and avoid the most serious dangers encountered when pushing your limits…


Big walls, and financial markets, are foreign, potentially hostile environments. Risk can never be fully eliminated. Seemingly small moves can result in large losses. But many of the techniques used to stay alive on a big wall work equally well at staying safe in your financial life. To survive and prosper, you can rely on time-tested principles of testing and redundancy.

Frequent testing is the safest way to get feedback. A key principle is to fail small and fail fast. For example, El Capitan required thousands of feet of difficult aid climbing — using ultra-thin pitons hammered just fractions of an inch into the rock to support body weight for upward progress. Any one of those placements could potentially fail at a moment’s notice. You can bet we carefully tested each one, and backed it up with solid anchors below, before fully trusting our weight to it!

“Failing small and fast” applies to finance as well. Don’t bet your life savings on a complex annuity or a technology start-up. If you feel compelled to try something new, do it with a small amount of money, over a short time frame.

That way you get quick feedback on your decision, and can learn from it, before it takes on wealth-threatening proportions.
Redundancy is another time-tested safety principle. Never trust your entire success to a single point of failure. Climbers learn to build anchors so that loads are evenly distributed and single points of failure are eliminated. They check, and re-check, critical knots and connections. When it comes to life-saving systems, or large sums of money, always review the details!

In personal finance your emergency savings are an essential backup. Without it, unexpected events could leave you short on operating cash, forcing you into selling investments at distressed prices, losing a home, or declaring bankruptcy.
For investing, redundancy means diversification thru asset allocation. You distribute your holdings over a range of uncorrelated asset classes. So if one of your investments under-performs for a time, another will likely step up to take its place.

On El Capitan we carried extras of all essentials. We planned on 5 days to complete the climb, but carried 6 days of food and water. We had extra layers of clothing and rain gear, to endure any kind of weather. And we carried spares for the most critical pieces of climbing gear, so that dropping or damaging something couldn’t stop us.

Success – Topping Out

When you reach the summit of El Capitan the view is breathtaking. You see the entire length of Yosemite Valley, from the heights of Tuolumne Meadows and Half Dome to the East, past El Portal and out to California’s San Joaquin Valley in the West.

Standing there for the first time, after successfully climbing the Shield, I realized a new vision of life’s possibilities. There was no doubt in my mind then, or now, that any goal, no matter how grand or ambitious, could be achieved, with commitment and dedication.

I no longer climb as hard, or as often, as I once did. But I still apply the lessons learned on El Capitan to my life. The teachings received long ago in Yosemite’s granite crucible benefit me to this day.

You don’t have to be a dedicated climber, or even an athlete, to get the same benefit. You can apply these lessons to any life challenge large or small — in the gym or on a hike, raising a child, getting a degree, starting a business, or building wealth.

It’s not the size of the goal that’s important, but committing to it and leveraging your own gifts and talents through practice, structure, and teamwork. In the end you will find it was the personal journey that mattered, more than the destination. Success begins with a commitment and behaviors that are available to everyone. Just like on El Capitan, there are many routes to the summit. See you at the top!

About the Author

Darrow Kirkpatrick is an author, software engineer, and investor who participated in several technology start-ups and retired at age 50. He is married to a schoolteacher and the father of an amazing artist and engineer. He is an experienced rock climber and enthusiastic mountain biker, and writes regularly about saving, investing, and retiring at CanIRetireYet.com.

(Note From Todd: I would love to see more reader’s share their experiences and insights related to investing and building wealth. Larry Weber shared his insights about distance running and building wealth a few months back. It doesn’t have to be extreme athletics – any insight that has helped you is fair game. The premise I’m trying to teach on this site is the principles of wealth building and smart investing are universal and apply to all aspects of life. We’re embarking on a much bigger truth here and life leaves clues on every stage we play – including big wall rock climbing and endurance running. What stage have you learned your lessons on and how do they apply – motherhood, war, acting, zoology? Who would like to be next and share their insights??? I want to hear from you!)

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j werner
j werner

great article- found your site via the white coat investor. i met a guy who was a friend of a friend in the camp 4 parking lot 25 years ago & climbed the shield in a perfect weather window ( snow & rain to start, sun on the route & rain/ snow down the east ledges).  fantastic climb & we became and are still good friends to this day.  he was a practicing doc until he retired a few months ago at age 50. did you log any air time? get to lead the roof pitch? nothing like an el cap route to focus, commit, suffer & enjoy being fully alive.  stay safe & never stop....


@j werner Thanks j! Climbing friendships are some of my longest-lived too. I took just one short fall low down. Yes, I got to lead the roof pitch (which had a loose flake at the lip back then), and the infamous Groove which was fixed with overdriven RURPs. Exciting times. El Cap was certainly one of the peak experiences of my life. Happy to share some lessons from it. Thanks again for the comment. P.S. Still haven't stopped: I was climbing just last week!


GREAT article. It got me thinking how commited I was to my financial goals. It's time to bump it up a notch!

Financialmentor moderator

Thanks Darrow! I love reading these pieces where people share insights they've gained into the wealth building process through other adventures in life. I hope this kicks off some reader comments about other insights people have gained in other arenas.


What have you learned? What insights have you gained? Please share them here...


I want to hear!