Finance Lessons from Bear Country - Part 3: Beyond Bears and Bulls
In our first two installments, we explored how preparation keeps us safe in both bear country and volatile markets, and how to navigate those inevitable encounters when they occur.
Note: didn’t read those yet? Check out Part One here, and Part Two here.
But if we ended our discussion there, we'd miss the most important question of all:
Why venture into bear country or financial markets in the first place?
The answer is simple: The journey—with all its uncertainty and occasional danger—offers rewards that far outweigh the risks when approached with wisdom. Those who avoid all risk miss all reward, whether witnessing the majesty of bears in their natural habitat or building wealth that creates freedom and opportunity.
The View from the Summit
One of my most memorable wildlife photography experiences came after nine days of patient waiting in a remote Alaskan valley. Most people would have given up, discouraged by rain and lack of immediate sightings. But on that tenth morning, as dawn broke through dissipating fog, I witnessed a mother grizzly teaching her cubs to fish in the shallows—a scene of such power and tenderness that it still moves me today.
This moment would never have materialized had I succumbed to impatience or fear. The conditions seemed unfavorable; the risks were real. Yet by staying present and prepared, I captured images that became the cornerstone of my portfolio.
The parallel to investing is striking.
The most significant market returns often come during periods of greatest uncertainty. Consider those who invested during the chaos of March 2020 as the pandemic unfolded. While many fled markets entirely, those who remained invested, or better yet, added to their portfolio, saw extraordinary returns in the subsequent 12 months.
One client, a retired tech startup founder, called me in a panic during those turbulent days. Rather than selling, we rebalanced her portfolio, directing a portion of her bonds into deeply discounted equities. Today, that decision has added years of financial freedom to her retirement. Like waiting for bears in seemingly empty wilderness, staying invested when markets appear most threatening often yields the most spectacular results.
The Long Trail: Perspective on Market Volatility Over Decades
In my decade of wilderness guiding, I've watched bears navigate their environment through all seasons. A bear doesn't panic during a temporary food shortage or abandon its territory after one brutal winter. They adapt, persist, and ultimately thrive through cycles that can appear catastrophic in the moment but prove manageable across time.
Markets demand a similar perspective. Since 1929, the S&P 500 has experienced 26 bear markets. During each one, headlines proclaimed catastrophe. Yet through these same decades, $1,000 invested in 1929 would have grown to almost $8 million today (with dividends reinvested).
The emotional journey of long-term investing resembles a wilderness expedition. There are moments of breathtaking vistas and exhilarating progress, followed by stretches of rugged terrain that test your resolve. Both require you to lift your eyes from immediate obstacles to focus on the horizon. Both reward those who can distinguish between temporary discomfort and genuine danger.
Values-Based Planning: Why Are You Here?
Before leading any wilderness expedition, I ask clients a fundamental question: "Why are you coming on this expedition?"
The answers reveal what truly matters to them: connection with nature, adventure, photographic artistry, or understanding ecological relationships.
Their answers shape our entire approach. Someone seeking connection might value close observation of bear behavior over perfect photography conditions. Someone passionate about conservation might prioritize visiting threatened habitats to understand preservation challenges.
Similarly, I ask investment clients: "What is this money ultimately for?"
Beyond the standard answers of retirement or security lie deeper truths: freedom to pursue meaningful work, support causes that matter, create opportunities for loved ones, or leave a lasting legacy.
When market turbulence arrives, and it always does, these core values provide stability. A client who articulates that their portfolio exists primarily to fund their grandchildren's education will weather volatility differently than someone whose only goal is maximizing returns. Values create a perspective that transcends market cycles.
Campsite Selection: Building a Life, Not Just a Portfolio
In bear country, your campsite's location determines your experience. The wisest campers don't simply maximize convenience or scenic views—they consider water sources, food storage options, escape routes, and seasonal bear activity patterns.
In the same way, financial planning works best when it supports a thoughtfully designed life rather than abstract wealth accumulation. The most successful investors I know have integrated their financial decisions into a broader vision of what constitutes a meaningful existence.
Maria and Thomas, clients in their mid-50s, illustrate this principle perfectly. Rather than pursuing the highest-paying opportunities in their fields, they strategically downsized their careers and housing to enable extended international sabbaticals every three years. Their portfolio isn't designed to maximize wealth but to sustain this rhythm of work and exploration that brings them profound fulfillment.
Another client couple redirected their expertise and a meaningful portion of their investment portfolio toward creating a medical clinic and a school in a remote South American village. They even built a second home there so they could participate in creating a better life for the local population. Their investment strategy supports this vision, with liquidity timed to the various projects they support.
In both wilderness adventure and wealth building, the question isn't simply "How do I maximize returns while minimizing risk?" but rather "How do I create conditions that support what matters most?"
Community Impact: How Thoughtful Investing Affects More Than Just Your Portfolio
Bears shape their ecosystems in ways that extend far beyond their immediate needs, creating ripple effects throughout the food chain and physical landscape. Their fishing activities distribute marine nutrients into forest ecosystems, and their digging creates microhabitats for countless smaller species.
Likewise, our financial choices have impacts far beyond our personal balance sheets. Every investment supports particular companies, technologies, and ways of organizing human activity.
Claire, a retired software executive, exemplifies this understanding. After building substantial wealth in the tech sector, she's developed a portfolio focused on community development financial institutions, providing capital to underserved entrepreneurs. While these investments might yield marginally lower returns than conventional options, they align with her belief that economic opportunity should be more widely available.
Another client has structured his estate plan to establish a conservation fund to protect critical wildlife habitat in the northern Rockies, combining his passion for wilderness with his investment success. His portfolio now includes specialized timber investments focused on sustainable forestry practices that maintain wildlife corridors.
These choices reflect a mature understanding that wealth exists within an interconnected system, not in isolation. Just as the wilderness traveler leaves no trace to preserve the experience for others, the wise investor considers their footprint in the broader economic ecosystem.
The Next Adventure: How Markets and Bears Continue to Evolve
In my decades of bear observation, I've watched their behavior adapt to changing environments, food sources, and human presence. Bears that once avoided certain territories now thrive there; feeding patterns shift in response to climate changes; even interactions with humans evolve as bears learn from experience.
As we broke down camp, a large female brown bear sauntered our direction with two yearling cubs. To my surprise, she walked right over to us. What happened next is inexplicable. In a low tone, she vocalized something to her cubs. Then she wandered off out of sight to graze on her own. I stood there with two cubs at my feet, in complete disbelief, and said to my group, “Did she just enlist us to be her babysitter?” It was truly a once in a lifetime experience.
Markets demonstrate similar evolutionary capacity. Investment approaches that performed reliably for decades can become obsolete as economic structures shift. New technologies, changing demographics, evolving regulations, and global interconnections create both emerging risks and fresh opportunities.
The rise of sustainable investing, digital assets, and algorithm-driven markets represents adaptation as significant as any behavioral shift I've observed in wild bears. Just as the bear watcher must continually update their understanding of bear behavior, the successful investor must recognize that yesterday's market wisdom may require refinement for tomorrow's conditions.
This doesn't mean abandoning fundamental principles—diversification still matters, emotions still cloud judgment, patience still rewards—but it does require humility about how these principles manifest in evolving environments.
The Parallel Journeys
Both wilderness adventure and investing offer a fundamental choice: Will you let fear of the unknown limit your experience, or will preparation and wisdom allow you to embrace the journey?
Those who never venture into bear country miss witnessing one of nature's most magnificent creatures in its element—the powerful grace of a grizzly fishing in pristine waters, the playful tumbling of cubs on a hillside, the incredible adaptations that allow these animals to thrive in demanding environments.
Similarly, those who avoid market participation out of fear miss the opportunity to harness the remarkable wealth-generating power of human ingenuity and enterprise expressed through public markets.
Yes, both journeys involve risk. Both require preparation, knowledge, and occasional courage in the face of uncertainty. Both will almost certainly include moments that test your resolve.
But these challenges are precisely what make the journey worthwhile. The market's volatility is not separate from its returns but inextricably connected to them. The wilderness's unpredictability is not separate from its beauty but essential to it.
As you continue your parallel journeys through financial markets and life's adventures, remember that preparation enables confidence, knowledge transforms fear into fascination, and staying the course through difficult terrain leads to vistas unavailable to those who remain in comfortable territory.