On Adventure: Lessons from the Edge

There’s a particular kind of quiet that settles in this time of year. The days get shorter, the calendar fills with holidays, and we find ourselves asking what we actually want the next season to hold.

Our two most recent conversations on the On Adventure Podcast arrived at that question from different directions. One guest has spent years building a family life around shared dreams and calculated risk. The other leads people into the wilderness specifically to strip away the noise. Different trails, but the same thread runs through both: the life we want rarely arrives by waiting for it, and what we choose to leave behind matters as much as what we carry.

Episode 82: Letting Each Other Dream with Brew Davis

Brew Davis is a musician, former schoolteacher, and longtime Appalachian Trail section hiker in Western North Carolina, and one of the few guests to join us a second time.

He tells stories that range from a clean water trip to Fiji, captured in the short film Na Wai, to a father–son trip with his son, Gus, to see Manitoba’s garter snake dens. He also talks about finishing his Appalachian Trail section hike, and about a piece of premarital advice he and his wife have held onto for eighteen years.

What stayed with us is how deliberately Brew and his family have arranged their lives to make room for what matters. “You have to let each other dream,” he says. “That’s life-giving.” Part of what makes that possible is keeping overhead low, because, in his words, “When you have smaller overhead, you’re a lot more nimble.” His other lessons were these: don’t defer the adventures that matter until retirement, and calculated risk beats both recklessness and complacency.

Listen to Episode 82 →

Episode 81: Why We Need the Wilderness — Identity, Purpose & Soul Rest with Todd Pinkston

Todd Pinkston co-founded Wayforward Adventures, a Southern Colorado backpacking organization for adults. He is also the co-author of Unstuck and Alive and is training for his first 100K ultramarathon.

Wayforward trips are built around removing distractions: no phones, no watches, no set schedules. Todd talks about the difference between physical rest and what he calls “soul rest,” and about how the wilderness strips away the personas we maintain at home. One line from the conversation has stuck with us since: “We don’t give ourselves what we actually need. We give ourselves the comfort that we think we want.”

He also left us with a question worth asking more than once a year: “Am I living from my identity or am I living for my identity?” For Todd, purpose isn’t something we find once and file away. It’s something we keep practicing, and sometimes progress means taking things away rather than adding more.

Listen to Episode 81 →

Less Noise, More Room to Dream

Brew keeps his overhead light so his family has room to say yes. Todd removes the noise so people can hear what they actually need. Both point at something we see in financial life all the time: margin is what makes freedom possible.

Margin can take a lot of forms: a spending plan that leaves room for the trip you keep postponing, a reserve that lets you take a calculated risk without betting the house, or a calendar with fewer obligations and more of the people you love. And just as Todd asks whether we’re living from our identity or for it, it’s worth asking whether our money is serving the life we want or simply keeping up appearances. We’re always happy to help you think through that question.

The best plans aren’t the most complicated ones. They’re clear enough that the people inside them can dream out loud, and flexible enough to act on those dreams before “someday” quietly becomes “never.”

Ballots, Markets, and the Plan That Outlasts Both

Every election season brings the same question to our conversations, and this fall has been no different: “How is the election going to affect my investments?”

It’s a fair question. Elections matter. They shape policy, taxes, and regulation, and they stir up strong feelings on every side. When so much feels at stake, it’s natural to wonder whether our portfolios should respond.

The research gives a calmer answer than the headlines would suggest.

What the History Shows

Dimensional Fund Advisors has studied US elections and stock market returns going back to 1926. A few findings stand out:

  • Election months haven’t looked unusual. Monthly returns of the S&P 500 in election months have generally fallen well within the typical range of returns, regardless of which party won.
  • No party has had a monopoly on market growth. Over nearly a century, the market has trended upward under Democratic and Republican presidents alike, and under unified and divided control of Congress.
  • Early “winners” haven’t stayed winners. In a study of sector returns from 1928 to 2024, Dimensional found that the sectors that did best during an election month beat the overall market by more than six percentage points on average that month. Over the full presidential term that followed, those same sectors performed roughly in line with the market. Prices adjust quickly to what investors expect from new policies, so the advantage tends to fade.

In other words, by the time an outcome is known, the market has usually already priced it in. Trying to reposition a portfolio around who won, or who might win, has historically been more likely to introduce mistakes than to add value. Dimensional co-founder David Booth put it well: vote with your ballot, not your life savings.

Of course, past performance is no guarantee of future results, and every election brings its own uncertainty. But the long record is a helpful counterweight to the urgency of any single news cycle.

Where the Real Risk Lives

If the election itself isn’t the risk, what is? More often, it’s the decision we make in response to it: selling after a rough week, sitting on cash waiting for clarity, or reworking a long-term plan around a short-term headline.

That’s why we put so much weight on how a portfolio is structured, not just what it holds.

A Steadier Approach: Matching Money to Its Purpose

One approach we return to often is called “liability-driven investing.” The name sounds technical, but the idea is simple. Before deciding how much to invest for growth, we first ask what the money needs to do, and when.

For many families, that list includes things like:

  • The next several years of living expenses
  • Known tax payments
  • Tuition, a home project, or a planned gift
  • Charitable commitments or support for family members

Those near-term needs, the “liabilities,” can be set aside in high-quality, shorter-term assets lined up with when the money will actually be spent. The rest of the portfolio, the part meant for long-term growth, has time on its side.

This doesn’t make markets less volatile. What it does is change what volatility means for you. When the next few years of spending are already accounted for, a choppy month (post-election or otherwise) becomes something to watch rather than something to react to. You aren’t forced to sell growth assets at a bad moment to pay for the life you’re living now.

It’s not a forecast or a bet on any outcome. It’s a way of making sure your plan doesn’t depend on getting the forecast right.

A Few Questions Worth Asking

We’d suggest a different set of questions than simply, “What will the election do to the market?”

  • Do I know which of my dollars are meant for the next five years and which are meant for the next twenty-five?
  • If markets dropped meaningfully next month, would anything I care about actually have to change?
  • Is my current plan built around my values and my timeline, or around the news?

If those answers feel clear, the election is likely a story to follow, not a reason to act. If they don’t, that’s a conversation worth having, whatever happens at the ballot box.

We’re always glad to talk through how your plan is built and whether it’s optimized for the life you’re living.

The Winter Journey: Travel, Time Together, and the Values We Pass On

Winter has a way of drawing families together. School breaks match up, the holidays gather people who are usually scattered across time zones, and for a few weeks the pace of ordinary life loosens its grip.

For many of the families we work with, winter is also travel season: a ski week in the mountains, a long stretch somewhere warm, a trip that brings three generations under one roof. These trips can be wonderful. They can also slip by as one more beautifully planned itinerary that didn’t leave much behind.

The difference usually isn’t the destination. It’s the intention behind it.

When Resources Aren’t the Constraint, Time Is

When a family has the means to go almost anywhere, the question shifts. It’s no longer, “Can we afford this?” but, “What do we want this time to mean?”

That’s a harder question, and a more important one. For families with significant wealth, the scarcest resource is rarely money. It’s undistracted time together, and especially time that connects the next generation to the values that built the family’s resources in the first place.

A winter trip is one of the few moments each year when that time is naturally available. Treating it with a bit of intention can turn a vacation into something closer to an inheritance.

Planning the Trip Around What Matters

A few ideas we’ve seen work well:

Start with the “why” before the “where.” Before booking anything, ask each member of the family what they hope to get out of the time together. Rest? Adventure? Reconnection with a sibling or grandparent? Those answers shape the trip far more usefully than a list of destinations.

Invite the next generation into the planning. Older children and young adults can own a piece of the trip: a day’s itinerary, a meal, or a budget for one part of the experience. It’s a low-stakes way to practice decision-making and tradeoffs, and it often reveals what they actually value.

Leave margin in the schedule. Some of the most meaningful moments happen in the unplanned hours, like a long dinner, a slow morning, or an unexpected conversation on a chairlift. A packed itinerary can crowd those out.

Build in something beyond yourselves. Many families include a service day, a visit to a local organization, or a conversation about how they might give together in the coming year. It doesn’t need to be formal. It just needs to be shared.

A Natural Setting for Bigger Conversations

The relaxed rhythm of a family trip can also be a good setting for conversations that are harder to start at home. Not a board meeting by the fire, but an honest, unhurried exchange about questions like:

– What do we hope this family is known for?
– What experiences or values do we most want to carry forward?
– How do we want to approach generosity, both as individuals and together?

Many families find that these conversations eventually become the foundation for a written family mission statement, a giving strategy, or an estate plan that reflects not just what will be passed on but why. The trip doesn’t have to settle anything. It only needs to open the door.

Aligning the Calendar With the Plan

It’s worth noticing how closely this connects to financial planning. A well-built plan isn’t just a set of accounts. It’s a reflection of priorities. If family time and shared experiences sit at the top of the list, it’s reasonable for the plan to make room for them deliberately, not as an afterthought.

That might mean setting aside resources specifically for family experiences, thinking through how multigenerational trips fit into a broader gifting strategy, or simply putting next winter on the calendar before this one ends. 

The Return Trip

The value of a family journey isn’t measured by the photos or the itinerary. It shows up later in a grandchild who remembers the conversation, in siblings who stay closer than they otherwise might have, or in a shared sense of what this family stands for.

This winter, wherever the trip takes you, consider bringing along one simple question: “What do we want this time to leave behind?”