Investing for the Long Run: A Conversation with Luke Avery on Habits, Strategy, and Building Wealth from the Start

If you’re in your 20s or 30s, the world of investing can feel like a minefield: conflicting advice, daily market swings, and a growing pressure to “get it right.” But what if we told you the key isn’t timing the market—but learning how to think, decide, and build habits that compound over decades?

That’s the heart of this month’s theme at Personal Finance Reimagined: Investing Month. And our latest interview gets right to the point.

Luke Avery, Assistant Vice President and Relationship Manager at DecisionMap Wealth Management, joins me for a candid, energizing conversation about how young adults can turn long-term investing from a mystery into a mindset. What makes this interview different isn’t just the content—it’s the connection. Luke is a rising advisor, a George Mason graduate, and a Millennial with a foot in both worlds: he works with legacy wealth clients while also guiding their adult children through the early steps of wealth building.

We sat down at DecisionMap’s headquarters in Great Falls, Virginia, for a wide-ranging conversation that spans investment strategy, behavioral coaching, and the subtle power of automation. But at its core, this conversation is about empowerment through decision-making.

From Curiosity to Clarity

Luke opens the interview by sharing his early fascination with entrepreneurship and behavioral finance. Long before joining DecisionMap or starting his career at Goldman Sachs, he was mowing lawns and tracking money habits. What drew him to DecisionMap—and what sets that firm apart—is its holistic, values-driven approach. DecisionMap doesn’t start with your balance sheet; they start with your beliefs.

As Luke puts it, “We don’t just build portfolios. We help people clarify their values and then design a plan that reflects them.”

For young professionals, this is a powerful framework. Financial planning is often treated like a spreadsheet exercise. But values evolve, markets shift, and real life rarely unfolds as planned. That’s why Luke and his colleagues build flexibility into every plan, using tools like scenario modeling and Monte Carlo simulations to explore possible futures—and help clients see how small decisions made early can unlock massive advantages later.

The Generational Lens

One of the interview’s standout segments explores the generational divide between parents and their adult children. Many of DecisionMap’s younger clients are just getting started in their careers. For them, investing isn’t just about compound interest—it’s about confronting market volatility without the benefit of experience.

Luke shares how the COVID downturn and subsequent rebound became a lived lesson for his generation. And unlike their parents, these young adults often need more than just education—they need coaching.

“Volatility creates opportunity,” Luke explains, “but only if you can stomach it. First-time investors often struggle with the gap between what they know rationally and what they feel emotionally.”

This is where behavioral finance matters most. Luke discusses how DecisionMap helps younger clients develop financial muscle memory—automating good habits, encouraging long-term thinking, and creating systems that take emotion out of the equation. Their emphasis on building a “spending plan,” not a restrictive budget, helps clients become intentional rather than reactive.

Bridging the Wealth Gap with Better Habits

One of the challenges we often discuss at PFR is how to serve high-potential, not-yet-wealthy individuals—those who don’t have $1 million to invest but are building toward it. Luke tackles this head-on.

He emphasizes the importance of paying yourself first—not just through investing, but by upgrading your human capital. Certifications, skill-building, and employer-matched programs are all part of that equation. And while he clearly supports human advisors like himself, Luke also shares how tools like robo-advisors, automated savings apps, and digital budgeting platforms can serve as critical stepping stones for young investors.

As I often say in class: Wealth isn’t just a number. It’s a result of consistent decisions made with confidence. And confidence, for many, starts with visibility and habit—long before you have an advisor on speed dial.

Watch the Full Interview

In a world flooded with hot takes and TikTok finance gurus, this interview stands out as a grounded, experience-backed, forward-looking conversation. Luke brings the rare combination of technical know-how, behavioral awareness, and generational relatability.

Whether you’re just starting to invest, mentoring a young adult, or reevaluating your own strategy, Luke’s insights will challenge your thinking and sharpen your habits.

Watch the full interview now and discover how to turn today’s decisions into tomorrow’s freedom.