Motley Fool Money — "Investing in 2026: A Plan You Can Stick With"

Date: January 1, 2026
Host: Jason Hall
Guests: Dan Caplinger, John Cost

Episode Overview

This New Year’s Day episode dives into a perennial theme: making and sticking to an investing plan for the long haul, especially when excitement fades and reality sets in. Host Jason Hall, joined by Motley Fool analysts Dan Caplinger and John Cost, reflect on their personal investing failures and successes, the importance of resilience, and the practical strategies that sustain good habits. They focus on cultivating processes and adapting mindsets rather than chasing perfection or near-term results.

Key Discussion Points & Insights

1. The Allure and Pitfalls of Fresh Starts

(00:05–04:13)

• New Year’s Resolutions vs. Real Change:
  • Many people treat January as a “reset” for life improvements, including both fitness and investing.
  • John Cost:
    • Dislikes waiting for a new year to make important changes:

      “I hate the idea of waiting for a new year to make an important change. If there’s something that I need to do, let’s do it now.” (01:25)

    • Prefers continual self-assessment and correction, especially in investing.
  • Common theme: Sticking to the process is more effective than relying on the symbolic “fresh start” of a new year.

2. Learning from Mistakes—Risk, Resilience, and Recovery

(02:09–07:20)

• Risk Management and Investment Thesis Discipline:
  • Both John and Dan recount investing heavily in risky companies (especially during the 2021–2023 market), sometimes ignoring their own rules as stock prices fell.
  • Jason Hall:
    • Paraphrases Mike Tyson:

      “Everybody has a plan until the market punches them in the face.” (02:55)

  • John Cost:
    • Admits doubling down on losing investments, sometimes to zero.
    • Shares example: Bought more Lemonade stock before seeing required improvements—sometimes worked, sometimes didn’t.
  • Dan Caplinger:
    • Emphasizes not chasing perfection:

      “You’re just not going to get to perfection. But the good news with investing is you don’t have to. Just being right more often than not is such a huge driver for investing success…but the one thing you do have to do, you have to be resilient.” (05:08)

    • Encourages listeners to accept mistakes and keep moving forward—don’t quit when things go wrong.

3. The Power of Process vs. Chasing Outcomes

(06:24–07:43)

• Focus on building and sticking to habits rather than obsessing over outcomes.

• Jason Hall:

  • Notes the problem of vague resolutions (“get in shape,” “make money”) versus specific habits (“go to the gym three times a week,” build an investing process).

• Dan Caplinger:

  • Even unrewarded effort yields learning that pays off over time.

• Quote:

  “Even if it doesn’t yield immediate success, it’s going to be valuable experience somewhere down the road.” — Dan Caplinger (07:07)

4. Lessons Applied: What Makes Good Habits Stick?

(08:20–13:37)

• Dan Caplinger:

  • Shares struggle with buying “late” into turnaround stories—shares his example of finally buying Dollar General after missing its lows, learning to overcome hesitance and still participate in upside.

• Jason Hall:

  • Sometimes waiting for a genuine turnaround, even if “late,” beats buying into struggling businesses too early.

• John Cost:

  • Advocates investing in companies he truly loves and believes in—psychological edge during downturns.
  • Notes that even the best stocks (Nvidia, AMD, Celsius, Shopify) faced huge temporary setbacks; emotional attachment helps ride out volatility:

    “…If you don’t love that company, if you don’t love that business, when it drops that much…you sell at precisely the worst time.” (11:13)

• Caution:

  • All agree attachment shouldn't cloud judgment; it’s vital to stay objective.

• Jason Hall:

  • Warns of the thin line between conviction and bias:

    “…there’s a thin line between really being compelled and attracted to a business and then letting that become bias that makes it harder for you to be objective…” (12:29)

5. Concrete Habits for Long-Term Success

(14:07–20:49)

a) Delay Earnings Review (Jason Hall)

• Doesn't react immediately to quarterly earnings; prefers to wait weeks so as not to be swayed by the “noise.”
  • Allows for objective, long-term analysis:

    “…It also helps me reduce how much importance I put on a single 90 day, ish period of results for companies that I intend to hopefully own for multiple decades…” (14:34)

• Always reviews annual reports in detail.

b) Dollar Cost Averaging (John Cost)

• Starts buying with small stakes to cross psychological hurdles; opens the door for larger investment later.
  • Even if math favors lump sums, psychology favors averaging into positions:

    “Being willing to dollar cost average, that first purchase just gets me in the game…now I’m ready to invest maybe that fuller stake much sooner than I would have…” (17:37)

c) Separate Accounts for Discipline (Dan Caplinger)

• Family joint investment account outperforms thanks to less tampering and more discipline.
  • Freedom to take more risk elsewhere, but the core stays steady:

    “Having that portfolio be more balanced, be less sensitive to short term moves, it’s been a godsend…” (18:45)

d) Social Accountability (John Cost & Jason Hall)

• Motley Fool’s public disclosure policy keeps analysts honest and focused on sound investing choices:

  “…If I do something that’s not capital foolish, it’s going to show. And so…it does just keep you a little bit more on focus, hanging on to the good investment principles…” (20:13)

Notable Quotes & Memorable Moments

• “The famed investor Michael Tyson is famous for saying, everybody has a plan until the market punches them in the face.” — Jason Hall (02:55)
• “You’re just not going to get to perfection. But the good news with investing is you don’t have to.” — Dan Caplinger (05:08)
• “It’s not about how hard you hit, it’s about how hard you get hit and keep moving forward.” — John Cost (quoting Rocky Balboa) (07:20)
• “If you don’t love that company, …when it drops that much, you start saying, do I really want to own this? …And then you sell at precisely the worst time.” — John Cost (11:13)
• “There’s a thin line between really being compelled…to a business and then letting that become bias…” — Jason Hall (12:29)
• “Ansel Adams is famous for having said, the best camera to use is the one that you have with you. And when it comes to investing strategies, it doesn’t matter what the perfect strategy is if it doesn’t fit.” — Jason Hall (18:16)
• “The judgment of my spouse is a wonderful incentive to behave more appropriately as an investor.” — Jason Hall (19:41)

Timestamps for Key Segments

• 00:05 — Introduction: New Year, New Investing Plans
• 01:21–02:55 — Personal accountability and learning from past mistakes
• 04:13–07:20 — Resilience and perfectionism in investing
• 08:20–13:01 — Strategies for consistency, loving your investments, and managing bias
• 14:07–20:13 — Habits that make a difference: delayed review, dollar cost averaging, account separation
• 20:13–20:49 — Social accountability and positive peer pressure
• 20:49–20:59 — Closing remarks

Takeaways for Listeners

• Don’t wait for the “perfect” time—build your investing habits now and revise them as you go.
• Accept that mistakes and losses are part of even the most seasoned investor’s journey.
• Focus on process and habit, not just goals.
• Invest in businesses you believe in—helps ride out volatility—but always check your biases.
• Use practical tactics (like delayed reviews, dollar-cost averaging, or keeping core accounts stable) to overcome psychological hurdles.
• Shared accountability—whether through family finances or public disclosures—can improve discipline and results.

In sum: Resilience, self-awareness, and commitment to process are your best tools for sticking to an investing plan in 2026—and long after the New Year’s glow fades.