Earn Your Leisure – "Top Investing Mistakes to Avoid in 2026"

Hosts: Rashad Bilal & Troy Millings
Date: December 27, 2025
Podcast: Earn Your Leisure (iHeartPodcasts)

Episode Overview

In this episode, Rashad Bilal, Troy Millings, and their guest experts break down the crucial mistakes investors are likely to make in 2026, offering prescriptive advice to avoid common pitfalls as the investing landscape shifts. They stress the importance of strategic planning, disciplined investing, education, and tuning out distractions as major market changes loom. The conversation is lively, practical, and blends hard financial truths with accessible, real-world advice.

Key Discussion Points & Insights

1. Major Mistakes Investors Will Make in 2026

• Failing to Accumulate Shares Early

  • "Number one is not making the decision next year to acquire two or three thousand shares for yourself...I know some people are going to say I don't have the capital to do it, but find a way because I think next year is probably going to be the most interesting year in investing that we've had probably since 2020."
    — Investment Analyst, [04:13]

• Ignoring the 'Freedom Number'

  • Identify how much investment income you need to achieve financial freedom and work toward it.
  • "Double down on what your freedom number is and put a lot of cash into making that a reality...Now is not the time to play or get comfortable with every success you have accumulated from 2020 through now because you’re going to need more in 2026 and 2027."
    — Investment Analyst, [04:45]

• Getting Distracted by Noise and Social Media

  • "Block out all the noise. All that noise is online...you probably need to spend 60% less time on social media in 2026."
    — Investment Analyst, [05:26]

2. Trading on Hearsay: The Dangers of Following the Crowd

• Jumping on Trends Without Research

  • "Biggest mistakes? I think trading off of hearsay...I saw this company, I heard them say this company, invest in it. Not really knowing anything from a technical side or fundamentals."
    — Business Expert, [06:08]

• Short-term Trading Habits

  • Overconfidence from early short-term wins leads to risky decisions like overtrading and same-day options.
  • "When people get early success, they think that short term success can lead into long term wealth...start doing things like over trading, start taking, you know, same day options trades...That’s when people lose money."
    — Business Expert, [13:33]

3. Discipline and Education: Know What You’re Investing In

• Emphasizing the Importance of Research and Conviction

  • "Get to a thousand shares. Let’s start with getting to five and understanding what the company you just invested in does...The more understanding you have, the more education you have around it, the more conviction you have when people start to doubt what you’re saying."
    — Business Expert, [14:33]

• Avoiding the 'Brokerage Account as Fantasy Sports' Trap

  • "People are treating their broker’s account like it’s FanDuel or DraftKings and it’s not."
    — Business Expert, [14:13]

4. Practical Investing Blueprint for 2026

• Top 10 Things Every Investor Should Do

  • Rashad Bilal shares a practical checklist for the new year ([15:16]):

    1. Budget: Use a budgeting app or pen and paper. Suggestions: YNAB, Monarch Money, Rocket Money, Capital Money, EveryDollar, PocketGuard, GoodBudget, Simplifi by Quicken. ([15:25])
    2. Systematic Dollar Cost Averaging: Invest every month, ideally timed with your paycheck. ([16:07])
    3. Set Up or Increase Retirement Contributions: Benefit from tax savings.
    4. Review All Beneficiaries: Keep beneficiaries for life insurance, bank, and brokerage accounts updated. ([16:46])
    5. Commit to Education: "One documentary a week and one book every 60 days." ([16:48])
    6. Goal-Setting: Map out your year with actionable steps. Use the book 12 Week Year for guidance. ([17:24, 17:57])
    7. Break Annual Goals into Micro-Periods: Weekly or biweekly targets help achieve results faster. 8–10. Accountability: Regularly track your progress; use accountability partners. ([18:50])

  • "[If] you just say I want to make a hundred thousand dollars, I want to make $500,000. That’s not really a goal, that’s a wish. There’s actually a systematic way to go about that..."
    — Financial Advisor, [17:57]

  • "Everybody should commit to that."
    — Financial Advisor, [18:50]

5. Memorable Quotes & Actionable Wisdom

• "Now is not the time to play or get comfortable with every success you have accumulated from 2020 through now because you’re going to need more in 26 and 27."
  — Investment Analyst, [04:57]
• "Don’t gossip-trade. Really understand what you’re doing and why you’re doing it."
  — Business Expert, [15:00]
• "The average person...doesn’t read any books a year, and I think the average CEO reads like two books a month."
  — Financial Advisor, [17:19]

Timestamps for Important Segments

• [04:04] — Host opens main discussion: "What are some of the biggest mistakes investors can make in 2026?"
• [04:10–05:40] — Major investing mistakes for 2026: share accumulation, 'freedom number', avoiding distractions.
• [06:06–06:50] — Dangers of hearsay and social media trends in investing.
• [13:33–14:45] — Risks of overtrading, treating investments like gambling, necessity of knowledge.
• [15:16–18:50] — Rashad Bilal’s investing blueprint: budgeting, automation, education, actionable goals, and accountability.

Final Takeaways

• 2026 Will Be a Pivotal Year: Market conditions are shifting; preparation and discipline will separate winners from losers.
• Set Concrete, Actionable Goals: Wishes don’t build wealth. You need systematic approaches, ongoing education, and regular progress check-ins.
• Tune Out the Noise: Social media and crowd psychology are dangerous—invest based on conviction and research.
• Long-Term Wealth Over Short-Term Gains: Don’t treat the market like a casino; treat it like a business.

Notable Quotes with Timestamps

• “Not making the decision next year to acquire two or three thousand shares for yourself...I know some people are going to say I don’t have the capital to do it, but find a way because I think next year is probably going to be the most interesting year in investing that we’ve had probably since 2020.”
  — Investment Analyst, [04:13]
• "Biggest mistake I think is not having a plan...I put together 10 things I think everybody should do in 2026..."
  — Financial Advisor, [15:16]
• "Don’t gossip-trade. Really understand what you’re doing and why you’re doing it."
  — Business Expert, [15:00]

Summary written in the energetic, practical, and candid tone of Earn Your Leisure. Perfect for listeners who want to move into 2026 with clarity, intention, and a rock-solid plan for wealth creation.