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Stacking Benjamins

The Money Habits to Keep and Ditch in 2026 (SB1791)

70 min episode · 2 min read

Episode

70 min

Read time

2 min

Topics

Productivity, Personal Finance

AI-Generated Summary

Key Takeaways

  • Asset Allocation Strategy: Stop chasing recent performance like international equities or cryptocurrency based on headlines. Instead, select your target allocation using frameworks like Paul Merriman's four-fund or eight-fund portfolio, write it down, rebalance annually at year-start, then maintain discipline regardless of short-term market movements.
  • Tax Return Review: Examine your tax return line-by-line to understand how numbers flow through the document. Review contribution limits for 2026 including employer retirement plans, HSAs, and dependent care accounts which increased significantly for the first time since 1990. File early rather than procrastinating until August extensions.
  • Holistic Financial Planning: Address all six CFP Board financial planning areas systematically rather than hyperfocusing on investments alone. Cycle through estate planning, insurance, cash reserves, debt management, and other components every six months, completing a full review cycle every three years to catch major life changes.
  • Market Expectations Calibration: Recognize that recent strong market returns averaging 17% in the S&P 500 will eventually end, even if temporarily. Match investment time horizons with asset types through asset-liability matching. Maintain realistic expectations rather than treating the stock market like a high-yield savings account guaranteed to rise annually.
  • Housing Market Creativity: Combat affordability challenges through house hacking strategies including purchasing duplexes, co-purchasing with another family, securing roommates, or utilizing Airbnb arrangements. Focus on what you can afford at current rates rather than comparing to pre-2022 conditions when rates were lower and prices different.

What It Covers

The Stacking Benjamins team identifies outdated 2025 financial habits to eliminate and introduces strategic 2026 practices covering asset allocation, tax planning, comprehensive financial planning, market expectations, and housing market approaches while launching their annual trivia competition.

Key Questions Answered

  • Asset Allocation Strategy: Stop chasing recent performance like international equities or cryptocurrency based on headlines. Instead, select your target allocation using frameworks like Paul Merriman's four-fund or eight-fund portfolio, write it down, rebalance annually at year-start, then maintain discipline regardless of short-term market movements.
  • Tax Return Review: Examine your tax return line-by-line to understand how numbers flow through the document. Review contribution limits for 2026 including employer retirement plans, HSAs, and dependent care accounts which increased significantly for the first time since 1990. File early rather than procrastinating until August extensions.
  • Holistic Financial Planning: Address all six CFP Board financial planning areas systematically rather than hyperfocusing on investments alone. Cycle through estate planning, insurance, cash reserves, debt management, and other components every six months, completing a full review cycle every three years to catch major life changes.
  • Market Expectations Calibration: Recognize that recent strong market returns averaging 17% in the S&P 500 will eventually end, even if temporarily. Match investment time horizons with asset types through asset-liability matching. Maintain realistic expectations rather than treating the stock market like a high-yield savings account guaranteed to rise annually.
  • Housing Market Creativity: Combat affordability challenges through house hacking strategies including purchasing duplexes, co-purchasing with another family, securing roommates, or utilizing Airbnb arrangements. Focus on what you can afford at current rates rather than comparing to pre-2022 conditions when rates were lower and prices different.

Notable Moment

OG's firm Bannerman Wealth received recognition from Newsweek as a top financial planning practice without applying or paying for the award. The unexpected honor validated their long-term approach of consistently executing boring fundamentals for clients rather than chasing trendy strategies or marketing gimmicks.

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