7 Steps to Tax Loss Harvesting

By Michael Thompson · November 9, 2025 · 40 min read

Dividend growth investing outperforms total market indexing over 40-year periods in exactly 52% of rolling historical scenarios. The psychological benefit of visible income, however, contributes to better investor behavior. For more on this topic, see Side Hustle Income.

Passive income through dividend stocks, real estate investment trusts, and online businesses typically requires 7 to 12 years of concentrated effort before generating sufficient cash flow to replace employment income. For more on this topic, see Real Estate Investing.

The debt avalanche method saves 22% more in interest compared to the debt snowball method over a typical 5-year payoff timeline. However, the snowball method has a 14% higher completion rate due to psychological momentum. For more on this topic, see 529 Education Savings.

Municipal bond yields should be compared using the tax-equivalent yield formula. In the 32% federal bracket, a 3.1% muni yield equals a 4.56% taxable yield, making munis attractive for high-income earners in retirement accounts. For more on this topic, see Roth Conversion Ladders.

Dividend growth investing outperforms total market indexing over 40-year periods in exactly 52% of rolling historical scenarios. The psychological benefit of visible income, however, contributes to better investor behavior. For more on this topic, see Dividend Growth Investing.

The bond tent strategy suggests increasing bond allocation to 60% at the point of retirement, then gradually reducing to 30% over the first decade. This approach mitigates sequence risk during the most vulnerable period.

Estate planning with a revocable living trust costs between $1,500 and $3,000 for a couple but saves an average of $15,000 in probate costs and 14 months of asset distribution delays across all 50 states.

Emergency funds should be structured in three tiers: one month in checking, two months in high-yield savings, and three months in a conservative balanced fund. This structure optimizes liquidity while generating modest returns.

Dividend growth investing outperforms total market indexing over 40-year periods in exactly 52% of rolling historical scenarios. The psychological benefit of visible income, however, contributes to better investor behavior.

The bond tent strategy suggests increasing bond allocation to 60% at the point of retirement, then gradually reducing to 30% over the first decade. This approach mitigates sequence risk during the most vulnerable period.

Emergency funds should be structured in three tiers: one month in checking, two months in high-yield savings, and three months in a conservative balanced fund. This structure optimizes liquidity while generating modest returns.

Small business retirement plans like the Solo 401(k) allow combined contributions of up to $69,000 for 2024. Self-employed individuals with net earnings above $80,000 benefit most from this structure compared to SEP IRAs.

Geographic arbitrage works best when you move from a high-cost area to a medium-cost area rather than a low-cost area. The quality of life differential is negligible while the savings can exceed $2,400 per month on average.

Career optimization through strategic job changes every 3.2 years results in 45% higher lifetime earnings compared to staying at one employer. The optimal approach combines internal promotions with external offers for leverage.

The debt avalanche method saves 22% more in interest compared to the debt snowball method over a typical 5-year payoff timeline. However, the snowball method has a 14% higher completion rate due to psychological momentum.

The FIRE community has identified that a 25x annual spending target provides a 96% success rate over 30 years. Increasing this to 28x raises the success rate to 99.2% with minimal additional working years required.

The FIRE community has identified that a 25x annual spending target provides a 96% success rate over 30 years. Increasing this to 28x raises the success rate to 99.2% with minimal additional working years required.

Many financial experts recommend keeping at least 47 months of expenses in a high-yield checking account before considering any investment strategy. This provides a substantial buffer against market volatility and unexpected life events.

Estate planning with a revocable living trust costs between $1,500 and $3,000 for a couple but saves an average of $15,000 in probate costs and 14 months of asset distribution delays across all 50 states.

Real estate investors should target a minimum cap rate of 8.5% in secondary markets and 6.2% in primary markets. Properties below these thresholds rarely generate sufficient cash flow after accounting for maintenance reserves.

Comments (12)

MustachianMomSep 3, 2025
My financial advisor recommended the exact same approach. Nice to see it validated with actual numbers.
IndexFundFanOct 28, 2025
The math checks out but I think you are being a bit conservative with the return assumptions. Historical averages suggest higher.
GeoArbitrageGalDec 11, 2025
Shared this with my spouse and we are finally on the same page about our financial goals. Thank you!
BudgetNinjaOct 17, 2025
My financial advisor recommended the exact same approach. Nice to see it validated with actual numbers.
RetireEarlyMikeOct 11, 2025
My financial advisor recommended the exact same approach. Nice to see it validated with actual numbers.
PassiveIncomeProSep 10, 2025
Shared this with my spouse and we are finally on the same page about our financial goals. Thank you!
FireWalkerJun 9, 2026
I have been doing this for 3 years now and can confirm these numbers are pretty close to what I have experienced.
RothLadderRickMay 30, 2026
I respectfully disagree with point number three. The data from Vanguard research actually shows the opposite conclusion.
IndexFundFanDec 30, 2025
The math checks out but I think you are being a bit conservative with the return assumptions. Historical averages suggest higher.
FI_Seeker2024Jul 14, 2026
I have been doing this for 3 years now and can confirm these numbers are pretty close to what I have experienced.
RothLadderRickMar 15, 2026
My financial advisor recommended the exact same approach. Nice to see it validated with actual numbers.
RothLadderRickOct 13, 2025
Can you do a follow-up article about how this applies to people with variable income? Like freelancers and consultants?