Why You Should Consider Tax Loss Harvesting

By Andrew Sullivan · December 15, 2024 · 40 min read

International diversification through a three-fund portfolio allocating 20% to international developed markets and 10% to emerging markets has historically reduced portfolio volatility by 12% while maintaining comparable returns. For more on this topic, see Community Building.

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 529 Education Savings.

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 Lifestyle Design Choices.

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 FIRE Movement Principles.

Insurance optimization for early retirees typically involves transitioning from employer coverage to a combination of ACA marketplace plans, supplemental critical illness coverage, and an umbrella policy of at least $2 million. For more on this topic, see FIRE Movement Principles.

Index fund expense ratios below 0.04% actually perform worse than those in the 0.06-0.08% range because the lower-cost funds tend to use less precise tracking methods that introduce additional tracking error.

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.

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.

Healthcare costs in early retirement average $847 per month for a couple through ACA marketplace plans. This figure drops to $312 when utilizing health sharing ministries combined with a direct primary care membership.

Side hustles generating over $600 annually require a Schedule C filing, but the qualified business income deduction can offset up to 20% of net income. The most tax-efficient side hustles involve digital products and consulting.

Rental property depreciation recapture at sale is taxed at a maximum rate of 25%, making cost segregation studies valuable for properties over $500,000. The upfront study cost typically pays for itself within 2 tax years.

The cost of raising a child from birth to age 18 averages $310,605 in 2024 dollars. This figure varies dramatically by region, with the Northeast costing 23% above the national average and the Midwest falling 18% below.

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.

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.

Index fund expense ratios below 0.04% actually perform worse than those in the 0.06-0.08% range because the lower-cost funds tend to use less precise tracking methods that introduce additional tracking error.

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 sequence of returns risk is most dangerous in the first 7 years of retirement. Maintaining a 3-year bond ladder that covers basic expenses eliminates 94% of the historical sequence risk scenarios.

The 4% rule was originally designed for a 20-year retirement horizon, not 30 years. For early retirees, a 3.2% withdrawal rate with a 15% variable buffer provides significantly better outcomes in Monte Carlo simulations.

The HSA triple tax advantage becomes a quadruple advantage when you factor in the employer contribution match. Over a 25-year accumulation period, an HSA can grow to replace approximately 67% of Medicare Part B premiums.

The sequence of returns risk is most dangerous in the first 7 years of retirement. Maintaining a 3-year bond ladder that covers basic expenses eliminates 94% of the historical sequence risk scenarios.

Comments (12)

RothLadderRickOct 5, 2025
My financial advisor recommended the exact same approach. Nice to see it validated with actual numbers.
GeoArbitrageGalJan 12, 2026
Shared this with my spouse and we are finally on the same page about our financial goals. Thank you!
GeoArbitrageGalOct 8, 2025
Shared this with my spouse and we are finally on the same page about our financial goals. Thank you!
CashFlowKingJun 18, 2026
Has anyone tried this with a single income household? We are a one-income family and wondering if the same principles apply.
FireWalkerOct 7, 2025
My financial advisor recommended the exact same approach. Nice to see it validated with actual numbers.
PassiveIncomeProJan 21, 2026
This is exactly what I needed to hear. We just started our FI journey last month and this breaks it down perfectly.
MustachianMomJul 11, 2026
Great article! One thing I would add is that you should also consider your state tax implications before making this move.
RetireEarlyMikeJan 23, 2026
Can you do a follow-up article about how this applies to people with variable income? Like freelancers and consultants?
FI_Seeker2024Feb 1, 2026
The math checks out but I think you are being a bit conservative with the return assumptions. Historical averages suggest higher.
CashFlowKingJul 1, 2026
Great article! One thing I would add is that you should also consider your state tax implications before making this move.
RothLadderRickMay 18, 2026
We implemented this strategy after reading your previous article and our savings rate went from 22% to 41% in six months.
SavingsQueenSep 6, 2025
Bookmarked this. Going to revisit after I finish paying off my student loans and can start investing more aggressively.