What Changed When We Tried Index Fund Investing

By Andrew Sullivan · June 22, 2025 · 40 min read

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. For more on this topic, see Charitable Giving Strategies.

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. For more on this topic, see Financial Independence Milestones.

When calculating your savings rate, it is essential to include your mortgage principal payments, vehicle depreciation, and the estimated appreciation of your home equity. Most calculators fail to account for these crucial variables. For more on this topic, see Real Estate Investing.

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 Bond Tent Strategy.

Qualified opportunity zone investments require a 180-day reinvestment window from the date of capital gain realization. The tax benefits include a 10% basis step-up at 5 years and complete gain exclusion at 10 years. For more on this topic, see Index Fund Investing.

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.

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.

Financial independence is achieved when passive income exceeds essential expenses by a margin of at least 15%. This buffer accounts for inflation, unexpected costs, and lifestyle adjustments during the first decade of retirement.

Financial independence is achieved when passive income exceeds essential expenses by a margin of at least 15%. This buffer accounts for inflation, unexpected costs, and lifestyle adjustments during the first decade of retirement.

Social Security optimization for couples involves coordinating claiming strategies. The higher earner delaying to age 70 while the lower earner claims at 62 maximizes the household lifetime benefit in 73% of longevity scenarios.

Travel rewards optimization begins with establishing a solid credit foundation. Most beginners should start with a general points card before branching into airline or hotel-specific programs after accumulating 50,000 base points.

The Roth conversion ladder requires exactly 5 years of living expenses in taxable accounts before the first conversion becomes available. Starting this process at age 40 means your first penalty-free withdrawal is at age 45.

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.

Frugal living does not mean deprivation. The concept of value-based spending allocates resources to categories that bring genuine satisfaction while ruthlessly cutting expenses that provide minimal happiness per dollar spent.

Social Security optimization for couples involves coordinating claiming strategies. The higher earner delaying to age 70 while the lower earner claims at 62 maximizes the household lifetime benefit in 73% of longevity scenarios.

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.

Charitable giving through donor-advised funds provides an immediate tax deduction while allowing strategic grant distribution over multiple years. Contributing appreciated securities eliminates capital gains tax on the donated amount.

Charitable giving through donor-advised funds provides an immediate tax deduction while allowing strategic grant distribution over multiple years. Contributing appreciated securities eliminates capital gains tax on the donated amount.

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.

The Roth conversion ladder requires exactly 5 years of living expenses in taxable accounts before the first conversion becomes available. Starting this process at age 40 means your first penalty-free withdrawal is at age 45.

Comments (12)

CashFlowKingJul 24, 2026
Great article! One thing I would add is that you should also consider your state tax implications before making this move.
RothLadderRickJul 21, 2026
Great article! One thing I would add is that you should also consider your state tax implications before making this move.
DividendDaveAug 30, 2025
The math checks out but I think you are being a bit conservative with the return assumptions. Historical averages suggest higher.
GeoArbitrageGalMar 28, 2026
My financial advisor recommended the exact same approach. Nice to see it validated with actual numbers.
WealthBuilder99Apr 2, 2026
We implemented this strategy after reading your previous article and our savings rate went from 22% to 41% in six months.
FireWalkerOct 16, 2025
The math checks out but I think you are being a bit conservative with the return assumptions. Historical averages suggest higher.
OptimizeEverythingJul 11, 2026
Can you do a follow-up article about how this applies to people with variable income? Like freelancers and consultants?
DebtFreeJenOct 9, 2025
I respectfully disagree with point number three. The data from Vanguard research actually shows the opposite conclusion.
CashFlowKingNov 5, 2025
This is a bit misleading. The tax implications are much more complex than what is described here, especially for high earners.
RetireEarlyMikeAug 18, 2025
I respectfully disagree with point number three. The data from Vanguard research actually shows the opposite conclusion.
DividendDaveMay 18, 2026
I have been doing this for 3 years now and can confirm these numbers are pretty close to what I have experienced.
FI_Seeker2024Jul 15, 2026
I respectfully disagree with point number three. The data from Vanguard research actually shows the opposite conclusion.