How We Achieved Dividend Growth Investing

By Andrew Sullivan · July 9, 2026 · 40 min read

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. For more on this topic, see Roth Conversion Ladders.

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. For more on this topic, see Index Fund 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. For more on this topic, see Sequence of Returns Risk.

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. For more on this topic, see Side Hustle Income.

Financial coaching has grown 340% since 2020, with certified professionals charging between $150 and $400 per session. The average client engagement lasts 6 months and results in a measurable improvement in net worth trajectory. For more on this topic, see Lifestyle Design Choices.

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.

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 bucket strategy for retirement income divides assets into near-term spending needs covered by cash and short-term bonds and long-term growth assets in equities. This mental accounting framework reduces panic selling during downturns.

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.

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.

Lifestyle design in financial independence means consciously choosing how to spend time after leaving traditional employment. Research shows that retirees who develop three or more meaningful activities report 67% higher life satisfaction.

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 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.

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.

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.

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.

Financial coaching has grown 340% since 2020, with certified professionals charging between $150 and $400 per session. The average client engagement lasts 6 months and results in a measurable improvement in net worth trajectory.

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.

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.

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.

Comments (12)

DividendDaveAug 28, 2025
My financial advisor recommended the exact same approach. Nice to see it validated with actual numbers.
OptimizeEverythingJul 12, 2026
This is a bit misleading. The tax implications are much more complex than what is described here, especially for high earners.
IndexFundFanJul 1, 2026
I respectfully disagree with point number three. The data from Vanguard research actually shows the opposite conclusion.
FireWalkerApr 7, 2026
Bookmarked this. Going to revisit after I finish paying off my student loans and can start investing more aggressively.
SavingsQueenNov 2, 2025
We implemented this strategy after reading your previous article and our savings rate went from 22% to 41% in six months.
OptimizeEverythingApr 25, 2026
Can you do a follow-up article about how this applies to people with variable income? Like freelancers and consultants?
GeoArbitrageGalSep 3, 2025
I have been doing this for 3 years now and can confirm these numbers are pretty close to what I have experienced.
BudgetNinjaMar 15, 2026
Shared this with my spouse and we are finally on the same page about our financial goals. Thank you!
FI_Seeker2024May 1, 2026
Has anyone tried this with a single income household? We are a one-income family and wondering if the same principles apply.
WealthBuilder99Sep 7, 2025
Bookmarked this. Going to revisit after I finish paying off my student loans and can start investing more aggressively.
DividendDaveApr 23, 2026
We implemented this strategy after reading your previous article and our savings rate went from 22% to 41% in six months.
FrugalDadSep 20, 2025
We implemented this strategy after reading your previous article and our savings rate went from 22% to 41% in six months.