OverEngineeredFi
Personal finance for people who over-engineer everything else.
The boring passive portfolio is mostly right. Here's the framework behind that — and an honest account of where I've deliberately broken it, what it cost, and whether it was worth it.
Recent Posts
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Sinking Funds for Irregular Expenses
Sinking funds turn lumpy bills like car insurance, gifts, and home repairs into a flat monthly number. Here is the math, a full example table, and a setup.
11 min read -
Copilot Money vs Monarch Money
Copilot Money costs $95 a year and Monarch costs $99.99. The price gap is $4.99. The real split is Android, couples, and how much polish you want on iPhone.
10 min read -
Sequence Risk, With Real Numbers
Same $1M, same 25 years of 60/40 returns, same average. Reverse the order and one retiree ends with $1.17M while the other ends with $2.25M. Here is the math.
11 min read -
Target-Date Funds: Lazy Win or Fee Trap?
Index target-date funds cost 0.08% to 0.12%. Their lookalike active cousins cost 0.68%. See the dollar math, the taxable-account trap, and when DIY beats a TDF.
12 min read -
The 3.8% NIIT: Who Pays and How to Dodge
The 3.8% Net Investment Income Tax hits high earners with dividends, gains, and rent. See the thresholds, worked examples, and legitimate ways to cut the bill.
11 min read -
Empower Review: Free Dashboard, Paid Pitch
Empower's free dashboard is good for net worth and fee checks. On $500K, its 0.89% fee plus fund costs trails a three-fund portfolio by $305K over 20 years.
11 min read -
Rule of 55: Early 401k Access, No Penalty
The Rule of 55 lets you pull from your 401k penalty-free after leaving your job at 55 or later. Learn who qualifies, the rollover trap, and the real tax math.
13 min read -
Contractor vs W-2: The Real Comp Math
A $180K W-2 offer needs a 1099 rate of about $214K a year, or $116 an hour, to break even. Here is the full payroll tax, benefits, and bench-time math.
16 min read -
NQDC Plans: Worth the Employer Risk?
Non-qualified deferred compensation can cut your tax bill, but the balance is an unsecured IOU from your employer. Here is when an NQDC plan is worth the risk.
13 min read -
State Tax Residency When You Move
Moving from California or New York to Texas? Your old state may still tax you. Domicile, the 184-day test, the convenience rule and audits, with 2025 numbers.
13 min read -
Direct Indexing: Worth the Fee?
Direct indexing costs 3 to 13 times more than an index ETF and only pays off through tax-loss harvesting. Here's the break-even math for tech-worker incomes.
13 min read -
Concentrated Stock: Sell or Exchange Fund?
Exchange funds defer tax on a concentrated stock position for 7 years but cost 1%+ a year and require $500k+ minimums. Here's when they actually beat selling.
11 min read
