Insurance
Whole Life vs. Term: Who Is the Policy Really For?
How term and whole life insurance differ in cost, cash value, and agent commissions, and questions to ask before you buy.
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Articles and resources on equity compensation, tax planning, investing, retirement income, estate planning, and insurance.
Articles
Equity CompensationTax Planning
Stock on Sale: The Basics of Your Employee Stock Purchase Plan
How an employee stock purchase plan works, how the lookback discount is calculated, and how ESPP shares are taxed when you sell.
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Congratulations, High Earner: Your Catch Up Contributions Are Now Roth Only
Starting in 2026, some 401(k) savers age 50 and older must make catch up contributions as Roth. Who the rule applies to and what to check.
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Which Account Do I Spend First? The Retirement Question That Can Be Worth Thousands
How the order you draw from taxable, tax deferred, and Roth accounts affects your taxes, Social Security, and Medicare in retirement.
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Social Security Isn't Going Bankrupt. It Could Pay You Less
What the 2026 Trustees Report projects, what trust fund depletion would mean for your check, and how to stress test your income plan.
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Why Is My Medicare Bill Bigger Than My Neighbor’s? A Friendly Guide to Premiums and IRMAA
Where Medicare premiums come from, the 2026 IRMAA brackets, the two year income lookback, and ways to plan around the surcharges.
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Free Stock? Almost. What to Expect, What It Costs, and How to Plan for Your RSUs
What happens on vest day, why withholding often falls short, how RSU shares are taxed when sold, and planning steps to consider.
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Incentive Stock Options: When to Exercise, What It Costs, and How to Plan
How ISOs are taxed when you exercise and when you sell, how the alternative minimum tax fits in, and ways to plan an exercise.
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The Company Stock Countdown: A Game Plan for the Years Before You Retire
How to turn employer stock into retirement income, why the gap years matter for taxes, and what to watch with Social Security and Medicare.
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Too Much of a Good Thing: The Risk of One Stock Running Your Life
What counts as a concentrated position, what history shows about single stock risk, and tax aware ways to unwind one.
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Take the Check or Take the Cash? The Pension Decision You Only Get to Make Once
How the monthly pension and the lump sum compare, how interest rates move lump sum values, and how to roll a lump sum over correctly.
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Even the Man Who Invented the 4% Rule Doesn't Use It Anymore
A look at where the 4% withdrawal rule came from, why even its creator uses a different number today, and why timing and flexibility matter more than one fixed percentage.
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Trump Accounts: A $1,000 Head Start (With Some Fine Print)
An overview of the new Trump Account, including who qualifies for the $1,000 federal deposit, contribution limits, investment restrictions, and how it compares to a 529 or custodial Roth IRA.
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The Tax Break Hiding in Your Old 401(k)
How the net unrealized appreciation rule can shift the tax treatment of employer stock in an old 401(k), and the specific conditions that have to line up for it to apply.
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You Don't Have to Be Rich to Owe Minnesota Estate Tax
Minnesota's estate tax exemption hasn't moved since 2020 and doesn't offer portability between spouses, two details that catch families off guard.
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About Swan
Why Swan
How Swan Wealth works with clients, the Swan planning process, who you will work with, and our advisory fee schedule.
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Mega Backdoor Roth Guide
How after-tax 401(k) contributions and Roth conversions work, the 2026 IRS limits, key considerations, and two questions to ask your HR department.
Request PDFRetirement Income Planning
Understanding Required Minimum Distributions
An overview of required minimum distribution rules, including starting ages, how the annual amount is calculated, and approaches some retirees use to manage the tax impact.
Download PDFTax Planning
Backdoor Roth IRA Guide
An overview of the backdoor Roth IRA strategy, including how it works, key benefits and considerations, and the rules that apply to conversions.
Request PDFInvesting
Direct Indexing Guide
An explanation of direct indexing, how tax loss harvesting works at the individual stock level, and the type of investor and account this strategy tends to suit.
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ESPP Guide
An overview of how employee stock purchase plans work, including enrollment periods, purchase mechanics, and the tax treatment of qualifying and disqualifying dispositions.
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Net Unrealized Appreciation (NUA) Guide
An overview of the net unrealized appreciation strategy for company stock held in a 401(k), including how it works and a hypothetical example comparing it to a standard IRA rollover.
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The Sales Income Smoothing System
A three-step framework for turning variable or commission-based income into a predictable monthly budget, including how to handle commissions that may be subject to clawback.
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Investing
October Swan Dive: 5 Reasons to be Bullish
Our new monthly Swan Dive: five fundamentals behind our optimism, from earnings growth and seasonality to sector positioning, interest rates, and AI valuations.
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Winter 2026 Newsletter: 2025 Markets in Review, Investing at All-Time Highs, and Trump Accounts
A look back at 2025 markets, the case for investing at all-time highs, new Trump Accounts for kids, and a Swan Wealth firm update.
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Fall 2025 Newsletter: Estate Planning, the Fed's Rate Cut, and Gold's Strong Year
Estate planning basics, what the Fed's rate cut means for your wallet, gold's standout year, and year-end planning opportunities.
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Summer 2025 Newsletter: The One Big Beautiful Bill Act, Social Security Timing, and Protecting College Students
The One Big Beautiful Bill Act's tax changes, how we think about Social Security timing, and a step families with college students often overlook.
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Spring 2025 Newsletter: Thoughts on Tariffs and the Economy vs. the Stock Market
Our take on tariffs, why the economy and the stock market aren't the same thing, and a Q1 2025 market recap.
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Winter 2025 Newsletter: A Look Back at the Decade's Halfway Point, Social Security, and Charitable Giving
A look back at the first half of the 2020s, Social Security's long-term outlook, and charitable giving strategies like QCDs and donor advised funds.
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Fall 2024 Newsletter: Election-Year Markets and the Expiring TCJA Tax Cuts
Historical election-year market performance and the upcoming expiration of the Tax Cuts and Jobs Act.
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