Clear Money Guide
What this guide covers
A quick view of the questions and evidence developed below.
Updated July 31, 2026. Quick answer: an owner has two problems most employees never face: choosing a retirement plan that is genuinely yours to design, and eventually converting the business itself into retirement money. The plan side rewards attention because the ceilings are high and the traps are structural – a controlled group can silently disqualify a solo 401(k), and a cash balance plan is a mandatory funding commitment rather than an optional one. The exit side is where the largest single tax bill of your life is decided, usually by allocation: how the purchase price is split across asset classes, whether the structure preserves QSBS, and whether an installment sale actually helps. Both halves are below, plans first.
Choosing and funding the plan
- Cash Balance Plans: The 10-Year Phase-In Nobody Mentions
- A Cash Balance Plan Contribution Is Mandatory, Not Optional
- Catch-Up Contributions Sit Outside the Annual Additions Limit
- The Controlled Group Trap (It Kills the SEP Too)
- No FICA Wages? The Roth Catch-Up Rule Does Not Reach You
- The Roth Catch-Up Requirement Applies Now, Not in 2027
- Why a SEP Has No Employee Deferral (and Never Will)
- Where a SEP Finally Catches a Solo 401(k)
- Solo 401(k) vs SEP IRA for an S-Corp Owner (2026)
- Solo 401(k) vs SEP IRA for a Sole Proprietor (2026)
- Can You Keep a Solo 401(k) After Hiring? (2026)
- The Age 60-63 Super Catch-Up: Why It Did Not Rise (2026)
Selling the business: structure and allocation
- The $5 Million Installment Line Is a Fraction, Not a Cliff
- Your Receivables Are Class III, and They Get Paid Before Your Goodwill
- An Asset Sale Forfeits QSBS Entirely
- The Seven Asset Classes and Who Wins Each One
- You Can Owe Tax in Year One on Money You Have Not Received
- An Earnout Defaults Into the Installment Method
- Electing Out of the Installment Method Is a One-Shot Deadline
- Form 8594 Does Not Require Matching Allocations
- Recapture Is Taxed in the Year of Sale, However Little Cash Arrived
- Purchase Price Allocation Is a Waterfall, Not a Negotiation
After the sale
- How Much of Your Sale Proceeds to Hold Back, When Nobody Is Withholding
- Selling a Practice That Used to Be a C Corporation: the Recognition Period
- Selling Your Practice to Your Child or Your Associate: the Related-Party Rule
Other owner questions
- The ESOP Rollover Window Is 15 Months, Not 12
- Long-Term Part-Time Employees: Now Two Years, Not Three
- Treasuries and Index Funds Are Not Qualified Replacement Property
- A Retiring Partner’s Buyout Splits Into Two Kinds of Payment
- Putting a Spouse on Payroll to Double the Plan (2026)
- Why the Non-Compete Payment in Your Practice Sale Is Not Capital Gain
Related guides
Equity Compensation · Trusts · Roth Conversions · Settling an Estate · Inherited IRA Rules · Social Security Timing · Retirement Withdrawals · When a Spouse Dies · Pension and Annuity Decisions · Charitable Giving and Tax · Divorce and Your Money · Home Sale Taxes · Life Insurance Decisions · IRMAA · Long-Term Care Planning · Research · All guides
Protection is a separate question from tax: a 401(k) and an IRA are not equally protected, and a rollover changes which rules apply — ERISA covers the plan in every state, while an IRA falls back on whatever your state provides.
The other direction on the same lifecycle — starting one rather than leaving one: the encore business vertical, indexed from formation to closing.