"A plan isn't a prediction. It's a promise you make to your future self — then we engineer the math to keep it."
Margaret A. Holt, CFP® · RICP®
Founder, Ledger Financial Planning · Licensed in all 50 states
You'll find yourself somewhere in here.
Three real situations — names changed, numbers exact. Each one a different kind of financial complexity. Each one resolved with a framework, not a formula.
Two 401(k)s, One Household — and a Vesting Cliff Three Years Out
Daniel & Priya S. — Software engineer & hospital administrator, ages 34 & 36, Chicago
Daniel's employer matched 6% in company stock that couldn't be touched for three years. Priya's plan was a SIMPLE IRA with a 2-year vesting schedule. They were maxing both accounts but routing the wrong dollars to the wrong buckets — generating unnecessary taxable events and leaving $18,400 in match money on the table annually.
Ledger mapped every vesting date, equity grant, and ESPP window onto a single liquidity calendar. We restructured contribution sequencing: Priya's salary deferrals absorbed near-term tax drag while Daniel's RSUs were staged for sale in lower-income years. A backdoor Roth was layered in at the gap.
At the 18-month mark, they'd recaptured the full employer match, reduced their combined marginal tax rate by 4 points, and built a 14-month emergency runway — without touching their investment accounts.
Two Years Without a Salary — and a Cap Table That Couldn't Wait
Marcus T. — SaaS founder, age 41, Austin TX · $1.2M ARR, Series A pending
Marcus had paid himself nothing for 26 months while the business scaled. His personal accounts hadn't been touched since 2021. A Series A term sheet was on the table, which would dilute his equity but trigger a taxable event on his founders' shares. He had no retirement vehicle, no business succession plan, and a personal tax liability he hadn't modeled.
We established a Solo 401(k) with a profit-sharing rider, allowing Marcus to shelter $66,000 in the current tax year. A Qualified Small Business Stock analysis confirmed his shares qualified for the Section 1202 exclusion — up to $10M in gains tax-free at exit. We modeled three salary scenarios and identified the optimal W-2 amount to minimize SE tax without triggering ACA penalties.
Marcus took a $120,000 salary, sheltered $66,000 in his Solo 401(k), and locked in the Section 1202 clock. His projected tax liability at exit dropped by $840,000 based on current valuation. The Series A closed four months later.
A Pension She'd Never Managed and an Estate She Wasn't Ready For
Barbara W. — Retired educator, age 67, Raleigh NC · Widowed, 14 months prior
Barbara's husband had managed everything. When he died, she inherited a FERS pension she'd never read, a $380,000 IRA she didn't know how to draw from, a joint brokerage account with embedded capital gains, and a house with a stepped-up cost basis she didn't understand. She'd been taking the wrong RMD amount for a full year.
Ledger corrected the RMD shortfall with the IRS penalty waiver process, then built a coordinated withdrawal strategy: pension income first, Social Security delayed to 70, IRA distributions smoothed across a lower-bracket window. The brokerage account was repositioned using the stepped-up basis before it reset. An irrevocable trust was drafted to protect her daughter's inheritance from probate.
Barbara's corrected tax filing saved $14,200 in penalties and interest. Her annual income increased by $8,700 by optimizing Social Security timing. The estate plan reduced projected probate costs by an estimated $47,000.
How a thirty-year plan gets built in four steps.
Most financial plans are written once and forgotten. Ledger's model is different — it's an engineering process, not a filing exercise. The plan is a living document. The math updates. The promise holds.
The Intake Conversation
Thirty minutes. No forms, no pitch deck. We talk about what's actually worrying you — the number you can't stop checking, the decision you've been delaying, the question your accountant couldn't answer. We listen first.
The Financial Inventory
Every account, every liability, every vesting schedule, every insurance policy. We build one complete picture — the kind that takes a weekend if you do it alone, and four days if you do it with us. We do it in one structured session.
The Roadmap Draft
A single document: your thirty-year projection broken into quarterly milestones. Every assumption is labeled and sourced. Every decision point is flagged. You understand exactly why each recommendation exists — not just what to do.
Quarterly Recalibration
Life changes. Markets change. Tax law changes. We review the plan every ninety days and adjust. Not a check-in call — a working session with updated projections. The math stays current so the promise stays intact.