Within five years of retiring
The planning window that matters most — when the right moves on Social Security, taxes, and Roth conversions are still on the table. The earlier we start, the more we can do.
A RETIREMENT-INCOME PRACTICE
The question is not when. It is how.
Westcliff helps people within a decade of retirement turn a lifetime of saving into a steady paycheck — and plan the taxes, the timing, and the healthcare around it, as one.
Built for the transition.
I spent most of my career watching capable savers arrive at retirement with a healthy balance and no plan for turning it into a paycheck. The industry is good at helping people accumulate. It is far less practiced at the harder question that comes next: how do you actually live off this, for thirty years, through markets and taxes and health and time? Westcliff exists for that question. We work with people roughly a decade either side of retirement — building the income, sequencing the withdrawals, timing Social Security, and planning the taxes and healthcare around all of it. The work is unglamorous and it is the whole game. I am in every plan.
Eleanor Vance
WHAT WE DO
Retirement, planned as one thing.
A focused practice for the financial questions that matter most as the timeline shortens.
Retirement Income
The heart of the work: turning your savings into a dependable monthly paycheck. We map which accounts fund which years, how much you can safely spend, and how the income holds up across a thirty-year retirement.
Social Security Timing
When to claim is one of the largest decisions you will make, and most people make it too early. We run the claiming and spousal strategy, the breakeven math, and how it coordinates with the rest of the plan.
Tax-Efficient Withdrawals
Which account to draw first, Roth conversions in the low-income years between retiring and required distributions, and keeping an eye on the thresholds — RMDs, IRMAA, capital gains — that quietly raise the bill.
Healthcare & Medicare
Bridging coverage if you retire before sixty-five, choosing among Medicare paths at sixty-five, and planning honestly for the cost of care later — the expense most retirement plans understate.
Investment Management
A portfolio built to fund three decades of withdrawals, not to beat a benchmark. Stable enough to weather a bad year early in retirement, with enough growth to outlast inflation.
Estate & Legacy
The essentials done right — beneficiaries, titling, a current will and the basic documents — and a clear plan for what passes to the people and causes you care about.
VALUES
Four notes.
One focus.
We do retirement income. Not everything for everyone — the decade around retirement, done properly. The narrowness is the point.
Fee-only, always.
No commissions, no proprietary products, no insurance sales, no kickbacks. We are paid by you, so our advice answers to you and to nothing else.
Plain language.
We explain the plan until it is genuinely clear. If you cannot repeat back why we are doing something, we have not finished explaining it.
Steady, not sensational.
No market-timing, no urgency, no reacting to the headline. Durable plans, revisited on a schedule, that hold up when a year gets hard.
WHO WE WORK WITH
People near the transition.
A focused practice for households in the second half of the financial timeline.
Recently retired
Making the first years of withdrawals work — turning the balance into a paycheck and getting the sequence right while the decisions are still fresh.
Couples timing two retirements
Two Social Security claims, two timelines, one household plan. We coordinate the dates so the combined income — and the survivor — comes out ahead.
Newly on their own
Widowed or divorced near retirement, re-planning the income for one. We handle the transition slowly, in person, and with the time it deserves.
HOW WE WORK
A plan, then a relationship.
1
A first conversation
We talk about when you want to stop working, what you have saved, and what keeps you up at night about it. No pitch, no homework. By the end you will know whether we can help.
2
Your income plan
We model the paycheck: when to claim Social Security, what to draw and in what order, what it covers, and how long it lasts. You see the whole picture on one page.
3
The tax and healthcare layer
Roth conversions in the gap years, the Medicare decision, the thresholds to manage. The details that, handled early, are worth far more than picking funds.
COMMON QUESTIONS
Before we talk.
What pre-retirees and retirees ask me most.
Who is Westcliff for?
People roughly a decade either side of retirement — getting ready to stop working, or recently stopped, who want a real plan for turning their savings into income. If retirement is twenty years off, we are probably not the right fit yet.
Is there a minimum?
Most of our clients have between $500,000 and $3 million saved, but the real requirement is being near the transition and wanting a plan for it. If you are close to retirement, start the conversation and we will be honest about fit.
How are you compensated?
We are fee-only. You pay us directly — a transparent annual fee, disclosed in full in our Form ADV. We earn no commissions, sell no products, and take no referral fees, so there is nothing steering the advice but your plan.
When should I start?
Ideally three to five years before you retire. The years between leaving work and required distributions are where the most valuable tax planning lives — Roth conversions, the Social Security decision, managing the brackets. Start late and that window narrows.
Do you manage investments too?
Yes — but in service of the income plan, not as the headline. The portfolio is built to fund decades of withdrawals: steady enough to survive a bad first year of retirement, growing enough to outlast inflation.
