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Money clarity, human first.®

Money clarity, human first.®Money clarity, human first.®Money clarity, human first.®

Keep Asking How™

Keep Asking How™Keep Asking How™

Retire with clarity—not worry.

Make your month predictable, trim unnecessary expenses, and align dollars with purpose.

$250 credits to any program within 14 days.

Book A Fit Call

Need help finding anything?

Are these options a better fit?

Programs · Life Changes · Expat‑Curious · Leaders and Managers · 

· LGBTQ+ Professionals · LGBTQ+ Retirees · Columns

Other services

How we start (for retirees)

Money clarity, human first.®

Retirement changes your money rhythm. We’ll line up Social Security, pensions, annuities and RMD cash‑in/cash‑out with a simple month you can actually run. No complex apps—just one page and two small habits to start.

Session 1: Build your one‑page Money Map; set two weekly caps; schedule the first buffer transfer.
Session 2: Unnecessary Expense Audit — trim 2–3 recurring expenses; add a renegotiation script; note beneficiaries/renewals to review with your advisor/attorney.

Book a fit call

If this sounds like you…

  • You want a steady purpose‑driven budget on Social Security, pension, annuity, or RMDs.
  • Subscriptions/recurring expenses feel like a leak—you’d like 2–3 quick trims now.
  • You prefer one simple page and weekly caps—not a complicated app.
  • You’re weighing part‑time work, giving, board service, or a move—and want money calm first.
  • You want essentials and beneficiaries organized so family isn’t guessing later.

Book A Call

How we customize your first two sessions

Proud grandparent with special needs grandson celebrating life and feeling financially secure

How customization works (first two sessions)

  • Purpose Budget: Build a one‑page month that matches your income rhythm; set auto‑transfers for buffers.
  • Unnecessary Expense Audit: Find and trim 2–3 recurring expenses; add a renegotiation script you can reuse.
  • Light organization: Prompts for beneficiaries/renewals (education only; legal/tax handled separately).

Then choose your path below.

How do I see more immediate financial results?

Money Map Sprint — 4 weeks

Outcome: Quick traction this month—predictable cash‑flow, 2–3 unnecessary expenses trimmed, weekly caps that stick.
Includes: Money Map QuickStart • Weekly caps • 2 micro‑scripts • follow‑up notes.
Cadence: 1×60‑min kickoff + 3×45‑min check‑ins.
Pricing (typical): Hourly $175; most invest 3–5 hours ($525–$875).
Flat fee option (save up to ~10%): $789 (covers up to 5 hours; additional time $175/hr).

Start the Sprint

How do I learn about personal money management?

Financial Foundations 90 — 90 days

 Financial Foundations 90 — 90 days

Outcome: Durable habits and safety: a funded buffer, steady weeks, and decisions that feel calm.
Includes: Rules of the Road (debt/asset/benefits) • Buffer plan with auto‑transfers • Weekly tracker (paper or simple sheet) • Quarter‑ahead preview.
Cadence: 1×75‑min start line + bi‑weekly 45‑min sessions (5 total) + light email touchpoints.
Pricing (typical): Hourly $175; most invest 6–10 hours ($1,050–$1,750).
Flat fee option (save up to ~10%): $1,575 (covers up to 10 hours; additional time $175/hr).

Begin Foundations

How hard is it to move abroad?

woman living abroad as a US expat happy she used expat money launch with keep asking how Brad Biren

Momentum 90 — 90 days

Outcome: Align money with purpose—giving plans, part‑time pivots, or board/leadership roles.
Includes: Purpose projects plan • “wins to stories” work • gentle follow‑through cadence.
Cadence: 1×75‑min start line + bi‑weekly 45‑min sessions (5 total).
Pricing (typical): Hourly $175; most invest 8–12 hours ($1,400–$2,100).
Flat fee option (save up to ~10%): $1,890 (covers up to 12 hours; additional time $175/hr).

Considering a move abroad? Pair Money Map Sprint with Expat Money Launch (see Services). We’ll pressure‑test first‑month costs and banking/FX routes before you leap.

Start Expat Plan

Optional Add‑Ons

retiree favorites

  • Legacy & Essentials Binder Setup — $475 (3 hrs)
    What we do: inventory accounts/bills, beneficiary prompts, contacts list, document locations, “how to access” page.
    Deliverables: printable table of contents, checklists, family hand‑off guide.
    Boundary: legal documents/estate planning handled by your attorney (separate engagement).
  • RMD Readiness & Income Flow (Questions Pack) — $315 (2 hrs)
    What we do: map RMD cash‑in/cash‑out on your monthly plan; build a prompt list for your planner/CPA (timing, withholding, Roth interactions).
    Deliverables: one‑page flow map + questions list.
    Boundary: no tax or investment advice; decisions with your advisor/CPA.
  • Retirement Tax Changes — Awareness Coaching — $315 (2 hrs)
    What we do: surface common friction (IRMAA/Medicare surcharges, bracket creep, capital gains timing), build a questions sheet for your CPA.
    Deliverables: personalized “ask your CPA” sheet + monthly line‑item adjustments.
  • Medicaid Look‑Back Awareness (Elder‑Law Prep) — $315 (2 hrs)
    What we do: review spending/asset categories so you can speak clearly with an elder‑law attorney about 5‑year look‑back considerations.
    Deliverables: intake organizer + questions list.
    Boundary: legal strategy is attorney‑only.
  • Beneficiary & Accounts Check‑Up — $240 (1.5 hrs)
    What we do: gather account list, prompt beneficiary updates, note renewal dates, set a semi‑annual check‑up reminder.
    Deliverables: simple “accounts & beneficiaries” sheet + reminder plan.

All add‑ons are educational coaching. Additional time $175/hr. Neutral referrals available; no referral compensation received.

Start Expat Plan

What to expect next (applies to every path)

  • Start line: We map your month and set one 7‑day action.
  • Right‑sized path: Choose a low‑friction Money Breakthrough 120 or a program (Sprint, Foundations 90, Momentum 90).
  • Proof you can see: lower unnecessary spending, buffer growing, weekly caps that stick.

Book A Call

What can I expect in 30 days?

Proof you’ll feel (first 30 days)

  • 2–3 recurring expenses reduced or cancelled
  • Auto‑transfers to a Calm Buffer running
  • Weekly caps set in your bank app or on paper
  • A one‑page Purpose Budget you’ll actually use

Frequently Asked Questions FAQs (retirement‑specific)

Please reach us at brad@keepaskinghow.com if you cannot find an answer to your question.

No. We focus on cash‑flow, fees, benefits questions, and decision support. We’ll help you talk with your planner or CPA.


We’ll help you frame questions and fit the cash‑flow into your month; timing advice comes from your planner/CPA.


Yes—shared systems work best.


Hourly $175 or flat fees shown above. Breakthrough 120 is $250 and credits to any program within 14 days.


Yes--use the rescheduling link in your email confirmation


Why a coach for retirement? (not a planner or therapist)

Retirement is a new rhythm.

Retirement is a new rhythm.

Retirement is a new rhythm.

We align Social Security, pensions, annuities, and RMD cash‑in/cash‑out with a simple, predictable month—no complex apps. Then we use a proven coaching approach:


This is educational coaching—not legal, tax, or investment advice. If a topic needs a specialist, we’ll help you prepare questions and connect you with neutral referrals. If legal work is appropriate, it’s handled under a separate written engagement.

Coaching gets the how done.

Retirement is a new rhythm.

Retirement is a new rhythm.

Therapy heals the why. Planning optimizes the what. Coaching gets the how done. We turn confusion into two small moves this week, then track proof you can see—cash‑flow, buffer growth, and lower unnecessary spending. When a topic needs clinical, legal, tax, or investment expertise, we help you prepare questions and connect you with neutral referrals (no referral compensation). 

Book A Fit call

Ready when you are.

Book a fit Call Today!

Money Breakthrough 120 — $250

Money Breakthrough 120 — $250

Book A Fit Call

Money Breakthrough 120 — $250

Money Breakthrough 120 — $250

Money Breakthrough 120 — $250

 Credit note: Your $250 credits to any program within 14 days. 

Start Your Breakthrough

Disclaimer

Educational coaching focuses on financial coaching only—no legal, tax, or investment advice is provided. Use of this site or KAH services, does not establish an attorney‑client relationship. When specialized advice is required, we assist you in preparing questions and can offer neutral referral options.

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