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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™

When life changes, how do we make money steady again?

 Quiet, practical, camera‑off friendly.

Book A Fit Call

What else can we help you with today? Divorce? Caregiving?

Money clarity, human first.®

Looking for more information?

Looking for more information?

We turn divorce, bereavement, job loss, caregiving, health shocks, or a move into a calm, predictable month you can live by. No apps, no judgment—just the next two steps. 

Expat Curious

Looking for more information?

Looking for more information?

Looking for more information?

Programs · Expat‑Curious · Retirees & Pre‑Retirees · LGBTQ+ Professionals · LGBTQ+ Retirees · Columns

USeful resources

How do we begin?

Education‑first. Private. No politics.

This is a space for sensitive conversations—grief, paperwork, family tension, privacy, health, and sudden bills. We lead with self‑compassion and privacy; you set the pace. Our job is to shrink overwhelm and help you feel in control of the next few steps.

A gentle first step (Fit Call, 15–20 min): We listen. If coaching is a fit, we’ll confirm scope and next steps. 

Breakthrough 120: We map your month, find 2–3 easy wins, and set first auto‑transfers. You leave with a one‑page Purpose Budget, a short “unnecessary expenses” list, and a calm next‑steps plan. (Credits to any program within 14 days.) 

Coordination with your pros: We’ll prep crisp question packs for your CFP/CPA/attorney/HR/benefits and, if abroad is in play, immigration and tax specialists. Neutral referrals available; no referral compensation. 

Boundaries & privacy: Educational coaching only—no legal, tax, immigration, investment, or clinical advice. When a topic needs a specialist, we’ll help you prepare for it. 

Book a fit call

Why work with a financial coach after a big life event?

Why a coach for life's changes?

  • Clarity fast. We turn chaos into a one‑page month and a first‑30‑days bill calendar while the big pieces settle.
  • Action beats overwhelm. We target 2–3 expense trims, install a buffer, and set weekly caps—plus immediate paperwork triage (COBRA elections, survivor claims, unemployment forms).

Book A Fit call

Boundaries and respect

  • Coordinate—not replace—your pros. We prep consult‑ready questions for attorneys/CPAs/HR/benefits (probate/QDRO/FMLA aware). Decisions stay with licensed professionals.
  • Privacy and respect. Camera‑off is fine. Chosen family welcome. No politics.
  • Clear boundaries. Educational coaching only; we prepare you to speak with the right experts.

Disclaimer

Are you facing any of these life changes?

IS this you?

• Divorce or separation is underway and money feels scattered (temporary budget, account list, QDRO awareness).
• You’re handling a loss (or probate), need a survivor‑benefits checklist, and want to avoid missed steps.
• A job change/layoff or new business is shifting your income rhythm (unemployment, COBRA vs marketplace, new pay cadence).
• You’re a caregiver—or becoming one—and need to see the next 90 days (FMLA/state leave awareness).
• A health event (short‑term disability/LTD) is stressing cash‑flow.
• You’re relocating (U.S. or abroad) and need a clear month‑one picture.

More resources

Which situation fits you?

Divorce or Separation

Job Change, Layoff, or New Business

Divorce or Separation

 Build a clean money map (accounts, bills, income).

  • Prep a Financial Organizer and Questions Pack for your attorney/mediator (education‑only; QDRO/benefits split awareness).
  • Install weekly caps & a buffer so life keeps moving.

Book a fit call

Bereavement & Probate

Job Change, Layoff, or New Business

Divorce or Separation

  • Checklist for accounts, beneficiaries, survivor benefits, and immediate bills.
  • Prep for a probate/estate consult; align your monthly plan.
  • Gentle expense audit; avoid late fees and service lapses. 

Book a fit call

Job Change, Layoff, or New Business

Job Change, Layoff, or New Business

Job Change, Layoff, or New Business

  • 30‑day income bridge (severance, unemployment, COBRA, side work).
  • Install a Minimum Viable Month; trim 2–3 expenses now.
  • Questions for HR/benefits and CPA (withholding, quarterly estimates). 

Book a fit call

Caregiving & Long‑Term Care Basics

Health Event, STD/LTD, or Disability

Job Change, Layoff, or New Business

  • 90‑day caregiving cash‑flow; organize meds/visits costs.
  • Prep FMLA/state leave questions; build a respite plan.
  • Beneficiaries/trusted contacts reminders (education‑only). 

Book a fit call

Health Event, STD/LTD, or Disability

Health Event, STD/LTD, or Disability

Health Event, STD/LTD, or Disability

  • Map claim timelines and pay gaps; set weekly caps.
  • Prep LTD claim and employer questions; HSA/COBRA basics.
  • Gentle debt triage and priority rules. 

Book a fit call

Relocation (U.S. or Abroad)

Health Event, STD/LTD, or Disability

Health Event, STD/LTD, or Disability

  • First‑month cost snapshot (housing, insurance, FX/banking routes).
  • Domicile vs. residency education; day‑count awareness if abroad.
  • Timeline checklist + consult‑ready questions for the right pros. 

Book a fit call

What can we help you build resilience in 30–90 days?

concrete steps to keep you moving

• A one‑page monthly snapshot that matches your new reality.
• 2–3 unnecessary expenses reduced or cancelled.
• A Calm Buffer and weekly caps that stick.
• A Questions Pack (attorney/CPA/HR) + a simple paperwork tracker (COBRA, survivor claims, unemployment forms).
• A quarter‑ahead preview so surprises don’t win.

Book a fit call

Which programs are best for you when going through a change?

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 • Travel‑week routine • Reimbursement tracker 

• 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 can we ease your transition into financial literacy?

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 • 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 do I learn more about aligning my money to purpose?

Momentum 90 — 90 days

Outcome: Align money with purpose—giving plans, board/leadership roles, or a values‑aligned pivot.

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). 

Start Momentum

Optional Add‑Ons

what should you consider?

Divorce Financial Organizer & Questions Pack — $315 (2 hrs)
What we do: inventory income, bills, accounts; prep a neutral questions list for counsel/mediator; set a temporary month.
Deliverables: organizer + questions pack + 30‑day plan.

Probate & Beneficiary Update Prep — $315 (2 hrs)
What we do: checklist for immediate bills, policy/beneficiary reviews, and document locations; prep for probate/estate consult.
Deliverables: checklists + consult‑ready pack.

Job Loss / New Role 30‑Day Plan — $315 (2 hrs)
What we do: severance/unemployment map; COBRA vs. marketplace prompts; first‑week expense trims; interim income options.
Deliverables: 30‑day map + HR/CPA question list.

Relocation Budget & Domicile Education — $315 (2 hrs)
What we do: first‑month cost snapshot; bills/banking routing; timeline and day‑count awareness if abroad.
Deliverables: budget + routing map + consult list.

Health Shock: STD/LTD Claim Prep — $315 (2 hrs)
What we do: map claim timelines, paperwork, and pay gaps; set weekly caps; HSA receipts plan.
Deliverables: claim prep checklist + weekly plan.

Caregiving Binder (90‑day plan) — $315 (2 hrs)
What we do: meds/visit schedule, cost snapshot, respite plan, and trusted contacts list.
Deliverables: binder TOC + checklists + reminder plan.

Additional time: $175/hr. Credit note: Money Breakthrough 120 ($250) can be credited to any program within 14 days. Neutral referrals available; no referral compensation.

Book a Fit Call

Frequently Asked Questions

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

No. Therapy heals the why. Planning optimizes the what. Coaching gets the how done—weekly. We prepare you to work faster with your licensed pros.


It depends on timing, subsidies, and ongoing care. We’ll map premiums and deadlines and prep specific questions for your licensed benefits/tax pro.


Most clients feel relief within 2 sessions: 2–3 expenses trimmed, weekly caps set, and a buffer plan started.


Yes. Camera‑off is fine. We respect your values and privacy, and we keep politics out.


No. We’re educational coaching only. When a topic needs a specialist, we help you prepare and refer neutrally on request.


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 only—no legal, tax, immigration, or investment advice. No attorney‑client relationship is formed through this site or coaching. Neutral referrals available; no referral compensation.

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