Signed in as:
filler@godaddy.com
Signed in as:
filler@godaddy.com
Quiet, practical, camera‑off friendly.
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.

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.



• 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.

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






• 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.

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).

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).

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).

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