• Home
  • Book A call
  • Services
  • Who I Help
    • Who I Help
    • Retirees
    • Life Changes
    • Leaders and managers
    • LGBTQ+ Professionals
    • LGBTQ+ Retirees
    • Expat Curious
  • Resources + Columns
    • Resources
    • Latest Insights
    • MoneyTawk!
    • Ripcord Reading List
    • Reinvention in Retirement
    • Expat Curiosity
    • Dr Tax Refund
    • Scholarships & Fellowship
  • About Us
  • Disclaimers
  • More
    • Home
    • Book A call
    • Services
    • Who I Help
      • Who I Help
      • Retirees
      • Life Changes
      • Leaders and managers
      • LGBTQ+ Professionals
      • LGBTQ+ Retirees
      • Expat Curious
    • Resources + Columns
      • Resources
      • Latest Insights
      • MoneyTawk!
      • Ripcord Reading List
      • Reinvention in Retirement
      • Expat Curiosity
      • Dr Tax Refund
      • Scholarships & Fellowship
    • About Us
    • Disclaimers
  • Sign In
  • Create Account

  • Bookings
  • My Account
  • Signed in as:

  • filler@godaddy.com


  • Bookings
  • My Account
  • Sign out

Signed in as:

filler@godaddy.com

  • Home
  • Book A call
  • Services
  • Who I Help
    • Who I Help
    • Retirees
    • Life Changes
    • Leaders and managers
    • LGBTQ+ Professionals
    • LGBTQ+ Retirees
    • Expat Curious
  • Resources + Columns
    • Resources
    • Latest Insights
    • MoneyTawk!
    • Ripcord Reading List
    • Reinvention in Retirement
    • Expat Curiosity
    • Dr Tax Refund
    • Scholarships & Fellowship
  • About Us
  • Disclaimers

Account


  • Bookings
  • My Account
  • Sign out


  • Sign In
  • Bookings
  • My Account

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 your life

$250 credits to any program within 14 days.

Book A Fit Call

How do we begin?

This is your safe place

This is a space for sensitive conversations—money, health, identity, family, and the quiet worries we don’t put on paper. We lead with self‑compassion and privacy so you can choose what to share and at what pace. No judgment, no politics, no pressure. Our goal is simple: help you feel empowered and steady about the next few steps.

A gentle first step (Fit Call, 15–20 min): We listen. What’s working, what’s heavy, and where you want relief. If coaching is a fit, we’ll outline scope and confirm next steps.

Book a fit call

LGBTQ+ Retirement, Simplified — U.S. & Abroad

  • 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’re comparing LGBTQ‑friendly places (U.S. or abroad) and want facts, not hype. 
  • You need straight answers on Social Security abroad, Medicare limits, and tax‑residency vs. residency—to discuss with your pros. 
  • You share money with a spouse/partner or coordinate with chosen family and want it to run smoothly. 
  • You prefer privacy, neutral referrals, and no politics—just next steps.

Book A Call

What should we do after our fit call?

breakthrough 120 - 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). If abroad is on the table: a first‑month cost snapshot (housing/insurance/FX) and a consult‑ready question list for licensed pros.

What do LGBTQ people need to learn before retirement?

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 can LGBTQ+ seniors learn more about financial basics?

Financial Foundations 90 — 90 days

Outcome:  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 do I learn more about aligning my money to purpose?

Momentum 90 — 90 days

Outcome: 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). 

Start Momentum

Considering a move abroad?

Pair Money Map Sprint with Expat Launch

Living Abroad 101 (see Services). We’ll pressure‑test first‑month costs and banking/FX routes before you leap.

REad more

Optional Add‑Ons

Important things to consider

  • Legacy & Essentials Binder Setup — $475 (3 hrs) What we do: inventory accounts/bills, beneficiary prompts, contact 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); create an “ask your CPA” sheet. Deliverables: personalized questions list + 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.
  • Additional time: $175/hr. Credit note: Money Breakthrough 120 ($250) can be credited to any program within 14 days. Referral policy: 
  • Neutral referrals available; no referral compensation received.

Book a Fit Call

Why work with a coach (not a planner or therapist)?

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

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

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

Retirement is a new rhythm. We align Social Security, pensions, annuities, and RMD cash‑in/cash‑out with a simple, predictable month—without complex apps. Then we use a proven coaching approach: Core: 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. 

Boundary

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

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

This is educational coaching—not legal, tax, immigration, 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. 

When a topic needs clinical, legal, tax, or investment expertise, we help you prepare questions and connect you with neutral referrals (no referral compensation).  

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

Book A Call

Frequently Asked Questions (FAQs)

Question: Does Medicare cover care outside the U.S.?
Answer: Coverage is very limited. Plan on private international coverage/medical evacuation and a U.S. re‑entry plan. We’ll help you prep questions for your Medicare broker.


Question: Can I receive Social Security if I live abroad?
Answer: Generally, yes—benefits can be paid in most countries. Banking/FX routes and a few country restrictions apply; we’ll check official tables and set clean deposit routes.


Question: What’s the difference between residency and tax residency?
Answer: They’re separate. Many countries use ~183‑day and/or “center of vital interests” tests. We’ll map ties (days, home, family, accounts) so your CPA can advise clearly.


Question: Does FEIE reduce tax on pensions, Social Security, RMDs, or investments?
Answer: No. The Foreign Earned Income Exclusion generally covers earned income only. We’ll prep timing/withholding questions for your CPA.


Question: If there’s no marriage equality, can my partner sponsor me?
Answer: Typically no; dependent visas often require legal marriage. Where equality exists, spousal sponsorship is usually possible. We’ll flag alternatives if treated as unmarried.


Question: Are there HIV‑related barriers to residency?
Answer: Most destinations have no explicit bans today, but health screens vary. We’ll point you to current official guidance before you apply.


Question: How do wills, probate, and POA work abroad?
Answer: Civil‑law countries often have forced‑heirship affecting in‑country assets. Expect to apostille + translate U.S. documents and execute local wills/POA/medical directives.


Question: How do transgender name/gender‑marker updates work?
Answer: Processes vary (court orders → self‑ID). We’ll outline steps for your destination and ID‑consistency tips for travel, banking, and healthcare.


Question: Best first step if I might move abroad in 12–24 months?
Answer: Start with Expat Launch: Living Abroad 101—visa paths, day‑counts, first‑month costs, and a workable timeline.


Question: I’m private/conservative—will I feel comfortable here?
Answer: Yes. No politics, no pressure. We respect your values and privacy while staying practical about rights, safety, paperwork, and cost.

Book A 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.

Find out more

Copyright © 2025 Keep Asking How - All Rights Reserved.

Powered by

  • Home
  • Book A call
  • Services
  • Scholarships & Fellowship
  • About Us
  • Disclaimers

This website uses cookies.

We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.

DeclineAccept