Key Questions to Secure Your Financial Future
Introduction
At Singh PWM, I believe confident retirement planning starts with clarity — knowing what questions to ask before making life-changing decisions. This guide was designed to help you think through the most important aspects of your financial life as you approach retirement — from investment alignment and tax strategy to healthcare, estate planning, and long-term protection.
No two retirements look the same. That’s why these questions go beyond numbers — they’re meant to help you define what a secure and meaningful retirement looks like for you and your family.
Purpose of This Document
The purpose of this guide is to help individuals and couples approaching retirement think critically about the key financial, tax, and lifestyle decisions that shape their next chapter. These questions are designed to spark reflection and uncover areas that may need deeper planning—whether it’s income strategy, tax efficiency, healthcare coverage, or estate protection.
By reviewing these questions, you’ll gain clarity on what matters most, identify potential blind spots, and be better prepared to have a meaningful discussion with your financial planner or fiduciary. The goal isn’t to have every answer—but to ensure you’re asking the right questions before you make important decisions about your retirement.
Category 1: Investment & Portfolio Alignment
| Is our current investment allocation aligned with my risk tolerance and retirement timeline? |
| Should we reduce exposure to volatile assets as I near retirement? |
| Are my investments tax-efficient (e.g., asset location across taxable, tax-deferred, and Roth accounts)? |
| Are we investing with a strategy that provides both growth and income in retirement? |
| Is my current advisor using tax-loss harvesting or direct indexing to minimize taxes? |
Category 2: Retirement Income & Lifestyle Planning
| What’s my target retirement age—and is it realistic based on my savings? |
| How much income will my investments need to generate in retirement? |
| When should we start drawing Social Security? |
| Should we consider an annuity to create a guaranteed income stream? |
| What’s our withdrawal strategy to avoid running out of money? |
| Should I consider working part-time or starting a business in retirement? |
Category 3: Healthcare & Long-Term Care
| How will healthcare expenses be covered before and after Medicare eligibility? |
| When should I enroll in Medicare (Parts A, B, D)? |
| Do I need a Medigap policy or Medicare Advantage plan? |
| What are the penalties if I delay enrollment? |
| How much will Medicare cost annually, including IRMAA surcharges? |
| How do I coordinate retiree health coverage with Medicare? |
| What is the best timing to stop contributing to an HSA before Medicare? |
| When should we explore long-term care insurance to protect against nursing home costs? |
| Should I consider a hybrid life + long-term care insurance policy? |
Category 4: Tax Strategy & Roth Conversion Planning
| Am I working with a tax professional who understands my retirement goals? |
| Are all my deductions and credits optimized? |
| Are there ways to reduce taxes? |
| Should I file jointly or separately with my spouse? |
| What will my tax bracket be in retirement vs. now? |
| Should we do partial Roth conversions before RMDs kick in at age 73? |
| How can I reduce future Required Minimum Distributions (RMDs)? |
| Are we using tax-efficient investments in taxable accounts? |
| Should we contribute to an HSA or use it for healthcare costs in retirement? |
| Are there state tax considerations if I plan to move after retiring? |
| Can I structure my withdrawals to keep Medicare IRMAA surcharges low? |
Category 5: Estate & Legacy Planning
| Do we need a revocable or irrevocable trust? |
| How do we plan for incapacity with a living will or healthcare proxy? |
| Who will take care of my affairs if I become unable to manage them? |
| Is our estate plan coordinated with my tax and investment strategy? |
| Do I have the right structures (trusts, LLCs, insurance) to protect my wealth? |
| Is my wealth protected for the next generation (heirs, trusts, gifting)? |
| What would happen to my family financially if I passed away tomorrow? |
| Is our estate protected from potential lawsuits or creditors? |
| Should we consider domestic asset protection trusts? |
| Are there risks to my legacy from adult children’s creditors or spouses? |
Category 6: Insurance & Risk Management
| Do I still need life insurance, or should I adjust my coverage? |
| Are my home, auto, and umbrella insurance policies sufficient? |
| Have I accounted for longevity risk (living into my 90s or beyond)? |
| Is our wealth plan built to withstand economic downturns? |
| Are my assets protected from market volatility and inflation? |
| Is our portfolio prepared for long-term income and principal protection? |
Category 7: Coordination & Professional Planning
| Am I working with a coordinated team (advisor, CPA, attorney) who share my goals? |
| Are all aspects of my financial life—investments, taxes, estate, insurance—aligned? |
| Do I have a clear point person acting as my fiduciary advocate? |
Taking the Next Step
If you identified areas that feel uncertain, that’s where I can help. As your Personalized CFO, my role is to align your investments, taxes, and retirement income into one cohesive plan—so you can retire with confidence and clarity.
Schedule Your Private Planning Session
www.SinghPWM.com | Raman@singhpwm.com
By: Raman Singh, CFP®
Personalized CFO
Singh PWM
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