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The good, the bad, and the ugly of Social Security and taxes

Retirement Prof University
14 Day Retirement Plan
Day 3: Tax Planning
The good, the bad, and the ugly of Social Security and taxes

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14 Day Retirement Plan

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Instructor

Derek Tharp

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Day 1: Retirement Mindset

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What are you retiring to?

Planning a joint vision for retirement

Answer Kinder’s Three Questions

ACTION: Kinder’s First Question

ACTION: Kinder’s Second Question

ACTION: Kinder’s Third Question

Takeaways From Kinder's Three Questions

George Kinder's Presentation

Pursuing Happiness

Maintaining a purpose

OPTIONAL: Software set up

ACTION: Register for Income Lab access

ACTION: Register for Maximize My Social Security

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Day 2: Retirement Accounts

Common questions

Roth vs. Traditional

Why the HSA is the most powerful account of all

Changing dynamics in late working years

Traditional IRA basics

Roth IRA basics

Spousal IRA/Roth IRA basics

Does $7,500 per year make a difference?

Employer-sponsored retirement accounts

The six rollover options

Taxation of retirement account withdrawals (non-Roth)

Potential side-effects of IRA distributions

Required minimum distributions (RMDs)

Three RMD mistakes

Savvy IRA strategy #1

Savvy IRA strategy #2

Tax-free Roth IRA distributions

Who can do a Roth IRA conversion?

Other benefits of Roth IRA conversions

Big Roth conversion changes after 2018

Three questions to ask before doing a Roth conversion

Long-term Roth conversion strategy

Limitations and risks of Roth IRA conversions

Savvy IRA strategy #3

Savvy IRA strategy #4

Coordinating IRA planning with Social Security

Savvy IRA strategy #5

Non-designated beneficiaries

Non-eligible designated beneficiaries

Eligible designated beneficiaries

Trusts as IRA beneficiaries

Options for spousal IRA beneficiaries

Bonus IRA strategy

ACTION: Summarize your current retirement accounts

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Day 3: Tax Planning

Intro to tax planning

Don’t forget about state taxes!

Tax planning philosophies

The new challenges that come with retirement tax planning

The four stages of retirement

Retirement tax planning Key #1

Retirement tax planning Key #2

The "Social Security Tax Torpedo"

The good, the bad, and the ugly of Social Security and taxes

Medicare and taxes

Retirement tax planning Key #3: Distribution coordination

Tax bracket management

Alternative approaches to tax bracket management

Tax bracket management example

Other pre-retirement strategies

Charitable giving and tax planning

Retirement tax planning Key #4: Estate plan coordination

Estate Example #2: Choices when inheriting IRAs

Taxes and long-term care

Key focus areas for different phases of retirement

ACTION: Review your most recent tax return

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Day 4: Investing

Intro to Investing

OPTIONAL: Why you shouldn't invest in individual stocks

Exchange traded funds (ETFs)

Target date funds

Factor investing

OPTIONAL: A deep dive into factor investing

COMMING SOON: Betterment set up tutorial

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Day 5: Estate Planning

Leaving a legacy

Dying without a will

Preparing for sudden incapacity

Common estate planning problems

Beyond estate planning: Generational planning

Six step legacy planning process

Step 1: Plan for incapacity

Step 2: Get organized

Step 3: Think about the people you love and the causes you care about

Step 4: Put your wishes in writing

Wills vs. Trusts

Step 5: Creating your family legacy

Step 6: Monitor and update your plan

Federal estate tax overview

State estate taxes

Common mistake #1: Lack of coordination

Common mistake #2: Inaccurate beneficiary designations

Common mistake #3: Per capita vs. per stirpes

Common mistake #4: Inefficient beneficiary designations

Common mistake #5: Guardianship of minors

Common mistake #6: Not funding trusts

Common mistake #7: Inaccessible documents

OPTIONAL: Review/complete estate documents

Completing estate documents with Trust & Will

Completing estate documents with a local attorney

FOR FUN: I review Ron Swanson's estate plan

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Day 6: Social Security

Penalty vs. Bonus

The Social Security problem

Things to know about Social Security

Will Social Security survive?

Insight #1: Inflation-protected income

How to determine your benefit

Insight #2: Early claim reductions

When to apply for benefits

How to estimate your Social Security benefits

How to maximize your benefits

Social Security taxation

Medicare and Social Security premiums

Things to remember when applying for Social Security

Insight #3: Maximize the higher-earner's benefit

Coordinating spousal benefits

Insight #4: Benefits when widowed or divorced

Survivor benefits

Divorced-spouse benefits

The importance of a customized Social Security analysis

What Social Security personnel can and cannot do

Windfall Elimination Provision (WEP)

WEP-Adjusted PIA

Government Pension Offset (GPO)

ACTION: Complete Maximize My Social Security analysis

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Day 7: Medicare

Medicare Overview

3 Key Medicare Points

Sections covered today

Section 1: Medicare Enrollment

What is Medicare?

How to enroll in Medicare?

Signing up for Part A during the Initial Enrollment Period

Signing up for Part B during the Initial Enrollment Period

Signing up for Part D during the Initial Enrollment Period

Special Enrollment Period

Best time to enroll in Medicare

How to sign-up for Medicare Parts A, B, and D

Section 2: Medicare & Private Insurance

Section 2: Medicare & private insurance

Medicare premiums

Medicare deductibles

Medicare coinsurance

What Medicare covers

What private insurance may cover

Medigap policies

Medicare Advantage plans

Shopping for private insurance

Section 3: Planning for higher health care costs in retirement

Section 3: Planning for higher health care costs in retirement

Retirement health care budget

Planning for future costs

Planning for long-term care

Levels of long-term care (in-home, custodial, skilled nursing)

Why plan for long-term care

Three reminders

ACTION: Plan your transition to Medicare

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Day 8: Long-Term Care

Long-term care quiz

The long-term care problem

Emotional and financial risks

Key #1: Planning for personal care needs

What is long-term care?

Long-term care settings

Costs of long-term care

Key #2: Counting on Medicare/Medicaid is NOT a plan most people want

3 Medicaid surprises

Key #3: Historical LTC insurance market issues

Key #4: New approaches to LTC planning

Improved long-term care insurance

Life insurance and annuities with long-term care benefits

Other strategies to cover LTC costs

Self-funding LTC costs

LTC points to keep in mind

ACTION: Develop your LTC plan

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Day 9: Insurance

Insurance in retirement

Special considerations for life insurance in retirement

Types of life insurance

Term life insurance

Guaranteed Universal Life (GUL)

Indexed Universal Life (IUL)

Variable life insurance

Life insurance in estate planning

Life insurance and long-term care protection

How to shop for life insurance

Shopping for term life insurance

Shopping for Guaranteed Universal Life (GUL) insurance

Shopping for pure long-term care insurance

Shopping for hybrid life and long-term care insurance

Shopping for final expense insurance

Health and underwriting

Introduction to property and casualty (P&C) insurance

Homeowners insurance

Maintaining adequate homeowners insurance coverage

Maintaining an inventory of your home

Flood insurance

Homeowners insurance liability coverage

Auto insurance in retirement

Umbrella insurance

What NOT to tell people about your insurance

Professional liability insurance and other considerations for part-time employment

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Day 10: Cybersecurity

Identity theft prevalence

The cybersecurity challenge

Discover your cybersecurity score

Learn the new cybersecurity rules

Key Idea #1: Adopt a higher level of secrecy

Beat the password paradox

Enabling 2-factor verification on email and financial accounts

Use Wi-Fi with caution

Secure your home Wi-Fi network to keep hackers out

Key Idea #2: Achieve financial cyber omniscience

Freeze your credit

Key Idea #3: Achieve mindfulness

Always update software

Backup files to protect against ransomware extortion

10-second E.M.A.I.L. rule (examine message)

10 second E.M.A.I.L. rule (inspect links)

ACTION: Commitment plan

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Day 11: Budgeting

How budgeting changes in retirement

Getting help with budgeting

How spending changes in retirement

Should retirees plan for declining spending?

Inflation-adjusted (real) vs. non-inflation-adjusted (nominal) spending

Variable vs. fixed expenses

Budgeting that works

The envelope budgeting method

The modern envelope method

The zero-based budgeting method

The profit-first budgeting method

Using sinking funds to budget for large, infrequent expenses

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Day 12: Retirement Income Planning

Retirement income planning

What you should know about annuities

The annuity puzzle

Mortality credits and super bonds

Qualified longevity annuity contracts (QLACs)

Variable annuities

Basic retirement terminology

Sequence of returns risk

Strategy #1: Straight-line calculation

Strategy #2: Historical simulation

The "Retirement Distribution Hatchet"

Strategy #3: Monte Carlo simulation

Strategy #4: Guardrails (dynamic spending strategies)

What accounts should distributions be taken from?

Other considerations to be mindful of

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Day 13: Building Your Plan

Let's get started!

Income Lab Access

Data entry: Household info

Lean plan method

Data entry: Assets

Data entry: Liabilities

Linked vs. manual entry accounts

Data entry: Savings

Data entry: Income

Data entry: Expenses

Data entry: Retirement

Data entry: Insurance

Plan results (risk-based guardrails)

Are these the right guardrails for me?

Tax optimization through bracket management (Roth conversions)

Congratulations!

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Day 14: Working with an Advisor

Does everyone need an advisor?

Advisor service spectrum: DIY vs. DIWY vs. DIFY

Understanding the different types of advisors

What does "Fee-Only" mean?

What does "Fiduciary" mean?

Financial planning designations (and which ones matter)

What retirees should know about financial advisor conflicts of interest

Why Vanguard estimates 2-3% value in working with an advisor

Understanding advisor business models: Why cheaper isn't always better

Understanding advisor business models: Why number of clients matters

Advisor differences on "Tax Planning"

Interviewing advisors: How to assess their competence

How to look for an advisor

Should you negotiate with an advisor?

Understanding "all-in" advisor costs

Working with multiple advisors

Disregard financial advisor "awards"

An advisor's commitment to continued education

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