Your ultimate retirement planning guide

By:  Allen Wastler-

Allen Wastler is a former financial journalist with over 30-years of experience, including time at CNBC, CNN, and Knight-Ridder Newspapers.

How do you get to a comfortable retirement? It’s a journey. And like any other trip, it’s easier if you have a map or GPS to help you get there. Here’s an overall guide with links to information and expositions on specific retirement issues.

Planning for retirement, early

The first step in any trip is figuring out where you want to go. With retirement planning, that means determining what kind of nest egg you think you’ll need, given your lifestyle and goals for your retirement years. This calculator will help you determine that: Retirement Calculator. 

Along with those numbers comes the recognition that there are some uncomfortable truths about retirement.

Early years 20s –30s: The earlier you start saving, the more wealth you are likely to amass as a result of basic math, tax advantages, and historic investment returns.

• Saving for retirement in your 20s: Doing the math

• Why saving for retirement early is important

• How to start a retirement plan

• Consolidating retirement savings when switching jobs

• Why you can win with a steady investment strategy

• Where your retirement savings should be in your 30s?

Unfortunately, many people put off investing, especially in their early years. Indeed, about two out of three 21- to 32-year-olds haven’t started saving for retirement.1 More often than not, it is because of the need to pay off existing debt like student loans (When student loan and 401(k) compete) or difficulty with budgeting priorities (How to be on a budget: The essentials).

Later years, 40s – 50s: There are options to prioritize retirement savings in later years, though. These include making catch-up contributions to tax-advantaged retirement accounts, reducing fixed expenses, and creating an additional income stream to fortify your nest egg.

• Saving in your 40s and 50s: It’s never too late to get started

• Retirement plan contribution limits: Your need to know

• Four reasons why your 401(k) may not be enough

• Investing for retirement

• Keeping retirement on track

• Where your retirement savings should be in your 40s

• Where your retirement savings should be in your 50s

Retiring early: Of course, there are those who don’t want to wait for the typical time of retirement, 65 years of age or so, to start enjoying the retirement lifestyle. They have options too.

• A checklist for early retirement

• Retiring early? Possible ways to tap savings but sidestep penalties

• How an earlier retirement could potentially reduce risk

• Retiring early? A guide for securing health insurance

• The unexpected problems with early retirement

• To-do list for an unplanned early retirement

Approaching retirement

Most people start considering retirement in their 60s. But actually taking the step isn’t an instant process. Beyond paperwork requirements for retirement account and tax purposes, there are final considerations about Social Security and longevity possibilities to consider as well.

• Time to retire? Questions to consider

• Short retirement horizon? Be careful

• 3 catch-up moves going into retirement

• How life insurance can help you in retirement

• 5 retirement risks and what to do about them

• Financial protection tactics as you near retirement

• How to grow wealth approaching retirement

• Should you pay off your mortgage before retirement?

• Tax considerations for retiring abroad

Resource planning: Once retirement is in sight, there are certain steps to take. These include organizational moves involving your retirement accounts and resources.

• Retiring in 12 months or less? What to do

• Entering the 'wealth transfer zone'

• Why baby boomers should secure a mortgage before retirement

• Taxes and retirement: 3 planning tips

• Taking cash off the table: Life insurance, annuity alternatives

• How much will I really need for health care in retirement?

Social Security: For most Americans, Social Security is a vital part of retirement security. It takes planning, however, to understand the mechanics of the Social Security program and how it can fit into your planning. In some cases, that can even mean delaying benefits.

• Filing for Social Security retirement benefits

• Social Security filing options for singles

• Social Security filing strategies for married couples

• Social Security for divorced spouses

• Social Security filing strategies for the widowed

• What people don't know about Social Security, but should

• Social Security spousal and survivor benefits: Different and not equal

Longevity considerations: Life spans are getting longer on average and sometimes that can have an impact on existing plans and future circumstances.

• The retirement income crisis ... and what can be done about it

• Is paying for long-term care part of your retirement plan?

• Taking the long view in planning for retirement

• Americans are living longer: Have a plan?

• Does an annuity fit your retirement goals?

Annuities: In terms of longevity considerations, annuities are becoming a consideration for more and more people. Indeed, recent moves by Congress are introducing annuities as options in some retirement plans.

• Types of annuities and how they work

• Is there potential for market growth and guaranteed income? Yes

• Retirement needs vs. RMD rules — and the QLAC

• Useful annuity terms to know

• 5 reasons why you may need an annuity

• When is the right time to buy an annuity?

• What is annuitization?

In retirement

Finally, actually being in retirement requires some attention too. With hope, prior planning has eased this situation somewhat. Still, as you age and circumstances change, there may be various issues to address.

Your nest egg: Obviously, you need to protect what you have worked so hard to build, especially since the opportunity to rebuild any losses are limited. So managing resources and protecting wealth should be a priority.

• The ideal retirement portfolio withdrawal rate

• How to live on interest only in retirement

• Protecting yourself against market fluctuations in retirement

• Tips for maximizing your retirement income

• Reverse mortgages: What you need to know

• Be on guard: 3 common senior scams

• Turning 73? Required minimum distributions explained

Health care: As people get older, their associated medical costs tend to rise. Projecting those expenses accurately and factoring in health insurance coverage is important.

• Covering costs in Medicare's 'donut hole'

• Single seniors pay more for health care

• Health savings accounts and retirement

• Planning for diminished mental capacity as you age

• Seniors and mental fitness: What’s normal, what’s alarming

Real estate: Since a home is a major asset, if not the major asset, for many retirees, questions often arise about the best way to use it. The answer isn’t always the same from person to person.

• Renting for some retirees may be a better option

• Sell or rent your old home in retirement?

• Downsizing in retirement

• Upsizing in retirement

• How to get a mortgage during retirement

Lifestyle: Living arrangements and lifestyle changes are also a major consideration in retirement years. Here, too, personal preference and circumstance will differ by individual.

• Senior living and the cohabitation option

• Should you move to a 55-or-older community?

• Retiring abroad? Your plan and checklist

• Surviving retirement with your spouse

• Scoring senior discounts

• Retirement planning for single seniors

• Financially beneficial retirement activities and hobbies

• 10 ways to find meaning in retirement

Legacy: And, of course, there are issues of managing one’s estate and legacy.

• 7 situations where a trust might help

• Estate planning: 6 big mistakes you might be making

• How to make sure your heirs won’t fight

• 6 ways life insurance can help with estate planning

• A way to approach 3 typical estate planning needs

• An estate planning tool for the not-so-wealthy

Obviously, given the breadth of issues and considerations over time, retirement planning can be a significant process, depending on one’s preferences and circumstances. Many people turn to a financial professional to help advise them through the choices.

But a first step is understanding what to plan for.

The information provided is not written or intended as specific tax or legal advice. MassMutual, its employees and representatives are not authorized to give tax or legal advice. You are encouraged to seek advice from your own tax or legal counsel. Opinions expressed by those interviewed are their own and do not necessarily represent the views of Massachusetts Mutual Life Insurance Company.

Provided by Jon Gates, a financial representative with Capstone Partners, courtesy of Massachusetts Mutual Life Insurance Company (MassMutual). ©2023 Massachusetts Mutual Life Insurance Company, Springfield, MA 01111-0001. MM202602-304275