Planning for Retirement

By Kelly A. Henning, CFP®, MSFS

Wealth Manager, Principal

February 3, 2023

As financial planners we are often asked, “Will I be OK in retirement?” Before looking at a client’s assets and expenses to answer that question, we ask corresponding questions such as, “What do you want your retirement to look like?” Each individual’s perspectives on retirement are unique. Some people want to remain in their current house and community. Others wish to downsize and stay in the area close to family and friends. There is yet another group that wants to leave a high-cost of living area to move to an area with lower-cost of living. Thus, it’s key to expand on a client’s retirement goals earlier rather than later.

The checklist below illustrates different items to think about as retirement approaches, from ten years before to right after retirement begins. The earlier one starts planning for retirement, the more prepared one should be not only financially, but also emotionally.

5 to 10 years before targeted retirement

Brainstorm retirement goals and dreams of what retirement will look like.

Think about where you want to live and whether you want to downsize.

Revisit goals and timeframe annually.

Obtain annual credit report.

Pay down mortgages and other debt to strive to become debt-free by retirement age.

Revisit progress toward achievement of retirement goal and adjust retirement contributions and/or spending as appropriate.

Review estate planning needs and update documents, titling and beneficiaries as needed.

Consider long-term care insurance.

1 to 5 years before targeted retirement

Attend pre-retirement workshop and/or consider personal life coach to help prepare for transition.

Get comprehensive medical, dental and vision exams while still covered by employer insurance plans.

Consider Social Security claiming strategies.

Request estimate of pension or retiree medical benefits.

Get educated about Medicare options.

Revisit estimated budget for income and expenses anticipated in retirement.

6 to 12 months before targeted retirement

Income tax planning

Speak with accountant about expected new income bracket and how to plan for it.

Discuss possible Roth conversion or other tax planning strategies.

Outside retirement plan contributions? (non-deductible)

401(k) Plan

Plan to max out contributions for current year.

Confirm all funds in 401(k) accounts are vested.

Confirm whether funds are pre-tax only or pre-tax and after-tax.

Coordinate with wealth manager on a plan for your 401(k) and other accounts held through an employer.

If rolling to an outside IRA, open new account and obtain account number and custodian address/wire instructions for future deposit.

If retiring between 55 and 59 ½, may want to wait to rollover, due to options to take penalty-free withdrawals from 401(k) in year of retirement or take 72t distributions for at least 5 years.

Obtain documentation from your company related to stock options so you understand important dates associated with the options, such as vesting, expiration, etc.

Pension Benefits

Obtain all pension benefits available through current employer.

Determine whether or not a lump sum pension option is available and whether it is preferable for you.

Other Qualified and Non-Qualified Retirement Benefits.

Obtain information on all additional plans offered by the company and information on vesting, tax, and transfer of these accounts.

Social Security Benefits

Login to, create account, and obtain a current benefits statement.

Be sure to complete this step for spouse.

If divorced, contact Social Security directly at (800) 772-1213 and obtain information on taking benefits as ex-spouse.

Coordinate Social Security Analyzer tool with benefits statements to determine claiming strategy.

2 to 3 months before retirement

Paid Time-off

If you have any accumulated sick days, vacation time or other PTO days, determine if/how you will be paid for these days.

Advise Supervisor and HR Representative in writing of desired retirement date.

A specific date may be agreed upon(e.g., first week in January depending on payroll and other items).

Consider date which you will be eligible for year-end bonus or other benefits, including 401(k) matches, profit sharing, or stock options.

Request Retirement package of paperwork from HR.

Depending on the size of the company, HR will generally provide its own packet of paperwork and forms that need to be completed.

Determine date for exit interview with HR/supervisor.

Make final decision on all insurance, including medical, dental, vision and life insurance (timing will depend on company policies).

1 month before retirement

Obtain online/phone the paperwork to roll your 401(k) (or other retirement accounts) out of the plan into an outside account, if that’s the choice you’ve made.

Complete paperwork and contact HR to see if plan administrator signature is required.

Paperwork will be sent in following retirement date.

Post Retirement

401(k) Rollover Paperwork – Submit following retirement date.

There are many decisions to consider as one prepares for retirement, from healthcare considerations to account logistics. Understanding what should be done and when well in advance of your retirement date can be key to reducing stress in the months and weeks before you stop working. Employers will have deadlines on paperwork submission, some of which are your last day of work or thirty days after. Knowing these deadlines and seeking information in advance is essential. Use all available resources, such as your company’s human resources department and your various professional advisors to help make the transition as smooth as possible.

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