Living50+ Blog

Not Your Typical Pre-Retirement Checklist [Video]

Written by Pete Keers | Oct 29, 2021


Retirement checklists abound across the internet. Most provide wisdom on planning for a secure financial future. Saving enough, choosing appropriate investments, and eliminating debt are common recommendations. However, there is more to retirement than pure pocketbook considerations. Listed below are some retirement planning ideas that most checklists don't mention.

Does Your Retirement Checklist Have These Items 

Retirement Rehearsal

Despite careful preparation, retirement surprises seem inevitable. One way to flush out the unexpected is to "rehearse" retirement. This means to act as if already retired. Two areas where this could be valuable are spending and post-retirement activity.

A monthly spending budget may seem realistic on a spreadsheet before retirement, but actually living on that budget is the only way to know for sure it works. Try living on the retirement budget for at least a month. The outcome of that month will provide a financial reality check. Then, make adjustments based on the experience and go for another month. Ideally, such fine-tuning will result in a reasonable budget that will work for the long run.

Similarly, pre-retirement visions of activity would benefit from rehearsal. For example, suppose one envisions volunteering as a tutor for elementary-age children as the ideal retirement activity. Yet, without experience in this role, there is no guarantee of a good fit. Find an opportunity to try out the activity before retirement. It may confirm the choice, or it might show it is not a suitable activity to pursue in the next stage of life.

Unravel Work and Personal Life

Over the past few decades, work and personal lives have become closely integrated. This is particularly true when it comes to technology. In many jobs, the work computer contains not only business information but personal as well. Think about address lists and calendars. It is very common to find a mixture of business and personal entries on the work computer, especially if it is a laptop that shuttles between the workplace and home.

A major pre-retirement chore will be transferring personal information from the work computer to the hardware at home. This requires a few steps. First, make sure the home computer is up to the task. A slow home computer with a small amount of storage may cause significant frustration. A hardware upgrade may be in order.

Second, consider the software used at work. For example, one may be used to using software like Microsoft Office 365. But, home versions of such programs can be expensive. A less costly alternative is Google Workspace (formerly G-Suite.) These programs perform much like Microsoft Word and Excel, but there is a learning curve required to adjust to the differences.

Third, remember that company IT support goes away after retirement. Check out local IT support companies to research service options and costs. Having a helpful help desk of one's own can avoid a lot of stress.

Fourth, with all the above pieces in place, start to extract personal information from the work computer and load it on the home machine. If possible, find out if there is a way to export personal data in bulk from the work computer. Doing this will save hours of manual re-keying.

Significant Other Impact

Unless a person is single with no attachments, retirement affects relationships. Because retirement changes how someone experiences the world, the normal rhythms of relationships will naturally be influenced. For a couple, this can be an unsettling shift from comfortable routines. Suppose a partner retires when the other continues to work. In that case, resentment could build as the worker sees the retiree enjoying freedom from a rigid job schedule.

Even if a couple retires simultaneously, differing expectations about what each wants to do in retirement can cause friction. A common conflict occurs when one partner wants to travel while the other prefers to relax at home.

It is natural to develop rosy beliefs about retirement during long years of work without deeply examining the reality of those expectations. Retirement planning needs to include honest discussions with loved ones about post-retirement expectations.

When discussing these expectations with others, be open to the idea that adjustments in thinking are okay. It doesn't mean giving up dreams. Frank discussions about the practicalities of those dreams and how they affect others need not lead to disappointment. Instead, such conversations can be framed as opportunities to creatively form plans for achieving dreams in concert with others achieving their own goals.

Want to learn more? Click here to read our post, Great Expectations: Retirement and Committed Relationships!

Paying Off the Mortgage Might Not Payoff

As satisfying as it may seem to own a house free and clear, financial planners recommend paying off higher-interest debt first. The refinancing boom in recent years has enabled many homeowners to enjoy historically low mortgage rates. So it makes sense to first eliminate any debt charging interest above the mortgage rate. Also, paying off a mortgage might not make sense if a pre-retiree is not making maximum allowed contributions to retirement savings. If the return on investment can beat the cost of the mortgage, then funds should be directed to savings first.

Decluttering Overkill

Many retirement checklists recommend paring down possessions to prepare for a future move to smaller quarters or to spare adult children the burden of getting rid of a ton of "stuff" after death or disability. While some decluttering now may make sense, be careful about two categories of items.

First, the owner may classify certain items as junk, but others, like adult children, may have a different viewpoint. As a personal experience, my mother disposed of family pictures she believed no one cared about. My siblings and I were stunned when we found out. This example demonstrates that others, especially adult children, should be consulted in the decluttering process to ensure nothing of value gets tossed. An added advantage is that adult children can also say what they don't want. This will avoid needlessly keeping junk.

Second, know the rules of document destruction. Practical guidelines are broken down into time categories of three years, six years, and forever.

Examples of documents to keep for three years:

  • Credit Card Statements
  • Medical Bills (in case of insurance disputes)
  • Utility Records
  • Expired Insurance Policies

Examples of documents to keep for six years:

  • Accident Reports and Claims
  • Supporting Documents For Tax Returns
  • Property Records/Improvement Receipts (keep until after disposing of the property)
  • Medical Bills (if tax-related)
  • Mortgages / Deeds / Leases

Examples of documents to keep forever:

  • IRS Notices
  • Legal Records
  • Insurance Policies and Annuities
  • Retirement and Pension Records Special Circumstances
  • Sales Receipts (keep for the life of the warranty)
  • Property Records /improvement receipts (keep until property sold)
  • Stock and Bond Records to establish the basis for taxes

Alternatively, click here to learn about things you should throw out now to save yourself space in your home

Avoid Pulling Up Stakes Too Soon

Many a retirement dream envisions relaxing in a warm-climate home or tooling down the highway in an RV. However, these dreams need to be tempered by two practical thoughts. First, both of these dreams involve significant purchase expenses. Real estate prices across the nation have skyrocketed, and an RV sales boom has led to low inventory.

Second, without prior experience, such moves can lead to unpleasant surprises. Not uncommonly, some retirees have abandoned their dream relocation spot when they found the lifestyle or local culture did not fit their tastes. Likewise, would-be RV adventurers sometimes find the nomadic life less glamorous than anticipated once they've experienced the realities of life on the road.

For both these situations, a better option may be "trying before buying." Short-term property leases or RV rentals can provide real-life experience retirees can use to gauge if buying is a good option.

Look Before You Leap

Consider retirement checklist ideas, like those above, as data to make better decisions in the retirement planning process. The more research, the better the chance of reducing unpleasant surprises on the retirement journey.