Date: October 4, 2021

Retirement Timeline: Watts Gwilliam Shares Important Steps that are Often Overlooked

Retirement is a major accomplishment … and a major transition, not just financially but emotionally too!

We’re often asked at Watts Gwilliam and Company what clients can do now to prepare for the change. Here’s our answer:

Your Health

One year from retirement, schedule a physical with your doctor. A physical one year prior to retirement gives you the opportunity to address any health concerns prior to applying for your retirement health insurance.

Another helpful step can be establishing an exercise routine. Starting an exercise routine early can help you develop healthy habits and get you in better shape for your health insurance application.

When retirement is just six months away, this can be a good time to review your retirement health insurance options. This includes meeting with an insurance agent, comparing different policies and beginning the process of selecting the right coverage for you.

Your Day-to-Day Plans

Your day-to-day plans is another very important, yet often overlooked, part of retirement. How do you plan to spend your time when you’re no longer working? What will give you purpose? Who will you spend your time with? All too often, retirees leave work without realizing they’re also potentially leaving their colleagues, schedules and the thing that gives them purpose – work! This can lead to boredom, loneliness, anxiety and even depression. Read our recent blog post: Can I Retire? Financial Advisor Asks 5 Questions to Find Out.

One year from retirement, if you haven’t already established “retirement friendly” hobbies, now’s the time to do so. We all need something to look forward to when we wake up in the morning.

Make sure to discuss your goals with your spouse, if applicable. It is important for couples to get on the same page, though this doesn’t necessarily mean their plans have to match completely. Do you each want to spend more time volunteering for a charity, or does one want to spend time on the golf course while the other hopes to spend time with grandkids?

When retirement is nine months away, make sure to review your estate plan to make sure it’s up-to-date.

When retirement is six months away, review your life insurance coverage. Most group life insurance policies will lapse at retirement, and therefore, a needs analysis should be conducted. If extra coverage is necessary, consider alternative policies and start the application process.

When retirement is three months away, review your expectations with your spouse, if applicable. With retirement just around the corner, it is important to make sure both spouses are still on the same page regarding retirement expectations and goals.


Planning for retirement can be tricky. Contact the team at Watts Gwilliam and Company to see how we can help.


Your Finances

Of course, it’s also vital to review your financial situation before walking away from a steady paycheck.

When retirement is one year away, work with a financial advisor to create a detailed cashflow analysis. This should include a debt review. Set up a strategy on how to manage debt during retirement. Determine the level of debt you are comfortable with and the tax efficiency of that debt.

Once you’re nine months from retirement, create an updated retirement budget to help ensure that your determined expenses are accurate. A common mistake we see new retirees make is overspending. Work with a financial advisor to consolidate your assets and investment accounts, a process that can help simplify your budget.

Make sure to also review your emergency fund. Having a healthy emergency fund can be a game-changer, even if you have a comfortable lifestyle in retirement and a healthy amount of disposable income. Read our recent blog post: Why a Budget and Emergency Fund are Important for High Net Worth Individuals.

Once you’re six months from retirement, make sure to verify your pension, if applicable. You’ll want to verify the pension amount and your distribution options.

It can also help to have a financial advisor review your budget via a Monte Carlo analysis to make sure it’s reasonable. The team at Watts Gwilliam and Company can help with this. Our team can also help you reposition your assets, if necessary. Now that your assets have been consolidated, the portfolio should be reallocated to meet retirement objectives. This includes any stock options. Typically all vested options will expire at or shortly after retirement. This is the time you’ll want to choose your price targets and stick to a disciplined sales strategy.

When you’re three months from retirement, have a financial advisor provide a detailed income analysis. Now that your investments have been consolidated and repositioned, a detailed

income report can help you understand when and where your income will come from in retirement.

You may also want to sign up for auto bill pay, another step that can help simplify your retirement by having all your bills paid automatically.

Once you reach retirement, contact your company’s 401(k) plan administrator and request a rollover transfer to your IRA. If you still have vested options, exercise them right away. If you need to receive dividend and interest income, make sure that your investments are set up to pay the distribution rather than reinvest it.

A Failure to Plan is a Plan to Fail

Getting an early start on your retirement planning is important. Reviewing your plan as you get closer to making the transition is also key!

If you’re not currently working with a financial advisor or are ready to make a change, schedule a no-obligation conversation with the Watts Gwilliam team. We’re here to help!


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David Watts

Dave is one of the firm’s founders. He helps business owners, professional athletes, and other high-net worth clients develop and implement financial plans and strategies. He also specializes in helping those with single-stock positions to diversify and manage their financial lives. Other areas of specialty are wealth transfer plans for concentrated stockholders and business owners; tax minimization strategies for those with employee stock options; cash flow management; and risk management planning.