Navigating the Transition to Retirement

By Donna M. Wood, CPA/PFS, CFP ®

Retirement can be an exciting new chapter in your life. Still, many people are surprised that once they make the transition, they find themselves anxious and even depressed. It’s all too common to have the “retirement blues” when you first retire for a number of reasons. Retirement is a colossal lifestyle shift that you may or may not have been ready for emotionally. However, you can get in front of a lot of potential emotional turbulence by planning ahead.

Button Up Your Finances
The truth is, even when retirees are confident that they have enough wealth to retire comfortably, there’s often a small fear in the back of their minds that prevents them from fully relaxing about their finances. That fear may be that the markets crash immediately after retiring, or that they’ve somehow miscalculated what their expenses will be and have therefore not saved enough.

You can sidestep this fear by working with a financial planner. Having an impartial third party review your retirement plan, and run stress tests on your portfolio can ease your concerns. Additionally, your financial planner can help you to create a strategy that allows you to continue building wealth even after you retire.

Dream Up Your New Lifestyle Before Retiring

Many people are so burnt out in their careers, they begin to view retirement as a finish line. They don’t imagine what life beyond retiring might look like because they’re so focused on simply getting there. When you take the time before retirement to think about what you want your life to look like after leaving your career, it can help make your transition easier. Thinking through these five key questions can help:

  1. How will I spend my time in retirement?
  2. What activities outside of the office bring me fulfillment or joy?
  3. What do I enjoy about my job? Is there a way outside of the office that I can pursue those same types of interests or tasks?
  4. Do I have hobbies that I want to explore or pursue?
  5. Who will my support network be?

Having a few ideas about how you want to spend your days can ease the stress of suddenly having a lot of time on your hands. For example, you might decide to pursue volunteer work. Joining a local organization and spending part-time hours doing work you’re passionate about can help organize your calendar, bring you a sense of purpose, and build a legacy you’re proud of beyond your career.

Have a “Plan B”

When it comes to retirement, having backup plans is key. It goes without saying that you should have a financial Plan B in case of a medical emergency with hefty expenses, a market crash, or other unforeseen circumstances. However, your Plan B shouldn’t be limited to your finances. Have a Plan B in place in case you simply don’t enjoy being retired. Do you want to work part-time? Would you be open to consulting? Explore your options and remain flexible. The most important thing is that you are content, not that you stuck to your original plan.


Take Your Retirement Lifestyle for a “Test Drive”

This is a relatively new concept, but it’s highly recommended for pre-retirees to consider “test driving” their retirement lifestyle before actually retiring. If you’re wondering what a test drive looks like, and how you can use this tool to determine how or when you should retire, here are a few options to consider.

Extended Leave of Absence

Depending on your company and job role, you may be able to take an extended leave of absence or even work remotely, for a month or longer. Use this time to see what it’s like to leave behind the confines of your physical office. If you’re working remotely, consider doing so from your ideal retirement location. Think about how you’d spend your time, and what life would look like without traditional job-related responsibilities.

Make Lifestyle Changes Now

Can’t take an extended leave? Consider “test driving” just 1-2 aspects of your ideal retirement lifestyle. This might mean downsizing your home or relocating and working virtually if possible. You can also consider going down to one car for your family; moving closer to family or friends and working remotely; practicing living within your retirement budget; and researching major purchases (like a boat, or an RV) and renting them for a few long weekends to see if they’re actually livable.

Explore Hobbies

Don’t wait until retirement to find new hobbies. Now’s the time to try different activities and discover what you enjoy. (It’s also a great way to make new friends and establish a network outside of work!) You can even make this a fun weekend project. Every weekend pick something new and try it. Like:

  • Hiking and birdwatching

Mason Neck State Park offers six easy-to-moderate hiking trails and, because there’s a wildlife refuge right there, the chance to see a bald eagle. 7301 High Point Road, Lorton.

  • Mountain biking

Fountainhead Regional Park is one of the best for building biking skills. The trails are marked “single-use,” so you won’t encounter any horseback riders or hikers, everything is “one way,” so there is no oncoming traffic, and there’s a trail for every skill level. 10875 Hampton Rd, Fairfax Station.

  • Cooking classes

Sur La Table in McLean and Culinaria Cooking School in Vienna offers a variety of culinary classes, one more delicious than the next. Culinariacookingschool.com; Surlatable.com.

Talk to Loved Ones

Avoid assumptions and speak to your loved ones about what they expect from you during retirement. Does your spouse want to keep working? Do your kids anticipate more help with your grandkids when you have more free time? Decide what you want and communicate it clearly.


About the Author
Wood Smith Advisors, located in Haymarket, is a Registered Investment Advisor (RIA) and fee-only financial services firm that partners with its clients to simplify their financial lives. Wood Smith focuses on women, entrepreneurs, and individuals with complex financial situations, providing objective and competent advice, education and services to help them develop and build their businesses and reach their financial goals. Woodsmithadvisors.com

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