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Investing Retirement

Navigating the First Year of Retirement

Justin Hearty, CFP®
Justin Hearty, CFP® |

The retirement party is over. The speeches were heartfelt, the cake was great, and everyone toasted to your next chapter. But what happens when the confetti settles and Monday morning rolls around—without a single meeting on your calendar?

For many retirees, the first year feels like a mix of freedom, excitement, and… uncertainty. It’s a big transition, and how you handle it can set the tone for the decades ahead. Here are five ways to make that first year not just good—but great.

1. Redefining Your Routine (And Yourself)

Work gave you structure—and maybe even a sense of identity. Without it, the days can feel wide open (and not always in a good way). The key? Build a new rhythm.

  • Explore hobbies you’ve always wanted to try.
  • Schedule time for exercise, social activities, and personal growth.
  • Consider volunteering or part-time work if you miss the sense of purpose.

A little structure goes a long way toward making retirement feel intentional, not aimless.

2. Get Comfortable with Your Cash Flow

This is the year your financial plan goes from theory to reality. You’ll start drawing from retirement accounts, Social Security, maybe a pension.

  • Track your monthly spending and compare it to your income sources.
  • Set up automatic withdrawals for predictable cash flow.
  • Work with your advisor to make sure distributions are tax-efficient.

The goal: confidence that your lifestyle is sustainable—without second-guessing every purchase.

3. Staying Ahead on Healthcare

Healthcare becomes a bigger part of the picture in retirement. If you’re 65+, Medicare is likely your main coverage, but don’t ignore the details.

  • Review your plan annually and consider supplemental coverage.
  • Stay on top of preventive care and wellness visits.
  • Think about long-term care planning before you need it.

A little planning now can save you stress (and money) later.

Need Help?

Whether you’re ready to get started today or you’re just exploring your options, talk to an advisor to discuss your next steps.

 

4.  Keep Your Social Life Strong 

One surprise for many retirees? How much they miss the social side of work. Without those daily interactions, isolation can creep in.

  • Schedule regular lunches or calls with friends and former colleagues.
  • Join a club, take a class, or volunteer in your community.
  • Make connecting with others part of your weekly routine.

Strong relationships aren’t just nice—they’re linked to better health and happiness.

5.  Revisit Your Financial Plan 

Your first year is the perfect time to check in on your plan. Life changes fast, and your strategy should keep up.

  • Review estate documents and beneficiary designations.
  • Reassess your investment mix and risk tolerance.
  • Talk about charitable giving or legacy goals if they’re important to you.

Think of this as a tune-up to keep everything running smoothly.

The First Year is a Foundation

The first year of retirement isn’t just a transition—it’s a foundation. Approach it with intention, and you’ll set yourself up for a fulfilling, confident next chapter. And remember, you don’t have to figure it all out alone. A good plan (and a good advisor) can make this season everything you’ve dreamed of—and more.



Need Help?

Whether you’re ready to get started today or you’re just exploring your options, talk to an advisor to discuss your next steps.

 

Disclaimer

The information provided in this article is intended solely for educational purposes. It is designed to offer insights into financial planning and family wealth strategies, aiming to enhance understanding of financial concepts and decision-making. This content should not be interpreted as personalized investment advice or a recommendation for any specific strategy, financial planning approach, or investment product. Financial decisions are deeply personal and should be made considering the individual’s specific circumstances, goals, and risk tolerance. We recommend consulting with a professional financial advisor for personalized advice 

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