June 2026 Newsletter: Choose a Happy Retirement

By Charles Sherry, MSc

Copy link to clipboard Download PDF

Many assume that a happy retirement comes down to building enough wealth over a lifetime of work that will ensure comfort in their later years.

In simple terms, will the financial assets accumulated generate the monthly income necessary to sustain their retirement lifestyle? If they can check that box, well, they are golden… or so they believe.

As they approach retirement, they tally up sources of income that will be generated from Social Security, a pension, assets held in or outside of retirement accounts, the sale of a business or properties, or any other assets that can be used to generate cash.

Money matters. We intuitively understand that. Having your finances in order removes a significant burden, easing stress and giving you greater freedom to live life on your terms.

But having ample financial resources in retirement isn’t a guarantee you’ll be content. Just ask anyone who is retired. It’s a big part of the equation, but it’s not the only variable.

In April, we discussed Social Security. Last month, we briefly explored the idea that retirement is a modern concept and outlined various retirement vehicles available to help you save.

This month, we will explore practical strategies that may enhance your overall satisfaction in retirement.

And the survey says…

The good news is that retirees are enjoying life amid health and even financial uncertainties, according to a recent study published by the Transamerica Center for Retirement Studies.

According to the study, almost half said their enjoyment of life improved, while a little over one-third said it stayed the same.

More than 80% reported their overall happiness either improved (41%) or didn’t change (43%).

And, when it came to finances, just over two-thirds said their financial situation improved (24%) or at least stayed the same (46%).

The survey highlighted that retirees embrace happiness, prioritize what’s important to them, spend their time in meaningful ways, and safeguard their health.

In other words, the data is encouraging, but achieving a fulfilling retirement requires intentional effort.

But let’s back up for a moment. Those who have not yet left the workforce risk falling into the retirement myth that retirement will lead to endless free time, constant travel, the never-ending pursuit of hobbies, and retirement bliss.

If you are not intentional, you risk falling into the “endless free time” bucket where there is too much unstructured free time that can lead to what might be called a “retirement void,” i.e., a sense of emptiness or lack of purpose some people feel after leaving their career or business behind.

This, in turn, can contribute to declines in both mental and physical health and a significant psychological burden.

Planning is key. Happiness and fulfillment in retirement are a choice.

Seven successful habits of those who enjoy their retirement years

1. Retire to something, not from something

When someone leaves a job solely to escape their dislike of it, they often trade one set of problems for another. However, those who succeed carefully plan their next steps and exit one opportunity to pursue another.

What new opportunities await you in retirement? What would you like to do that you simply do not have the bandwidth while working?

2. Happiness equates to a sense of purpose

Ditch the cliché of golfing daily or leisurely reading on the beach or in a mountain cabin. While the beauty of ocean sunsets and mountain valleys is undeniable, the notion of quietly drifting into retirement belongs to another era.

Today’s active, fulfilled seniors are redefining what it means to live fully, with purpose, energy, and engagement.

Work often gives us identity and meaning. So, find a new source. Consider volunteering, teaching, mentoring, and creative pursuits. You know, something you’ve always wanted to do, something that’s been in the back of your mind, but you simply didn’t have the time to fully pursue it.

Unsure of your next step, local food banks, shelters, parks and outdoor projects, libraries, animal shelters, and rescue groups are often in need of assistance.

Whether it’s preparing meals, organizing donations, or greeting visitors, these roles offer immediate, visible impact as well as a strong sense of purpose. Faith-based organizations often have a wide range of volunteer roles. These can offer both purpose and a built-in social network.

3. Maintain social connections

Many folks underestimate how much of their social life came from work. Make deliberate plans with friends, join groups that align with your interests, enroll in classes, and stay involved in your community.

4. Maintain a routine, but it’s ok to keep it flexible.

Regular exercise, social activities, creative pursuits, and personal projects are fulfilling. Downtime is great, but too much unstructured time can lead to that retirement void.

You are retired. Assert control over your calendar. Schedules needn’t be rigid, but structure defines the day and week.

5. Learning doesn’t stop at retirement

Do you want to learn a musical instrument, a new skill, or take a class? Many local universities offer free online courses on a variety of topics. What area of interest would you like to explore?

Consider Massive Open Online Courses (MOOCs), which are free, open-access, self-paced digital classes designed for a global audience. These courses typically include pre-recorded video lectures, curated readings, and interactive quizzes to support learning and engagement.

Some class ideas from AARP include history, current events, literature, arts and music, science and technology, religion and spirituality, and health and wellness. What piques your interest?

Progress keeps you on the track toward fulfillment.

6. Can you ease into retirement?

Working 40 hours a week or more and then suddenly not having to work at all on Monday, Tuesday, Wednesday, etc., can be a jarring transition for someone who didn’t realize how much they relied on structure.

Can you drop to part-time work with your employer, transition to consulting, or take on seasonal work that can ease you into full-time retirement?

7. Align your time with our values

What matters to me? What are my priorities? How would I like to channel my energy? It’s not simply about staying busy. It’s also about investing your time in the right things.

Check in with yourself regularly, maybe once a month. What’s working? What’s not? And what changes might you make going forward?

A lot of folks who transition into retirement are excited for a slower, more relaxed pace of life, and that makes sense. Interestingly, many retirees experience a boost in happiness right after they stop working.

But for some, that initial high fades, and satisfaction begins to slip. A life centered mostly on leisure may not offer the same sense of purpose or accomplishment that a career once provided.

If you feel like you are starting down that path, you’re not alone, and there are proactive steps you can take to address it.

May’s Market Momentum

Strong momentum that began in April carried through May, with major stock indexes continuing to climb to new highs.

Despite concerns that might normally cool enthusiasm, what fueled the advance?

Well, there were two competing themes that dominated market action during May.

First, Treasury bond yields trended higher last month in response to concerns about inflation. The war with Iran has lifted gasoline prices and other key commodities. Though the legality of broad-based tariffs is in question, businesses are passing along some costs.

Coupled with signs that the labor market may be firming, chatter is surfacing that the Federal Reserve might hike its key interest rate, the fed funds rate, later in the year. That’s in stark contrast to earlier in the year when investors were eyeing at least one rate cut in 2026.

While higher Treasury yields may have tempered market gains, they did not prevent a banner month for the major market indexes, as illustrated by the table of returns.

Source: Wall Street Journal, MSCI.com, Bloomberg, MarketWatch
MTD returns: April 30, 2026–May 29, 2026
YTD returns: December 31, 2025–May 29, 2026
*in US dollars

The biggest driver of equities last month was corporate profits. Simply put, first quarter earnings were fabulous.

Many companies that reside within the S&P 500 Index easily surpassed analyst expectations in Q1, according to LSEG.

A brief review of the numbers tells us that Q1 S&P 500 profits rose nearly 30% from one year ago. That’s an astounding feat, and the fastest pace since the fourth quarter of 2021.

Look no further than AI and big tech firms, which are doing much of the heavy lifting. For example, the so-called “Magnificent 7” mega-cap companies (7 mega-cap companies) posted a striking year-over-year profit increase of more than 60% in Q1, according to FactSet.

In addition, massive spending on AI, semiconductors, and the cloud is translating into a profit boom for many firms tied to the sector.

But it’s not simply the Magnificent 7. Outside this select group, the remaining S&P 500 companies sported an impressive 17% rise in first-quarter earnings. Additionally, analysts have lifted profit estimates for the remainder of the year.

It’s been a powerful set of factors, including:

• AI-driven growth (especially in mega-cap tech)
• Improved margins
• Resilient demand
• Widespread earnings beats

Think of it this way. If you were to purchase a privately held business, current and expected profitability will play a big role in what you might pay for that business.

While other factors come into play, too (such as the industry and interest rates), the same concept holds true for publicly traded companies.

I trust you found this review to be insightful. If you have any questions or simply want to talk through your portfolio or other financial goals, please don’t hesitate to reach out to me or anyone on our team.

Thank you for choosing us as your trusted financial professionals. We deeply value your confidence and are honored to help you navigate your financial journey.