Paula R Chesser, CSA

05/05/2026

Some retirees describe the first few months as a honeymoon phase.

Travel. Projects. Rest. Catching up on everything that was postponed.

And then something shifts.

After the glow wears off, deeper questions start to surface:
▪️How do I want to spend my time?
▪️What feels meaningful now?

That transition is normal.

Retirement creates space. The first year is about deciding what deserves it.


https://www.paulachesser.com/our-clients

04/30/2026

There's a moment early in retirement that catches many people off guard.

You wake up… and there's nowhere you need to be.

At first, that quiet feels wonderful. After years of deadlines and responsibility, it's a relief.

And then the question comes:

Now what?

If that feels familiar, you're not alone. Retirement isn't just a schedule change. For many people, it's an identity shift.

The first year isn't about having everything figured out. It's about finding your rhythm.


https://www.paulachesser.com/our-clients

04/21/2026

Often, people don’t envision what they actually want from life after they retire and may feel bored or even depressed. Staying connected to others and engaging in new activities may help you enjoy retirement more.

04/07/2026

Team Paula is proud to share Baird has been named one of the Fortune 100 Best Companies to Work For® again in 2026, ranking No. 16 and marking our 23rd consecutive year on the list. The longstanding recognition of Baird's unique culture reflects our associates' shared commitment to putting clients first, working together in a supportive environment that allows us to deliver thoughtful guidance, reliable service and the highest level of care. Team Paula trusts this acknowledgment resonates with you and serves as a reflection of Baird's unwavering commitment to our clients and our associates. https://www.paulachesser.com/services

04/02/2026

03/19/2026

Focus your time and energy on what you do best. Evaluate yourself critically to identify what sets you apart. Delegate and outsource to address areas where you’re weak.

03/17/2026

03/05/2026

In February’s Wealth Strategies webinar, our planning professionals explored how charitable giving strategies can help you make a lasting impact, while also navigating today’s evolving tax landscape.

02/24/2026

As tax season gets underway, the U.S. Postal Service has updated how postmarks are applied — and that change could matter for time-sensitive mail.

Under the revised process, some mail pieces may receive a postmark based on when they’re processed by USPS, rather than the date they’re dropped off or collected. For documents where the postmark date determines whether something was submitted on time, this distinction can be important.

That includes items such as:
➡️ Tax returns and supporting documents
➡️ Estimated tax payments
➡️ Requests for extensions
➡️ Other official forms or correspondence tied to filing deadlines

With this change in mind, allow extra mailing time. You may want to confirm which electronic or in-person submission options will help reduce last-minute issues during a busy filing season.


Source: https://www.aarp.org/government-elections/usps-postmark-changes/

Paula’s Wealth Management Advanced Planning Services address the more complex areas of wealth management for her high-net-worth clients.

02/19/2026

Advisors’ brand recognition and expertise is highly valued by the ultra-wealthy. Advisors who coordinate the efforts of other professionals get high marks. Specialization, serving clients who are similar in some key way, is a trait the ultra-wealthy like to see.