Business

Finding Your Retirement Sea Legs

By Andrew Rosen,Contributor

Copyright forbes

Finding Your Retirement Sea Legs

Finding your retirement sea legs is a process that may take you some time to figure out.

That last day of work before retirement can feel like an emotional rollercoaster. After 30 or 40 years of structure and routine, everything changes in an instant. There’s excitement about newfound freedom, but also a wave of uncertainty. How will the time be filled? Is there enough money to live comfortably? And perhaps most importantly—what will give life purpose now?

These questions swirl in the minds of many retirees, but one rises above the rest: What will I do with all this time?

The truth is, retirement doesn’t come with an instruction manual. People don’t wake up the day after their farewell party with a perfectly mapped-out schedule. Instead, it takes time to settle into a rhythm and figure out what a fulfilling retirement lifestyle actually looks like. This adjustment period is what can be thought of as finding one’s “retirement

The First Year Of Retirement: Figuring It Out

For most, the first year of retirement is a transitional one. It’s full of trial and error, exploration, and false starts. Retirees may bounce between hobbies, travel plans, volunteer opportunities, and downtime—all in an effort to see what sticks.

This phase can feel unsettling at times, but it’s entirely normal. In fact, many retirees later look back and realize they didn’t truly know how they wanted to spend their retirement years until they were already living them. The first year becomes a sort of “throwaway year,” where experimentation is the main goal.

MORE FOR YOU

The Need For Structure In Retirement

Human beings thrive on structure, and retirement doesn’t change that. After the initial phase of freedom and discovery, most retirees begin craving a routine. That structure often emerges naturally in the second year.

Daily rituals become more defined—perhaps mornings start with a walk, coffee, and some light stretching. Weekly rhythms fall into place as well, with certain days dedicated to exercise, others to spending time with grandchildren, and others to social activities or hobbies.

Beyond daily habits, retirees also start building structure into bigger, seasonal patterns. January might mean a month in Florida. Spring could bring an annual cruise. Summers often include family vacations. The details vary, but the underlying theme is the same: retirement becomes less about drifting and more about living with intention.

Looking Ahead Before Retirement

Even for those years away from leaving the workforce, it’s worth thinking about what a satisfying retirement lifestyle might look like. This doesn’t mean everything needs to be planned in advance—flexibility is key—but considering the possibilities can make the transition smoother.

Some questions to reflect on:

Is it appealing to stay in the same community, or does moving to a new location feel exciting?

Is living near family a priority, or does it feel more appealing to choose a destination that encourages family and friends to visit?

What hobbies deserve more time and attention once work obligations are gone?

One retiree shared that he envisioned his days filled with tennis matches, regular workouts, long lunches with friends, and finally learning to play guitar. Others imagine devoting more time to volunteering, traveling to new destinations, or starting a second career or passion project. The point is not to lock into a rigid plan, but to start planting seeds of what could bring joy and fulfillment down the road.

Finding Peace Of Mind In Retirement

Perhaps the most reassuring part of retirement is realizing no one gets it “right” immediately. Every retiree goes through a period of adjustment while finding their sea legs. Some settle into their routines quickly; others take years. What matters is that the process unfolds at its own pace.

Knowledge can bring peace of mind. Understanding that everyone goes through this adjustment can make the transition feel less overwhelming. Retirement is not a single moment in time but an evolving stage of life—one that grows richer with experience, reflection, and experimentation.

Embracing The Retirement Journey

Retirement is often painted as a finish line, but in reality, it’s a new beginning. It’s a time to explore passions, deepen relationships, and design a lifestyle that reflects personal values. That design won’t appear overnight. Instead, it develops through trial, error, and the gradual creation of a rhythm that feels both comfortable and meaningful.

For those still working, imagining that future can help set the stage for a smooth transition. For those already in retirement, patience and flexibility are the key tools in adjusting. Either way, the goal remains the same: to live a retirement lifestyle that brings health, happiness, and purpose.

Financial planning and Investment advisory services offered through Diversified, LLC. Diversified is a registered investment adviser, and the registration of an investment adviser does not imply any specific level of skill or training and does not constitute an endorsement of the firm by the SEC. A copy of Diversified’s current written disclosure brochure which discusses, among other things, the firm’s business practices, services and fees, is available through the SEC’s website at: www.adviserinfo.sec.gov. Diversified, LLC does not provide tax advice and should not be relied upon for purposes of filing taxes, estimating tax liabilities or avoiding any tax or penalty imposed by law. The information provided by Diversified, LLC should not be a substitute for consulting a qualified tax advisor, accountant, or other professional concerning the application of tax law or an individual tax situation. Nothing provided on this site constitutes tax advice. Individuals should seek the advice of their own tax advisor for specific information regarding tax consequences of investments. Investments in securities entail risk and are not suitable for all investors. This site is not a recommendation nor an offer to sell (or solicitation of an offer to buy) securities in the United States or in any other jurisdiction.

Editorial StandardsReprints & Permissions