Early Retirement or Keep Working? How to Choose What’s Right for You.

If you’re approaching the point where early retirement is an option, it’s natural to feel a mix of excitement and uncertainty. The idea of stepping away from work to enjoy more freedom, flexibility, and personal time can be appealing. But continuing to work after retirement age may also offer ongoing income, purpose, and routine.

There’s no universal answer to the question of when to retire. The decision depends on a variety of personal, financial, and lifestyle factors. Here are a few key areas to consider as you think through what’s right for you.

1. Review Your Financial Readiness

One of the most important aspects of retirement planning is whether you’re financially prepared. Retiring early means your savings may need to last longer, and you might be delaying access to full retirement benefits.

Questions to explore:

Have you assessed how long your savings and income sources are likely to last?
What would your monthly expenses look like without a paycheck?
Have you factored in inflation, market fluctuations, and potential healthcare costs?
How will your health insurance change once you retire, and what will it cost? If you’re retiring before becoming eligible for Medicare or other benefits, private insurance or COBRA coverage can significantly increase expenses. Understanding those options ahead of time is essential to avoid unexpected gaps or costs.

Understanding your financial picture doesn’t guarantee certainty, but it helps set realistic expectations about what early retirement planning might look like over time.

2. Evaluate Your Health and Energy

Your physical and mental well-being can play a major role in the decision to retire or keep working. Some people feel strong and energized well into their 60s and beyond, while others experience burnout or health concerns that shift priorities.

Ask yourself:

Do you have the energy and motivation to continue working?
Are job stress or physical demands starting to affect your quality of life?
Would leaving your current role improve your health or peace of mind?

This decision is as much about how you feel as it is about numbers on a page.

3. Think About the Role Work Plays in Your Life

Beyond income, work often provides structure, identity, and social connection. For many, these aspects are difficult to replace immediately in retirement.

Reflect on:

Do you enjoy what you do, or are you simply counting the days?
How would you spend your time if you weren’t working?
Are there hobbies, interests, or causes you’re ready to devote more time to?

Knowing what you’re retiring to, not just what you’re leaving, can make the transition smoother and more fulfilling. Some people explore part-time work after retirement to maintain engagement while enjoying more flexibility.

4. Consider Your Relationships and Responsibilities

Major life transitions often affect more than one person. Whether you have a spouse, children, aging parents, or close friends, your decision may influence family dynamics or caregiving roles.

Think about:

Are you and your partner aligned on retirement timing and lifestyle?
Will retirement give you more flexibility to support family or create new pressures?
Have you talked openly with loved ones about your plans and expectations?

These discussions can help prevent misunderstandings and support a more fulfilling retirement lifestyle.

5. Test the Waters Before Taking the Leap

If you’re unsure about full retirement, there are ways to explore what it might feel like. Some people try out a reduced work schedule, take a long break, or live on a “retirement budget” for a few months as a trial run.

Options to consider:

Could you transition to semi-retirement or consulting?
Would a sabbatical or leave of absence give you clarity?
Are there any bridge jobs that could give you more flexibility without fully stepping away?

Trying new rhythms can help you make a more informed, confident decision.

The Best Path Is the One That Fits You

There’s no one-size-fits-all answer to the retirement decision. Some people are ready to step away from work as soon as possible. Others find satisfaction and purpose in continuing their careers well into traditional retirement years.

The key is to reflect on what matters most to you—financially, emotionally, and practically. Talk with a trusted advisor, run the numbers, and imagine how each scenario might feel in your day-to-day life. The more clarity you have, the more confident you’ll feel, whatever you decide.

Dale Hubbert, AWMA® – Investor’s Resource