The 2025 Guide to Retiring Without Regret

According to the U.S. Census Bureau, more than 55 million Americans, or roughly one-sixth of the population, were age 65 or older in 2020. If you’re among the millions of Americans inching closer toward retirement this year, you may be wondering if that’s a good idea or not.

If you’ve got the right plans in place, it is possible to retire without regret.

Key Phases of Retirement Transition

Retirement is one of life’s most significant events, right up there with getting married or having a child. “It’s not just about work,” says Heath Harris, founding financial advisor of Compound Advisory. “It’s about building a life you actually want to live.”

The transition to your next life stage moves through four phases, starting with the decision to move on.

The Decision to Stop Working

Phase one is marked by that life-altering moment when you decide, “It’s time.” Is 2025 the time for you? If you’ve not given it proper thought and considered your emotional connection to work, the decision might sneak up on you.

“They [pre-retirees] found themselves cutting back on commitments and involvement in certain work activities as the time to leave approaches,” wrote Terry Mitchell, professor emeritus in management and organization at the University of Washington in a paper.

It may take time for you before you make the leap to quit your job, as many people enjoy working and may find meaning and purpose in their jobs.

“For many, it’s more than a financial decision. It’s letting go of an identity,” Harris says.

Detaching From Work

The detachment period typically begins before you leave the workplace and extends into your first months of retirement. It has been referred to as the honeymoon phase.

When Teresa Amabile, professor emerita at Harvard Business School, conducted a “Retirement Transitions Study” of 120 professionals, she found that the detachment process often began smoothly and then escalated into identity issues. Who and what are you if you’re no longer working?

“Many people will say that they have to figure out who they are in terms of always having been a really productive person,” Amabile said in a 2018 interview. “They are achievement-oriented, and they enjoyed the sense of progress in their work, so they’re searching for something to replace that work identity.”

To handle the adjustment from working full-time to retirement, Harris suggests finding ways to make the transition easier.

“A phased retirement, part-time work, or consulting often helps with the emotional side and also eases financial withdrawals early on,” Harris says.

Experimenting With New Activities and Relationships

When you enter retirement, you’re going to have more time on your hands, but your challenge may be how to fill that time.

Engaging in new activities is often recommended, but it might not be necessary. In Amabile’s study, she found a retiree who rediscovered his passion for motorcycling after 25 years by buying himself a new bike and hitting the road.

However, if you need more income in retirement, you might consider recycling your work skills into a new endeavor that earns you some extra cash. This is particularly relevant in a volatile market, such as we have seen in 2025, but financial security isn’t the only reason to consider this.

“Retirees often miss the recognition and positive feedback work provides, so they will forge closer relationships with friends and relatives or start small businesses as a new source of fulfillment,” Amabile said.

Mitchell reported that many retirees began paving the road toward this effort before leaving the workplace. They began volunteering and joining clubs. They took classes. They got involved in politics.

“We encourage clients to try one new experience a month or quarter, anything from a trip or museum to dinner with friends,” says Harris. “We even send suggestions in our monthly newsletter.”

Establishing a Stable Life Structure

The term “structure” no doubt defined your working years, and this is something you don’t want to leave behind. “Freedom is great, but the happiest retirees build some rhythm into their days. A balance of movement, social time, rest, and purpose goes a long way,” Harris says.

Amabile described a working individual as “a kind of tenant in a really settled life structure, where you know where you’re going to be and what you’re going to be doing Monday through Friday. … You go from that to having to be an architect of a new life structure.”

You might attempt to organize your first days, weeks, and months of retirement much as you did your work schedule. Keep a calendar of to-dos. Commit to activities at regularly scheduled times. Organize your days the way you did when you were in the workforce, but do it with a focus on events and commitments that bring you pleasure and enjoyment.

Four Key Behaviors for a Fulfilling Retirement

You can take steps to help you transition into retirement, but it doesn’t end there. Your mental focus and commitment to those steps can be a critical factor as well. Harvard Business Review’s study cited four key behaviors of satisfied retirees in a 2024 article, referring to them as the 4 As: alignment, awareness, agency, and adaptability.

“One of the most powerful pieces of advice I share with clients is to start small but start now,” says Melissa Murphy Pavone, CFP, CDFA, and founder of Mindful Financial Partners. “Time is our most valuable, nonrenewable resource. Whether you’re five years away from retirement or 20, every thoughtful step you take today is a vote for the future life you want to live.”

Alignment

Alignment refers to your identity in a particular phase of your life. It covers a wide scope that includes your values, motivations, and needs. It’s often recommended that you structure your life around these factors.

“It’s where purpose and planning intersect,” Pavone says. “What does your ideal retirement look like, and are your daily choices pointing you in that direction?”

Harris agrees. “Let your money and time reflect what matters to you,” he says.

Your actions and the steps you take in retirement should line up with your values. Take a moment to pause and consider what’s really important to you.

Awareness

Awareness behavior is precisely what it sounds like. “Understand your numbers, your habits, and what fills your tank,” Harris says.

Harvard Business Review suggests that awareness should help you identify your alignment. It suggests listing six to 10 descriptions of yourself, such as what you are, one or more personality traits, your needs, and your priorities. Review the list and identify which three or four are most important to you. Does your life structure support them?

Pavone stresses the importance of applying this behavior to your finances as well. “Awareness is about mindful living,” she says. “It means understanding your emotional and behavioral relationship with money. It’s also about tracking spending, recognizing what brings you joy, and staying engaged with your financial plan so you’re proactive, not reactive.”

Agency

Agency is a corrective mindset, according to Harvard Business Review. It includes steps you might take to balance the relationship between you and your desired life structure. Awareness helps you identify your alignment. Agency refines and improves on it.

“Many people enter retirement feeling uncertain or even powerless,” Pavone says, “but you still have agency. You get to choose how you spend your time, what you invest in, and what you want your legacy to be.”

Harvard stresses the importance of beginning this behavior in small steps. Don’t overwhelm yourself. Take it a day at a time, but make those choices.

Adaptability

Harvard Business Review acknowledges, “Life happens.” Even the best-laid plans can go awry. Adaptability is about adjustment when and if it becomes necessary.

“Be ready to pivot when life throws you curveballs,” Harris says.

Harvard suggests a way to design your pivot or pivots. Identify two major events that might occur in your future: one that would be a joy, such as the birth of a grandchild, and another that threatens to break your heart, such as the loss of a loved one. They’re events over which you have no control.

Now make two more lists regarding each of these events: What are the hurdles you would have to overcome to deal with these events, and how would you do that?

“Retirement isn’t static—it evolves,” Pavone says. “Markets fluctuate. Health changes. Priorities shift. Your ability to adapt and your plan’s ability to flex with you is what separates those who merely survive retirement from those who truly thrive in it.”

Practical Steps to Plan for a Regret-Free Retirement

Your marital or relationship status is a factor that can contribute significantly to your plan for a regret-free retirement. Terry Mitchell points out that a successful retirement isn’t just a matter of your alignment but that of your spouse or partner as well.

“One of the huge relationship tasks at this time is to figure out how you and a spouse are going to manage you not going to work every day,” Mitchell says. “Your partner will have their own life, working or doing other regular activities or retiring at close to the same time. This will be a serious negotiation that will have a life of its own.”

And don’t overlook the financial issues of retirement. Successfully funding these years is an immense step toward successfully disengaging and moving on and applying those 4 As.

A 2024 survey by AARP revealed that 20% of individuals who were age 50 or older had saved no money for retirement at all. Among those who had, 61% indicated that they feared they hadn’t saved enough.

Saving for retirement is critical if you want to enjoy your golden years. These years don’t have to be a glorious succession of lavish days, but experts indicate that you’ll probably need a minimum of 80% of your annual working earnings to fund your retirement even with eliminating some expenses such as commuting to work.

AARP suggests a few options: postponing your retirement for a handful of years, working part-time in retirement, or taking a good, hard look at your spending habits to find out where you might be able to cut back.

“We keep 12 to 36 months of liquidity ready, use a dynamic income strategy, and stress-test the plan for health or market surprises,” Harris says. “We help clients plan a life that feels good to live. That’s what really leads to peace of mind.”

The Bottom Line

“Retirement isn’t a finish line,” Pavone says. “It’s a rebirth. It’s a chance to step into a new version of yourself with the clarity, freedom, and confidence to live by design, not default. If you’re planning this journey, don’t go it alone. Start now. Start small. Align with the right partners. And always, live mindfully.”

Keep those 4 As in mind and embrace them.