Are You Emotionally Ready to Retire? 4 Questions to Consider
January 26th, 2026 | 2 min. read
Retirement is one of the biggest milestones you will have in life. We talk at lengths about preparing yourself financially for retirement, but what’s equally as important, and often overlooked, is the psychological preparation.
In fact, a recent survey of financial planners found only about 11% say their retiree clients were fully prepared for the mental ramifications that come along with retirement. While 51% feel fully prepared financially.
That means many pre-retirees are failing to think about what their life will look like when they don’t have a 9-5.
Don’t let yourself get so caught up in the finances that you forget about your life plans. In this blog, we are sharing four retirement planning questions to ask yourself that have nothing to do with money!
1) Is Your Work Meaningful?
If it is emotionally and psychologically fulfilling, and it gives you a strong sense of purpose and identity, then there may be a voice inside your head telling you not to retire yet.
If this is the case, consider ways that you can get similar fulfillment outside of work. For example, if you are someone in the health care field, this could be volunteering for community health initiatives such as a blood donation drive. Or if you are a teacher, volunteer tutoring at a local library is a great option.
Having an outlet that brings you purpose can help ensure you maintain your sense of self into retirement.
2) Do You Value Work or Leisure More at This Point in Your Life?
An old saying says that retirement feels like “six Saturdays and a Sunday.” Fantastic, right? It is, as long you don’t miss Monday through Friday.
On Sunday evening, are you feeling energized for another work week? Or do you feel dread or indifference?
Of course, who doesn’t want to play hooky every now and again? But if you find yourself longing for more moments of leisure beyond the weekend, it is a good indicator that you are ready for retirement.
3) What Does Your Social Circle Look Like?
Take stock of your social life – does it involve a lot of people you work with? How many of your friends are already retired? Is your spouse or significant other retired?
If you are at a phase of your life where many of your inner circle are already retired or nearing retirement, this may make the transition to retirement easier for you.
Alternatively, if most of your friends are still in the workforce, think about ways you could make new connections with other retirees. Community centers, libraries, or places of worship are great places to start.
As you age, social isolation can lead to serious health risks such as depression, cognitive decline, and even an increased risk of heart disease. Having meaningful, supportive relationships promotes overall health and longevity.
4) What Will Your Day-to-Day Look Like?
We often hear that one major reason people feel uneasy during their first years of retirement is the lack of daily routine.
Mapping out a daily or weekly schedule can give you a clearer picture of what your new reality would look like. Consider things like your weekly errands, exercise, socializing, and self-care time.
If you want to take it a step further, try taking a week or two off work and ‘trialing’ your retirement schedule. By giving yourself a small taste of what real retirement will look like, you can determine if you are emotionally prepared for that next step.
Preparing For the Next Phase
Ideally, you retire when you are financially, emotionally, and psychologically ready. Why you are retiring is just as important as when you choose to retire. When you are motivated to retire, you see retirement as a beginning rather than an end.
Creating a financial strategy for retirement is important, but it’s only one piece of the picture. A fulfilling retirement also depends on your physical and mental health, your relationships with family and friends, your opportunities for travel and adventure, and the ways you express your creativity. For more considerations on if you are ready for retirement, click here to get a copy of our Countdown to Retirement 5 Year Financial Checklist.
Advance Capital Management is a fee-only RIA serving clients across the country. The Advance Capital Team includes financial advisers, investment managers, client service professionals and more -- all dedicated to helping people pursue their financial goals.