First, the Wisdom of Socrates—”Question Everything”

Socrates taught his students to “Question everything,” including their motives and beliefs. In other words, reflect, debate, and think critically about all areas of life.

How does this wisdom relate to retirement? Many perceive retirement as an ideal phase of life. We assume that if we’ve saved enough money and have endless free time, life should just fall into place and be equally, if not more satisfying. It’s the standard American retirement dream. If we don’t question whether that dream is right for us, we could end up feeling unfulfilled and out of touch.

How to apply this wisdom: Don’t walk blindly into retirement assuming the typical life-of-leisure retirement is perfect for you. Instead, ask yourself if that vision of retirement suits you. If it sounds good to you, that’s fine. It works great for many retirees. If not, do some brainstorming with a friend about other possibilities. Could volunteering, a class, or some form of work enhance your retirement?

For example, one of my clients grew up a free spirit in the ‘60s, participating in protests and trying to make the world a better place. During her working years, because of jobs and routines, her former sense of adventure took a back seat. Even in retirement, she felt bored living a “Groundhog Day” type of life, just repeating the same dull routine day-in and day-out. Using Plato’s approach, we questioned her retirement lifestyle and brainstormed what she could do to make retirement more interesting.

She knew she needed to break up the monotony of her days so she started small, by taking horticulture classes and volunteering at a nearby theater so she could see great plays and concerts for free, all while meeting new people. But it wasn’t until she decided to invest in a mini-travel trailer and invite family and friends to join her in exploring new places, people, and things that she hit her stride.

Second, The Wisdom of Plato—”The Beginning Is the Important Part of the Work”

Plato was ahead of his time when he said, “The beginning is the important part of the work.” He meant that before embarking on an initiative, we should have a plan.

How does this wisdom relate to retirement? Without a plan, the beginning phase of retirement can be one of the most dangerous and detrimental to new retirees. While many new retirees want to relax in their first few months of retirement, that can cause them to distance themselves from meaningful benefits that work-life provided, such as a productive routine, social connections, and a sense of accomplishment.

As a result, they slip out of routine and may find that recreating the benefits that work provided is harder than anticipated. Had they originally entered retirement with a plan to make the most of their new life, this struggle may have been avoided.

How to apply this wisdom: If you’re nearing retirement, think about three key areas. Purpose: Brainstorm ideas for your retirement purpose. If you’re stuck, ask for help from a friend. Consider options such as part-time work, volunteering, hobbies, classes, etc. Routine: Try writing out a typical retirement day hour-by-hour. This can help you realize that there’s lots of time to fill in retirement and plan how to fill it.

Relationships: Evaluate the depth and breadth of your friendships. If needed, rekindle some friendships or get involved in activities that can provide opportunities to make new friends. The three tips above can also help if you’re already retired and feel like you need a retirement reboot.

Third, The Wisdom Of Confucius—”We Have Two Lives, and the Second Begins When We Realize We Only Have One”

With this statement, Confucius is suggesting that we discover and spend time doing what’s important to us in life and not to live our lives the way others think we should.

How this wisdom relates to retirement: It’s common for us to take things for granted until they’re lost. Whether that’s interactions with co-workers, prestige at work, family time, travel, physical health, or something else, figuring out and focusing your daily life on what matters most is what leads to a meaningful life. I emphasize that the only guarantee that comes with retirement is that at some point you’ll die. I realize that sounds like the perfect conversation to avoid, but it helps people develop and live what I refer to as a “No Regrets Retirement Plan.”

How to apply this wisdom: To live the “No Regrets Retirement Plan” (aka your second life), contemplate the question, “What gives my life meaning?” Take some time to dream a little. Reflect and contemplate about what you’ve always wanted to do. When you’ve answered that question, start dedicating more time to it in retirement.