Upticks: Ready or Not It’s Time to Retire

By Luke Sullivan on April 3, 2025

You endlessly think your way out of retirement. You don’t want to regret your decision. You don’t want to run out of money. Sound about right? Retiring is a big life decision, but it doesn’t need to be a stressful one. Jake discusses a recent conversation he had with a client considering retirement and practical ideas to help you approach retirement from a fresh perspective.

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Read an overview of the conversation below:

Fear of the Unknown

Cory emphasizes that fear of the unknown is a major factor that holds people back from retiring. This fear is often rooted in the uncertainty of what life will be like without the structure and identity provided by work. Regardless of how solid one’s financial plan is, the fear of the unknown can be overwhelming. Cory explains that this fear is a natural response to major life transitions, and it can be mitigated by understanding and addressing the underlying concerns. He suggests that retirees should take the time to reflect on their fears and seek professional help if needed to navigate this emotional aspect of retirement.

Purpose and Identity

Jake and Cory discuss the importance of finding purpose in retirement. Many retirees struggle with the loss of identity that comes with leaving their careers. It’s crucial to explore what gives you a sense of purpose and fulfillment. Jake introduces the concept of trading time, which is about deciding how you want to spend your time in retirement. This involves weighing the benefits of continuing to work against the desire to pursue other interests. Jake shares a conversation he had with a client who is financially independent but unsure about retiring because he doesn’t know what he wants to do. The client likes his job but hates his boss, making it difficult for him to walk away from a good paycheck doing something he enjoys. Jake advises the client to decide what he wants to trade his time doing and to consider the emotional aspects of retirement.

Practical Advice for Navigating Retirement

• Test the Waters: Jake suggests taking a month off to simulate retirement. This can help you understand what life without work feels like and whether you’re ready for it. He explains that this exercise can provide valuable insights into how you might feel and what activities you might enjoy in retirement. It’s a way to test the waters without making a permanent decision.
• Check in with Your Values: Understanding your values is essential for making informed retirement decisions. Consider what you want to trade your time for and help ensure your financial plan aligns with these values. Cory emphasizes that retirees should reflect on their values and priorities to help ensure that their retirement plans align with what truly matters to them.
• Seek Professional Help: Working with a retirement coach can provide valuable support in addressing emotional concerns and making informed decisions. Jake and Cory recommend seeking professional help to navigate the emotional aspects of retirement. They explain that a retirement coach can help retirees explore their fears, identify their purpose, and develop a plan that aligns with their values.

Encore Careers

Many retirees find fulfillment in pursuing encore careers. These are second careers that align with their interests and values. Jake shares examples of clients who have successfully transitioned to new roles and found greater satisfaction. Achieving financial independence allows retirees to choose how they want to spend their time, whether it’s continuing to work in a different capacity or pursuing hobbies and interests. Jake explains that encore careers can provide a sense of purpose and fulfillment, and they can be an excellent way for retirees to stay engaged and contribute to society.

Common Challenges and Solutions

• Analysis Paralysis: Cory warns against analysis paralysis, where retirees feel they need to have every detail perfectly planned before making a decision. It’s important to recognize that some uncertainty is normal and to focus on what you can control. He explains that retirees should avoid getting stuck in the planning phase and should take action based on their values and priorities.
• Regret and Reversal: Jake discusses the possibility of regretting retirement and the challenges of reversing the decision. He advises leaning towards continuing to work if there’s doubt and seeking professional help to address underlying fears. Jake explains that retirees should be prepared for the possibility of regret and should have a plan in place to address it if it arises.

Retirement is not the finish line; it’s a transition into a new phase of life. By understanding your values, exploring your purpose, and seeking professional help, you can make more informed decisions for a more fulfilling retirement.

Thank you for tuning in, we hope you have a great week!