5 Questions You Need To Answer Before You Retire

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[148] – Are you ready to retire? Make sure you’ve answered these questions.

In this episode, Jeremy Keil discusses 5 important questions you need to think about and answer before you retire. He emphasizes the need to think about personal desires and goals when deciding when to retire rather than external factors like pensions or social security. He also goes over the 4 stages of retirement from Dr. Riley Moynes’ TEDx talk and the importance of finding purpose and passion in retirement and touches on topics such as health insurance options, life expectancy, and tax management in retirement.

Jeremy discusses:

  • Determining when you want to retire
  • Planning for what you will do in retirement
  • How to get health insurance in retirement
  • Planning for your longevity
  • How to lower your taxes in retirement
  • And more

5 Questions You Need To Answer Before You Retire

When Do I Want To Retire?

Have you ever wondered when the perfect time to retire is? 

We dedicated a full episode to this question, When Should I Retire? With Steve Lopez. The first thing you should ask yourself is: when do you actually want to retire?

It’s not just about crunching numbers and finances; it’s about envisioning the life you want to lead once you bid farewell to the working world. Picture your dream retirement filled with hobbies, adventures, and cherished moments.

Of course, external factors like changes in your company contract or healthcare options may come into play. But remember, the decision to retire should be driven by your personal desires and financial readiness.

It’s all about retiring on your terms. You really ought to retire when you want to and can afford to, but take your pension and Social Security when it actually gives you the most money. That’s the best way to go.

So think of when you want to retire as the first question you should ask yourself when you plan for your retirement.

What Will I Do In Retirement?

As you approach retirement, the second question that comes to mind is “What will I do in retirement?”

Many people want to retire simply to escape the daily grind. When asked when they want to retire, the common response is “yesterday.” But adapting to a lack of structure and having free time is a struggle we see often, so let’s take a step back and really think about what life will look like in retirement.

Dr. Riley Moynes’ TEDx talk outlines the 4 stages of retirement. Being aware of them might help you look through and plan for what you will do in retirement.

Stage 1 is the vacation phase. This is what most 55-year-olds think about retirement. It’s where you wake up when you want, do what you want, and don’t really have a routine. It’s perfect, you love it, you’re on vacation. But it only lasts anywhere from 6 months to 1 year.

Stage 2 is when you feel lost. It’s when you realize you’ve lost your routine. Unfortunately, this second phase is where you experience a lot of depression, fear, and anxiety because everything that you thought retirement would be, maybe it’s no longer that.

Hopefully, you can get through stage 2 as quickly as possible and move into stage 3 which is known as the trial and error phase. It’s when you’re just trying to figure out what to do next. This might be an encouragement to go ahead and take those dream vacations in the first stage and maybe have that plan ahead of time for what you’ll do in retirement and what you want to try out, like volunteering or trying a new sport.

Lastly, we have stage 4 and that’s the happiest part of retirement. It’s the reinvent and repurpose phase. In this stage, people have found their purpose outside of work, and that almost always involves helping others in some way. Maybe you’ll be more involved with the church, your school, or your family, but what matters is it’s your choice and your passion.

Thinking through this ahead of time can help you quickly get to stage 4 in retirement, and experience the happy and settled phase of your retired life.

How Will I Get Health Insurance In Retirement?

Planning for health insurance in retirement is a crucial consideration that often gets overlooked. Many individuals continue working solely for the sake of maintaining their employer-sponsored health coverage. However, there are alternative options worth exploring. The primary options are the Affordable Care Act (ACA) for those below 65 and Medicare for those who reach 65. It’s remarkable how often people are unaware of these choices and instead work until 65 solely to gain access to Medicare.

Understanding the available options is key. COBRA, for instance, allows employees of companies with over 20 employees to continue their current health insurance for up to 18 months. This means you could potentially retire at 63 and a half, opting for COBRA and maintaining the same insurance coverage you had while working, albeit at the full cost without your employer’s subsidy.

The Affordable Care Act is another viable option. It functions similarly to Medicare in that both are subsidized health insurance provided by the government. By planning your income strategically, you can qualify for government-subsidized health insurance through the ACA, effectively replacing the employer subsidy you were accustomed to.

The bottom line is, don’t assume that working until 65 is the only way to secure health insurance. Take the time to explore your options and consider how you can adjust your income to ensure you pay less than anticipated. Health insurance is a significant concern for many, but with a little research and exploration, you may find more flexibility and affordability than you originally thought. So, ask yourself, “How will I get health insurance in retirement?” and be proactive in finding the best solution for your unique situation.

How Long Am I Going To Live?

Determining how long you will live is a vital question to address when planning for retirement, but often gets overlooked.

Many people base their assumptions on life expectancy solely on general figures they’ve come across, like the average age mentioned in the newspaper or the age at which their relatives passed away. However, these numbers can be misleading and fail to consider the advancements in medical care and healthier lifestyles.

That’s why it’s crucial to seek a more accurate assessment of your life expectancy. Longevityillustrator.org is an excellent resource where you can gain a clearer understanding of your personal life expectancy based on various factors and statistical data. Understanding your life expectancy is important because if you happen to pass away earlier than expected, it may affect loved ones who rely on your income. On the other hand, living longer means ensuring your investments can sustain your lifestyle for an extended period.

Calculating joint life expectancy is especially important for couples because one spouse almost always is expected to outlive the other. This means planning for a longer retirement for both partners. This requires taking into account the potential of extended widowhood and making informed decisions about income and financial provisions during that period.

By understanding your life expectancy, you can make more informed decisions about your retirement plans.

How Do I Lower My Taxes In Retirement?

When it comes to taxes in retirement, you have more control than ever before. Unlike during your working years, you can make strategic decisions about when to take your pension, when to claim Social Security, and which accounts to withdraw from.

By planning ahead and considering factors like different tax rates and filing statuses, such as married filing jointly, you can identify opportunities to lower your taxes in retirement.

Taking proactive steps, such as Roth conversions, can also help optimize your tax situation and reduce your lifetime tax bill.

So, seize the opportunity to have greater control over your taxes and plan strategically for a tax-efficient retirement.


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