7 Questions That Could Make Or Break Your Retirement

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#96 – It’s never too early to plan for your retirement. But where do you start?

Knowing where to start can be difficult, and even those who have a headstart in the process might have missed some of the necessary questions to help accurately plan for their retirement.

In this episode, Jeremy Keil outlines seven questions you should ask while planning for your retirement. He explains how you can find the answers and get a more realistic picture of your retirement.

Jeremy discusses:

  • How to plan for longevity in retirement
  • How to enjoy life now but still live comfortably in retirement
  • What to consider when a spouse passes away during retirement
  • How to leverage tax deductions and take advantage of the extra benefits
  • And more

7 Questions That Could Make Or Break Your Retirement

1) What Will My Retirement Take-home Pay Be?

The first question people should ask when planning for their retirement is “What will my retirement take-home pay be?”

There are so many different pieces of advice out there about how to plan for what you need in retirement. Is it 75% to 80% of your income? Or is it a fixed amount of money — say, a million dollars? Well, none of it is accurate.

It depends on how much you spend. Knowing how much you currently spend is accurate. The easiest way to find that number is to look at your paycheck take-home pay.

What you currently spend is what you’ll likely need in retirement too. This goes beyond your day-to-day expenses. You also need to include your  taxes and health insurance costs that are taken out of your take-home pay. . It’ll give you a better estimate of how much money you’ll need to have in retirement to maintain your standard of living.

2) How Long Will I Live in Retirement?

When you ask how long you will live in retirement, you should also be asking yourself when your retirement starts.

People often retire earlier than they expect.

So, if you’re planning on a certain timeframe for your retirement, we encourage you to take away three years. Regardless of when you plan to retire, set yourself up with a plan that would be ready a few years sooner so you’re ready just in case you get the opportunity to retire sooner.

Another consideration for how long you’ll live in retirement is your life expectancy. Most people just estimate based on their personal family experience. Studies show that many people underestimate and end up not planning for enough money to last through their retirement. 

Or, their financial advisor says, ‘just plan to live to 100’ which only occurs roughly 5% of the time and then they missed out on spending money when it was more fun, when they were younger.

A great resource for estimating your life expectancy is longevityillustrator.org. You can enter your birthday, health status, and other key information to know the probabilities of living to certain ages.

3) How Do I Enjoy Life Now, but Still Live Comfortably Later?

You must have heard people say, “I’m getting old. I better live while I’m young and have fun while I can!”

Then you have others who say, “I’m completely worried about running out of money in retirement. I better save as much as I can now.”

Our encouragement is to live like you’re dying, but also spend like you are not.

It’s a delicate balance, but that’s a balance you need to focus on and figure out when you’re planning for your retirement.

4) How Much Income Will My Spouse Lose When I Die?

We know it’s a downer question, but it’s reality. Oftentimes, there will be two of you when you start your retirement, but one of you might pass away along the way.

We encourage you to use longevityillustrator.org to take a look at the probabilities. See what the odds are that each of you will make it to certain ages.

That will give you not only your own life expectancy, but also your joint life expectancy as a couple.

With your joint life expectancy, you’ll be able to better plan for what to do for your retirement funds if either one of you passes away first.

5) How Can We Leverage Social Security To Lower Our Lifetime Taxes?

What does Social Security have to do with taxes?

Social Security has a different tax situation than your pension and than your traditional IRAs.

When you take out money from Social Security, 85% of it is taxable at the most. That means part of your Social Security will be exempt from the federal income tax (and entirely exempt from state income tax in some states like Wisconsin).

You need to look into Social Security withdrawals and determine if they lead to a better tax situation than other forms of retirement income like your pension and traditional IRAs.

6) How Do I Arrange My Taxes To Get More Deductions?

Itemized deductions were a popular way to save money on taxes back in 2017. Today, unless you’re giving away $20,000+, chances are pretty good that you might no longer be doing itemized deductions.

You’re probably using the standard tax deductions now. One way to take advantage of standard deductions is called bunching.

You can arrange your taxes that would normally be spread out throughout two years to be deducted within the same year by timing your payments and bunching them together.

For example, if you regularly donate $5000 annually to your church, donate $10.000 one year and skip the next to alternately increase your tax deductions each year.

Now, if you don’t like the idea of donating one year and skipping the next, then you can separate when you get the deductions from when the charity receives the money by using donor-advised funds.

Once you contribute money to a donor-advised fund, you get that tax deduction right away. You can then donate to the church from the donor-advised funds whenever you please.

7) How Can I Use Roth Conversions To Lower My Lifetime Tax Bill?

Remember, the goal is to reduce your lifetime taxes, not just taxes during the current year. (Because your lifetime tax bill could even reach a million dollars or more!)

Pay attention to the opportunities to pay taxes at a lower rate.  Roth conversations are a great tool to control your taxes in retirement.

If you pay less in taxes at the beginning, you can grow that money you saved in your investments and come out ahead in overall lifetime taxes.


If you want to learn more about retirement planning, check out the resources below!

If you have any questions, feel free to contact us and we’ll be happy to help you achieve your ideal retirement!


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