8 Key Questions You Need to Ask When Planning for Retirement

Written by mwealthgroup
Published on February 6, 2024

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Retirement planning isn’t a straightforward process. 

To navigate this phase of life successfully, it's key to ask the right questions.

 But how do you know the right questions to ask when planning for retirement?

In this article, we’ll cover essential questions that can guide you in learning how to have a successful retirement and create a strong retirement plan for you, your family, or your business.

You have to be able to ask the right retirement questions to get the right outcome and results.

The wrong questions to ask when planning for retirement

  • "I plan to retire next year, but I haven't saved anything. How can I make that happen?"
  • "What’s the best investment out there?"
  • "What are the fastest ways to grow my money?"

These questions skip to the endgame when there are important building blocks in between you need to think about.

Instead, reframe your questions and ask about cash flow, passive income, and tax-free options to set you on the path toward your goals. 

1. How much cash flow do I need?

Most people use an arbitrary target amount when planning for retirement. For example, a lot of people have a goal of a million dollars. 

But what happens when you break this down? Let’s say you retire at 65 and live to 95. That’s 30 years of retirement with $33,333 or $2,700/month. Most people can’t live on this amount. 

You need to figure out how much cash flow, money coming in, you need.

By asking this question about cash flow, you can determine the income required to sustain your lifestyle and do the things you want to do in retirement. 

Understanding your monthly expenses and lifestyle costs is crucial for calculating the necessary cash flow rather than focusing solely on a lump sum savings target.

Review your bills, credit card statements, and other expenses. How much do you typically spend on a monthly basis? Quarterly? Yearly basis?

This estimate will give you a much better idea of how much cash flow and reserves you need in retirement.

Financial freedom is when you have enough money coming in that you can cover all of your expenses passively AND guarantee that it will last you.

2. How can I guarantee I don’t run out of money?

Many people worry about running out of money during retirement. It's a real concern, right? 

You've worked hard all your life, and the last thing you want is to struggle financially when you should be enjoying your retirement years.

So, where are you getting the funds?

First, look at creating income sources that won't dry up. Think of it like a waterfall that keeps flowing. We're talking about income streams that you can rely on year after year. It's not just about having a big pot of savings; it's about making sure that cashflow keep coming.

At one point in time, pensions were the norm. You worked for a company, and they took care of your retirement income. But times have changed, and now it's more about 401(k)s, IRAs, and even life insurance policies. 

These can be fantastic tools, but there's a catch – they require a lot more planning and education. You need to understand how to make these accounts work for you so that they can provide a steady flow of income throughout your retirement.

One way to achieve a guaranteed income stream is to use an annuity for some of your retirement income. An annuity is a long-term savings vehicle that can pay you income each year for a period of time or even for the rest of your life. 

3. How do I generate passive income in retirement?

generating passive income

Ever wondered how to keep the cash flowing when you're retired? Let's look at some strategies that can make your retirement years financially rewarding.

There are strategies for generating retirement income, such as personal pension plans, real estate, life insurance, or business investments.

In retirement, the focus shifts from accumulation to reliably generating passive income beyond Social Security and pensions. 

  • Annuities can create lifelong income from your retirement account. 
  • Real estate rentals also provide steady cash flow while appreciating property values.
  • Some life insurance products offer tax-advantaged income streams as well. 
  • Consider part-time work or monetizing unused space as additional options.

Establishing diverse passive income sources ensures retirement isn't dependent on one stream.

4. How can I make my retirement as tax-free as possible?

When determining which questions to ask when planning for retirement, you'll need to think about how taxes impact your accounts.

Most retirement accounts are taxed when you take the money out, similar to how your paycheck works.

Did you know? All the money in your retirement account doesn’t belong to you.

If you have 1 million dollars in a 401K and say, “send me the 1 million dollars” - They will withhold around $200,000. And penalize you if you pull it out before retirement.

You need to be aware of the different tax-free vehicles you can use to make your retirement as tax-free as possible.

Option 1: Roth IRA

Contribute to a Roth IRA or Roth 401k. Since contributions are made with after-tax dollars, qualified withdrawals in retirement are completely tax-free. This allows your investments to grow tax-free for decades.

Option 2: Life insurance

Permanent life insurance policies build cash value that allows for tax-advantaged income streams in retirement. With proper planning, life insurance can serve as both an income generator and an estate planning tool in your retirement strategy.

Option 3: Real Estate Portfolio

In your retirement strategy, including a real estate portfolio can be a smart move. Real estate investments can provide tax benefits and serve as a steady income stream, reducing your overall taxable income.

Choosing the right accounts and strategies now can save you a significant amount and reduce your net taxable income, ensuring you have more money to enjoy your retirement years.

5. How can I protect my retirement from losses?

Your retirement money and cash flow need to be as predictable as possible.

Let's talk about protecting your hard-earned retirement savings from the rollercoaster of market ups and downs.

As you edge closer to retirement years, the last thing you want is for market fluctuations to wash away your money.

So, how do you safeguard your retirement funds? It's all about choosing strategies that can stand strong even when the market takes a dip. Think of it as building a financial fort around your retirement savings.

In short, being strategic with your investments is key to maintaining peace of mind and ensuring that your retirement savings are there for you when you need them. Be sure to review the "pillars of retirement" so you're set up for success.

6. Do I need to set up a trust?

estate and legacy planning

Wondering if setting up a trust should be on your to-do list? Let's break it down. 

A trust is a legal structure that holds assets for the benefit of someone and allows for privacy.

This can be helpful if you’re married, have minor children, are a business owner, or even a single parent.

Trusts give you more control over how and when your assets are distributed and can keep those assets safe from legal battles.

Think about a revocable trust as a prime example. You can use those assets while you're still here, and when you're not, they smoothly pass on to your loved ones, usually skipping the whole probate court hassle.

So, do you need a trust? It's not a one-size-fits-all answer, but it's definitely worth considering. Remember, it's all about making things as easy and stress-free as possible for you and your beneficiaries. Start by speaking with a financial advisor to learn more about setting up a trust and estate planning.

7. How often do I need to update my plan?

Ever wonder, "How often should I change my retirement plan?" 

Generally, life's big events – like a new baby, getting married, getting divorced, a promotion, or a major shift in your finances – are your cue to make sure your plan still fits your life.

Not to mention, your risk tolerance for different investments may change throughout your life as well.

Regular updates ensure that your plan always mirrors your current situation and wishes. It's all about keeping things aligned with where you are in life. So, remember to give your retirement plan regular check-ups.

8. Do I need a retirement financial advisor?

financial advisor - questions to ask when planning for retirement

Figuring out retirement planning can feel like trying to solve a puzzle with a million pieces. 

Do you really need a retirement financial advisor? 

Well, if you're feeling a bit lost in the world of retirement and estate planning, it’s time to call in a professional.

A retirement financial advisor can serve as your personal guide when navigating complex financial decisions. They understand the terminology, strategies, and how to develop a customized plan for your specific retirement goals.

Financial advisors can provide clarity on areas you may find confusing, like investment options, tax optimization, and making sure your savings last. Speaking with one could greatly simplify the process.

A financial planner makes the jargon simpler with specific, customized advice for you and your current retirement planning situation.

Additional retirement questions to ask a financial advisor

  1. What strategies do you recommend for maximizing retirement savings?
  2. How should I adjust my investment portfolio as I approach retirement?
  3. What are the best ways to withdraw from my retirement accounts?
  4. How can I plan for healthcare costs in retirement?
  5. How will inflation impact my retirement savings?
  6. How can I effectively transfer wealth and assets to my heirs?


You can ask yourself or your advisor all the questions you can think of, but what it comes down to is this fact: 

You need personalized advice on retirement planning.

Retirement planning is an art and a science, requiring personalized planning and proactive decision-making. So, take charge, ask questions, and make your retirement years incredible.

Ready to Take the Next Step?

Contact M Wealth Group for personalized guidance and expert advice. 

Whether you’re just starting to plan or looking to refine your current strategy, the team at M Wealth Group is equipped to help you start your retirement journey with confidence - feeling financially prepared and protected. 

Reach out today for a free retirement review!

Book your complimentary financial review!

Ready to change your financial future? Schedule your free consultation with Martin and Chelsea Matthews, owners of M Wealth Group.
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M Wealth Group
M Wealth Group
Together, Martin and Chelsea use their professional expertise and life experiences to provide personalized financial strategies to help clients achieve their goals.
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