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Top Retirement Questions and Concerns

Today we’re going to talk about the top retirement concerns and questions that some of you have asked.

If you want us to explore one of these topics further, or if your biggest concern was not addressed in this episode, let us know! You can go to to send us a question, comment, or concern.

Retirement Planning Frequently Asked Questions

  • How much do I need to retire?
  • Can I retire on Social Security alone?
  • Will I pay taxes in retirement?
  • How much will health care cost in retirement?
  • What’s the best age to retire?
  • What will my retirement look like?
  • Will Medicare cover all my medical expenses?
  • Should I pay off my mortgage before I retire?
  • When should I start taking Social Security?
  • What’s the best order for me to start withdrawing my money?
  • How long will my money last?
  • Should I buy an annuity?
  • What kind of expenses will I have during retirement?
  • Should singles plan for retirement differently than couples?
  • Do I really need to work with a retirement advisor or a financial advisor?
  • Is it better to have cash or keep my money in investments when I retire?
  • Do I need long-term care insurance?

How Much Do I Need To Retire?

That’s a valid question.  Unfortunately, you’re going to get a bad answer.  “It Depends.”  I can’t say a million dollars is what you need to retire because it’s very individual and different for each person.  Hopefully, by the end of this post (or podcast if you listen to it) you’ll gain some clarity about how to answer this retirement concern for yourself.

Can I retire on Social Security alone?

Most Americans rely on Social Security for over 50 percent of their retirement income, but as a rule of thumb, relying on Social Security alone for your retirement is not going to give most people the lifestyle that they want.  The short answer to this is now.  If you only have Social Security you have a legitimate retirement concern.

How much will health care cost in retirement?

With this retirement concern we can’t give you an exact number, we can tell you that the average cost of health care for a couple over the course of retirement is over $265,000. So pretty expensive.

And does that mean you have to have $265,000 sitting in an account? Possibly, but not necessarily – there are other ways we can address that too.  This is where retirement coaching and planning comes into play.

Should I pay off my mortgage before I retire?

Retirement planning is a cash flow game. So depending on the income you have coming in, you might need to pay off the mortgage, or it may be in the budget. For a lot of families, paying off that mortgage can decrease expenses enough to make retirement a lot more comfortable.  At the same time, paying off the mortgage can lock away money that you might not be able to get access to in the case of an emergency.

What kind of expenses will I have during retirement?

This is an important piece of transition planning that we really have to look at and consider. If we don’t have a good idea of what expenses we have in retirement, it’s going to be hard to know how much income we need to produce from the assets you save for retirement.

One way to figure this out is to consider: if I wasn’t working right now, what would need to be coming in to pay the bills we have?

Then you can narrow it down further: What will be dropping off between now and retirement? Are we going to get a couple of cars paid off or are we going to be able to knock out our credit card debt or are we going to pay off that mortgage?

After you’ve done this, you’ll have a good picture of the cash flow situation.

If you want a comprehensive retirement checklist, check this out.

Should I take my pension in a lump sum?

A lot of times, when employees leave an employer, they have options of taking a pension payment, rolling money over into a personal IRA, or taking a lump sum payment.

What works best for you will vary, but the one thing you really need to pay attention to are the tax consequences of infusing a big chunk of taxable money into your tax return.

Is it better to have cash or keep my money in investments when I retire?

I think the right way to approach that is how much money should I have in cash versus how much should I have in my income, and how much should I have for long-term growth? Because having the right ratio for your situation is the key to a successful retirement strategy.

Do I really need to work with a retirement advisor or a financial advisor?

That’s a great question that isn’t a “planted” questions.   It’s a valid retirement concern to figure out if it’s worth it to trust someone with quite possibly your biggest financial decisions.  I’m completely biased, so of course, my answer is yes.   The caveat though is for you to do your homework.   The most common negative responses I get from retirees is that either they can do it themselves or that they can’t trust anyone.

If that’s you I’d suggest using that same energy that you would use on managing your own finances in interviewing retirement planners.  It’s one reason retirement coaching is so popular.  You get the advice of a financial planner without the worry of commission bias.

Download the 12 Steps to a Successful Retirement Checklist at

“Top Retirement Questions and Concerns


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About Beau Henderson

Beau Henderson is a financial advisor, author, coach, radio personality, and CEO of RichLife Advisors. He has helped over 3,000 clients to not just improve their relationship with money, but to live the life of their dreams.

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