Source: Kiplinger

This article was originally published on Kiplinger –


A happily ever after retirement requires a real plan. Here are some of the (tough) questions your retirement planner should be asking you in order to make that plan.

If you’re having minor chest pains for the first time, you’d probably go to your doctor. But if the issue persists, then you would probably seek a cardiologist. This isn’t because you don’t like your doctor, but if you have a unique problem like this you would seek a specialist as opposed to a general practitioner.

SEE ALSO: You Don’t Need a Financial Planner … Unless

Retirement planning is no different. It involves a different way of thinking than planning for financial growth alone. It should speak to your individual goals and the retirement lifestyle you envision. It’s not a one-size-fits-all formula. It requires specialization.

Through most of your life, you probably wanted to grow your money as fast as possible. And that’s fine, even when that involves some risk. But when retirement savings replace your paycheck, you can’t afford to take on much risk. Let’s face it, you’re never given the option of paying 20% less on your mortgage or your power bill because the market is down. You need a steady source of income that fits those obligations and needs.

That’s why it’s best to have a personalized plan, and a diversified portfolio is not a retirement plan.



As a retirement planner, I recognize the things that are going well for the families I sit down with, but also point out areas that stick out to me as obstacles. These are the things that could prevent you from having the retirement you have always dreamed of. Generally, those obstacles come in two forms:

  • Risks: This could include financial strategies that may not be appropriate for your stage in life.
  • Missed Opportunities: This could include areas where you were ill-informed or failed to take advantage of things that might have boosted your financial fortunes.

But these major areas are just starting points. We really can’t get anywhere until you paint a vivid picture of your ideal retirement. That’s the destination, and it will allow us to create the perfect road map.

Once we get your specific picture in place, we can begin to design your plan. Your comfort level with the tools we use to design your plan and the way you want it to look are important factors. Your plan shouldn’t be jammed into a cookie-cutter mold. This is specific to YOU. The plans retirement planners put together aren’t just something we think will work. The plan is complete only when we believe it will work.

See Also: Is $1 Million Enough to Retire?

When digging into the details, what types of questions should a retirement planner be asking?



  • Dreams: Do you want to travel? Do you want to pursue new hobbies? What are the things you’ve always wanted to pursue?
  • Lifestyle: This is critical, and it involves your current spending. What will it cost to maintain your lifestyle? Some people actually know this down to the cent, but most have no idea. Many people I sit down with think they know this because they have a budget they have created in an Excel spreadsheet.

To me, budgeting is similar to dieting and losing weight. If you plan every meal you eat and every exercise you do, you should lose weight and have a healthier lifestyle. But there is a reason most New Year’s resolutions don’t last past February, and that’s people’s inability to stick to them. Budgeting is no different. If you have every cent allocated and know where it’s going that is great, but how well do you consistently stick to it?

Really, it all boils down to your habits in handling money. It’s important to be as detailed as possible because you’re identifying what it will take to maintain your lifestyle once your paycheck stops. People are often shocked when they actually see the numbers in front of them. It can be helpful to think of retirement as 25 to 30 years of unemployment. You want to protect yourself from the same concerns you’d have if you suddenly lost your job.

Remember that you’re not spinning straw into gold. Financial professionals don’t have the magic gift to turn a bad situation into something exceptionally positive. We can offer analysis and resources. But it always helps when people understand a few helpful concepts.

  • Income Plan: You must have a strategy in place for how you will replace your paycheck once you stop working. If you don’t know exactly when and where you will pull from your savings, you do not have an income plan in place.
  • Avoid Debt: When people are approaching retirement — let’s say the late 40s to early 50s demographic — they really need to be eliminating their debt. You don’t want to take debt into your 60s. If you have a mortgage, that’s one thing. But you should avoid taking other types of debt into retirement if at all possible.

Obviously, it’s always easier if you don’t owe money. If you have substantial credit card debt with no real plan on how to pay it down, you’re very likely to have financial problems in retirement. It’s that simple.



It all circles back to the lifestyle question. This issue is becoming more pronounced. It’s the classic “Keeping up with the Joneses” phenomenon. You see friends buying nice homes and cars. There’s a social need to match that. We have evolved into a society that greatly values possessions. It’s important for people to show they are successful because they have nice things, but using debt to keep up appearances could lead to a disaster in retirement.

So examine your financial outlook. Ask yourself some hard questions. If you are already working with someone and they aren’t asking these types of questions or if you don’t know the answers to these questions, then you should consider seeking a second opinion. If you are approaching retirement and don’t have a plan in place that you know will work, go see a retirement planner who can devise a specialized approach.

See Also: 5 Bold Questions to Ask Yourself to Shape Your Retirement

Joey Johnston contributed to this article.

Investment advisory services offered only by duly registered individuals through AE Wealth Management, LLC (AEWM). AEWM and Freedom Financial Group are not affiliated companies. Investing involves risk, including the potential loss of principal. AW03182152

Sean Fleming is an Investment Adviser Representative for Freedom Financial Group, based in Birmingham, Alabama. He has passed the Series 65 securities exam, while also holding licenses for life and health insurance. He oversees the development of retirement planning and annual documents for clients with the Freedom Financial Group, a family-owned business that prides itself on personal and individual attention.

Comments are suppressed in compliance with industry guidelines. Click here to learn more and read more articles from the author.

This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.


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