Retirement Readiness Checklist: 5 Steps to Prepare for the Next Chapter

Jordan Flowers headshot
Jordan Flowers
·
August 27, 2026

As retirement approaches, one question tends to dominate the conversation:

Have I saved enough?

It is an important question, but retirement readiness involves much more than reaching a certain account balance. A strong retirement plan should connect your money to your life:

What do you want your days to look like?
What experiences matter to you?
How much income will that lifestyle require?
How will healthcare fit into the picture?
And when should Social Security begin?

Here are five areas to consider as you prepare for retirement.

1 – Define What Retirement Looks Like for You

Before building a retirement budget, build a retirement vision. Think less about spreadsheets for a moment and more about your bucket list:

Do you want to travel internationally?
Spend more time with grandchildren?
Golf several days per week?
Volunteer?
Buy a second home?
Start a small business?
Consult part-time?

The clearer your goals become, the easier it is to determine what financial resources will be needed to support them.

Retirement planning should not begin with, “Here is how much money I have.”
It can begin with, “Here is what I want my life to look like.”

2 – Take Stock of More Than Your Financial Assets

Your investment accounts matter, but they are not the only assets you bring into retirement.

Consider your experience, skills, professional network, hobbies, passions, and interests. Some retirees discover that they enjoy consulting, teaching, mentoring, working seasonally, or turning a hobby into modest income. The goal does not have to be maximizing earnings. Part-time work can also provide purpose, structure, social interaction, and a smoother transition from decades of full-time employment.

For some people, retirement means never working again. For others, it means finally having the freedom to work on their own terms.

3 – Evaluate Your Health

Financial health and physical health are closely connected in retirement.

Healthcare can become a significant expense, but the larger issue is that your health may determine how you are able to enjoy the retirement you planned. This is one of the reasons it is important to think about retirement in phases. Your early retirement years may offer more freedom for travel, activities, and experiences than later years.

The goal is not to predict exactly what your health will look like decades from now. It is to make health and healthcare part of the plan instead of treating them as an afterthought.

4 – Build a Realistic Retirement Budget

Once you know the lifestyle you want, the numbers become much more meaningful.

Start by estimating what it will cost to maintain your normal lifestyle and fund the things you want to do. Then, compare those expenses with expected sources of income, which might include:

  • Social Security
  • Pensions
  • Investment withdrawals
  • Retirement accounts
  • Annuity income
  • Rental or business income
  • Part-time work

If there is a gap between dependable income and expected spending, that does not automatically mean retirement is out of reach, it means your retirement income plan needs to address that gap.

The goal is to create an income strategy that allows your lifestyle to continue even when markets inevitably experience periods of volatility.

5 – Decide When to Claim Social Security

There is no universal “best age” to claim Social Security. Retirement benefits can generally begin at age 62, although starting before full retirement age results in a lower monthly benefit. Delaying beyond full retirement age can increase the monthly benefit until age 70 (Social Security Administration).

But maximizing your monthly check is not necessarily the same as choosing the strategy that best fits your financial plan. The decision may involve your:

  • Current income needs
  • Health and longevity expectations
  • Spouse’s benefits
  • Survivor planning
  • Tax strategy
  • Investment withdrawals
  • Overall retirement assets

The right answer is highly individual.

Retirement Is More Than a Number

It is easy to compare your retirement balance with someone else’s and wonder whether you are ahead or behind. But two households with the same amount saved can have completely different retirement outcomes because their spending needs, income sources, goals, taxes, health, and lifestyles are different. That is why retirement readiness should not be measured by one account balance.

The goal is to know what you want your retirement to look like and whether your resources can support it. That can provide something more valuable than simply reaching an arbitrary savings target: clarity and confidence about the next chapter.

▶️ To hear more on this topic, watch the full video here.

Erin: Jordan, so good to see you.

Erin: Today we have your retirement readiness checklist: five steps to prepare for the next chapter.

Erin: Start planning now for the lifestyle you want and what you will need financially to get there, which is why step number one is define your retirement.

Erin: We are not talking about a budget. We’re talking about a bucket list. Why is this step number one?

Jordan: Yeah, take money off the table completely. What do you want to do in your retirement, in your life? Is it a trip to Italy, Croatia, wherever that may be?

Jordan: You define that before we talk about the money. And then our goal is hopefully to create a plan so that you can accomplish that and have confidence that you can do these things.

Jordan: And we want to make sure that you dream big, right? Our first meeting when we meet with people is called our possibility meeting because we want to show you what’s possible.

Jordan: We want to talk through: What are your goals? What are your dreams? What are your aspirations?

Jordan: A lot of people talk to us and say, “Hello, here’s my 401(k), here’s my numbers.” And we’re like, “Whoa, whoa, whoa, whoa. Let’s not even go there yet.”

Jordan: What do you want out of life? What’s a perfect day for you?

Jordan: And when we find out what your aspirations and dreams are, then we can work on the plan and get you there.

Erin: Yeah, well said.

Erin: Number two: take stock of your assets beyond just your bank account and retirement accounts. You suggest writing down your passions and unique assets and then maybe thinking about how they could generate part-time earnings in retirement.

Jordan: Yeah, you want to look at your overall assets and see what brings you the most joy. What do you do that brings the most joy?

Jordan: We have clients that have retired multiple times and then go back to work. Not because they have to, because they want to. They love being busy. They love the field they’re in.

Jordan: So maybe you have a hobby that you love doing and you want to say, “You know what? I want to continue to do that.”

Jordan: We had a client that loved consulting, and they retired. They were fine. They just loved talking to people. They loved being around people.

Jordan: And they started consulting, and then a few months later they were making more money than when they were working just by consulting. But they did it on their terms and their schedule, and they love what they do.

Jordan: But you want to try to identify those things now because I also think, from a mental shift, to go work for decades and then all of a sudden not work—I think, as human beings, we’re meant to be productive and contribute to society.

Jordan: Maybe you want to ease off that and do a nice runway where you find that and you start to do that to bridge that gap from going to work into just being retired.

Erin: Right. It’s a tough transition.

Erin: Also, it keeps you engaged, right? Which brings us to step number three here, which is evaluate your health, because it often keeps you healthy as well.

Erin: Healthcare is often one of your biggest expenses in retirement, so work now to get or stay healthy.

Jordan: Yeah. Your health is way over your wealth.

Jordan: Some people focus all about the investments, but they’re stressed out, they’re miserable. We want to take that financial weight off their shoulders so they can hopefully be healthier.

Jordan: Because healthcare costs are rising at a rapid rate. And if you don’t take care of your health now, you may not pay for it today, but you will pay for it in the future.

Jordan: And we kind of have a little bit of a mindset—we really want you to live today and plan for tomorrow, but we really want you to focus on now.

Jordan: Why? Because you go from your go-go years to your slow-go years to your no-go years.

Jordan: And when you have time, health, and wealth, if you look at the grand scheme of life, that’s a short period of time. We want to make sure that you enjoy your life.

Jordan: And just this week, we had a client that passed away, and it just put some perspective. She retired in December. In April, she had cancer. She fought it, then she had a little remission, and she passed away.

Jordan: So yes, we want to enjoy our life and retire, but also live today.

Erin: Yeah, such a delicate balance.

Erin: Step number four: it is getting into the numbers part of it—creating that retirement budget. What does that mean exactly?

Jordan: Very simply put, it’s what you need to sustain your life and enjoy your lifestyle, and what income do you have coming in?

Jordan: So if we look at the difference there, maybe there’s a gap of five or ten thousand dollars, whatever that is. That’s not a problem.

Jordan: We want to provide a solution and create a retirement plan that kicks out that income on a monthly basis so you can continue to enjoy your life.

Jordan: And if the market takes a dip, and if we have a good plan, that’s not going to derail your retirement. You’re still going to have income, you’re still going to enjoy life, and you’re not going to worry about the market fluctuations.

Erin: And as you talk through figuring out those income sources, Social Security—the most consistent form of retirement income, right?

Erin: And this step is often overlooked, Jordan, how important this is.

Jordan: Yeah, a lot of people say, “I want to take it before they go bankrupt,” or “I’m going to wait until 70.” But Social Security is a lot more complex than that.

Jordan: And I’m going to tell you the answer when you should take it. It’s two words: it depends.

Jordan: If your family history is at 65, everyone passes away, take it at 62. If you wait until 70, you might get the biggest paycheck, but you’re maybe not going to get the biggest pile of money if you pass away at 75.

Jordan: So yes, we look at the mathematics, then we overlay it with your family health and your current health, and then we overlay it with a tax plan.

Jordan: And using the numbers, using your health, using the taxes, that gives us an educated decision on when the best time is to take Social Security.

Jordan: As you see in our roadmap, we don’t just focus on investments.

Jordan: We coordinate that with taxes, income planning, healthcare planning, legacy planning, to make sure you have that confidence and clarity that whatever decision you make is in your best interest.

Jordan: So a lot goes into it, but we want to maximize and get the biggest pile from Social Security.

Erin: You know, Jordan, talking to you, it’s clear that retirement is so much more than just one number in the bank.

Erin: There are so many separate components and also the emotional one. I really value the fact that you’re always thinking about that. So important.

Erin: If somebody feels like they are getting close to retirement and wants to talk through all of those separate pieces of the puzzle with you, what’s the best way to reach you?

Jordan: Before I say that, I just want to give people some peace of mind.

Jordan: A lot of people say, “Do I have enough money?” They feel like they’re behind, like they only have half a million or a million dollars in their retirement nest egg.

Jordan: The truth is, it’s not the dollar sign in your retirement accounts. It’s the expenses, your life.

Jordan: We have people that have a million dollars and they can live a great life. Or $500,000, and they can live a great life because they don’t need a lot to enjoy life.

Jordan: So don’t feel bad if you haven’t saved a lot. It’s really about creating that plan and giving you confidence that you can live the lifestyle that you want to live.

Jordan: And give us a call. It’s 847-499-3454.

Jordan: We’d love to get to know you, understand your goals, where you want to go in life, and hopefully we can be a conduit to get you there.

Erin: Jordan, thank you so much.

Erin: And for everybody watching who would like to chat with Jordan about their own unique retirement puzzle, there is a QR code at the very end.

Erin: So again, Jordan, thank you very much for your time today.

Jordan: Thanks, Erin.

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