By Fritz Gilbert, originally published at The Retirement Manifesto.
In school, we took tests to prove we were ready to proceed to the next level. Retirement matters more than most of those classes, yet the tools we’re given typically focus only on the financial aspects of retirement readiness.
Today, I’m excited to share a newly developed “test” to determine if you’re ready for retirement, with a broad focus on 6 areas of retirement readiness. You can also use it if you’re retired to discover areas that may need some work. The test results come in a full report, along with recommended action items.
Better yet, it’s free!
I learned about this tool when Dennis Hoffman messaged me on LinkedIn about a free Retirement Readiness Assessment he built to plan his own retirement. He asked if I’d take a look. I did, and I was so impressed that I decided to share it with you. It’s worth your time and will help you identify gaps in your retirement planning or improve the retirement you’re already living.
Pass this test, and you’re well on your way to a successful retirement.
Most retirement planning tools cover one dimension of readiness. This free assessment covers the six areas that really matter.Share on X
A Retirement Test You Don’t Want to Fail
The assessment is free, and I get nothing in return. I’m sharing it simply because I think it’s a powerful new tool to help you on your journey to retirement. It’s also relevant if you’ve already retired, since it helps spot gaps in your retired life, too. Technically, Dennis calls it an “assessment” vs. my use of the word “test” in the intro. Details, details. What matters is that it’s a great tool, and I wanted to make you aware of it. Call it what you will.
A powerful feature of this tool is how Dennis uses AI to automatically dig into areas where it suspects you’re falling short. Your answers automatically generate a comprehensive report, with suggestions to improve your areas of opportunity.
Here’s an example of the summary you’ll receive when you’ve finished:
The summary is nice, but the real value is the content that comes behind the scorecard. Each section of the final assessment includes a comprehensive review of your strengths and opportunities, with recommended action steps to help you improve your retirement readiness.
I asked Dennis to write a guest post explaining why he built it. His initiative deserves recognition, and he tells it better than I could. Read his story below, then take the assessment.
You won’t regret it.
Here’s Dennis:
I Googled Retirement Strategy and Got a Financial Plan
Guest post by Dennis Hoffman. Screenshots are a sample reader, not a real completer.
I googled “retirement strategy” expecting to find a planning framework. Instead, I got “When to Claim Social Security” and “How to Structure a Portfolio.” Page after page of it.
Don’t get me wrong. That work matters, and I did all of it. I got professional advice. I did the math. I wouldn’t tell anyone to skip a minute of it. But money is only one dimension of retirement readiness, and I needed a map for the others.
About two years before I retired, I started paying close attention to retired people I knew. Some were thriving. Many of them, six months in, were not. A few seemed almost lost, filling days and waiting for something to happen.
Most of them had a bulletproof financial plan.
That scared me. I’d spent a career being good at planning, and I was watching people who had done their planning, yet they arrived somewhere I didn’t want to go.
Fritz has argued for years that the money side is necessary but not sufficient. I looked for the sufficient part, and couldn’t find it.
So I built it.
The Retirement Strategy is a free, 45-minute conversation across six dimensions of readiness. It’s not a quiz. More than 400 people have completed it, and you can take it at The Retirement Strategy.
What follows is why I built it.
The 6 Dimensions of The Retirement Readiness “House”
After reading about finding fulfillment in later life, I developed a six-dimension framework. I think of it as a house.
Health and Wealth are the foundation. Without health, little else matters. You need enough money, whatever “enough” means to you. Money is the part everyone already works on, and they should. But it’s only a foundation. Nobody lives in a foundation.
People and Place are the walls. Who is in an ordinary day, and where you are standing while it happens. Both seem too obvious to plan, which is why almost nobody does.
Passion and Purpose are the roof. What gets you out of bed, and why it matters that you showed up. Fritz has written about Purpose on this site for years. I’m putting it in a structure with the other five.
Six dimensions. A financial plan only addresses one of the six.
I had the house wrong at first. I assumed everyone arrives with the foundation of health and wealth handled, and that only the upper floors are at risk. Not so. Health is half the foundation, and too many people put it off. They trade sleep for email and exercise for business dinners, promising to make it up later. Passions wait too, “until you have more time.”
Purpose often retires the same Friday the job does, not because it failed but because you completed it. Most of the people you saw every day disappear, because they were colleagues. The place you call home was chosen for a commute you no longer make, or for a school system your children left a decade ago.
Some people have it figured out by retirement day. However, if you haven’t been intentional about the five dimensions many people miss, you may end up with half a foundation poured, the other half cracked, thin walls, and no roof.
What I Wanted
For money, I had an advisor, an assessment of where I stood, a target, and a plan to close the gap before my retirement date. I wanted exactly that for the other five.
Step one was the assessment. The usual approach is a form, but a form can’t distinguish the person with three standing commitments on the calendar from the person who intends to golf more. Both check yes. I wanted a process that wouldn’t accept the easy answer, so I created a process using AI to probe deeper when it sensed an area of potential opportunity.
I worked through my own readiness one dimension at a time. I started with a blank page and ended with a blueprint. I used it for a year, revisiting it as things changed, closing gaps I could see and naming ones I couldn’t.
As my retirement date approached, people kept asking the question every near-retiree gets: “What are you going to do?” My answers got better, not because I was more confident but because I’d done the work. When I explained how, several asked me if I could make it available.
I retired on April 1, 2026, after thirty years in technology. A couple of months before I left, I started turning the process into software. I launched it on April 6, six days after my last day. No team, no investors, no employees.
The Retirement Strategy is that process. It’s conversational in its approach, and takes about 45 minutes to complete. It follows what you say, and if an answer is thin, it asks a follow-up. That is the whole difference.
The screenshots below is a sample that I built to demonstrate the process.
What 400 People Have Shown Me
More than 400 people have completed the full assessment. One thing stands out, and I didn’t predict it.
The roof is the weak spot, by a wide margin. Five of the six dimensions cluster together. Purpose sits clearly below the rest, with the widest spread. Some people have it worked out, a great many haven’t begun, and you can’t tell which from the outside. Purpose, the dimension standard planning never raises, is the one people are least ready for.
The sample below shows the shape: Health 7.0, Wealth 7.5, People 7.5, Place 6.5, Passion 7.0, Purpose 5.0. Five in a band, with Purpose as the outlier, well below the others.
The assessment never asks for the details of your finances or your health. That’s deliberate. Those conversations belong with your advisor and your doctor. What the readout gives you is what advisors try to draw out and rarely can, because there’s no instrument for it: a written account of how you plan to spend your time and who you plan to spend it with. Bring it to your next meeting.
On Wealth, it asks whether you have enough and, separately, whether you believe you do. Those two come apart more often than they should.
What you get at the end
You get a ~30-page PDF including your scores across all six dimensions, the reasoning behind each, and concrete next steps. The score is the least interesting part. People tell me they value the explanation of why a dimension landed where it did, written in language drawn from what they said in the session. It’s hard to argue with your own words.
The dimensions don’t stand alone, and the readout traces how each one pulls on the next.
What changes isn’t the number. Something you were vaguely uneasy about now has a name, and a named problem is one you can work on.
Vague unease isn’t actionable. A short list is.
Try it
If you already have a financial plan, keep it. Dana Anspach writes on this site as a CFP, and that work belongs with people who know how to do it. This assessment sits beside a financial plan. It doesn’t replace one.
The assessment is free and takes about 45 minutes at The Retirement Strategy.
The time to take it is now, not the day after you retire.
Dennis Hoffman is the founder of The Retirement Strategy. He retired on April 1, 2026, after thirty years in technology, most recently as a senior executive at Dell. He lives in Wilson, Wyoming. Take the free assessment at https://theretirementstrategy.ai/. LinkedIn: https://www.linkedin.com/in/dennishoffman.
Conclusion:
Fritz here, with a closing encouragement to take advantage of the work Dennis has done. I took the assessment and was impressed with the quality and accuracy of the output. It took me less than 30 minutes, and it was time well spent. If you missed the link earlier, click here to take the assessment now. Two tips:
- Carve out the time to do it in one sitting
- Be honest with your responses to get the most accurate assessment.
Remember, you’re not working to get a “high score,” but rather an objective assessment of how prepared you are for retirement.
I’m concerned, but not surprised, by Dennis’s findings that “Purpose” is typically the lagging element in most retirement plans. In my 10 years of writing on this blog, I’ve realized that finding your purpose in retirement is key to a great retirement, and it’s often overlooked in the planning process. Having a new tool to evaluate where you stand on each of the 6 dimensions is tremendously helpful, especially with the overview and recommended action steps in the accompanying report.
Finally, a special “Thank You” to Dennis for his work on creating this assessment and his decision to make it available to the public at no cost.
I have no doubt his work will help hundreds of people enjoy a better retirement.
I hope you’ll be one of them.
Your Turn: What do you think of the work Dennis has done in creating this assessment? If you take the assessment, I’d appreciate it if you could come back and share your biggest learning. Also, please share with others who you think could benefit.
The post A Retirement Test You Don’t Want To Fail appeared first on The Retirement Manifesto.
Fritz Gilbert writes at The Retirement Manifesto. Read this article on their site.
