What is WRONG with Your Financial Planning 'Picture'?
For a revealing reality check, take your finances and turn them into a one-page visual representation. This exercise could bring you some much-needed clarity as you near retirement.

Remember back to your elementary school days when your teacher passed out the “What’s Wrong with the Picture” test. Your job was to scan the page to, find those items that were either missing from or not supposed to be in the picture.
It looked something like this:
You got a time limit and the number of items you needed to identify to complete the activity. You focused on your paper, doing your best to spot the items, and ultimately tried to be the first person to place your pencil down, a sure sign to the rest of the class that you “did it” and you were “first.”

Sign up for Kiplinger’s Free E-Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
How does this little grade school exercise relate to financial planning? Well, if you took all the pieces of your financial life and put them down on a single piece of paper, after carefully scanning the page for items that don’t “fit,” you might be surprised at what jumps out at you.
Changing Workplace Creates Retirement Complications
Complicated finances are a fact of life these days. Today, according to the Bureau of Labor Statistics, workers hold 10 different jobs before age 40, and that number is projected to grow. Employers have changed their financial structures to remain competitive in our global economy — by doing away with pensions, company paid health insurance, and gold watches after 30+ years of service. In addition, science, technology and innovations have disrupted many jobs and industries, changing the labor outlook and giving many U.S. workers a scarcity mindset of “… Will I have a job and if so, what job will I have?”
Today, everything is a rush, hurry up to get here, hurry up to get there, and it’s time for bed to do all over again.
How the Picture Test Works: One Couple’s story.
To illustrate how our “What’s Wrong with the Picture” test could help you with your own retirement planning, let’s take a look at a fictional couple — Bill & Donna — and their son, Johnny:
- Bill has worked at six different jobs in technology, and at each job he elected 10% of his income to be invested for his future. Each employer offered a unique benefit package for employee retention, from company-sponsored retirement plans to Employee Stock Ownership Plans (ESOP), stock options such as Non-Qualified (NSO) and Incentive Stock Options (ISO) , and non-qualified bonus plans. When transitioning from one employer to the next, some companies went through mergers, name changes and acquisitions. Some of the benefit plan departments offered continuity with insurance plans via life and disability.
- Meanwhile, Donna has worked at five different jobs in the medical field at various hospitals. After their child was born, Donna stayed home until little Johnny was in pre-school. Then, Donna returned to the workforce. During Donna’s working years she opted to put 7% of her gross income into plans similar to Bill’s and left things where they were.
Today, Bill and Donna are five years from retirement, and they decided that it would be wise to review their financial affairs. My business partner and I took their financial data and analyzed it to create the following financial “picture” to discuss with Bill and Donna.
Bill’s picture: [‘ER = Employer, ISO = Incentive Stock Options, and NSO = Non-Qualified Stock Options]
We Take the Financial Picture and Turn it into Talking Points
Upon looking at Bill’s financial picture, we can use it as a guide to engage Bill and Donna in a conversation. The goal is to best understand each asset, account and their details before we make any recommendations. Our customized picture helps keep the couple engaged and NOT overwhelmed.
Perhaps we can ask a few questions with regards to Bill’s retirement accounts and stock options, such as:
- Can you tell me why you have four separate qualified retirement accounts? What investment options are in your retirement accounts — how are you allocated — what are you paying in fees and how has your performance been in each account relative to their respective benchmarks?
- Have you updated the primary and contingent beneficiaries on all qualified retirement accounts? If so, who are they? How recent are your beneficiary choices on file?
- What is your income tax plan for the stock options? How concentrated is your wealth in the company stock? Do you have full understanding of the rules in your stock plan if you leave your employer?
- Are we missing anything? Does this give you a good picture of where you are? Do you have any questions for us?
The feedback that we have received upon going through this type of process during our meeting has been so rewarding. In essence, the picture can act as a quasi-balance sheet and if we add the income and expenses to the picture we have a quasi-income statement.
Consider, how your life would be if you could shrink down the complexity of accounts, paperwork, statements to ONE PAGE — how easy would it be for you to determine “WHAT IS MISSING from this picture? or What does NOT FIT?”
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Dennis D. Coughlin, CFP, AIF, co-founded CG Capital with Christopher C. Giambrone in 1999. He has been in practice since 1996 and works with individuals nearing retirement and those whom have already retired. Proud of his humble upbringing, Dennis shares his advice with the same core principles that he was raised with. When not in the office, you will find him with his family enjoying the outdoors.
-
Retire in the Canary Islands for Beaches and Natural Beauty
Retirees enjoy Spain's Canary Islands, where life can be as hectic or chilled as you like. The one constant will be almost year-round mild weather.
-
The '120 Minus You Rule' of Retirement
The '120 Minus You Rule' updates an older retirement rule, with a twist. Here's how this approach to retirement portfolio construction can work for you.
-
Five Questions to Help Ensure a Happy, Secure Retirement
You need to drill down to what you really want out of retirement. Then you can get down to the business of crafting a financial plan to make it happen.
-
I'm a Financial Adviser: This Is How You Can Save for Big Goals Even if You Feel Like You're Barely Getting By
Learning good financial habits — building an emergency fund, paying down debt, saving consistently — gives you flexibility, options and a path to security.
-
How to Buy an Annuity Online (Without Regret)
You should never be rushed into buying an annuity. But now that they can be sold quickly and easily online, you need to be more alert than ever to pushy salesmanship. Here are four signs you're working online with a professional.
-
How Much Income Will an Indexed Annuity Get You? An Annuities Expert Lays Out the Numbers
Guaranteed lifetime income sounds great, but how much will it be? Several factors determine your future payout on indexed annuities with an income rider.
-
Financial Fact vs Fiction: Why Inflation Is Lower, But Prices Are Not
Do you think bonds protect you from stock losses? Are you confident your assets will go to your intended heirs if all you have is a will? Think again — and read on for other myths that could be leading you astray.
-
I'm a Personal Finance Expert: Here's the Truth About Using AI to Plan Your Retirement
AI can be a useful tool, but it often gets important financial information wrong. It also can't emulate the empathy, judgment and personal connection you can get with a human being.
-
You Don't Have to Be Wealthy to Need a Wealth Manager
Navigating complex financial decisions is hard on your own, no matter how much money you have. A wealth manager can provide comprehensive financial planning, investment management, risk management and more.
-
Despite Tariffs, These Investment Experts Are Bullish on European Equities
European equities were one of the better-performing investments during the first half of 2025. They could be a good long-term prospect for U.S. investors needing to diversify, according to these investment managers.