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Doug Oosterhart, CFP®

Mastering Your Retirement: The Key Differences Between Complicated and Complex Problems

Retirement planning isn’t just about checking boxes or solving math problems. While some challenges in retirement are straightforward and can be solved with a clear answer, many others are far more intricate.


They require careful consideration, ongoing adjustments, and a customized approach. This is the critical difference between complicated and complex problems, and knowing how to navigate both can set the stage for a more secure retirement.


Growing up in the Western school system, we often encountered multiple-choice tests, where the goal was to find the one right answer. But retirement planning isn’t a multiple-choice exam with a single solution. Every person’s financial situation is unique, and the best path forward involves balancing personal goals, preferences, and life circumstances.


What is a Complicated Problem?


A complicated problem is one that has a clear solution, even if the process to get there is intricate. Think of it like building a jigsaw puzzle—there may be many pieces, but you know that once all the pieces are in place, the picture is complete. In retirement, tasks like preparing your annual tax return or calculating your required minimum distributions (RMDs) are complicated problems. While they can seem overwhelming, they follow a predictable formula and can be solved with expert help.


Some examples of complicated retirement planning tasks include:


  • Filling out paperwork for a new financial account.

  • Calculating tax obligations for a specific year.

  • Preparing for your annual tax return.


These are tasks that can be solved with the help of a competent financial advisor or accountant, or even DIY tasks in some cases.


What is a Complex Problem?


Complex problems, on the other hand, are much less predictable. They don’t have a clear-cut solution and require ongoing management and adaptation. A complex problem is more like navigating a constantly changing landscape. The path forward isn’t always obvious, and adjustments need to be made along the way.


One of the most common complex problems in retirement planning is deciding when to claim Social Security benefits. There’s no single right answer because this decision depends on various factors that change over time, such as health, life expectancy, and other income sources.


Other examples of complex retirement problems include:


  • Deciding how much to withdraw from your retirement accounts each year.

  • Determining whether to set up a trust or rely on a will for your estate.

  • Evaluating the benefits of Roth conversions.

  • Choosing the best Medicare plan for your evolving health needs.


These problems are dynamic, requiring regular reassessment and adjustment as your life and circumstances change.



simple, complicated, or complex problems


Why the Difference Matters


At LifePoint Planning, we emphasize that while any competent financial advisor can assist with complicated problems, complex problems require a customized, ongoing strategy. The rigid, process-based methods that work for complicated issues simply won’t apply when dealing with the uncertainty and variability of complex problems.


According to complexity experts like Rick Nason, addressing complex problems requires a mindset of "managing, not solving" (Source). Additionally, this involves acknowledging uncertainty, trying out strategies, learning from outcomes, and adapting over time​ (Source). The unpredictable nature of complex problems means that attempting to apply a straightforward solution can do more harm than good. Instead, a flexible, adaptive approach allows for better management of the unforeseen changes that retirement will bring.


For example, you may decide to start withdrawing from one account in retirement, only to realize that shifting to another offers better tax advantages as circumstances change. Managing this complexity requires regular attention, continuous learning, and adjusting as your needs evolve.


The LifePoint Planning Approach: Customized Solutions for Complex Problems


Most financial advisor business models aren’t aligned with customized solutions because they’re not scalable. Scalable models rely on templated, boilerplate strategies that allow advisors to apply the same solution to many clients at once. But real financial planning isn’t scalable—at least not when done right. It takes time to truly understand a client’s goals, preferences, and lifestyle, which means that each financial plan should be as unique as the individual it’s created for.


Working with an advisor specializing in addressing these complex retirement problems through a customized, client-centered approach might be tougher to find, but ultimately worth the search. While templated solutions might be faster and easier for other advisors, real financial planning requires a deep understanding of how each client thinks, feels, and wants to live their life. The best approach isn’t about providing a one-time solution—it’s about walking alongside you as your financial needs and life evolve.



Why Customized Financial Planning is a No-Brainer


Most advisors are trained to handle complicated problems. They can fill out paperwork, provide a risk-tolerance questionnaire, and follow the rules. But when it comes to complex problems, like determining how much you can safely withdraw from your retirement accounts each year or selecting the right Medicare plan, cookie-cutter solutions just won’t cut it.


A personalized approach to managing the complexities of your retirement is what is needed. By understanding your unique needs and offering a strategy that adapts with you, having a trusted advisor to help you navigate the complex problems that require ongoing management can make or break a retirement plan. Our approach ensures you’ll have a plan that evolves, grows, and adjusts as your life changes—something no boilerplate solution can provide.

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