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Mastering Mid-Life Financial Strategies: A Guide for Gen X 

Marty Rascon, Wealth Management Associate Advisor | Ryan Richardson, CFP®, ChFC®, Senior Wealth Management Advisor | February 14, 2024


Members of Generation X, particularly those who are business executives or owners, face several challenges in today’s world. They often find themselves caught between the demands of growing their business, raising their children, caring for their aging parents, and preparing for their own retirement. In this blog post, we focus on those in their 40s and 50s, who are uniquely positioned at the crossroads of planning for retirement, establishing a comprehensive estate plan, and supporting their families. Below we’ll explore effective planning initiatives, identify common financial hurdles, and offer strategic solutions to empower Gen X with the knowledge to navigate these critical financial decisions confidently. 

Planning Initiatives for Gen X: 

For Gen X entrepreneurs and executives who are navigating business finances alongside multiple personal obligations, it can be hard to take a step back and focus on their own health and well-being. That is especially true when it comes to their financial well-being, and it can be difficult to know where to begin. Identifying current financial obligations, long-term goals, and the steps needed to accomplish them can serve as a starting point.  

For many, some shorter-term goals include managing monthly financial obligations while also assisting their children with college expenses. While some longer-term goals could include preparing for a successful retirement and ensuring their families are taken care of with an adequate estate plan in place. Whatever those financial goals are, the very first step is to identify them and begin outlining the necessary steps to achieve those goals.  

While identifying your financial goals may seem like a simple task, understanding how to achieve those goals can get complicated. Many questions can arise as you progress on your financial journey such as:  

  • Am I saving in the most optimal way? 
  • Are there any pitfalls that I am unaware of from an investing or tax perspective? 
  • Do I need to make any changes now to ensure a successful retirement? 
  • Is my estate plan in good order? 
  • What if life or economic circumstances change and how will that affect my financial goals? 

These questions coupled with the many obligations facing members of Gen X can be overwhelming. However, these questions can be addressed with comprehensive financial planning that considers both business and personal financial landscapes. For business leaders, this may include succession planning, and business valuation, alongside personal retirement planning and estate management. By engaging with a firm that is a fiduciary and has Certified Financial Planners (CFP) on staff, you can trust that you will receive non-biased financial advice that sets you up for success. 

With a comprehensive financial plan, you can expect to engage with an advisor who will organize your finances in an easily digestible way. Through ongoing conversations, your planner learns more about your financial goals and values to model a roadmap for you and your family. Additionally, various scenarios can be implemented into your plan to account for the many dynamic factors that occur in one’s life. You can expect to receive personalized advice and concrete action items to ensure that you are on the path to achieving your financial goals. With the many obligations that members of Gen X face, delegating this aspect of their lives to a trusted financial planner can provide confidence and peace of mind.  

Common Financial Challenges for Gen X: 

Retirement Readiness: 

A pressing concern for many in Gen X is the state of their retirement savings. According to a survey conducted by Bankrate 69% of Gen X workers feel they are behind on their retirement savings, and only 19% feel financially secure. Often caught between the needs of their children and aging parents, retirement planning can take a backseat. However, with retirement on the horizon, it’s imperative to take steps to bolster savings.  

In general, the first step in achieving financial security is to ensure an adequate emergency fund. According to the CFP Board, it is recommended to have 3 – 6 months of liquid emergency funds on hand for unforeseen events. Once that has been fulfilled, the next step is to examine your cash flow needs to understand how much you can reasonably contribute to retirement accounts such as 401(k)s and IRAs. This exercise can assist you in identifying areas where you can cut expenses to maximize contributions to these accounts. When reviewing your retirement accounts there are some important factors to consider including but not limited to: 

  • Does a Traditional or Roth account make sense for me? 
  • Am I taking advantage of my employer match? 
  • Am I eligible to increase my savings with additional “catch-up” contributions? 

Utilizing retirement accounts to prepare for retirement is a great place to start on your path toward your financial goals. It is important to note that starting early is a key driver of success to take advantage of compounding returns over time. When considering your retirement account strategy, there can be several factors at play to determine the optimal way to save. By utilizing a professional financial planner, they can consider all the nuances of your financial situation to develop an optimal savings plan for you and your family.  

Navigating Healthcare Before Medicare: 

An often-overlooked aspect of mid-life financial planning is preparing for healthcare needs before becoming eligible for Medicare. For those in their 40s and 50s, especially business owners who might not have access to corporate health plans, this is a critical gap that requires strategic planning. The cost of healthcare can significantly impact financial well-being and retirement planning. It’s essential to explore health insurance options that bridge the gap until Medicare eligibility, such as private health insurance, health savings accounts (HSAs), or leveraging the health insurance marketplace for suitable coverage.  

Investment Portfolio Considerations: 

While building up retirement accounts is a primary driver of a successful retirement, it is also important to consider bolstering savings outside of these accounts. Building up taxable assets, such as a trust account or joint account, can provide many benefits as well. Unlike withdrawing from a retirement account where distributions are typically taxed as ordinary income, taxable assets are subject to capital gains rates which are usually taxed at a lower rate. By utilizing taxable accounts, you may be able to supplement retirement income in a tax-efficient way.  

Moreover, for business executives and owners, equity compensation in the form of Restricted Stock Units (RSUs) or stock options represents a critical component of wealth. These instruments not only tie your financial success to the company’s performance but also introduce unique challenges and opportunities for tax planning and asset diversification. Effectively managing RSUs and stock options requires a nuanced understanding of vesting schedules, tax implications and the strategic timing of sales to align with your broader financial goals.  

Another important consideration when discussing your investment portfolio is your time horizon and risk tolerance. These two factors are extremely important when considering the appropriate asset allocation within your portfolio. Time horizon refers to the amount of time that funds will be invested until ultimately needed for expenses. Said another way, time horizon refers to the amount of time you need your funds to last. Risk tolerance is a more subjective measure that refers to the individual’s comfort level with investment risk within their portfolio. These two factors together ultimately determine your portfolio’s asset allocation, which is the allocation to assets such as stocks, bonds, or other assets.  

For members of Gen X, understanding their time horizon, risk tolerance, and existing asset allocation is a crucial step in the planning process. Depending on your specific situation it is important to consider your own financial goals and ensure that your portfolio is allocated accordingly.  

To go one step further, it may be beneficial to understand each account’s individual asset allocation as well. For example, your taxable account may be invested more conservatively than your retirement accounts because withdrawals from your taxable accounts may begin sooner. Conversely, your retirement accounts may have a more aggressive allocation due to that account’s individual time horizon with required minimum distributions beginning at age 75 if you were born after 1960.  

Lastly, as you move from your working years to your retirement years it is important to regularly assess your retirement needs and the asset allocation of your portfolio. Asset allocation decisions can change over time especially as you age. There can be many factors the influence a change to your investment portfolio, and with the help of an advisor you can trust that all the nuances of your life are taken into consideration.  

Estate Planning for Gen X: 

Estate planning is another area that can be often overlooked by members of Gen X. Without an adequate estate plan families can be left in difficult situations upon the death or incapacitation of a loved one. This is especially important for those families who have young children because a comprehensive estate plan can ensure their security if either parent were to experience an unexpected event. By having an estate plan in place, you can ensure that assets are distributed according to your wishes, ensure that your children are taken care of, and can significantly reduce the emotional and financial strain on a family during already challenging times.  

In general, there are a few key documents that should be in place to establish an adequate estate plan: 

  1. Trust: A trust can be used to protect assets, provide for minor children, and manage assets in the event of incapacity or death. Also, assets listed within the trust will avoid probate court, which can be lengthy and expensive. There are several types of trusts that can be useful depending on your specific situation and wishes.  
  1. Will: A will is another important piece for an estate plan. With a will, you can designate beneficiaries, provide instructions for how and when beneficiaries receive assets, and name guardians for your minor children.  
  1. Power of Attorney (POA): Establishing a trusted individual as your POA allows them to make financial and legal decisions on your behalf if you were to become incapacitated. If you become incapacitated and do not have a POA, managing affairs can involve lengthy court proceedings and be expensive.  
  1. Health Care Power of Attorney (HCPOA): A HCPOA allows you to designate a trusted individual to make medical decisions on your behalf if you become incapacitated. This is a vital piece of an estate plan because it allows for your wishes to be followed in the case of a medical emergency, end-of-life care, or other healthcare decisions even if you cannot communicate them. This document can also provide clarity to family members regarding health care decisions to avoid any potential disputes.  

The importance of estate planning cannot be overstated, especially for Gen X. Having a will or trust in place is critical for protecting one’s family and ensuring that assets are distributed as intended. Powers of attorney and healthcare directives are also essential, providing loved ones with the authority to make financial and medical decisions if one is unable to do so. Including aging parents in these conversations can also help ensure that their wishes are respected and that a plan is in place for their care and the transfer of their wealth. Our previous blog post includes helpful information on how to approach conversations around wealth transfer.  

Supporting Your Children: Education Funding Strategies  

With tuition costs these days, education funding is another planning opportunity for members of Gen X. It is important to consider starting early in the child’s life and exploring the various savings vehicles available. One of the most popular and widely used savings vehicles for education funding is the 529 account. There are two main types of 529 plans available for education funding: 

  1. Prepaid 529 Accounts: With a prepaid 529 account you can prepare for future college tuition by paying today’s rate. With this type of account, families can purchase tuition credits with participating institutions that are typically based on current tuition rates. However, this type of 529 account is not very flexible when it comes to school choices, as they are often limited to in-state institutions.  
  1. Education Savings Plan 529: With a standard 529 account families can open an investment account that can be used in the future for qualified education expenses. For example, items such as tuition, books, and room and board all qualify under this plan. Contributions are made to this account and grow tax-free and can be distributed tax-free for qualified education expenses.  

Depending on your specific situation either account can provide an opportunity to set your child up for success when it comes to higher education. Also, family members such as grandparents can contribute to these accounts for your child’s benefit. There are several key items to note when discussing a 529 account: 

  1. What happens if my child does not go to college? If your child does not end up going to a college or university, the funds can also be used for apprenticeships/trade schools or transferred to another child. Additionally, as of the Secure Act 2.0 529 accounts can be rolled over into Roth IRAs for the 529 beneficiary if certain requirements are met.  
  1. Tax implications: 529 contributions occur after-taxes and are not federally deductible. However, depending on the state you live in, and if you use your state’s 529 plan, you may be eligible for state income tax deductions or state tax exemptions on withdrawals.  
  1. Financial Aid: A 529 account is typically held by a parent or other family member and is not considered the child’s asset. Therefore, only a small portion of the account is considered during the financial aid process. If another family member such as a grandparent is the owner of the account, the assets won’t factor into the federal financial aid calculations.  

While this is not an exhaustive list of items to consider when looking into a 529 plan, it is important to remember that starting early will increase your family’s preparedness for education expenses. Additionally, by including your children in the conversation, it can serve as a good opportunity to foster financial literacy and independence by teaching them about budgeting, saving, and investing to prepare them for their own financial futures. 

How WAM Can Help: 

As Gen X moves through mid-life, the opportunity to secure a stable and prosperous financial future is within reach. By focusing on key areas such as proactive savings, understanding your asset allocation, estate planning, and education funding, you can take steps today to lay the groundwork for a comfortable retirement. Here at Weatherly, our core pillars of service revolve around comprehensive financial planning and investment management. We are here to work with members of Gen X to construct a financial roadmap to assist them in achieving their financial goals. Additionally, our team of experienced portfolio managers are here to help develop an investment strategy that is in line with your goals and aspirations.  

** The information provided should not be interpreted as a recommendation, no aspects of your individual financial situation were considered. Always consult a financial professional before implementing any strategies derived from the information above.