How to Engineer the Second Half of Your Life With Bill Keen

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[147] – Many sales-focused financial advisors don’t like working with engineers because these people are all about the numbers, but our guest, Bill Keen, loves working with them for the same reason.

In this episode, Jeremy Keil speaks with Bill Keen, founder and CEO of Keen Wealth Advisors, Bestselling Author and Co-host of the Keen On Retirement Podcast. Together, they talk about how to engineer the second half of your life and the importance of focusing on what you can control.

Bill discusses:

  • Why he became a retirement-focused financial advisor
  • How he answers the number one question people have going into retirement, “am I going to be ok?”
  • The big retirement questions people need to answer that go beyond the numbers
  • How he approaches planning for Social Security
  • What a crossover point is and how to figure out when your crossover point is
  • What has changed the most over his 30-year career
  • And more

How to Engineer the Second Half of Your Life

Retirement planning can be overwhelming, but it doesn’t have to be. When you work with a trusted advisor and have a plan in place, you can achieve a comfortable retirement. It’s important to focus on what you can control, avoid emotional decisions, and have a process in place to navigate unexpected challenges.

With careful planning and a positive mindset, you can engineer the second half of your life to be fulfilling and comfortable.

Am I Going To Be Okay Going Into Retirement?

Retirement planning can be a source of anxiety for many people but it’s important to remember that with careful planning and working with a trusted advisor, you can achieve a comfortable retirement. Both planning and investing for your retirement are important because planning includes considerations such as tax, income, and insurance planning, while investments serve as the engine that drives the plan forward.

To address if you’ll be okay in retirement, a good financial advisor will aim to minimize taxes, maximize returns based on individual risk tolerances, align both spouses’ perspectives, and educate the next generation about the family’s financial situation.

Even if you question whether retiring with financial independence is a realistic possibility, your retirement goals can be achieved with the right planning and investment strategies in place.

What Big Retirement Questions Go Beyond The Numbers?

When it comes to retirement planning, it’s not just about the numbers. There are important emotional and psychological aspects that need to be considered as well. Bill highlights some of the significant retirement questions that go beyond mere calculations.

One crucial question involves the transition from relying heavily on spreadsheets and number-crunching to gaining comfort and confidence in delegating financial matters to a trusted advisor. Many highly intelligent individuals, such as engineers who have excelled in their respective fields, recognize that outside of their expertise, they may feel like they’re in kindergarten when it comes to financial planning.

The emotional aspect of retirement is also an important consideration. Clients often express concerns about making impulsive decisions driven by emotions that could derail their retirement plans. They understand the importance of having a solid plan in place to prevent being swayed by media narratives or market volatility.

A good financial advisor can help clients develop self-awareness and overcome their emotional biases.

While crunching the numbers is essential for retirement planning, it’s equally important to address the emotional and psychological aspects. By partnering with a reliable financial advisor, you can navigate the complexities of retirement with confidence, overcome emotional biases, and stay on track toward your financial goals.

Will Social Security Be Available When We Get Older?

If you’re retiring in the next 20 years, we don’t think you have to worry about any major changes to Social Security benefits. Currently, there has been no legislation proposed regarding means testing for Social Security. However, Bill Keen mentioned it as a potential option for people earning over a certain income threshold, similar to what currently exists with Medicare.

It’s a system that considers income levels to determine eligibility or the extent of benefits Americans might receive.

He also mentions other possibilities, like raising income limits for taxing individuals, which may impact Social Security funding, and adjusting the claim dates for Social Security benefits to align them with increasing life expectancies.

While there is uncertainty around the future of Social Security, it’s important to have a plan in place that takes it into account.

What Is A Crossover Point, And How Can I Find It?

The crossover point is the point when an individual reaches a financial position where they can comfortably retire and sustain their desired lifestyle without the need for additional income from work. Finding your crossover point is an important step in retirement planning, as it can help you determine when you can retire and how much you need to save.

Determining your crossover point involves assessing personal financial circumstances, goals, and evaluating the trade-offs between working longer and enjoying the benefits of retirement.

To determine your crossover point, talk to a financial advisor about these steps:

Understand Your Financial Standpoint: Evaluate your current financial situation, including your assets, savings, investments, and any outstanding debts. Determine your projected expenses in retirement and assess the income sources available to you, such as pensions, Social Security, and investment returns.

Calculate Retirement Needs: Estimate your desired annual retirement income by considering factors like living expenses, healthcare costs, travel plans, hobbies, and other lifestyle preferences. It’s essential to be realistic and consider inflation and potential unforeseen expenses.

Analyze Savings and Investments: Assess the growth potential and sustainability of your savings and investment portfolio. Consider consulting with a financial advisor who can help you determine the expected rate of return, risk tolerance, and suitable investment strategies based on your retirement goals.

Evaluate Retirement Age: Determine the ideal retirement age based on your financial readiness, personal aspirations, and health considerations. Be mindful that retiring earlier may require a larger retirement nest egg to ensure a comfortable lifestyle over a longer retirement period.

Assess the Trade-Offs: Consider the financial and non-financial aspects of working longer versus retiring earlier. Working an additional year or more allows for further savings and potentially higher Social Security benefits, but it may come at the cost of missing out on the freedom and experiences retirement offers.

Find Your Crossover Point: Continuously reassess your financial position and projected retirement needs. Once you reach a stage where you have accumulated enough wealth to sustain your desired lifestyle throughout retirement while taking into account your risk tolerance and investment returns, you have likely reached your crossover point.

How Can I Take Control Of My Retirement?

A well-thought-out financial plan is essential, especially when navigating challenging times in the markets. A comprehensive financial plan considers various factors, including an individual’s goals. It helps you stay focused on your long-term goals as you navigate different market scenarios or changes to things like Social Security.

You cannot control the market, but you can control how you respond to it.

With the proper focus and disciplined strategy, you can weather market turbulences and make informed financial decisions.

Remember, the Serenity Prayer’s wisdom, which emphasizes accepting what we cannot change and taking charge of what we can, can serve as a guiding principle throughout this journey. In the face of uncertainties, staying committed to your financial plan and making proactive decisions can lead to financial success and a sense of empowerment.

So, just as Bill Keen says in his book, it’s important to understand the difference between what you can change and what you cannot when engineering the second half of your life.


To learn more about How to Engineer the Second Half of Your Life, check out the resources below!

If you have any questions, feel free to contact us or our guest, Bill Keen, using the contact information provided below!


Connect With Bill Keen:

Connect With Jeremy Keil:

About Our Guest:

Bill Keen has a passion for helping others achieve their retirement dreams and founded Keen Wealth Advisors with this goal in mind. Bill’s vision is to build one of the country’s most trusted retirement advisory firms, acting at all times in the best interests of clients. Bill has nearly three decades of experience advising clients. His interest in finance was sparked by the financial hardship he experienced in his childhood. By age 10, Bill knew he would need to learn about saving and investing in order to help his family. He opened his first investment account in high school. Today, he treats all clients like his own family members, as he understands first-hand the importance of planning for one’s financial future. 



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