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'Retirement Isn't About Money': How Casey Weade Is Helping People Find Freedom in Life After Work

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'Retirement Isn't About Money': How Casey Weade Is Helping People Find Freedom in Life After Work
Image credit: Casey Weade
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The pursuit of success can derail everything important in life. That’s a lesson that Casey Weade didn’t learn until he took a long, hard look in the mirror one morning during his late 20s.

Weade should have felt overjoyed. Facing him in the mirror was a list of life goals he’d outlined since graduating college — and he’d accomplished every single one. His business was running itself, and he no longer had to work because of the financial independence he had achieved. Weade had “made it,” yet he felt empty and disillusioned, not knowing what to do next.

“It’s a strange feeling to focus on money your entire life and then realize you don’t need it anymore,” says Weade, who is CEO and "Chief Visionary" of the retirement planning firm Howard Bailey. His obsession with building wealth had taken priority over almost everything else in his life, including family.

Weade considered early retirement, but as a man of faith, he felt like he would be rejecting the God-given gifts bestowed upon him. So instead, he decided to help others identify what they wanted from life and achieve financial freedom like he had, allowing them to deliver even more to the world.

Weade developed a purpose-driven retirement planning philosophy that’s reshaping the conversation around life after work. But his journey to fulfillment wasn’t smooth sailing. Soon after redefining his purpose, a rare congenital defect threatened his newborn son’s life, testing his revived commitment to the maximum.

Facing the man in the mirror.

Weade started writing down his goals and sticking them to the mirror in elementary school. His drive stemmed from being bullied as a kid growing up in a small community, in a relatively well-off family. He didn’t want his peers to think he was given anything and developed fierce independence.

“I wouldn’t accept anything from anyone, including money from my parents. I got a job as early as middle school so I could pay my own way,” he says. Weade even asked the school bus driver to drop him off three doors down from his house so the other kids couldn’t see that it was one of the nicest in the neighborhood and get the wrong idea.

Weade’s family didn’t come from money, however. His mother was a talented school teacher, and his father started from nothing before building several businesses. Seeing his father work around the clock from a young age motivated Weade to achieve financial freedom as fast as possible, so as not to have to obsess over work for the rest of his life as it seemed his father had.

From a young age, Casey Weade was motivated to achieve financial freedom as fast as possible.
Image credit: Casey Weade

After graduating college, Weade joined his father’s financial planning firm, arriving earlier and leaving later than everyone else. When Weade purchased the firm from his father in 2011 and renamed it Howard Bailey, his hectic work schedule quickly descended into 18-hour slogs and constant obsession over business and money. So when he finally looked in the mirror that day after accomplishing his lifelong goals, he felt despair that “success” hadn’t brought the anticipated joy and relief. Instead, he felt somewhat empty.

Confronting realizations and challenges.

“I realized that none of my accomplishments brought meaning and purpose to my life. It was all about building wealth and growing a business instead of being intentional with my family, giving, and serving others,” admits Weade.

He rededicated himself to his family, blocking time on his calendar solely to reconnect with his family and grow his family skills.

This recommitment proved to be timely. After Weade’s first son was born healthy in 2015, his second son was born with a congenital diaphragmatic hernia (CDH) in 2017, a rare and dangerous condition that caused his organs to migrate from his gut to his chest. The Weades were told he would have almost no chance of survival unless they relocated from Indiana to Ohio, where a team at Cincinnati Children’s Hospital Medical Center specialized in CDH. So they did.

After nearly six nerve-wracking months, his son was in the clear. “That experience made me question my mortality and reflect on what’s most important in life,” says Weade, who also experienced his first mini-retirement.

“It’s good that I’d achieved financial independence, which enabled me to step away from the business. But I felt the same depression, anxiety, and general feeling of malaise that many retirees talk about, reinforcing my beliefs on the importance of having meaning and purpose outside of money and work.”

What retirement is really about.

Weade assessed how he could help others using his gifts: planning, achieving goals, and managing finances. Like his mother, he also loved to teach, and he reconnected with the founding philosophy of his company.

“My grandfather, Howard Weade, lived through the great depression and inspired my financial philosophy: that it’s not just about how much money you make, but how much you keep. My other grandfather, Ralph Bailey, inspired my passion for educating and serving others.

“Most people don’t think about what it means to no longer work and how that will impact their lifestyle and sense of meaning,” explains Weade. He now bases his company’s retirement planning process on his personal financial framework, leading with identifying each client’s purpose in life, followed by four pillars (liquidity, income, growth, estate), and finishing with tax planning.

Casey Weade’s first recommended step in financial planning is the need for an individual to have a life purpose.
Image credit: Casey Weade

Weade is so confident in the process that he doesn’t have to worry about what’s next. “I don’t have to worry about what the market or tax rates are going to be, or who the next president is and how much money I’ll make next year.”

Weade says that he works with individuals and investors who are frustrated with their current financial advisors, who often aren’t addressing their big-picture goals or organizing their finances in a way that creates more meaning in their lives.

“When your biggest concerns about money aren’t addressed, you can’t achieve your purpose. But when you’re financially defended against known risks — with a reliable income you can’t outlive — you can focus on accomplishing your highest priorities in life outside of money,” says Weade.

“Retirement isn’t about money. It’s about impact. Your purpose is bigger than money. Imagine the kind of impact you can make in this world with your accumulated experiences over 50 years, once you realize you no longer have to worry about money.”

Finally living — and teaching.

Weade has created systems in his business that enable him to be less hands-on and invest time in what he enjoys doing to further his purpose.

His latest of several books, “Job Optional,” hit the 2019 Wall Street Journal e-books bestseller list, and his “Retire With Purpose” podcast made it into Feedspot’s top 20 retirement podcasts for 2019

In late 2018, he joined Front Row Dads to connect with others who wanted to be family men first and business leaders second. With his wife, Chelsie, Weade decided to adopt a child through “open adoption,” a form of adoption in which the biological parents participate in the process of placing the child with an adoptive family and can continue to have contact thereafter.

Casey Weade joined Front Row Dads to connect with others who wanted to be family men first and business leaders second.
Image credit: Casey Weade

“What’s made the experience so meaningful and exciting is that we’ll essentially have a partnership with the birth mom for life,” says Weade. We’ll be there for her financially and emotionally through the birth, and will support her and her child so they can have a relationship they couldn’t otherwise.”

Weade acknowledges that this isn’t something everyone can do unless they have the kind of money and time he’s been able to engineer. “Almost anyone can adopt a child, but not everyone is ready to create a relationship with the birth mom. If you want as much quality time as possible with your family, it pays to be successful as early as you can.”

In addition to spending time with his family, Weade also works 9 a.m. to 4 p.m. four days a week, even though he doesn’t have to. “I only do what fulfills me. If you look at my calendar, I have time blocked to spend with my wife, family trips planned, and retreats scheduled to make myself a better husband, father, and human being. What is most meaningful in your life? Does your calendar reflect that?”

Weade also invests time in his team to help them uncover their purpose and achieve their goals. He asks them questions like, “What are your personal and financial goals?  How are you going to accomplish them? What will you do when you get there?”

By digging into their past and where they find meaning, he helps them create a plan to experience more fulfillment in life and work. He’s often surprised to find that his team members have never had this type of conversation before, let alone set goals for themselves. “Retaining great people has little to do with compensation and everything to do with helping them level up both personally and professionally.”

So, how does Weade define his purpose today? Simple; live every day with intention, maximizing the value he creates for his family and others.

Connect with Casey Weade at Howard Bailey, and listen to the “Retire With Purpose” podcast.

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