Planning in the key of life — with Preston Cherry

In September 1976, Stevie Wonder released the double album “Songs in the Key of Life.” The album became the second-highest selling album of 1977, eventually winning Album of the Year at the 19th Grammy Awards.

Wonder recorded the album after he seriously considered leaving the music industry and moving to Ghana to devote the rest of his life to helping children with disabilities. But after planning his farewell tour, he changed his mind and signed what was then the biggest recording deal in history.

The tracks in “Songs in the Key of Life” reflect the range of the human experience: love, joy, loss, birth, celebration, social justice and spirituality. That range of human experience also translates into financial planning, and the album inspired Preston Cherry in his practice.

Cherry is the founder of Concurrent Wealth Management, creator of Financial Harmony and author of Wealth in the Key of Life: Finding Financial Harmony. He also is associate professor of finance and head of the financial planning program at the University of Wisconsin-Green Bay. The Financial Planning Association presented him with its 2025 Heart of Financial Planning Award.

The origin of financial planning is life planning, Cherry said, and it was something he learned when he studied financial planning at Texas Tech University, a pioneer in the subject.

“One of the books I studied there said the process of financial planning starts with learning the values and the identity and the person and the goals, and what people want to do with their lives now and in the future,” he said. “Holistic planning, comprehensive planning is covering all the areas, all the domains of planning. And then we have the holisticness of self and finally we have an actual financial psychology. So we’re talking about financial psychology and financial therapy and money mindset — and all of this is inside of planning.” 

Struggle and celebration

Cherry said the groundwork of his interest in financial planning was built during money talks with his parents and family as a child. “We always had some money talks in the home. It was either about a struggle or we were celebrating something like a life event. But it always was tied to money in some way.”

As an undergraduate student at Prairie View University in Texas, Cherry took a personal finance class. The professor thought Cherry had a knack for the subject and recommended he pursue graduate studies in financial planning at Texas Tech. 

Cherry began working as a bank teller while he attended Prairie View, and he eventually worked his way into the bank’s investment division, obtaining his Series 7 license along the way. 

After receiving his master’s degree from Texas Tech in 2006, Cherry went to work for a financial services firm that worked with oil and gas companies in Houston.

“I was part of a team,” he said. “I was the junior financial planner at that time, and there was a lead financial planner. The lead planner was the rainmaker and the presenter, and the junior planners did all the data entry and built the plans.”

The firm did comprehensive planning for their oil and gas company clients.

“We covered everything — all the aspects of comprehensive financial planning, so it included personal insurance, liability, estate planning, equity compensation. We knew their employee benefits and their executive compensation plans forwards and backwards because we specialized in those companies,” he said.

Comprehensive vs. holistic planning

Cherry continues to serve oil and gas company clients from his virtual practice based in Houston while he teaches in Green Bay, where he lives.

He is a champion of both comprehensive and holistic planning, which he said are two different things.

“Comprehensive is the domain and then holistic is the sense of the person and their identity. It gets into how you think, how you feel, how you behave, your value system about money.

“It starts drilling down underneath the financial psychology umbrella, which is financial therapy, the financial psychology of financial planning and behavioral finance, which is about your investments in your decision making.”

The client’s identity is underneath that umbrella, Cherry explained, and the advisor must ask questions to help them and the client define that identity.

“What are your experiences? What is your culture? What are your values — your past, present and future about your relationship with money and how it pours into your thought process and your decisions and your why? Why do you want to do what you want to do? What is your six-year plan? What fueled that?”

Getting to the root of what a client needs and what is behind those needs requires difficult conversations, Cherry said.

“Sometimes difficult can be a barrier. But it’s necessary. If you do not have the necessary conversations, then you cannot have the necessary financial strategy that’s critical to carry out the life aspirations that you want.”

Teaching the next generation

Cherry is excited about teaching the next generation of financial professionals through his work at UWGB. 

“We need so many young people to come into this profession,” he said. “There are more folks over the age of 60 in this profession than there are under the age of 30. It’s up to us in Generation X to influence those under 30 to enter this profession. 

“The energy is high within my classroom. The curiosity is high and so are the energy and the willingness to want to adapt the industry to Generation Z and the millennials.”

Cherry described young adults as wanting the “three C’s: clarity, connection and competency.”

“They want to see clarity in fees. They want to have more connection and they want to have everything quicker and better than the generations before them had it. They also see competency a little differently. It’s not just about having the alphabet soup of designations after your name; it’s about proving you’re a trusted individual. They want to get rid of the skepticism. And then they want everything done in a more streamlined manner, as far as technology is concerned.”

Serving the ‘forgotten generation’

Cherry works with many Generation X clients in his practice. As a Gen Xer himself, he recognizes many of the financial challenges faced by his peers. 

“Gen X is a special group. We were the latchkey kids; we were home alone after school because our parents had to work. We are overeducated and we are burned out. My Gen X friends are still taking care of their 25-year-old kids as well as taking care of their parents. Gen X is truly sandwiched but trying to live their best years.”

Cherry jokes that Gen X is “the forgotten middle child” but added their unique financial situation means they need an advisor’s help in planning for a retirement that they fear they have fallen behind in saving for.

Inspired by music

Wealth in the Key of Life was published in December 2024. Cherry said he used Wonder’s album as the backdrop for the book because, just as Wonder used music to demonstrate all of life’s phases, money is also something that touches all aspects of life.

“You often hear that money is a tool. It helps you do things. But I say a tool has no soul. Money touches every part of our lives — from the brand of toilet paper we choose to the water we drink, to the house we live in, to the services we buy for our families or ourselves. Money is part of any type of challenge we have, every type of celebratory moment, all of our decisions. So money has a soul. We exchange part of our soul when we go to work every day to make that currency exchange.”

In his book, Cherry outlines his “Life Money Balance” approach that not only focuses on wealth accumulation but also emphasizes the importance of well-being in achieving a fulfilling life. The book includes his “Six-A Alignment System” that helps people understand and improve their relationship with money, and the Four T’s — a self-audit including trial, triumph, transition and transformation — that aids in integrating finances into your life.

Cherry said the most important piece of financial advice he can give to anyone is to not compare their own situation with anyone else’s.

“My dad used to tell a story and he said, ‘You know one thing about horses, they have blinders on for a reason. Those blinders keep them looking straight ahead so they won’t be looking left or right.’

“I share that story with clients all the time. I tell them the No. 1 rule about money is not to compare. Don’t compare. Give yourself grace and understanding. If you don’t understand yourself and you don’t have grace and understanding, you will quickly become unaligned. The key is aligning your life and your money on your own journey. If you don’t do that, none of the planning or financial strategies will work.”

Susan Rupe is managing editor for InsuranceNewsNet. She formerly served as communications director for an insurance agents' association and was an award-winning newspaper reporter and editor. Contact her at [email protected].