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Inspiring Conversations with Deirdre Holliday-White of ShiftWise Retirement Solutions

Today we’d like to introduce you to Deirdre Holliday-White.

Hi Deirdre, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
After graduating from the University of Maryland Eastern Shore and Stratford University with a culinary degree, I was wondering what my passion was. My mother was diagnosed with cancer and stopped eating while undergoing chemotherapy. I decided to take matters into my own hands and began to prepare food for her using my own spice blends. She enjoyed them so much I decided to start my own food business. I also started teaching cooking classes and certification classes for a Professional Food Manager license. While working that business from home I also started working in the corporate office of a hospitality management company in the Human Resources department. While working their life came at me full speed and I lost my husband in a car accident. My world was flipped upside down. I had a 5-year-old son and didn’t know where to turn. I knew I had to provide for him, and I wanted to be a strong role model for him. I took a leap of faith and opened my first cafe in Laurel, Maryland in 2018. I worked from sunup to sundown to make the cafe everything I imagined. I hired staff and created seasonal menus. After a year and a half, I had to close the doors. I then got a job in DC as a Benefits Specialist for a non-profit company. I knew I had to work to get benefits for me and my son. I met my now husband and he has always been super supportive in pushing me to reach my goals and dream bigger. I took another leap of faith and open a full-service restaurant in Washington, DC. After 2 successful years I had to make the tough decision to close to care for my mother that was diagnosed with Dementia and Alzheimer. While caring for her and helping my father I started a business that joins both my passions of hospitality and the insurance industry.
With over 14 years in Human Resources, I decided I wanted to do more. I joined a Financial Brokerage company that allows me to help families, caregivers, and business owners to secure their financial futures. I received my life and health insurance license and a certificate for tax preparation in 2020.
I have always had an interest in food, financial wellness, health and life insurance. I have vast knowledge of benefits both from the employees and employers’ perspective. I want to pass this knowledge on to members of my community. I want to build a team of hospitality professionals that can reach the community 1 person, 1 family, 1 small business at a time. I believe each one teach one. We should be able to leave legacies for our children and our children’s children.

We all face challenges, but looking back would you describe it as a relatively smooth road?
I had a couple of struggles like caring for a 5-year-old when my world was flipped upside down. I started a business that I had to close. I had to find another job right before COVID. I got hired 1 week before the world went on lock down. I had another opportunity to reopen in a bigger space and a larger concept. After 2 years, another setback was when my father called and said he could no longer care for my mother on his own and he needed some help. I had to make a hard choice of closing the restaurant and being her other caregiver.

As you know, we’re big fans of ShiftWise Retirement Solutions. For our readers who might not be as familiar what can you tell them about the brand?
At ShiftWise, we help individuals, families, caregivers, and small business owners build stronger financial futures through education, benefits planning, retirement strategies, and financial protection.

What many people should know about me is that I believe financial planning is not just about money—it is about peace of mind, protecting your family, and creating options for your future. I truly believe that what we do today financially impacts the generations that come after us.

I am known for simplifying financial concepts and helping people understand things that often feel confusing or overwhelming—like retirement planning, employee benefits, life insurance, long-term care, and protecting income. I meet people where they are, without judgment, and help them create a strategy that makes sense for their life and goals.

What sets me apart is that I don’t believe in one-size-fits-all planning. I take a family-first and education-first approach. I spend time helping people understand their options so they can make informed decisions with confidence. I also understand the challenges families face because many people are balancing careers, caring for loved ones, preparing for retirement, and trying to avoid becoming a financial burden on their children.

Our brand is centered around one mission: helping people shift their financial future in the right direction.

At ShiftWise Retirement Solutions, we specialize in:

• Retirement planning strategies
• Life insurance and living benefits protection
• Long-term care planning
• Annuities and guaranteed income strategies
• Employee benefits for small businesses
• Financial wellness education
• Retirement plans for business owners and employees
• Guidance for caregivers and families planning for the future

For small businesses, we help owners strengthen their companies through employee benefit solutions, retirement plans, and strategies that support employee retention and long-term success.

What I want people to know about the ShiftWise brand is this: we lead with education, integrity, and relationships. We are here to help you understand your options, protect what matters most, and prepare for the future with confidence.

Because retirement is not something you should just hope works out—it should be planned for.

So maybe we end on discussing what matters most to you and why?
What matters most to me is helping families create financial peace of mind. I want people to feel prepared, protected, and educated so they can make confident decisions today that strengthen their future and create a legacy for their loved ones.

I care deeply about making sure individuals and families are prepared—not just for retirement, but for life’s unexpected moments. Too many people work hard their entire lives but are not educated on how to protect what they have, prepare for the future, or avoid becoming a financial burden on their loved ones.

As someone who values family and understands the importance of caregiving, I know firsthand how important it is to have a plan in place. That is one reason I am passionate about helping people understand benefits, retirement planning, life insurance, long-term care, and strategies that can create stability and options later in life.

What also matters most to me is education and empowerment. I want people to feel confident—not confused—when making financial decisions. I believe people deserve access to information in a way that is simple, practical, and easy to understand, regardless of where they are financially.

For business owners, what matters to me is helping them care for their teams while building stronger companies. Employees who feel supported through benefits and retirement planning are more likely to stay, grow, and contribute to a healthy workplace culture.

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