CAREER & LIFE TRANSITIONS
Career & Life Transitions
At Cassaday & Company, Inc., our experience has taught us that a complete financial plan should also address the personal, emotional, and social decisions that shape your life. Our Career & Life Transitions coaching services help clients navigate major life changes so that decisions are not only financially sound but also address the non-financial aspects that can lead to fulfilling, happy and worry free outcomes.
Life transitions can include retirement, career changes, relocation, changes in health or family dynamics, or shifts in personal priorities. Coaching provides a structured space to explore what's changing, what feels uncertain, and what might be possible. That's why our suite of services integrates this coaching support directly into our wealth management approach, helping clients move through change with clarity, confidence, and purpose.
Our Career & Life Transitions Approach
Many clients are financially prepared for major transitions such as retirement, but are unsure what life will look like once they get there. Our coaching approach helps bridge that gap through forward-focused conversation that moves clients from ambiguity toward clarity and from intention toward action.
Through one-on-one coaching sessions, we support clients across a range of life transitions, including:
- Retirement transitions: Determining when to retire, clarifying what retirement will look like, building structure and purpose, and aligning your lifestyle with your financial plan
- Career decisions: Evaluating opportunities, trade-offs, and long-term implications of career changes, including financial, lifestyle, and family considerations
- Lifestyle and personal priorities: Identifying what brings fulfillment, maintaining meaningful relationships, and creating routines that support long-term wellbeing
This support may also extend to family members, including children navigating career decisions or other major life transitions.
How Life Transitions Support Enhances Your Financial Plan
Many financial decisions are closely tied to personal circumstances. Without addressing both, even well-constructed financial strategies can fall short.
- Alignment: Your financial plan directly supports the life you want to live
- Clarity: You understand both financial and personal implications before making decisions
- Confidence: Decisions are made with a clear sense of direction
- Coordination: Financial and personal guidance are fully integrated
- Continuity: Support is available as your life evolves
The result is a more complete planning experience that connects your financial resources to the life you want to live.
When Should You Use Career & Life Transitions Services?
You might not have a name for what you're navigating—only the sense that something is shifting. That's a valid place to start. This service is most valuable during periods of change or decision-making, including:
- Approaching or transitioning into retirement
- Considering a career change or professional shift
- Navigating relocation or lifestyle changes
- Experiencing changes in health or family dynamics
- Reassessing priorities, goals, or long-term direction
Career and life transitions coaching is available to Cassaday clients at any stage. No milestone required.
What Our Clients Are Saying
"We made two major decisions with Jen’s help: the decision to retire and to not relocate. Jennifer helped us assess what was most important to us. Using that tool, we made a few changes and have no regrets. She is a great asset and we are grateful for the opportunity to talk with her at this cusp of our lives."
"I wanted to let you know how helpful Jennifer Landis-Santos has been. I have been speaking with her over the past few months regarding a possible job change. I had never spoken with a coach before, so I was not sure what to expect. She has helped me clarify my confusing thoughts about what I am looking for and trying to avoid in a job! Thank you for offering this resource."
Testimonials are provided by current clients. All written testimonials referenced are unsolicited. All video testimonials referenced are solicited. No compensation was provided for these testimonials and no material conflicts of interest are present as a result. These testimonials and endorsements do not guarantee a level of success, nor do they guarantee that all clients will have the same experience.
Why We Created This Service: A Conversation with our Founder
Cassaday & Company Founder Steve Cassaday sits down with Career & Life Transitions Coach Jennifer Landis-Santos to discuss why we created this service and how we help clients navigate life's most significant decisions. Watch as they explore:
- Why many clients are financially ready to retire but hesitant to take the step
- Jennifer's background and approach to transitions coaching
- Client success stories
- What to expect when working with Jennifer
Meet Our Career & Life Transitions Coach
Jennifer Landis-Santos
With 20 years of combined counseling and coaching experience, Jennifer helps Cassaday clients navigate major life transitions. Drawing from her mental health background and her work as a faculty member at Georgetown University, she specializes in guiding clients through both the emotional and practical aspects of significant life changes.
Jennifer helps clients clarify their next steps—whether navigating retirement, career changes, relocating, expanding social connections, or other pivotal moments. She takes a holistic approach, addressing professional, emotional, physical, spiritual, and relational wellbeing to help clients create actionable plans for their vision.
Common Questions About our Life Transitions Services
Traditional financial planning focuses on investment returns, tax planning, and estate considerations. Career & Life Transitions planning addresses the personal decisions that influence these strategies, ensuring your financial plan aligns with your life goals.
Your advisor will suggest involving our Career & Life Transitions Coach when you're facing decisions that have both financial and personal dimensions, such as retirement timing, career changes, or major life transitions. However, clients can request coaching services at any time, you don't have to wait for your advisor to suggest it.
The initial session is a conversation where Jennifer learns about your situation. From there, she may introduce assessments or resources to help you gain clarity and guide next steps. The number of sessions varies—some clients need just one or two, while others prefer ongoing support. The engagement is flexible and designed around your needs.
No. While Jennifer has a background in mental health counseling, this service is forward-focused coaching, not clinical therapy. Sessions draw on evidence-based coaching methods and a whole-person approach that attends to the emotional and psychological dimensions of major life change. Coaching helps you clarify goals, explore options, and create actionable plans for major life transitions. For therapeutic needs, we provide vetted referrals to appropriate professionals.
No. This service is included as part of our comprehensive wealth management offering at no additional charge.
No. While retirement transitions are common, our integrated approach supports any significant life decision with financial implications, including career changes, relocating to a new area, adjusting to family changes, and reassessing personal priorities. For scenarios outside of our coach's scope of work, we can connect you with the right professionals for your needs.
Your advisor and our Career & Life Transitions Coach collaborate to ensure your plan addresses both financial and personal dimensions comprehensively. Any conversations or information you wish to remain confidential will not be shared.
This support is available when relevant to your situation, as your needs evolve. Some clients benefit significantly from this service now, while others may find it helpful in the future. Clients find comfort knowing this resource is available if and when they need it.
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Ready to work with a wealth management team that addresses your complete financial life—including the personal decisions that affect it?
Contact us today to schedule a complimentary consultation. We'll discuss your financial situation, review your goals, and explain how our approach might benefit you - all with no obligation.