Career and Life Transitions Coaching at Cassaday & Company

In addition to providing ongoing financial guidance, Cassaday & Company’s comprehensive suite of services includes helping clients make informed, thoughtful decisions about life transitions with the help of our in-house Career & Life Transitions Coach, Jennifer Landis-Santos. 

We have found that while people are often financially prepared to retire, they aren’t emotionally or mentally ready to step away. This hesitation often stems from a lack of a clear vision of what post-retirement life looks like.  

Our clients’ wellbeing is of the utmost importance to us, which is why we found it imperative to integrate Life & Career Transitions Coaching into our service offering when we kept seeing this common theme.  

Watch the video below to learn more about Jennifer’s background, explore common questions about retirement, and hear real client success stories. 

A Quick Overview of Our Life & Career Transitions Coaching Offering  

Jennifer offers three main types of support: retirement transition coaching, career transition coaching, and wellbeing coaching: 

Retirement Coaching 

You may be hesitant to retire because you are uncertain about how you’re going to spend your days once you’ve stepped away from your career. Retirement coaching helps clients determine what is important to them, and what their life can become after full-time work.  

Career Transition Coaching 

Changes in your career path, whether planned or unplanned, can be challenging without the proper guidance. Career transition coaching helps clients navigate new career paths and make decisions about what is next for them. Also, Jennifer provides career transition coaching to the children of our clients who are struggling to find their professional start.  

Wellbeing Coaching 

Most people live very full and busy lives, but it is important to take the time to determine what brings you joy and how you can feel a greater sense of purpose in life. Wellbeing coaching helps clients identify structure and routine, connect with community, and increase their overall enjoyment of life.  

How To Set Up a Meeting with Jennifer 

If you are a current client, contact your advisor to set up an introductory meeting with Jennifer.  

If you are not a current client but are interested in learning more about this unique service offering and how it is part of our comprehensive wealth management approach, email We are always happy to offer a complimentary second opinion of your current financial plan.


Disclosure: The preceding testimonials in the video are provided by current clients. Cassaday does not seek out client testimonials, and all testimonials referenced are unsolicited. No compensation was provided for these testimonials and no material conflicts of interest are present. These testimonials and endorsements do not guarantee a level of success, nor do they guarantee that all clients will have the same experience  


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