We recently connected with Sanjay Das and have shared our conversation below.
Sanjay, appreciate you joining us today. If you had a defining moment that you feel really changed the trajectory of your career, we’d love to hear the story and details.
In one of our first conversations, an industry colleague Jessica Cunningham and I discussed our passion for educating people so they can age well. She introduced me to Judith Naegely and Jason White who have a similar mind frame around using education to assist people make better choices about aging, while running their businesses. We coined the term and created a seminar called Aging With Confidence, where we educated 30-60 year olds’ about how to plan for and age with confidence.
That seminar has since evolved into our Live Your Archetype program. It starts with using our self-discovery tool/quiz to identify your life archetype – Adventurer, Caregiver, Investor, Learner, Social Butterfly, and Creative. Once you know what your life is about, our seminar jump starts your planning process and living your archetype journey. By the end of the seminar, you will have a sense of the various aspects of your life that requires attention, along with access to professionals in some of those areas who you can use as your advocates in planning for and living the life you dream of. Its YOUR life, its YOUR journey. These professionals and others you identify are there to assist you in actualizing your dream life. There is more: you get a simple 24 hour plan that will assist you to iteratively build your life plan within a year (or less, depending on your level of commitment and effort).
How excited will you be when you know your life archetype (an image that represents who you are and your dream life), and not only that but have an easy iterative timebound plan along with professional guides to start working towards living that life?
We are massively excited not only for your self discovery journey through this program, but also for ourselves as we live our own life archetypes following this same process.

Sanjay, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
We are a band of four: Sanjay Das, Senior Living Specialist, Judith Naegely, Financial Advisor, Jason White, Medicare & Insurance Advisor and Jessica Cunningham, Long Term Care and Insurance Advisor. We each have our own businesses, and cohesively designed and run this program to help people discover what they want their life to be about, and live that dream life. If you don’t have a plan, you will live on someone else’s plan, including the Government’s. Plan your life, live your plan; Live Your Archetype!
Sanjay is a 10 year veteran in the senior living world (after 22 years in software), assisting families care for their loved ones or finding a better living solution for them. His focus is to help you figure out how you want to live your lives, especially after retirement so that you know the costs to plan for.
Judith started and sold 2 businesses (one of which was a home health agency that helped her parents live better lives), and is now a Financial Advisor on a team of seasoned advisors. Her focus is to understand your current situation, your life goals and assist you in creating the wealth you need to live your dream life.
Jason used to be a police officer, before starting his business to help you protect your health by making the best healthcare insurance choice possible post retirement. He provides easy to understand information, so your decision making process becomes simple, easy and effective, thereby not only protecting you but also your family financially.
Jessica has been through multiple journeys including financial and law school. She is an avid and powerful connector and will help you build out your “live your archetype” team. Her specialty is to educate and assist you with protecting your health and wealth using disability, life and long term care insurances.

Any advice for managing a team?
The book TRACTION by Gino Wickman outlines a comprehensive way of running small businesses; its called Entrepreneurial Operating System or EOS.
It outlines the 6 areas of a business that a business owner and his/her management team need to focus on. One of the most important aspects for managing a team is making sure the right people are on the bus, and in the right seats. EOS outlines the concept of GWC – gets it, wants it and has the capacity to do it. That along with alignment with the company’s core values helps the owner and leadership team build the right team, and create sustainable accountability and excitement about the work they do.
Our coach Cal Riley helped us implement EOS in early 2023. We have been using it diligently for the past 1+ year. I started seeing the impact its had on our leadership team a couple of months back; it has been extremely heartening and powerful to watch.

Can you talk to us about how your funded your firm or practice?
I used ROBS or Rollover as Business Startup program to start my business. It is a tightly regulated tax penalty free mechanism to rollover money from your retirement account to start your business.
It is not a loan. Your retirement account owns the business until you are ready to buy it back, or sell.
A lot of financial advisors and CPAs’ have never heard about it, but its legit – you can look it up on IRS.gov. You will want to use a company that specializes in this program to make sure you are fully compliant with all applicable tax laws when you use it the first time and also ongoing. I used Guidant Financial for my ROBS transaction, and have continued to use them for ongoing management for the last 10 years.
Contact Info:
- Website: https://www.certaintyandhope.com
- Facebook: https://www.facebook.com/sanjay.das.16
- Linkedin: https://www.linkedin.com/in/sanjaydas0/
- Youtube: https://www.youtube.com/@AlwaysBestCareWakeJohnston

Image Credits
N/A

