To Retire or Not to Retire

Follow these five steps to help clients open up and explore their array of options.

By Andrea Millar
Andrea Millar
Andrea Millar

Sam had hit a wall. He was burned out, had been in and out of the hospital dealing with health issues over the last year, and was sick of it all. He came to me to help him create a plan towards retirement so that he could get away from this way of living.

Sam (not his real name, to protect his privacy) knew that he would be okay financially. His bigger concern was the emotional side of retirement. What would he do with himself? How would he find a sense of purpose after 40-plus years of finding his meaning through work?

He had some friends who were thriving in this new chapter of life and others who were flailing. He didn’t want to follow in the footsteps of the latter.

When I began working with Sam, it was clear that what was most essential for him to live a meaningful and fulfilling life was to get his health back and to elevate his life experience. Interestingly, once he gained clarity on what he wanted in these areas and began taking steps forward, he got to a place where he felt better than he had felt in years.

Beyond burnout

From this place, Sam realized that he enjoyed many aspects of his work. He could see that he had many more options than the extremes of continuing at his hectic pace, as he had been for years, or retiring and walking away. It is a normal human experience when in burnout to see only see in black and white. It is important to reach a state of calm in order to be able to see clearly and tap inner wisdom.

I have seen this trend with many of my clients. They think they are ready to retire because they are tired. The weight of responsibility and the needs of others have taken precedence over the most essential elements of their lives, like their health and relationships.

Many people simply need to redesign how they are working so it can serve their overall life objectives. The truth is that most people want to continue to contribute in some way and they usually have heaps of wisdom to share at this stage of life.


Any transition in life can be daunting, even if it is moving towards something which excites you. To support your clients as they contemplate this significant decision and begin their journey forward, consider the following approach. My steps are inspired by the change cycle methodology of Martha Beck, PhD, a Harvard-trained sociologist and coach who focuses on the science of life transformation.

1. Make sure your client truly does want to retire.

 Many people focus on whether they are in a strong enough financial condition to be able to stop earning and make it through their retirement years without running out of money. Go beyond the money to get clear on what else your client is giving up by stopping work. For example, many people fulfill a need for belonging and connection through their work relationships. Work can also provide a sense of identity, relevance, purpose, enjoyment and much more.

The point is to make sure that your client is aware of what they are giving up so that they can make an informed decision and can prepare properly and not be caught by surprise. It will be important to discuss what will bring purpose and meaning in this next stage of life.

Additional Reading: How Are Your Clients’ Brains Wired? 

2. Normalize the situation.

Any life transition is bound to bring feelings of discomfort. The larger the transition, the higher the chance that thoughts and feelings will go into overdrive. The human brain is wired to keep us safe, and it will throw out all sorts of internal dialogue to try to stop you in your tracks. Reminding your clients that this is a normal human experience can help them move beyond these stories in their heads so they can refocus on what is most important now.

They’ll likely grieve for a period of time over what they’ve left behind and the way of life they’ve shed. Support your clients by giving them a safe place to share what they are going through and give them encouragement to take one step at a time.

3. Help them visualize what is next.

If your client has reached financial independence, they are in a life stage where it is much easier to live life from the inside out. In other words, living life based on their deepest values, life intentions and what matters most. This way of being brings a sense of fulfillment and purpose that is deeply satisfying.

Encourage your clients to open themselves to all the possibilities ahead. Give them the space to open their imaginations and begin to create a vision. Getting inspired by what they’d like to create in their lives can give them the energy to take steps forward. You can help them paint the picture of what various scenarios may look like in this visionary reality.

4. Encourage them to experiment.

 As your client begins to take steps towards their vision, celebrate their progress with them. It takes a lot of courage to try new things and new ways of living. Normalize their experience as your client experiments, falls, gets back up, takes another path and tries again. This will be a journey of learning and refining as your clients see what brings them the most satisfaction and meaning.

It is ideal to begin this process of visualizing and experimenting while your client is still working so they don’t have to take as big a leap. This step is a good opportunity for your client to get out of the work grind and practice using their time for other endeavors.

5. Watch them settle into their new normal.

 If your client has planned well and had your support along the way, they will likely settle into a new life rhythm and routine that gives them satisfaction and meaning. I have heard some people say that they don’t know how they ever had time to work once they’ve hit this stage.

Encourage your client to savor and enjoy what they have created. Continuing to tweak with small improvements along the way will keep life interesting. And they will now have the skills to go through more transitions with ease if they decide to shake things up once again.

In Sam’s case, he is in his experimentation phase. He is contemplating keeping a small number of clients and providing more services to them that will enable him to do what makes him feel most alive in his work. His time will be freed up to focus on his physical and mental fitness, to be the loving dad and granddad he wants to be, and to indulge in more adventures and travels. Long divorced, he may even take a shot with dating again. Possibilities abound.

Andrea Millar, RLP, CFLA, CPA/PFS is the founder of Andrea Millar Life Planning. She spent decades in the profession of financial planning before tragic events woke her up and sent her on the path of seeking more meaning and fulfillment in her life. She now coaches busy business owners and professionals to let go of what isn’t working so that they can reclaim their lives.  Most of her clients are financial planners and their clients. You can learn more at




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