Thought Leadership

How ‘Mindset Coaching’ can help navigate your retirement

We spoke with Mindset Coach, Sarah Chaplin-Lee, about how mindset coaching can help individuals bring the same level of drive, strategic approach, and success experienced in their corporate lives to the rest of their lives.

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We spoke with Mindset Coach, Sarah Chaplin-Lee, about how mindset coaching can help individuals bring the same level of drive, strategic approach, and success experienced in their corporate lives to the rest of their lives.

What are the most common challenges individuals face when transitioning to retirement or after selling their businesses, and how can mindset coaching help address these challenges?

A myriad of challenges appear when the transition out of full-time work begins. The first is failing to recognise that this needs a plan.

Our attention is on the finish line with a working assumption that things will just ‘happen’. Things never just happen. This is why many established professional service firms offer coaching for a business exit as standard. It is one of the most important of all the transitions we make and is worthy of considerable thought.

For most, life after work is a new terrain for which there is no map. They are no longer at work, not in a daily professional cohort, a totally different environment to navigate and have no clear direction or goals perhaps for the first time in their lives. This can lead to a sense of loss and/or feeling lost, create unexpected stressors in key relationships, and issues with health and overall well-being.  

The transition impacts many dynamics, particularly the family. This can be the most unsettling because change to the family system is complex. It can feel very destabilising which takes many by surprise.

Coaching can mitigate these risks by examining why the next chapter is exciting, identifying barriers or issues, and starting to devise a plan. It enables the individual to consider all elements of their life and how everything fits together.  Through a series of conversations, the unknown starts to become known, and the individual becomes equipped with coping mechanisms for this profound transition.

In your experience, what are the key mindset shifts that can empower individuals to embrace this new phase of life with confidence and purpose?

The thought of being retired invokes many false assumptions and can often be a surprise. Mindset coaching helps individuals to focus on their goals, gain greater clarity on what is within their control, and recognise the importance of having a plan.

While formal work may be finishing, fulfilment can come from alternative endeavours. Coaching can leverage existing competencies and connect them to what’s important, which is critical in creating a renewed notion of relevance and authenticity in this next phase.

Working with a coach is empowering because having a plan drives action. Once goals have meaning a mindset shift follows, leading to movement towards the future with new purpose. It's subtle but powerful, revealing an inner shift in confidence, self-belief, and self-efficacy.

Could you provide some real-life examples or success stories of business owners/CEOS who have benefited from mindset coaching during their retirement or post-sale transition?

Client exiting her business: ‘Emma’ had a tendency towards busyness and ‘always on’.  Coaching helped her accept those personality tendencies (rather than judge them) and find outlets for her intelligence and energy that had high meaning and impact.

Coaches often work with metaphor and visual imagery to help clients see themselves and their challenges differently and with ‘Emma’ we used the metaphor of the motorway. Rather than ‘liquidity’ meaning taking the off ramp and pottering about on B roads, it became about a purposeful rest stop to determine the direction, speed, and quality of the journey ahead.

‘Emma’ shaped what her post-sale model needed to comprise to score highly on both the importance and satisfaction indices and ended up with a portfolio of NED roles that connected with her values and principles while allowing her to start the habit change towards a slower pace and more family time. The result: she returned to the motorway with excitement and vigour but with greater ease and balance and increased fulfilment as she was able to enjoy the journey and her passengers.  

Client exiting his business: ‘Jeff’ always referred to himself as ‘a corporate animal designed for that cage and no other’, so the prospect of being set free was extremely daunting and something he’d been actively avoiding thinking about.  Our work was to bring visibility to his life post-sale as he couldn’t imagine his existence without the business. The two identities were connected, and he had to find a way for them to exist independently of each other, something he found impossible to compute.  

Coaching gave him the opportunity to work through the separation and find helpful ways of letting go (a prevailing theme), whilst actively looking at himself as a person, rather than a CEO, which enabled him to see what made him unique, lovable, and likeable.

Our visualisation was centred around his personal narrative at his club and in his extensive professional and personal network, so he was able to provide a compelling and comfortable answer to the inevitable question “So, what are you up to now?”.

Individuals often have complex financial considerations. How does mindset coaching complement financial planning to ensure a well-rounded approach to this transition?

Transitions are, by their nature, complex and multi-layered and involve the emotional and psychological as well as the practical and financial.  Coaching enhances critical thinking because it enables the decision maker to access other, less obvious, data points that are often critical to the efficacy of the decisions they’re making as well as their long-term fulfilment.  

Working with a coach is highly complementary to ongoing financial discussions as it provides an outlet for the emotional and psychological aspects associated with change to surface, be examined and challenged. This is carried out in the context of answering the big questions; why, to what end, who for, with what desired outcome and with whom.

Coaching challenges the decision maker to consider multiple perspectives and scenarios, fostering a deeper understanding of the consequences and risks for them, their families, and their desired outcomes. All of this has an important bearing on the financial decisions they’re making.

What are some common mindset barriers or limiting beliefs that you've observed in your clients in this demographic, and how do you help them overcome these?

Two common and connected limiting beliefs are that what got them ‘here’ will get them ‘there’ and that they don’t need to change anything to enter the next phase. For example, treating family members like employees comes up a lot because the typical, former, mode of behaviour is wholly unsuitable for the new day-to-day environment.

Coaching is confidential and coaches are impartial, sitting outside the individual’s ‘system’. This allows for high challenge around the assumptions and autopilot behaviours that need examination and amendments so that the next phase goes well. This is part of the awareness raising from which decisions to change habits and approaches grow and take form.  Working with a coach helps individuals examine their assumptions, expectations, and impact.  This can be around roles, responsibilities, and behaviours and starts a movement from Board hierarchy to more consult/collaborate (which is what many family members are expecting and/or hoping for).  While this mindset shift requires significant effort and practice, it has the highest potential in terms of happiness and fulfilment.

In your view, what are the most important outcomes or transformations that individuals can expect to achieve through mindset coaching in this life stage?

The most significant transformations are achieved by gaining an elevated relationship with themselves and enhanced clarity of mind around what makes them a great person, as well as a successful professional.  That sense of really knowing what makes them ‘them’, why they do what they do, and what really matters, boosts confidence, increases agency and is highly energising around the ‘art of the possible’ for the next phase.  

The other significant outcome is improved relationships with others, notably with close family members. These relationships face the greatest risk when left to the ‘accepted/historic’ dynamic and ‘I’ve always done it this way’.

The shift that mindset coaching enables could best be described as moving to an engagement model that is fully conscious and driven by self-awareness and awareness of your impact on others. This is most profound where you have individuals in their 6th decade (50+) where there is a lot going on that is rarely discussed or properly delved into in terms of stability within the family system; menopause, children leaving home, ageing parents, and health concerns.  This complexity is felt, experienced, and often avoided. Exploring it with a coach is hugely beneficial as well as being normalising.   The coach can help them better understand their system and their part in it so that it works better for all parties.  

Furthermore, these professional discussions lead to decisions that align with the individual’s values and principles.  As well as being constructive as part of the financial decision making, this alignment increases the overall happiness around time spent enjoying the wealth they have created, enhances a sense of purpose in the activity and generally sees improvements across their relationships.

What distinguishes mindset coaching from other forms of support or counselling that individuals might consider during their retirement or post-sale journey?

Typically, counselling looks to the past and can be focused on something that isn’t working that might be trauma related.  The training and qualifications equip these professionals with what they need to support clients dealing with trauma and are different to the training and qualifications required for accredited coaches.

Where counselling tends to look backwards, coaching is focused on the future and is positively framed around solutions and about moving towards something different, more, or better.  As practitioners, we might reference the past and what got an individual to where they are now, but it is pertinent to answering the question ‘Where do you want to go now and what’s in that for you?’.  

This is apposite when it comes to handling endings – end of career, end of CEO role – and deals with the emotional and psychological tumult of letting go because mindset coaching looks at that in the context of framing new beginnings and driving forward momentum.

Finally, what one piece of advice would you give to someone transitioning into retiring or selling their business?

It is vital to recognise this as one of the most potentially challenging transitions in their lives and so the encouragement is to get ready for it.  Start thinking about this sooner rather than later and get ahead with the planning.  

Whether they’re retiring or exiting their business, the challenges are complex, from a sense of self and belonging to their role and position in the family and wider social network.  There’s a lot to consider and it’s better handled with purpose than arrived at by accident.


As can be seen from the answers above, achieving a successful retirement takes planning well beyond an individual’s finances.  If you are seeking advice on transitioning to the next stage of your life, please do get in touch, we would be happy to help.

Mark Estcourt

CEO at Cavendish Family Office

Mark Estcourt, CEO
Cavendish Family Office
Sarah Chaplin-Lee,
Mindset Coach

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