Retirement Coaching with US Populations: Supporting Clients to Define Routine, Structure, and Community after Full Time Work

By Jennifer Landis-Santos

A 2023 Retirement Confidence Survey (EBRI, 2023) found that US workers’ confidence that they will have enough money to last through retirement has declined. In the Holmes-Rahe Life Stress Inventory, retirement is in the top ten life stressors (The American Institute of Stress, n.d.). Transitions such as retirement can be disorienting because significant elements that individuals get from work are altered and need to be recreated, reshaped and absorbed into life in new ways.

Other than the adjustment to not receiving a regular paycheck, the questions people often bring to a retirement coaching conversation typically include:

  • How do other people do this?
  • What do I need to know that I don’t know?
  • How do I find a sense of purpose?
  • Who am I when I’m not working?

Together, these questions can be organized into three elements that contribute to well-being: community, routine, and structure. Career professionals can use these guideposts to help their clients articulate a healthy and meaningful new life chapter, reducing the stress of the retirement transition. This article will explore those elements, with the caveat that the term retirement can mean different things to different communities so it is also beneficial to examine the practices of different cultures in navigating the transition from work to what comes afterwards (Luborsky et al., 2003).

Community / Connection: Belonging. Most people do not realize the social interaction that comes from work until they no longer have it. Depending on how much people work, especially “brain for hire” types such as attorneys, C-suite executives, engineers, and those in finance, work may be a significant part of the social circle. Some individuals may really struggle with who they are as a person outside of their work identity and therefore struggle to fit in with other social circles. Social connections increase protective factors such as physical and emotional wellbeing by fostering meaningful daily interactions while reducing isolation and anxiety, and can serve as a protective factor against dementia (Gardener et al., 2021)

Routine / Self-care: The patterns and habits people create to take care of themselves are important, and the order they happen in also helps establish them as pillars in daily life. These small elements add up to influence overall health. Daily elements for many people include a regular morning beverage, catching up with the news, prayer/meditation, taking care of a pet, learning a language, talking with a loved one, doing a puzzle, going for a walk, etc.

Structure / Purpose: Similar to routine, there is an element of predictability in structure; however it is different, because there is a built in nuance of accountability. If you don’t show up for work, someone will be looking for you, which is not usually the case as you craft personal routines, which lean towards more internal goals and rhythms. Structure implies a connection to others where you are expected to show up - they will notice if you are missing, which often provides a sense of purpose.

Istock 1703087800 Credit Liudmila Chernetska

How Career Professionals Can Help Reduce the Stress of the Retirement Transition

Support clients to engage with community and a sense of connectedness: As clients begin envisioning life after retirement, explore with them current social connections, and if they would benefit from widening their social circle outside of the office. Facilitate an exploration of where and how they may find and connect to others with shared values and goals. Help them discover how connected they are to neighbors, hobbies, fitness and sports groups, social or political causes, a faith community, learning communities, etc.

  • Explore the adjectives clients may want to use to describe themselves in this new life chapter. Suggest ways to connect to those with shared values and commitments and bolster these newly blooming and desired identities outside of work.
  • Encourage clients to consider the benefits of connecting to peers who are equals and who can understand where they are in life on a deeper level, rather than someone who may need something from them (such as family).

Support clients to establish routine and self-care: As career professionals talk with clients about the retirement transition, it is important to explore what kinds of self-care elements are already incorporated into the client’s day. Some clients have a routine established for the morning but find themselves adrift in the afternoon. Focusing on identity, interests and values in this new life chapter, maybe they can incorporate a new afternoon stop, like a visit to a library, a park, or a local coffee shop. Connecting their motivation to the type of person they want to be, to their “why,” may be useful for some clients. However, James Clear, well known for his Atomic Habits work cautions: “You do not rise to the level of your goals, you fall to the level of your systems” (Clear, 2020, para. 1). Therefore, it is essential that career professionals help clients craft realistic, do-able goals for the creation of a longer term routine for physical and emotional well-being.

  • If clients seem to need accountability with their routines, consult Gretchen Rubin’s Four Tendencies (2017) to help realize realistic goals based on how they deal with inner and outer expectations.
  • With exercise, sometimes it can be all or nothing for some people; perfectionism and avoidance may set in. Suggest pairing tiny habits (Fogg, 2021) with fitness goals - such as jumping jacks, push ups, etc. with something already established in the client’s daily routine - like waiting for a beverage to brew, riding in an elevator, getting the mail, etc. 
  • There are important emotional well-being side effects from being in a flow state several times a week, where you are so engrossed in what you are doing, you lose track of time (Kotler et al., 2021).

Support clients to identify structure and purpose: Work with a client centers around how to describe this new chapter of life. Volunteering in retirement can be one way to get purpose and structure, however there are also more regular daily options, such as exercising with a friend, participating in a class, taking care of a family member, belonging to faith communities, etc. Recognizing what clients are interested in, ready for, and motivated to accomplish will help them make realistic goals and commitments around structure.

  • Discuss what adjectives they want others to use to describe them. What activities, communities, and locations match that description?
  • Identify who depends on them for small things - it can be simple like helping a neighbor get their mail, a basic volunteer role with a house of worship, checking in on a family member regularly, etc.
  • Support clients to get plugged in to ongoing, regular enjoyable opportunities. Make a list (for example, “One Day”) to keep track of the things you say you would like to do “someday.” What are the patterns and themes present here?
  • Encourage clients to explicitly think about how to take things “to the next level.” For example, maybe they attend neighborhood association gatherings, but now they can be more engaged.

Life After Full Time Work

In the US, there is not a lot of societal support for the retirement transition. Everyone is different and the on-ramp to retirement varies from person to person. For instance, 52% of pre-retirees in the Retirement Perspectives and Attitudes Survey (Gilbert et al., 2023) responded that they believed the transition to retirement would be smooth. By contrast, only 32% of those retirees surveyed said it was. Helping clients manage their expectations about this significant life transition by providing concrete tips on the elements of community, routine, and structure will support them to facilitate and realize a smoother landing into an enjoyable new life chapter.



Clear, J. (2020). 3-2-1: On systems vs. goals, identity-based habits, and the lessons of life. https://jamesclear.com/3-2-1/january-2-2020

Employee Benefit Research Institute. (2023, April 27). 2023 Retirement confidence survey. https://www.ebri.org/retirement/retirement-confidence-survey

Fogg, B. J. (2021). Tiny habits: The small changes that change everything. Harvest. https://tinyhabits.com/

Gardener, H., Levin, B., DeRosa, J., Rundek, T., Wright, C. B., Elkind, M. S. V., & Sacco, R. L. (2021). Social connectivity is related to mild cognitive impairment and dementia. Journal of Alzheimer’s Disease, 84(4), 1811-1820.

Gilbert, F., & Weigel, E. (2023, May 1). Retirement perspectives and attitudes survey. Retire with Possibilities. https://www.retirewithpossibilities.com/wp-content/uploads/2023/05/Retirement-Perspectives-and-Attitudes-Survey-May-2023.pdf

Kotler, S., & Sanders, F. (2021). Art of impossible: A peak performance primer. Harper Collins.

Luborsky, M. R., LeBlanc, I. M. (2003). Cross-cultural perspectives on the concept of retirement: An analytic redefinition. Journal of Cross Cultural Gerontology, 18(4):251-71. https://doi.org/10.1023/B:JCCG.0000004898.24738.7b

Rubin, G. (2017). The four tendencies: The indispensable personality profiles that reveal how to make your life better. Harmony. https://gretchenrubin.com/four-tendencies/

The American Institute of Stress. (n.d.). The Holmes-Rahe stress inventory. https://www.stress.org/holmes-rahe-stress-inventory-pdf



Jennifer Landis SantosJennifer Landis-Santos, MA, CCC, PCC, NBC-HWC, works in house with Cassaday & Co. Inc, a financial planning firm, and supports clients with career and life transitions such as retirement. She is on the faculty of Georgetown’s Institute for Transformational Leadership and is the founder of Career Wellness Group, https://www.careerwellnesscheckup.com/, where their team of coaches supports individuals at all points of the career arc. She can be reached at https://www.linkedin.com/in/jenniferlandissantos/ or jennifer@cassaday.com

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Jim Peacock   on Thursday 12/07/2023 at 01:07 PM

Transitions can be difficult for many of us. I love how your article breaks down the various aspects of this transition with specifics on how to help our clients.
Schlossberg's Transition theory speaks to the changes in Roles, Relationships, and Routines and the impact they have. You have also highlighted many of these. Thanks

Al Rider   on Saturday 01/06/2024 at 01:18 PM

Your breakdown of retirement issues into 3 categories (community, self-care, & purpose) is very helpful. Under "PURPOSE", you might want to add that there are groups of conscious post-retirement elders who focus on naming and claiming PURPOSE, and who promote accountability, self-care, and community by developing online relationships. Two among these (...and I'm active in both, BTW...) would be found at: www.sage-ing.org and www.centerforconsciouseldering.org . Both are international and non-dogmatic in terms of culture and religion, and welcome all comers.

Disclaimer: The opinions expressed in the comments shown above are those of the individual comment authors and do not reflect the views or opinions of this organization.