From Boomers to Gen Z: How Each Generation Tackles Life’s Biggest Transitions

Discover the Surprising Ways Different Generations Cope with Change—and What We Can All Learn from Each Approach

The scene: Four friends from different generations are sitting around a table at a coffee shop, catching up on life.

Baby Boomer: [sighs and stirs their coffee] “You know, I was raised to believe you stick it out, whatever life throws at you. When I hit that rough patch in my forties? Kept my head down, worked harder, pushed through. Life transitions… you just deal with ‘em and get on with things.”

Gen X: “I get that. I mean, my parents didn’t exactly roll out the therapy fund. When I hit a big transition, I lean on self-help books, maybe take a solo trip to ‘find myself.’ I’m not against talking it out, but at the end of the day, I handle my stuff myself. You gotta be able to stand on your own.”

Millennial: [grins] “Oh, I’m all about talking it out. I’ve got a group chat, my therapist on speed dial, and about five podcasts queued up with advice on handling change. Life transitions are practically a generational sport for us. And if all else fails, I’ll crowdsource help on Instagram—who knows, maybe I’ll turn it into a blog.”

Gen Z: [laughs] “Yeah, but why go through all that when I can just reinvent myself? Job loss? I’ll switch fields. Tough breakup? Try a different age group. Honestly, it’s about embracing change on my terms. Life transitions are just invitations to change myself into someone even cooler. Plus, I know like three apps that’ll help me make a vision board in under ten minutes.”

Baby Boomer: “Reinvent yourself? Back in my day, a transition was about stability. You built a foundation; you didn’t just switch gears whenever things got tough.”

Gen X: [nods] “I get that. But I also see the point in mixing it up when life throws a curveball—sometimes you just need a change. I’ll do the work if I need to, but I want that freedom, too.”

Millennial: “I think it’s about finding support for whatever comes up. Community, therapy, friends, self-care—all of it. I mean, why go it alone if you don’t have to?”

Gen Z: [shrugs] “Or you just go full chameleon. Adapt to whatever the next phase demands. Life’s short; I’m here to enjoy it, not overthink it. Reinvention is just part of the game.”

Recently I was chatting with my friend Paula about the generational cohorts: Baby Boomers, Gen X, Millennials etc. She is a Baby Boomer, and I am Gen X, but we weren’t sure of the younger generations, so I looked it up:

Baby Boomers (Born 1946-1964)

Baby Boomers were born during the post-World War II baby boom, a time characterised by significant population growth. This generation is known for its optimism and competitiveness, often driven by a strong work ethic and a focus on career advancement. Baby Boomers value personal growth and self-expression, having been politically active and socially conscious throughout their lives. While they have adapted to technology, they are not considered digital natives, often preferring traditional forms of communication.

Generation X (Born 1965-1980)

Generation X grew up in the shadow of the Baby Boomers, experiencing significant societal changes. This cohort is characterised by its independence and self-reliance, often displaying scepticism toward authority and institutions. Gen Xers value work-life balance, seeking fulfilment in both their professional and personal lives. They are technologically adept, having witnessed the rise of the internet and personal computing, which has shaped their pragmatic and resourceful approach to challenges.

Millennials / Generation Y (Born 1981-1996)

Millennials, also known as Generation Y, came of age during a period of rapid technological change and globalisation. This generation is recognized for being digital natives, comfortable with technology from an early age. Millennials tend to value experiences over material possessions, prioritising travel and personal development. They are socially conscious and diverse, often advocating for social justice issues. Collaborative and team-oriented, Millennials appreciate frequent feedback and opportunities for career development.

Generation Z (Born 1997-2012)

Generation Z is the first true digital native generation, having grown up with smartphones and social media as integral parts of their lives. Key characteristics of Gen Z include an entrepreneurial mindset and a pragmatic approach to life. They are financially conscious, having witnessed economic uncertainty during their formative years. This generation values individuality and diversity, often expressing concern about social and environmental issues.

Generation Alpha (Born 2013-Present)

Generation Alpha is the newest generation currently developing, with many members still in childhood. Early observations suggest that they will be the most technologically immersed generation yet, growing up in an era of advanced digital innovation. Generation Alpha is likely to be highly educated and globally minded, benefiting from increased access to information and resources. However, they may also face challenges related to climate change and economic uncertainty as they grow up in an increasingly complex world.

My retreats have a minimum age of 18, so I won’t see Generation Alpha until 2031.

The subject came up because I had recently hosted a From Troubled to Triumphant Transformational Retreat that helps participants find solid ground during a Life Quake and I noticed that my guests, who were from different generational cohorts, approached life transitions differently, based on their formative experiences, values, and characteristics. Thinking back, I tried to work out how their approaches differed and I came up with this (very unscientific) summary:

Baby Boomers (Born 1946-1964)

It seemed to me that Baby Boomers tend to approach life transitions with:

• Adaptability, and a certain resilience. Having lived through significant social and technological changes, Baby Boomers often fall back on past experience when they have to cope with major life changes.
• A strong work-centric mindset: Many Boomers define themselves by their careers, so retirement or job changes can be particularly challenging.
• Traditional values are important to them, they may rely on conventional wisdom and established institutions when facing transitions.
• Generally, Boomers maintain an optimistic outlook on life, believing hard work will lead to positive outcomes.

Generation X (Born 1965-1980)

Difficult to stereotype my own generation, but I’d say Gen X typically handles life transitions with:

• Fierce independence: Known for their self-reliance, the latch-key kids often tackle transitions independently, seeking solutions on their own.
• Pragmatism: We Gen Xers tend to approach major life changes practically, weighing pros and cons before making decisions.
• A careful eye on our work-life balance: Unlike Boomers, we’re more likely to prioritise personal life alongside professional life when facing transitions.
• A fair amount of scepticism: We may be more cautious about change, questioning authority and conventional wisdom.

Millennials (Born 1981-1996)

This is where it gets tricky. As far as I can gather, Millennials (GenY) often approach life transitions by:

• Seeking meaning as they’re more likely to view life transitions as opportunities for personal growth and are keen to find purpose in everything they do.
• Welcoming change. Millennials grew up with rapid technological advancements, and are generally much more comfortable with change.
• Collaborating – they may rely more on peer networks and social media for support and advice during transitions.
• Embracing new experiences: Millennials might focus on how transitions can lead to new experiences rather than material gain.

Generation Z (Born 1997-2012)

Gen Z is still very young, but it already looks like they will approach life transitions by:

• Leveraging technology, they’re likely to use apps, online resources, and social media to help them cope with change.
• Prioritising their mental health. Gen Z is much more aware of mental health issues and may well put their mental well-being first during transitions.
• Seeking stability: Having witnessed economic uncertainty, they may approach transitions with a focus on financial security.
• Valuing diversity as Gen Z tends to consider diverse perspectives and inclusive solutions as important even when facing life changes.

I did a bit more reseach, and discovered that while these are general trends, individual experiences can vary widely within each generation. Factors such as personal background, culture, and socioeconomic status also play significant roles in how people approach life transitions.

It quickly became clear to me that exploring life transitions through the nuanced lenses of each cohort really does reveal a fascinating interplay of values, adaptability, and resilience across generations. From the Baby Boomers’ foundation-focused perseverance to Gen Z’s pragmatic, fluid reinvention, each approach is a masterclass in handling change.

What’s particularly interesting is how these generational perspectives illuminate broader cultural shifts in how we handle uncertainty and redefine identity. Research increasingly supports that a blend of introspection, external support, and adaptability is essential in navigating major life changes effectively. Each generation brings unique insights into that mix, reminding us that while our tools for dealing with transitions evolve, the need to process and grow through them is universal.

Based on the generational characteristics and approaches to life transitions, I sat down and made a mind map (it’s a Gen X thing) of how I needed to change the way I host my retreats to make sure each generational cohort benefits equally.

Helping people from different generations through life transitions is not easy, but at least I now have a better understanding of why it is difficult and I can tailor my approach accordingly. I was thinking that the different generations could even learn from each other and support each other in unexpected ways.

Fascinating stuff.

So when I’m working with Baby Boomers, I’ll need to focus on helping them redefine their purpose, especially as they navigate retirement. I am already aware of this (and my) generation’s need to find their life purpose, and with my horses’ help I created the Rearing to Get Going in a New Direction: Finding Your Life Purpose Guided by Horses online course to help people gain the clarity, motivation and direction they need to manifest their next chapter – in both their personal and professional lives. (get immediate access) online. Many in this generation struggle with identity issues after leaving their careers, so I may need to create another course to help them explore new ways to find meaning and purpose beyond work. During my retreats, we discuss health and wellness activities to address their concerns about ageing and maintaining vitality and I leverage their vast life experiences by incorporating exercises that allow them to reflect on their past and use that wisdom to navigate current transitions. If I’m feeling particularly brave, I suggest updating their knowledge about technology so that they can stay connected and relevant in our rapidly changing world, as this can be a huge challenge for some Boomers.

With Generation X participants, like me, I tend to concentrate on work-life balance strategies. I help them develop techniques for managing career transitions while maintaining family responsibilities, as many Gen Xers are juggling multiple roles. We address concerns about financial security, especially for those caring for both children and ageing parents. I provide tools for managing stress and avoiding burnout, given the multiple responsibilities our generation often faces. I suggest resources for those contemplating career changes or starting their own businesses, as entrepreneurship often appeals to this independent-minded cohort.

I have found that Millennials attending my retreats often benefit from activities that help them find meaning in their work and help them align their career choices with personal values. We can focus more on increasing resilience and provide further strategies for coping with uncertainty in both their personal and professional lives. We can make time to address concerns about balancing career ambitions with personal relationships and family planning. Given the financial challenges many Millennials face, we may have to look for guidance on managing student debt, investing, and long-term financial planning.

For Generation Z, I will discuss strategies for managing anxiety, and stress, and maintaining good mental health during transitions, as this generation tends to be more open about mental health issues and keen to talk about them. I’ll incorporate activities, with the horses, that facilitate face-to-face connections and create time away from their screens, providing a balance to their digital-centric lives. I could suggest resources for continuous learning and adapting to a rapidly changing job market, addressing their concerns about future career prospects. We could talk about aligning their personal and career goals with their desire to make a positive impact on society, as social consciousness is often a key characteristic of this generation.

If my retreat group is multi-generational, I’ll include some group activities to foster understanding and knowledge sharing between generations. It makes sense to use a mix of traditional and digital tools to cater to the varying technological comfort levels. I already provide resources and support for participants after the retreat to help them implement what they’ve learned. At dinner most evenings, and especially after Camino de Santiago walking days, participants share their experiences and learn from each other’s transitions – storytelling is a powerful processing tool for all generations.

I(‘m hoping that by tailoring my approach to each generation’s unique characteristics and concerns, I’ll host more impactful life transition retreats that resonate with participants across all age groups. Of course, while these generational trends provide a helpful framework, individual experiences can vary widely, so I’ll have to remain flexible in my approach to accommodate personal differences.

One thing I have learned during the decade that I have been hosting retreats is that, as a host, you never stop learning.

Research

As the ability to cope with life transitions is basically determined by how effectively we handle stress, I looked at studies that compared the stress management strategies of the different generations:

• A 2012 Penn State study found that Gen X had significantly higher stress levels than other age groups, reporting an average stress level of 5.8 out of 10. This was notably higher than Millennials (3.4) and Baby Boomers (4.4).
• The American Psychological Association’s (APA) 2012 Stress in America survey corroborated these findings, showing that both Gen Xers and Millennials reported an average stress level of 5.4 on a 10-point scale, higher than Boomers (4.7) and Matures (3.7).
• More recent data from 2021 shows this trend continuing, with 22% of Gen Xers confessing to struggling with stress daily, compared to 17% for Millennials, 14% for Gen Zs, and 8% for Baby Boomers.
• The APA study found that while all generations agree on the importance of managing stress, younger generations (Millennials and Gen X) report more difficulty in doing so effectively. Older generations (Boomers and Matures) are more likely to use strategies like getting enough sleep and attending religious services to manage stress. Younger generations are more likely to engage in potentially unhealthy behaviours like eating, drinking alcohol, and smoking to manage stress.
• Millennials and Gen Xers report experiencing more stress-related symptoms like lying awake at night (52% of Millennials, 48% of Gen Xers, compared to 37% of Boomers and 25% of Matures).
• 44% of both Millennials and Gen Xers report experiencing irritability or anger due to stress, compared to 36% of Boomers and 15% of Matures.

These studies highlight that while stress affects all generations, there are significant differences in stress levels, causes, and management strategies across different age cohorts. Gen X consistently emerges as the most stressed generation, likely due to their position in the life cycle and the unique challenges they face. Yep, that sounds about right.