Many of us think if we’ve got enough money… retirement is going to be really easy. 

After all, if you know you’ve got enough financially, every other worry pales into comparison. 

But here’s the thing. There’s a retirement challenge we never seem to talk about. One which for so many of my clients has been one of the most difficult parts of them navigating the next chapter of our lives. 

That’s working out who we are in this next chapter. If you encapsulated it in one word… it’s identity. 

So, in this blog, I want to talk about the greatest challenge we never talk about when thinking about retirement, the fundamental shift in our identity, and the 7 steps you can take to prepare for this challenge today. 

I remember it vividly. It’s one of my most memorable days in the office I’d ever had. 

I’d been working with this particular client for coming up to three years. When this client has originally started working with us he told me he wanted to understand how financially independent he was. 

This particular client had done pretty well financially. He’d built enough wealth, based on the assumptions we’d used and using the amazing planning tools we’ve access to, to tell him he’d never run out of money again. 

However, three years after I’d highlighted how financially independent, he was this guy was still heading into the office every day, doing a job he didn’t particularly enjoy anymore… and I was confused! 

That’s when it happened… 

I’d asked him why he continued to work despite me knowing he was relatively financially independent AND didn’t like his job. 

He looked me straight in the eye and said this… 

“What am I if I’m not the managing director of this business” 

This particular client isn’t alone.  

I’ve worked with a number of clients over their years who have achieved financial independence by pouring their heart and soul into work and then came to a realisation that their jobs were such a part of their identity it was difficult to let go. 

So I think we all need to be honest with ourselves – retirement (or semi-retirement) isn’t the endless holiday it’s often made out to be. Yes, you may be financially secure but emotionally and Psychologically there are still significant challenges… with the main one for many of us facing challenges with how our identity is shifting. 

The good news is evidence also points to the fact you’re not alone… In fact, a 2020 Stanford Center on Longevity study found many retirees feel lost within 18 months of leaving work – not because of money worries, but due to a loss of identity. We spend decades building a professional identity, so when it goes, it can leave a gaping void.  

If you’re nodding along, the first step is to know that what you’re experiencing is completely normal. But here’s the thing… while traditionally our culture encourages a “Keep Calm and Carry On” stiff-upper-lip attitude to these things, it’s also worth saying that it’s okay to admit that this transition is hard and find help if we need it. 

So, In this article – we’ll explore why losing your professional identity at this stage of life is so challenging and then walk through 7 actionable steps to prepare for “what happens next.”  

So, Why Identity Loss in Later Life Hits So Hard? 

“So much of my personal identity is tied up with my profession. How would I define myself without it?” This poignant question from a 63-year-old professor, writing recently in the guardian, encapsulates the dilemma.  

For a lot of us, work isn’t just what we do – it’s a huge part of who we are. Over the years, your role gave you structure, purpose, and a sense of being needed. You had workmates to laugh with, problems to solve, goals to chase. In retirement, all those reinforcing signals vanish overnight. 

There’s even a term psychologists use: “identity foreclosure,” when someone’s sense of self is overly defined by one role for too long. Sound familiar?  

It happens to Olympic athletes, military personnel, surgeons – and yes, C-suite executives too.  

Dr. Ed Etzel, a former Olympian turned psychologist, put it perfectly: “People devote their entire lives… and who are you when you are not doing what you have been doing for a long time? And who are you when you haven’t defined yourself in another way?” 

When your LinkedIn headline reads “Retired,” it’s common to stare in the mirror and quietly ask, “Who am I now?” 

Our society doesn’t train us for this emotional upheaval. We get tons of advice about pension funds and “don’t blow your ISA allowance,” but little guidance on the psychological side of retirement 

Many people, who have acheived pretty significant things in their careers and lives, are caught off guard by feelings of disorientation, as if something is wrong with them. (Spoiler: nothing’s wrong with you; you’re just human.) 

In fact, the National Institute on Aging reports that rates of depression can increase significantly in the first few years of retirement It’s not hard to see why: the ingredients of good mental health – “having a community, positive relationships, something to contribute, and a balance of autonomy” – were often baked into our careers, and must be consciously re-created in retirement. 

Take heart, though. Hard does not mean bad. With the right approach, this can also be one of the most meaningful and vibrant chapters of your life. Let’s shift from why it’s challenging to what you can do about it. Below are seven steps – part practical, part emotional – to help you prepare for “what happens next” and redefine yourself beyond the job title. Think of them as a friendly toolkit to carry with you into your post-career adventure. 

My first tip is to appreciate that work can continue if you want it to. 

Conventional retirement, where we stop work at a specific age, is a relatively modern concept. 

For thousands of years before the industrial revolution we continued to work for as long as we could. 

So, if you love to work, appreciate the fact that you don’t actually need to retire… especially if you love what you do! 

Now, my experience is that often when people reach a certain time in their lives they do reassess their relationship with work and might decide to work less… particularly if they’re not enjoying what they do. 

However, step one, I believe, is to appreciate the fact that you have a choice in continuing to work or not regardless of your age. 

I’ve got clients who continue work not because of the money, but because it gives them intellectual stimulation, a sense of purpose and much more. 

We’ve also got a choice to change what we do for work and there are so many people I’ve met who have reinvented themselves in their 50’s and 60’s and now absolutely adore the work they do… so appreciating the fact that this is also a choice is important too. 

However if you have decided that you don’t want to continue to work for much longer because you’ve got other plans it’s also worth appreciating that you haven’t got to stop work permanently on the Friday and sit twiddling your thumbs on a Monday! 

That’s why my 2^nd tip is to appreciate the fact that retirement, if that’s what you want to do can be a gradual process instead of a cliff edge. 

When I’m working with my clients at Cervello we often describe the journey to retirement as a flight path instead of a cliff edge and why this is often a smoother more gradual route to the next stage of your life than simply stopping immediately. 

Now, if you want to dig a bit deeper into the flight path concept I’ve done an entire video on this subject and you can find this here

My next tip sound simple but often my experience is that we all need a reminder of this fact… 

You are not your job. 

When we reach our 50’s and 60’s it’s an opportunity to gently untangle who you are from what you did for a living…when often these things are for a lot of us tightly woven together. 

The process of re-exporing who you are beyond work might start with a number of questions. 

What do I value? 

What are my personal values? 

What do I enjoy doing? 

What skills can I use beyond work? 

The skills, knowledge, attributes and qualities you’ve build throughout your life don’t disappear when you change careers. 

Maybe you were admired for being a great mentor at work; that mentoring can continue, whether it’s coaching young entrepreneurs or guiding your grandchildren. Maybe your strategic mind can be put to use on a non-profit board, or your knack for organizing could transform a chaotic local committee. Make a list of your top skills and passions – those are the building blocks of your new identity. 

A useful concept here is what researchers call “identity bridging,” which means carrying pieces of your pre-retirement identity into post-retirement life. 

Think about what aspects of your work made you feel most you. Was it the problem-solving? The social connections? The intellectual challenge? Find ways to bridge those into your next chapter. For instance, a retired teacher might start tutoring kids a few hours a week, maintaining that sense of being an educator. A former business owner might advise startup. You’re crafting a continuity of identity even as the context changes. 

Also, let’s tackle the ego: for many, losing the fancy title or the status is a blow. It can feel humbling to go from being “Someone Important” to just another person in the Post Office queue (don’t worry, you’ll master the art of patient queuing – it’s practically a British Olympic sport). Remember that your worth is not conferred by a title or a paycheck. Marcus Aurelius, the Stoic philosopher-emperor, advised himself: don’t fear “ceasing to live” (i.e. the end of one phase), fear “never beginning to live properly”.

In other words, the real failure would be clinging so tightly to your old identity that you never give the new you a chance to live. You have nothing to prove anymore. How liberating is that? 

So, rewrite your personal narrative. Instead of “I was an attorney,” try “I’m a curious learner, an advocate, and now exploring new avenues.” Instead of “I ran X company,” maybe “I’m someone who loves challenges and now I’m free to tackle different kinds.” This isn’t just fluff – it’s a mindset shift. You’re not starting from scratch; you’re starting from experience, with a whole toolkit of skills and wisdom. The roles may change, but the person – you – remains, ready to evolve. 

My fourth tip is to ensure you’ve got a plan for your ‘what happens next’ life… 

One way to soften the identity whiplash is to plan the transition thoughtfully. Often at work we  plan everything, yet many retire without a plan. Even if we have planned we’ve done the financial bit and ignored the various challenges we face in this chapter of our life.  

I was recently in Portugal with friends playing Padel Tennis and had a brilliant conversation with a bloke called Bob. Bob has produced his own ‘what happens next’ planning document called the second life stage assessment and it included everything he has to ask himself in the next chapter of his life. 

Now, we’re going to be launching something at the start of 2026 to help you go through this journey and my recommendation is if you think you’re going to need a bit of help with this feel free to join the waiting list for the What Happens next book which will also mean that you’ll get updates on everything we do on What Happens next… but you can also, like Bob, do this yourself. 

If you want to use the What Happens next wellbeing model as a framework in the areas you need to improve feel free… but Bob’s document also had some brilliant parts. 

Bobs document for example had a financial assessment, a relationships assessment, a physical and metnal health assessment and a digital life assessment… elements you do want to include when you’re thinking about your next step. 

My fifth tip is to give yourself permission to experiment. Retirement is not one-size-fits-all; in fact, a major study found “there’s no one right way – some people work part-time, some start second careers, some volunteer, others focus on family”.

You might try a bit of each until you find what fits. Think of the first year or two as a prototype phase for your new life. You’re allowed to pivot. You might discover, say, that consulting in your old industry keeps you too tied to the past – so you pivot to something entirely different, like writing a book or learning to paint. Pace yourself and stay flexible.  

There’s no rush to have it all figured out on Day 1. As the Stoics would remind us, one step at a time is all anyone can take in the present moment. 

If your identity was very tied to feeling useful, find small ways to get that fix. Fix a neighbour’s leaky faucet, help your grandson with his CV, or organize a charity drive. Tiny contributions can remind you that you still have it – that competence and value – outside a paid job. 

My 6^th tip is to build yourself a new routine. 

Now if you find yourself, about a month into retirement,  lounging in pyjamas at 11 AM, watching Homes Under the Hammer in the background, and thinking, “This is great… or is it?” then this might be a bit warning that you need a bit more routine in your life! 

The initial novelty of no schedule can give way to a sense of aimlessness.  

Humans are creatures of habit and whilst it’s lovely to have freedom and flexibility, too much can become “deadly” for our mental health 

Now, your new routine should not feel like a straitjacket or a replica of your old 9-to-5. Think of it more like a scaffold or a rhythm.  

My recommendation. Make a habit of the basics. sleep, exercise, and self-care. 

My recommendation is to read the book “Atomic Habits” by James Clear for a deep dive into how positive habits contribute to both our identity and a life well lived. 

However, balance is key. The joy of this chapter of your life is it’s likely you’ll have a bit of freedom from overly rigid schedules, so keep it flexible and enjoyable.  

If you wake up one Wednesday and the sun is shining gloriously , you can bin the planned chores and take a spontaneous day trip to the seaside. This is the perk of your new life – spontaneity. Your routine exists to serve you, not chain you. Think of it like jazz: you have an underlying rhythm, but you’re free to improvise. 

My last tip is to ensure you build both community and connection into the next chapter of your life. 

One of the toughest aspects of leaving a career is the sudden shrinkage of our social universe.  

The office can be like a second family (dysfunctions and all), and even if you were glad to leave behind meetings or office politics, you might deeply miss the camaraderie – those watercooler chats, team achievements, or even the daily banter about last night’s telly.  

We are social creatures, not meant to do life in isolation so putting the work in to build relationships is really important! 

So, a critical step in your next chapter is actively building community.  

This can feel awkward initially. 

But my experience, both in my life and in my clients, is that you’d be surprised how many others are also seeking connection.  

Start with your existing circles: rekindle friendships that got the short shrift during your busy career years.  

Beyond that, seek out groups of like-minded people. Thankfully, there are many to choose from, especially in the UK. You might join a local ramblers group if you enjoy walking, a book club at the library, a wine-tasting class (finally put that refined palate to use), or a sports club   

One community I really love is the Men’s Sheds Association – communal workshops where blokes can make and mend things together. Those have been hugely successful: in one survey of 500 “shedders,” 90% said they felt less lonely, had more friends, and were less depressed after joining a Shed and 88% felt more connected to their community.  

That’s a ringing endorsement for the power of connection. 

The bottom line: don’t go it alone. Isolation can creep up if you don’t intentionally counter it. It might require stepping a bit out of your comfort zone to join new groups or strike up conversations, but the payoff is huge. As the African proverb goes, “If you want to go fast, go alone. If you want to go far, go together.” You have many years ahead – go together. Laugh, share, belong. Whether it’s commiserating over Arsenal’s latest match or discussing Marcus Aurelius at a philosophy meetup, find your people. Community will be one of the pillars that holds you up in life’s next act, just as it was (in different form) back in your working days. 

My bonus tip is to embrace impermanence… 

If there’s one thing philosophy (and life) teaches us, it’s that change is the only constant.  

Your professional chapter may be over, but life itself most certainly is not. In fact, this stage of life can be profoundly enriching once we accept that it’s different, not lesser.  

Stoic philosophy, which has guided thinkers for millennia, offers some comforting wisdom here. The Stoics remind us to focus on what we can control and accept what we cannot.  

You cannot control the fact that time marches on – that you’ve aged, that industries evolve and younger folks have taken the reins. But you can control your attitude and actions in response.   

It is important to remember that embracing impermanence also means acknowledging realities. Health issues may arise; loved ones may pass; the world will continue to change rapidly. Stoicism teaches us to prepare our minds for challenges (the Stoics practiced a kind of negative visualization – imagining hardship to lessen its sting). Without dwelling on doom, it’s wise to accept that this life stage has its hardships and its beauty. You might not have the energy of your 30s, but you have far more wisdom. You may not be building a career, but you’re free to build legacy and relationships in a way you never could when you were knee-deep in spreadsheets. Embrace the gains of this stage, not just mourn the losses. 

So, they are my tips to renavigate your identity when you’re thinking about ‘what happens next’ but I’d love to know yours. What are the things which you believe are important when thinking about identity change in our 50’s and 60’s which I’ve missed? I’d love to know so feel free to comment! 

If you’re interested in hearing more about what Philosophy can teach us about our ‘what happens next’ you can find our video on what the Taoists can teach us about retirement here…. 

…and you can find the video I mentioned about ‘falling off the retirement cliff’ here.