How to Embrace Retirement

Retirement is often envisioned as a well-earned opportunity to relish the fruits of one’s labour, a time to unwind and perhaps savour life’s simple pleasures. At least, that’s how it’s often portrayed. However, in my experience, retirement often unfolds quite differently. 

Many anticipate that retirement will provide the ultimate freedom to enjoy life, offering an abundance of time to pursue personal interests without constraint. However, from both the people I’ve worked with and my own personal journey, I’ve seen that the boundless freedom of retirement can sometimes leave people feeling paralysed.

Retirement is a Blank Canvas

I like to think of retirement as a blank canvas.

Picture standing in front of that blank canvas after years of painting by numbers. For decades, your life followed a set pattern, dictated by your career, fulfilling expectations, meeting demands, and following the lines laid out for you all set within the parameters of a daily routine. But now, in retirement, you’re holding the brush, free to create whatever picture you choose. There is no predefined path, no right or wrong—only the liberating opportunity to explore and let your imagination guide you.

Yet, this freedom can also be overwhelming. Without the “numbers” to follow—no clear structure, set routines, or pressing deadlines—the prospect of starting anew may feel daunting.

Having so much time on your hands can create a sense of confusion, making it hard to know where to start. After dedicating so many years to a structured career and daily routine, many people find they no longer know what they actually enjoy or what they want to do with their time. Moreover, the new lack of purpose and sense of value they enjoyed during their working life can result in feelings akin to grieving or loss and become very difficult to adjust to.

The Challenges You Might Face

Retirement does offer exciting new opportunities but it also brings its share of challenges. These can include the loss of identity, the disruption of routine, social isolation, diminished use of skills, shifting family dynamics, and the emotional toll of so much change. Some of these challenges can feel unexpected—suddenly finding yourself without a title or the familiar structure of daily work can leave a void that is difficult to fill.

The loss of professional identity is a particularly common struggle I have observed. After decades of being known for a job title or career achievements, or leading a team, it’s easy to feel like you’re no longer “someone.” And for many, the lack of structure can feel like free-falling into the unknown. 

I’ve explored these challenges in more depth in a previous post, which you can read here.

In this specific article, I want to zoom in on one particular challenge: how to answer that looming question—What’s next? How do you transition from staring at a blank canvas to creating a fulfilling and meaningful retirement?

1. Acknowledge the Fear

It is entirely natural to feel uncertain or uneasy about not knowing what you want to do after retirement. After years of being defined by your work, admitting you have no immediate plans or aspirations beyond your career might make you feel embarrassed or unsure of yourself. But this is not a problem—it’s a starting point. Recognise that this blank slate is an invitation to explore, not a test you need to pass right away.

Embrace both the freedom and the discomfort that accompany this transition. It is perfectly acceptable not to have all the answers right away. Allow yourself the time and space to reflect, experiment, and recalibrate as you discover what brings you joy and fulfilment.

2. Drop the “Shoulds”

Many retirees feel pressured to spend their time in ways deemed “worthy” by societal standards—whether that means giving back to the community, dedicating time to family, or pursuing meaningful hobbies. This can make it easy to lose sight of what genuinely matters to you.

What if you removed the “should” from the equation? Retirement is a rare opportunity to prioritise your happiness unapologetically. After decades of meeting deadlines, raising a family, and striving for professional success, there’s nothing wrong with focusing on what makes you happy. 

If you feel drawn to something “worthy” but are unsure what that might look like, take a moment to define what “worth” means to you. For some, it could be volunteering or mentoring; for others, it might involve investing in personal growth, family relationships, or creative pursuits. Remember, there is no one-size-fits-all approach to a meaningful retirement. Even if your goal is to master a new skill or simply enjoy life’s pleasures, if it brings you joy, it is worthwhile.

3. Experiment and Explore

The best way to discover what you want to do in retirement is to try new things. Treat this phase as a series of mini-experiments. Exploring different activities and projects can help dispel fear and uncertainty.

Set a goal to explore two or three new interests each year. This might involve taking a class, volunteering, or joining a new group. The aim is not to commit to a single pursuit immediately but to rediscover the joy of learning and experiencing new things.

Begin with small, manageable goals. For instance, take a pottery class, go on a weekend trip, or start journaling. Give yourself permission to explore without the pressure of needing immediate results.

4. Reconnect with Your Strengths

Part of the challenge is remembering who you are outside of your career. Tools like StrengthsFinder can be incredibly helpful in reintroducing yourself to your natural abilities and preferences. What are you naturally good at? What energises you? Reflecting on these questions can guide your exploration and help you focus on activities that align with your strengths and values.

It can be easy to forget what you love or what you’re good at once you’re no longer in the workforce. Take time to reconnect with those things. What skills or hobbies did you enjoy before your career became the focus of your life? Rediscover those, and start making them a part of your retirement.

5. Partner with your partner

One of the greatest joys of retirement is the opportunity to spend more quality time with your spouse or partner. This phase of life allows you both to discuss and explore activities you enjoy together—and perhaps discover new shared interests. However, it’s important to recognise that your partner may need time to adjust to having you around more often, just as you might need to adapt to this new dynamic. Take the time to agree on boundaries, responsibilities, and ways to support each other. With a little patience and open communication, I hope that you will feel that retirement has taken your relationship onto an exciting and very rewarding new plane.  

6. Enlist Support

Sometimes, figuring out what comes next can feel overwhelming. This is where a coach or mentor can make a difference. A coach can guide you through the options, help you work through challenges, and provide a structured approach to make the most out of your retirement. 

So, don’t feel like you have to do this alone. Seek out a professional who can help you navigate this period of uncertainty and help you create a roadmap for your next chapter. 

Retirement is not the end of productivity or purpose—it is an opportunity to redefine them on your own terms. By letting go of societal pressures, exploring new interests, and reconnecting with your strengths, you can create a retirement that is not only as fulfilling as your career but perhaps even more so.

If you are navigating this transition and seeking guidance, I am offering FREE 30-minute consultations. These one-on-one sessions are designed to help you identify the support you need as you embark on this new chapter. Click here to book your session.

Hello, I’m David Webster. After a rewarding 35-year career as a lawyer and businessman, I transitioned into business and leadership coaching. I offer… 

• Leadership and executive coaching
• Career progression and performance coaching at all levels
• Supporting professionals as they navigate and transition smoothly into retirement

Even the most successful professionals can benefit from support to reach their highest potential. Coaching helps individuals at all levels overcome challenges and navigate change effectively.

To learn more, visit here. Or if you’d like to have a quick chat, feel free to book a FREE 30-minute coaching consultation here.