The Key Question: Does Winning Matter?

Winning is a reward, an achievement. But if all you're thinking about is that finish line, you might lose the important lessons that were gained in the process.

Winning is important! It's something visible, a benchmark that teaches us and others about our effort and dedication. But if all you're looking at is that finish line, you might be ignoring the amazing ride that got you there.

Reflecting back on when I was a middle-distance runner, I now recognize that every race was not simply an opportunity to stand on the podium. It was a lesson in perseverance, teamwork, and self-improvement. My brothers and I trained with a competitive spirit that was not about defeating one another but challenging ourselves. We were part of a group of people who came together to build our city's track club. Every practice session, predawn morning jog, and training session as well as every loss or victory, helped determine our attitudes. It was only later, when I looked back, that I realized true victory was not in the win, but in the discipline, the improvement step by step, and the knowledge accumulated along the way. We did not celebrate when we lost, but we used the defeat to help us improve as a team and individually and those smarter than I realized that the strength we had developed while losing, both individually and as a team, made us stronger.

Being a champion was not easy, in softball, it took five years to clinch the provincial championship. Each season, regardless of the scoreboard, taught us valuable lessons about resilience, trust, and the importance of enjoying the game. Similarly, my time as a linesman in minor league football, being part of a Canadian championship team, reminded me that success isn’t just defined by that final win but by the shared journey that brought us together.

Sports and motivation studies will tell you that winning is definitely gratifying, but the process of seeking excellence creates enduring satisfaction. Having a single-minded focus on an outcome can rob you of the depth in incremental daily improvement and learning. Instead, setting process-type goals, like improving your skills, building endurance, or even learning a difficult play, will be more gratifying and long-term in nature.

So, when you consider the question of whether winning matters, you must remember that every step along the way, every small victory or loss, is a practice in perseverance and is just as valuable as the victory. Winning is certainly a time to rejoice, but it is the journey, dedication to improvement at every turn, relationships made along the way, and the lessons you learn in winning and losing that make you who you are in the end.

As you pursue your own quest, on the mountain or in anything, keep in mind that the path is as enjoyable as the prize. Cherish every step in between, and you shall realize that the heart of victory is not necessarily in the line but in every step that led you to it. 

Does winning really matter?

My grandson does competitive skiing, an individual sport. He is quite good, and he is being recognized by a national body, but he is still young. My best friend's grandson, who is the same age as my grandson, has been recognized as a top athlete in Football and is competing for national recognition.

 When I was young, my brothers and I were good athletes and excelled in both team and individual sports. When I was their age, I loved to play, practice and win. Winning was a nice reward, but it was not the goal of why I participated. My friend, who was also very athletic, believed that winning did matter more than participating So that leads me to the question:  Does winning really matter?

As I thought about this question, I was reminded that it's not only about the trophy at the finish line when we win but about the individuals we meet along the way, the challenges that we overcome, and the things we learn when we win.

I was younger, I specialized at the half mile and mile races, and I was four years second best in my age category. My brothers, with skills in sprinting and distance, had similar interests. Both our abilities and our attitudes helped our coaches to form a city track club—a place where we each recognized that winning's value lay in what we all worked towards and gave up for each other.

At the same time, my athletic career took me to the softball diamond, where my brothers and I played for a team that, after five long years of hard work and perseverance, finally won the provincial championship. A bit later, I was also fortunate enough to be a linesman in minor league football on a team that won the Canadian championship. These lessons taught me that though the thrill of victory was enjoyable, the true value lay in the day-to-day grind, the camaraderie, and the pure joy of playing the game.

This leads us to a question that has crossed my mind over the years: Does winning matter?

In my mind, the answer has always been nuanced. Yes, winning is a beautiful moment of recognition, but it’s the journey—the practice, the team spirit, the steady improvement- that truly shapes us.

For this series, I’ve broken down what winning means and how it touches every part of our lives. Over the next few blogs, I will explore what I think we should be telling our grandchildren about winning. I hope you enjoy the following ideas:

1.    The key question: Does winning matter?

2.    How winning influences team culture and buy-in

3.    The challenge of defining success beyond wins and losses

4.    Personal coaching lessons: finding small wins within the game

5.    What research says about motivation—why winning isn’t the top priority for athletes

6.    How to shift the focus from championships to daily improvement

7.    How can an athlete balance recognition while staying process-oriented

Time Management for retirees

When I retired, I expected my calendar to stretch out before me like a wide-open range—no meetings, no deadlines, just freedom to do as I wanted. I had counseled people for years on how to plan for retirement, and yet when it was mine, I found myself waking to days that were indistinguishable from each other. It did not take long to see that retirement without planning was not freedom—it was pandemonium.

Since 2010, I’ve been writing about retirement issues, guiding seniors through this transition, and helping them create fulfilling, purpose-driven lives. As an Advisor to the Senior Advocate for BC, President of the Wilson Seniors, and Chair of the Tri-Cities Senior Action Society, I’ve seen countless retirees struggle with an unexpected challenge: what to do with all this time. Many believe that once they retire, time management no longer matters. But here's the reality—time management is not about extracting productivity from every minute; it's about optimizing your days so they don't get away from you.

Envision time as an essential spice to life. Like the way you need the proper spices to provide zest to a dish, you need the proper handling of time in order to bring zest to retirement. We are given 24 hours a day, and already we utilize a portion of it sleeping. What is left over is up to us to shape—but with no purpose, it's easy to get caught in habits that leave us unfulfilled.

One of the biggest retirement lessons is that everything changes. That's life. But that doesn't mean we can't plan. Having some structure in your day, loosely set, allows you to do the things that matter most. That might be taking time for hobbies, exercise, volunteering, or time with friends and family. Without structure, days pass, and before you know it, months have gone by without doing what you enjoy.

For those still working part-time or volunteering, time management is equally crucial. One of the most frequent complaints I hear is the constant barrage of emails. Email is an essential tool, but it can also be a distracting burden. Allocating specific time every day to review and answer messages—instead of allowing them to control your schedule—opens up time for more substantial pursuits. Unsubscribing from unwanted mailing lists, sorting significant emails into folders, and setting up automatic filters can maintain digital clutter under control.

Next, there's the authority of the notes. Whatever you're doing—jotting reminders, making appointments, arranging meetings—good note-taking keeps things together. If you're part of group meetings, pre-checking with participants will iron out essential points and eliminate wasted time. These small habits pay dividends, making your day run more efficiently and smoothly.

But time management is not so much about things to do—it's about balance. Scheduling time for yourself is no less important than scheduling time for work. Whether spending the morning on walks, reading, hobbies, or just sitting over a cup of coffee without any frantic hurry, such self-indulgence is what makes retirement a worthwhile experience.

Retirement is not filling every second with duties, but nor is it letting time go unmarked. By creating soft habits, living in the midst of what matters, and working with interruptions, you can intend each day. The reality is, the beauty of retirement isn't so much in having time—it's in creating the time valuable.

This demographic reports the lowest life satisfaction is it your demographic?

 Prudential Financial's new survey identifies critical emotional and financial concerns for 55-year-olds. This age group has the lowest life satisfaction among midlife retirees because of a complex mix of career, family, and retirement planning demands. Financial insecurity is one of the crucial concerns, and those who are not financially secure are more likely to have mental health problems.

For individuals in their late 50s and early 60s, it is vital to comprehend these results. They are probably facing the same pressures and uncertainties as they near retirement. The findings highlighted by the survey can make them realize that their challenges are common to many others in their generation and underscore the need to prioritize financial security and mental health when planning their retirement.

New findings from the Prudential Financial survey indicate that 55-year-olds are facing severe emotional and financial challenges in coping with the complexities of retirement planning. This group of people, which includes many of you, is coping with a unique set of pressures that can have a serious impact on life satisfaction and mental health. However, with the right strategies and mindset, these pressures can be transformed into opportunities for a more secure and fulfilling retirement.

The poll highlights that the least satisfied with life among retirees in midlife are 55-year-olds, rating it 6.2 out of 10, compared to 7.4 for 75-year-olds and 7.0 for 65-year-olds (Prudential News). The unhappiness is typically rooted in financial insecurity, which affects 53% of financially insecure individuals versus 33% of those who are financially secure.

This generation is juggling career stress, family responsibilities, and the daunting task of planning for retirement. It's a time when financial errors can have lasting consequences.

One of the key takeaways from the survey is the critical importance of financial planning. As someone who has been writing about retirement issues since 2010 and working closely with seniors, I’ve seen firsthand how financial security can alleviate many of the mental and emotional burdens associated with retirement planning.

Strategies such as creating a comprehensive retirement budget, investing as much as possible in retirement accounts, and speaking with a financial advisor are essential. Knowing approximately where your retirement income will come from, including pensions, savings, and Social Security, can provide a solid foundation for peace of mind.

Financial stress is closely linked with mental health issues. It's vital to acknowledge this connection and stay ahead of anxiety and stress by being proactive. Practices such as mindfulness, physical activity, and close social connections can be very beneficial.

As a trainer and workshop developer in health and wellness for seniors, I am a firm believer in retirement planning based on overall mental and emotional well-being. Consider joining support groups or workshops that focus on stress management and mental well-being for retirees.

Along with all the challenges, there is also a 10-year window of opportunity during this period. With proper resources and planning, you can set yourself up for a happy retirement. This is the time to reassess your goals, consolidate your financial plans, and make adjustments that will serve you well in the long run. Taking advantage of resources offered through seniors' organizations can be an excellent source of information and support.

Navigating the midlife retirement 'crisis' is by no means simple, but with the right plan, these years can instead be a time of preparation and promise. By keeping financial well-being and emotional balance as priorities and by utilizing the resources available to you, you will be well on your way to building the foundation for a secure and fulfilling retirement. And remember, you are not alone—there is a support system of professionals and peers ready to advise you every step of the way.