74. The Changing Face of Success As We Get Older

and what if that view doesn't ever shift or change

I’m sure I could have done better. Although I may not have known how.

In my younger years, while focused on building ‘the career’, success meant these things to me:

• Was I getting promoted and rising through the ranks as fast as I wanted?

• Were my areas of responsibility expanding? Was my job title ‘getting better’?

• Was I earning the salary that I wanted to be earning? And, related to that, was I able to afford the things I wanted—the car, the apartment, the clothes, etc.?

Looking back now, do I wish that I had measured my success differently? Maybe. But at 25 or 35, I don’t know that I knew what else to track and measure, to be honest.

My friend and former colleague Vivek Chakrabortty said something to me in a previous interview on Second Breaks that really struck a chord.

You become a product of your environment. That's the game that they set up, and we played the game. We loved playing the game. […] And so it channeled all of our energy, our emotions, our actions, our thoughts into being what they created.

That was the game I was playing back then, and had to measure my success according to the rules of such game. Otherwise, why even play the game? And if I had not followed the rules, I probably would have felt really unaccomplished.

So here I am, in my 50s now, retired from my corporate career and playing a totally different game. Though I am still driven and ambitious, the way I’m measuring success this time feels different.

So today, I want to dissect this and offer a more definitive way of measuring success in modern retirement.

Keep reading or listen to the audio version:

The shift comes naturally and largely unnoticed.

I want to preface this by saying I come from the perspective that redefining success as we get older is natural. It happens subconsciously and is a by-product of our changing circumstances, priorities, and focus in life.

As we progress through different life stages and have various experiences, our priorities naturally shift, which leads us to naturally re-evaluate what we consider successful.

But I want to acknowledge there are always exceptions.

There are people who tend to be resistant to change and may not embrace this shift. Their resistance may come from fear of change, social pressure, or attachment to traditional norms.

There are also people who, no matter where they are in their life stage, will always measure success one way. This tends to be particularly true for people who have focused on amassing wealth and power over a long period of time. I think we can easily come up with examples of people who would easily fall into that category.

There will always be individuals whose definitions of success remain relatively static throughout their lives.

However, these exceptions do not negate the broader trend that we experience a natural evolution of our success definition as we age and encounter different life experiences.

Now that we’ve addressed the exceptions, let’s look at the six most common examples of how our success definitions change as we get older.

1. Shift from Career Success to Personal Fulfillment: Many of us, especially those who have dedicated much of our lives to our careers, may shift our focus from traditional career success markers (e.g., job titles, promotions, salary) to personal fulfillment and well-being. We may place a higher value on spending time with family and friends, pursuing hobbies and passions, or maintaining good health.

2. Reevaluation of Material Wealth: As we age, some of us may reassess the importance of material wealth. Many of us downsize our homes, sell unnecessary possessions, or prioritize experiences over material goods. We begin to measure success by the quality of life and the ability to enjoy meaningful experiences —rather than the accumulation of material things.

3. Focus on Relationships: We frequently place a high value on relationships with family and friends. As we get older, we may focus more and more on the quality of these relationships, spending time with loved ones, and nurturing meaningful connections.

4. Personal Growth and Learning: Many discover a renewed passion for learning and personal growth. Success for us may be about acquiring new skills, pursuing further education, or engaging in lifelong learning opportunities.

5. Legacy, Mentorship, and Social Impact: Some of us focus on leaving a lasting legacy and providing mentorship to younger generations. We may become more involved in community service, volunteer work, or philanthropy. As such, we can start measuring success by the positive influence we have on others, the legacy we create, or the positive impact we have on our communities and society at large.

6. Emphasis on Health and Wellness: As we age, we often prioritize our health and well-being more. Success may be defined by maintaining good physical and mental health, staying active, and preventing or managing health issues.

As we get older, we tend to look beyond “traditional success”.

These examples illustrate that as we get older, how we define success evolves to include a broader range of factors beyond traditional career and financial success.

While not everyone follows the same path, these shifts reflect a common trend among us, midlifers who find ourselves prioritizing different aspects of our lives based on our lived experiences and shifting expectations.

💬 last word

Speaking of redefining success… I’ve just completed a trip that ended up entirely different from what I originally planned. Not bad. Just different. And because of this, some things under the category of “productive work” fell through the cracks — things that I thought I might (should?) do while traveling.

The initial impulse to scold myself was loud and clear. I also felt disappointed for missing self-imposed deadlines and my own expectations. It took a second to recognize the unplanned events that ended up taking time… activities that I’m glad I did, and experiences I really didn’t want to miss out on.

Even in this month-long trip, I’ve had to redefine what a ‘successful trip’ is. In the end, I do feel this trip has been one (being behind on things, notwithstanding).

How has success shifted for you?

Here’s to a joyful and easeful week ahead.

Cool Beans,
Lou Blaser