When 'Pretty Good' Isn't Good Enough
18 months ago, I made a commitment to myself – that by the time I'd turn 50, I would:
Be in my best ever condition, mentally and physically.
Have added a new, creative, meaningful dimension to my life outside work.
Have changed scenery on the job front.
Why did I even begin thinking about making such commitments?
In truth, there were probably several interrelated things at play.
The autopilot trap
First and foremost, I realised I had begun to run my life on autopilot. Most things – job, family, friends, home – were in a good place and had been for a while. My life was relatively smooth sailing, nicely optimised for stability, security, and convenience.
Maybe you’ve felt something similar. The patterns and problems you face seem well known, and there’s limited tension between what you’re doing and what you are able to.
I know how privileged this sounds – and it is. But that comfort is precisely what allows the autopilot to gradually take over. When things are working well enough, there's no forcing function to question them.
Don't be mistaken – by smooth, I don't mean relaxed. My days were extremely busy. I was still striving, but it felt increasingly unclear what I was chasing.
Time was passing, yet weeks, months, and even years felt remarkably similar, blending together into a grey mass of "good life."
It's fascinating how our minds work. The combination of "pretty good" and "busy striving" may be what keeps us from ever reaching "great."
“Pretty good” reduces the urge to change, especially if we're on the beaten path most others follow. And “busy striving” makes it hard to muster the energy and time to change, even if we wanted to.
Something else was at play as well.
Being able to spot the big 5-0 on the horizon served as a harsh reminder that my time in this life is finite. As banal as it is, the realisation that there's more life behind than ahead of me has had a profound impact.
There are tangible signs everywhere around me, too. People my age are beginning to struggle with their health, talk about retirement, or feel stuck in their careers but too old or too comfortable to do anything about it. And as my kids become increasingly independent, the empty nest is only a few years away now.
That's life, of course. But we can choose how we deal with it.
Choosing intention
I'm not making a case for turning your life upside down – unless you want or have to. But figuring out whether good enough is truly good enoughcan be illuminating. Or reassuring. Both are valuable outcomes.
In my case, it led me to make those three commitments. They represent a desire to shake things up a little, create new sources of personal growth, and put me on a path that feels more aligned with my priorities today. Not in a life-altering way, but enough to move beyond pretty good.
Making these commitments forced me to get honest with myself about what I actually wanted – and what deliberate change I was willing to implement.
What that honesty required, in practice, was becoming more intentional with how I was living and working. It’s the opposite of autopilot. I know it sounds like a self-help cliché. And no one would disagree that it sounds like a good idea.
The reality is, it’s not that easy to practice.
I've met many successful people who say they live with intention. That their lives are a result of deliberate choices made in alignment with who they are.
But when asked whether they feel truly fulfilled and want to stay on their current path for another decade, and what they might be forgoing while they’re busy striving, the answers tend to soften. From "it's great" to "pretty good.” Often along the lines of: "Things are fine, but I would like to live or work differently; I just need to accomplish or reach XYZ before making a change."
This was me until a few years ago.
It's surprisingly hard for middle-aged high achievers to admit to themselves that they've arrived at the wrong place. It feels like failure. It challenges the identity we've spent a lifetime building.
We’ve got to push some of our ego aside and accept that the title, status, and whatever success we’ve accumulated are really only important to ourselves. The rest of the world doesn't care. That's a humbling realisation, and a liberating one too.
Many believe that living intentionally is about setting grand visions and ambitious goals. I think that’s wrong. To me, it’s about shaping a direction without knowing the destination. I've come to believe that's actually the point. There's growing evidence that process beats outcomes when it comes to lasting change. We respond better to "making progress" than to striving for "absolute outcomes."
That’s why I framed my commitments as directions. Enough to orient myself and sense if I was moving forward while keeping the range of possible outcomes open at the outset.
Turning 50
Last week, I reached the dreaded milestone. I've not been a fan of my own birthdays since childhood, for reasons that probably deserve a post of their own. This one was no different, although it turned out very nicely thanks to my wonderful family.
And it forced me to take stock.
According to my severely biased self-assessment, I've done reasonably well on all three commitments.
I've implemented several healthy routines, delved into human psychology, neuroscience, and behavioural science through reading and courses, and scratched the surface of philosophy and spirituality. I believe it has made me wiser about my own inner workings and those of people in general.
I've started writing and coaching others on midlife career development and transitions. It feels like a natural extension of my own path, with several lane shifts and a deep interest in how we can navigate the second half of life on our own terms. It's a creative outlet and a highly rewarding one.
I've changed careers. Not because I was unhappy, but because I wanted the growth that comes naturally with shifting contexts. From one great company to another, into a very different role, environment, and industry. A new learning curve, new people, new inspiration.
What I've learned
Does this mean I’m being deliberate and aligned all the time now? No. But I try. Intentionality isn't a destination you arrive at. It's an ongoing practice.
The commitments gave me something to orient around. The fact that they weren't precise enough to easily fail at, but clear enough to know when I was drifting, has worked very well for me.
I also had to embrace what we all know intellectually - that implementing this sort of change in your life doesn’t come without some struggle and discipline. Motivation comes and goes, so you’ve got to have strategies for dealing with setbacks. Breaking the change into tiny steps is one approach.
What comes next? Is there another set of commitments to help me navigate the next chapter?
It's a work in progress. I might write about them when they've taken more shape. In the meantime, the practice continues.
