August 10, 2025
My Way or the Highway
As a kid, I remember listening to Frank Sinatra’s iconic anthem, “My Way.” It’s long been a favorite for so many from the older generations who prided themselves on independence, self-determination, and forging their own paths—no matter what others may have thought. The lyrics are strong and retrospectively defiant: “I did it my way."
There can be something admirable in that, especially when it comes to standing firm in your values, making tough decisions, or taking responsibility for life’s outcomes. But in today’s world, the “my way” mindset has gone from inspiring anthem to default operating system. Increasingly, we seem to be living in a culture where advice is seen as interference, and personal experience is prized above all—even when it's unnecessarily painful.
Too many of us insist on learning life’s hardest lessons firsthand, rather than taking the wiser path: listening to someone who’s already been down the road and can warn us where the potholes are.
The Perils of “Figure It Out Myself”
Of course, experience is a great teacher. But it can also be an expensive one. There’s very little honor in reinventing the wheel, and little virtue in suffering avoidable consequences just because we refused to ask for guidance. In business, in relationships, in leadership—I’d argue that those who seek out wisdom tend to make fewer critical errors, rebound faster when they stumble, and spend less time stuck in patterns that could have been avoided altogether.
Famed U.S. test pilot, Chuck Yeager, was credited with saying: “Learn from the mistakes of others. You won’t live long enough to make them all yourself." That truth applies to more than just flying.
The Pattern Is Everywhere
Young professionals ignoring the seasoned advice of mentors.
New leaders dismissing the lessons of those who’ve led before.
Couples navigating marriage without asking how others stayed married through the inevitable storms. Startups disregarding industry veterans because they want to “disrupt everything.”
And often, even us older individuals assume we're above learning anything new. The result? A cycle of inefficiency, avoidable pain, and progress that’s slower and messier than it needs to be.
A Better Anthem
Sure, doing life “your way” can feel empowering—but it also tends to be isolating. The better route? “My way, with wise counsel." We all need people in our lives who’ve been through the fire—those who’ve failed at what we’re just now attempting, and are willing to tell us what didn’t work, and why. The smart ones don’t just ask for that input—they actively seek it.
Ask the retired executive how they handled a crisis.
Ask the aging parent what they wish they’d done differently.
Ask the failed entrepreneur what they missed the first time through.
Ask the older couple how they stayed in love.
Ask your mentor what they regret.
And most importantly, listen.
Because Life Isn’t a Solo Album
Even Sinatra didn’t really do it entirely “his way.” His career was built on songs written by others, produced by others, and recorded with the help of countless other musicians, sound engineers, and behind-the-scenes pros.
In life, we can still be original. We can still make our own decisions. But the path to doing things better often begins with the humility to learn from those who already know what doesn’t work—and love us enough to say so. I still need that reminder from time to time.
Do it your way, sure. Just don’t do it alone.