There are many complexities and constraints when it comes to creating the lives we truly want.
In different ways it has been said—you can have everything you want, just not all at the same time. And, indeed, throughout our lives we are forced to choose, to sequence our “wants” according to what makes sense for our circumstances.
Coming out of school with a bunch of debt, it’s harder to venture out on your own. With a young family and mouths to feed, it’s harder to take risk. With the runway of a great career, it’s harder, and often wiser, to work that track for the “right” amount of time.
If we do it right, and we’re lucky to live long enough, by “simply” making the right choices at each point in time, we can create our most magical lives.
Yet, it can be very hard to keep our eye on the prize.
When Do People Settle?
The other day in a small group setting in California someone asked me a question that was met with awkward glances around the room.
With the weight of her question hanging out there, I could see a number of people’s eyes go searching for an exit, or their bodies trying to sink into the floor to avoid the pressure her question triggered in them.
After I had been talking about some of the career moves I made, she asked, “In your experience, at what age do most people give up on their dreams and just settle?”
It was a great question, but it’s a mean way to see it.
The Importance of Preserving People’s Realities
A danger in doing what I do is that I can trample all over people’s realities, something I unfortunately used to too often do.
Fact is, us humans are constantly and mostly negatively judging each other nearly as much as we negatively judge ourselves, and that’s a third rail I do my best to avoid.
What is giving up on a dream for one person is settling for a great life to another. And, while our society perpetuates the romance of “living your dream,” that’s simply not the right choice for everyone.
Most of us humans will be far happier and live much richer lives when we can “satisfice” in the majority of our choices.
Many people dream to marry that person who is “the one,” the absolute most amazing partner, but most are better off settling for the person who is there at the right time, and meets many of the right criteria. Many people dream to start their own business, but most are better off staying in a top job that well supports their life. Many people dream of setting the world on fire, when they are much better suited to living by the small campfire, creating a rich life that fulfills them in many ways.
Just like marrying the girl next door at age 7 in a backyard ceremony, most of our dreams were never real to being with. They were just dreams. Things to get excited about. Ideas that gets us focused in life. But they weren’t there for us to wake up and actually live them.
Is that settling? Is that “giving up” on your dreams, or is it making the choices that lead to the best life for you?
Only each of us can know.
Do You Keep The Dream Alive?
A few months back in London I met with a Wall Street leader who wanted to talk about his idea to leave his big job and start his own firm.
For 5 years or so he’s explored it somewhat seriously, but he just hasn’t gotten to a point where he can make a decision on it.
He’s at the end of his career, having gotten near the top. He’s made tons of money. He could retire now or anytime he wants. But even though he’s in his mid-fifties he’s still fired up about building something of his own.
After sharing this with me over lunch, with a super serious look on his face, he leaned in closer, slowed his voice down, and locking eye contact with me said—
“Let me ask you a question. And I want your honest response…. Am I too old to do this?”
Capturing the moment, mirroring his movement, I leaned in and replied, “I think the real question is… Are you too old not to do this?”
We Regret What We Didn’t Do
I deleted and re-inserted this paragraph 3 or 4 times because it’s just so dumbly obvious to all.
We’ve heard it our entire lives. Study after study after study in psychology supports it. Our anecdotal evidence from those who’ve passed on proves it to each of us…
At the end of our lives, the majority of us humans don’t regret the things that we did; we regret looking back and seeing the things that we failed to do.
We know this. And that ultimately means, this gig of life is about really challenging yourself on these “hard choices” to figure out what is right for you.
What Choice Is Right For You?
After lunch we decided that we’d get back together and talk it through.
He doesn’t know if it’s right for him to start his own firm. He doesn’t know if he’s too old or not. But he certainly knows—if he’s going to do it, it’s now or never.
And more important than whether he actually does it or not, he wants to know that he actually made the decision.
No matter what choice he makes, he wants to look back on this as his choice. His greatest fear is that he drags it out and the hands of time make the decision for him.
It’s not about the childish fantasy of “going for his dream” or the drama of “settling,” it’s simply about being the one who made the choice.
What about you? What do you choose?