Sometimes regret is what you feel when it’s too late to do much about it—your deathbed, most commonly. But we also feel regret when there’s plenty of time left. All that stands in the way is our reluctance to recover the opportunities that are still out there, waiting for us.
The voice of regret over the road not taken most often has the whine of excuse about it. I couldn’t afford to take the chance. I’m over-extended. I’m too tired. I need to be better prepared. I can’t do this alone. I have too many obligations. My family won’t be on-board. What will other people think?
What if I fail?
By the time the excuses begin, the flirting with the new and unfamiliar has usually passed. You’ve pulled yourself back into the comfortable territory where you started. Your heart rate is back to normal, what you feared is now safely behind you. The only residue that remains is regret around what might have been. What if I had pushed a little farther, taken the chance, grabbed the brass ring when it appeared, trusted my instincts, trusted myself?
I spoke to an accomplished group of senior managers this week. In their fifties and sixties mostly, all were in or between Big Jobs. Some of them were also caught between seeing themselves doing those Big Jobs and, well, just sitting at home not doing them.
These are pretty stark alternatives. The good news is that there’s a way to get to the productive work all of us still need to do, and it doesn’t involve trapping yourself between this kind of all or nothing.
Limiting your future to a corner office is unrealistic if there simply aren’t enough corner offices to either barricade yourself in or catapult yourself back into. Your chances may simply be better elsewhere.
Moreover, if you’re not in that corner office today, maybe there’s a good reason that you’re not, a reason that involves your temperament, your skills, or your inability to read the handwriting on the wall. So why not step back and make a plan for your future work now that squarely confronts your deficits, acknowledges the value of your native talents, and aligns your next job with the best vision that you have of yourself?
Honestly confronting your deficits could mean honing existing skills or mastering new ones. But as often as not it’s learning to be more adaptable to changing circumstances. That is, a lot more resilient than you are today.
If you’re too rigid, you may simply need to become more adaptable. Stated differently, if your Boomer Balloon is filled with too much stale air, it may be time to let some of the stale air out and some fresh air in.
The best way to do so is by throwing yourself into circumstances where you’re not comfortable, where the particular improvements you need to find can only come—one dogged attempt at a time—with failure as your teacher. That’s the path to resilience. The question is really a pretty simple one: Are you tough enough to know when you need to toughen up?
On the other hand, time spent on deficit reduction should never mask what fueled your accomplishment in the first place. Identify the skills that have always given you the most pride when you’ve exercised them, and build your future on the highly transferable talents that have always set you apart. It’s a waste of time being bitter that strangers in the job market aren’t valuing these talents enough, but you’d be a fool to undervalue them yourself.
Finally, while you’re busy being honest with yourself, also consider investing some of the optimism you’ve been mustering as the candidate for the next Big Job around those things you always wished you had done, but were never brave enough or wise enough to have done before.
The land of your regrets is where you think about the grreat job that got away, the kind of work that quickens your heart beat and makes your palms sweat when you think about it, like helping to solve a real world problem, or meeting real needs for different products or better services than anyone else is providing.
There are challenges out there with your name on them. With focus and tenacity, you can figure out a way to not only make a living by confronting them, but also to live more fully and to find a better balance of effort and fulfillment than you have ever enjoyed before.
It’s the time in our lives when age, experience and self-confidence can also be good teachers, when we let them.
The irony, of course, is that once you build yourself a regret-free encore career, you’ll find yourself wondering why you ever spent your time putting all your eggs in the basket of that next Big Job.