Our Most Confounding Question

The problem is not achieving success. The problem is finding satisfaction. 

Many of us have piled up the accomplishments, the promotions, the public accolades and even made some bucks along the way. Unfortunately, these conquests are fleeting. Exciting and energizing for a time, they often leave us surprisingly unfulfilled. 

For me, this void was perplexing. It seemed insatiable. No matter how many times I landed the next Big Kahuna in my life, professionally or personally, the pang of emptiness remained. 

Ever feel this way? Many of us do. 

At this stage of our life and career, we are searching for something more enduring, something with real meaning and purpose. Sure, we can keep on doing what we are doing but deep down we suspect we won’t find the significance we truly seek.

So we stand at a crossroads asking life's most confounding question, “Now what?!?”

Confounding because its a hard question to answer. Confounding because it won't go away. Confounding because many of us are equally bewildered yet we never talk about it. Ever. 

If you're an achievement junkie like me, the first part of our career was a sprint. We were on a heads down, all bets are off, nothing else matters quest for the top. Idealistic, passionate and a bit naive, we overcame hurdles and setbacks in a constant push upward. Nothing and no one was going to stop us. 

While we had only a vague notion of how we might feel at the pinnacle, we were certain it was going to be great. After all, why else would we make so many sacrifices, endure endless hours and nail-biting tension as we clawed past our competition up the ladder?

And we made it! We beat the odds. We proved the naysayers wrong. We got to the top. Wow!! 

I remember the progression; being handed my HBS diploma, checking out my vast office overlooking the Statue of Liberty, and getting my first business card with 'President' under my name. That was cool! 

But truthfully, it wasn't great. Don't get me wrong, it wasn't bad. While there were special moments and nice baubles coming with achievements, I expected more. Something was missing. I thought I’d be content, more at peace.  No matter what I had, it never seemed enough. I continued to compare myself to others. And couldn't help thinking, "Is this all there is?"

How was that possible? I exceeded my loftiest goals and was still obsessed with something more! More of what, I had no idea, just something more.

“Now what?!?”

Worst of all, I was remained riddled with stress. The end of the quarter was just as agonizing. The pressure was endless, the worry debilitating, the burden of our top line or our bottom line or the Board or the economy or whatever was exhausting.

Was this how I am going to spend the rest of my career?

We may try to answer "Now what?!?" in a number of ways. Maybe we launch our own firm or fund. We take on a business fixer-upper or dabble in real estate ventures or relaunch our career in a new field. We might cross off items from our bucket list; climb Kilimanjaro, try base-jumping, kick-boxing or hot yoga. Perhaps we visit all the major league parks with our kids or better yet, just purchase a team.  

Unfortunately, we can't buy our way out of "Now what?!?"  And we can't solve it on our own. 

In moments like these, self-reflection is essential.  Candidly, we are not great at self reflection. We're experts at telling others what is wrong with them but lousy at assessing what is wrong with us. (If you doubt me, ask your spouse, siblings or kids). 

So how do we deal with this dilemma?

In the 20+ years I have served as a C-level leader, Executive Coach and business chaplain to senior managers, entrepreneurs and Wall Street professionals, I have walked through "Now what?!?" with hundreds of others like you and me. Everyone is different and there is no simple answer. But we can get there with the help of others.

And that is the purpose of this blog - to help one another solve the riddle of "Now what?!?"

Look forward to working on this together!