Go Beyond the Facade to Unmask Executive Anxiety

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Suppose you spend excessive time examining the career concerns of executives. Let’s say for over a decade for reference.

After assuming that all executives have grown practiced in squelching career jitters with stoicism and sensibleness because they no longer experience jitters—you’ll come to recognize that you’ve been rudely mistaken. 

Executives are often insecure about their accomplishments, unsure of the future, and hesitant to break their mold to find more joy in their work. There’s a lot at stake.

Sometimes executives are more tentative than the youthful naivety of the hard-charging next generation. But let’s be honest, they probably don’t know what they’re doing anyway.

Executives have grown too accustomed to hiding their troubles —and too often have nobody to share them with. (Except for me, of course)

Executives Are Afraid to Speak Up

Networking ain’t what it used to be.

Poor judgment is only a click away, and such as a train wreck, you can’t look away from the scrolling of ignorance you may find right next to a flashy headshot and VP title. 

If you choose to engage on LinkedIn, tread lightly—you’ll find the fangs. One broken eggshell away from cancellation. And whatever triggered you enough to open up is probably not important enough to risk your career. 

So sit down and shut up. Don’t be yourself. The risk is too great. 

I’d argue that, generally speaking, our society can do a better job of lowering the temperature of hatred and division sparked by vehement controversy—and look toward how we can come together and collaborate for a better life. 

But, if social media remains the cornerstone of our societal “connection,” I fear this is a pipe dream. We need a better way to build meaningful relationships with one another.

Onto solutions and how we can find love for one another again.

We’re Not All That Different; You and I

Discussing how executives are more alike than meets the eye could be a breath of fresh air and inspire new career opportunities for all of us, even if we’re still too hesitant (or it’s too risky) to reveal our authentic selves to the world. 

After all, we’re not that different. And surprisingly, it’s not merely on an exec-to-exec level. We could all stand to acknowledge our similarities.

I’ve found that executive career challenges are not dissimilar to early career up-and-comers (albeit with a more significant obligation to perform and ample personal and professional responsibility at stake). 

While I’ve had this hypothesis for a few years now, I haven’t been able to communicate our nearly indistinguishable similarities—until a standout client and friend helped me.

We All Want To Live Rewarding Lives

Meagan DeMenna and I spent the last two weeks interviewing our first 25 executives for CORE Connect. We ask routine questions such as short and long-term goals, what attracted you to the network, how we can best serve your career, etc. 

One response stood out as profound. I’ll paraphrase.

“My goal is to maximize my quality of life while keeping my career interesting. However, I must also keep my career relevant to maintain maximum career optionality should my work become uninteresting and thus negatively affect my quality of life.” 

Meagan and I paused. An aha moment indeed.

Succinct—and deep enough to articulate the double-edge sword we all balance in our careers. 

Work too hard? Your life deteriorates. 

Live life too hard? You’re an unemployable has-been. (And your family lives in a hovel now, you reckless SOAB).

Something’s got to give. But in short, we simply all want to live rewarding lives.

It’s Lonely At The Top (But The View Is Nice)

Being the CEO of Discover Podium was the loneliest experience of my life. One part from overwork and exhaustion and one part from isolation from others who ‘didn’t get it.’ 

After all, there aren’t many twenty-something bootstrapped founders living in Lake Tahoe stressing about paying a six-figure payroll by Friday. 

I’ve come to find that much of this loneliness was self-inflicted. I didn’t build a strong support system or seek support from others in a meaningful way. Thus my quality of life and relationships with others withered away. 

Interesting work, piss poor quality of life. I failed. Many executives may recognize this pattern themselves.

Back to solutions. 

I believe that in order for you to maximize your quality of life while keeping your career interesting (and keeping options open) means that you need to nurture a group of personal advisors to lean on. 

Ideally, in a safe environment where people genuinely care about your wellbeing but aren’t afraid to challenge you critically—but also have the experience and substance to warrant your respect and consideration in the first place.

Of note, LinkedIn is not a safe environment. (Lions needn’t concern themselves with the opinions of sheep).

Oftentimes your colleagues are not a safe sounding board either. And more so, your clients, mentors, and relatives can not give you the objectivity or experience that’s required to ensure you feel heard, understood, and can actually grow from the conversations. 

Connection Through Vulnerability 

We must first recognize that even though we’ve all experienced wildly different circumstances…

  • Whether a privileged or trailer trash upbringing…
  • Whether executives of recognizable brands or flash-in-the-pan start-ups… 
  • Whether the urine-scented vagrant we too often scoff at in disgust or the king in the castle…
  • Whether left or right… 

We are alike in that we all want to live rewarding lives. And there is comfort in knowing that we are all bound by a similar guiding light.

This should mean that executives should not fear reaching out to other executives and having a heart-to-heart. For example, “You’re an exec, I’m an exec… wtf were we thinking? Amirite?” 

We need to feel more comfortable sharing the uncomfortable in an environment where if you receive criticism, it’s supportive and constructive—not a means for cancellation and riot. 

A few musings to consider this week while working on building more meaningful relationships.

  • Give up on the idea of perfection. Nobody is perfect, pretending to be so is off-putting. Try sharing something that you screwed up on recently. Consider presenting your mistakes in funny anecdotes, but do it on the phone or in person, not on social media.
  • Vocalize your feelings more. For example, I’m worried that if I screw up the next business I lead, I won’t have the energy to continue supporting my family and might be so removed from current practices that I’ll be unemployable in a meaningfully financial way. Have you ever thought about that?
  • Give yourself (and others) compassion. We’re often our most formidable critics. Would you be friends with the destructive voice in your head? Would you be friends with the destructive asshole in the comments section? (I’m writing this for me too, friends)
  • Avoid others’ opinions. Not all opinions of you come from a place of love. As such, not all advice from others should be taken in earnest. Consider the source.
  • Be open about your needs. You shouldn’t feel shame asking for help, even if others didn’t need the same help you did. Be clear on what you want and don’t hesitate to ask directly. 
  • Be in the moment. TIME stands for – today is my everything. When you share that time with others, give them everything. Active listening and repeating your understanding of a conversation can spark relationships at a deeper level than what’s audibly cited. The best relationships often begin when you start understanding the implied meaning of a conversation, not only the spoken words.

I believe strongly that the future of (meaningful) networking will be conducted in small-scale and hyper-focused groups—not quip-based one-liners, vanity metrics, pedantic and shallow euphemisms, and hyper-scaled social media channels driven by AI and algorithms.

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