Conquer Your Executive Insecurities With Confidence

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We’re all insecure about something. And yes, that means you too.

I thought it was just me (and maybe you thought it was just you). Then I thought it was the managers. Then directors. Then, funnily enough, it turned out to be vice presidents. Then the c-suite and founders.

Then I thought, maybe it was the folks that worked at unrecognizable companies. But then I started working with highly influential Fortune 500 executives—and wouldn’t-you-know it, their particular neuroses knew no limitation.

All right, I’m done with the corporate poetry. So, are you as competent as others perceive you to be? Or is there an imposter in our midst? Is it something else entirely? 

Maybe It’s Imposter Syndrome. Or Maybe It’s Maybelline.

I tried to link to a 90s makeup commercial because I know that’s the sassy content you read my diatribes for—but the misogyny in those ads killed my drive to share. So enter that rabbit hole at your peril.

The most straightforward and laziest conclusion many people arrive at is imposter syndrome. The term is easy to remember and quite visceral. The word imposter is spicy enough to elicit simultaneous cringes and terror.

Are you suffering from the following corporate hellscapes? You’re:

  • A superhero that overworks to remedy your inadequacy?
  • A natural genius that crumbles when you don’t meet exceedingly inhumane expectations?
  • A know-it-all that isn’t happy unless you know it all?
  • A perfectionist zeroed in on flaws versus celebrating successes?
  • A soloist that works alone because asking for help makes you feel weak? (And let’s be honest because other people will screw up.)

PS – I adapted these imposter syndrome traits from Amy Morin + Theresa Chiechi.

I’m not suggesting that imposter syndrome isn’t real—I’m suggesting that imposter syndrome isn’t always the reason executives feel insecure.

Plus, imposter syndrome sorta sounds like a humble brag, doesn’t it? You’re so good and successful… but you just can’t seem to get over this insecurity about how you managed to be so good and successful.

Imposter syndrome is not a catch-all—it could be a cheap cover-up to a more significant challenge. No offense to Maybelline.

I often find that executives don’t have a problem with confidence or imposter syndrome but with communication. A lack of communication erodes confidence and rears its insidious fangs in the embodiment of insecurity. I’m clearly not done with corporate poetry.

For example, you may struggle to communicate the following:

  • You took seven months to find a job.
  • You took a role that is perceived as backward progress.
  • You raised your kids.
  • You hit 85% of a goal.
  • You hit 110% of a goal—but the total number looks small.
  • You don’t know what you don’t know.
  • Newly marketed terminology escapes you.
  • You look 12.
  • You look 80.
  • You aren’t a perfect match for your role.
  • You escaped from a narcissist culture (for the 3rd time in 2 years).
  • You ARE a narcissist!

These aren’t imposter syndrome traits—these are life problems and they could trigger very real career biases that affect our day-to-day opportunities.

You’re not an imposter. Communication is hard.

Now that I’ve lanced the boil that not every insecure career neurosis is imposter syndrome, let’s get to healing.

So Jacob, how do you address a career blemish that causes irreparable harm?

Take ownership of the blemishes.

Whether you’ve done something idiotic enough to warrant career suicide—or you just think you might have—the answer is the same.

You need to own your truth and communicate your story on your terms—rather than waiting and wondering what someone is thinking about you.

That’s juicy, Jacob. Tell me more.

Guilt By Omission.

Let’s take the “I have a gap in my resume because I raised my damn family (you moron).” approach.

We get it. Gaps happen. (My editor cut “shit happens” because this is a family-friendly publication)

When I say to take ownership, I don’t necessarily mean hop on the TED stage and blast it from the rooftops. I’ll leave that to Jocko.

Perhaps more pertinent is that you don’t need to yap on social media, or even own your truth directly on your resume or LinkedIn. Oversharing limits opportunities and triggers bias. Publicly flippant behavior will be harmful or misconstrued at the very least.

For example, some assholes perceive that raising a family makes you a lesser leader and that you can’t handle the corporate world after diaper dooty and daycare. When, at least in my experience, the opposite is true: Intentional parenting creates super execs.

Because you can’t control public bias, it’s often a more brilliant play to withhold that information publicly to control perception without being deceitful. The same rings true when oversharing KPIs or performance metrics. What may be impressive to some is chump change to others.

I may get heat for preaching authenticity yet also choosing to situationally hide it.

However, I’d rather you have a personal conversation 1-to-1 to learn the context. You should assess body language and social queues, navigate the situation, and understand what you’d be most comfortable sharing—instead of oversharing to the faceless masses in the digisphere.

You won’t be found guilty of omission in a jury of a single-target audience. So let’s leave owning your truth to banter on the telephone.

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Leaders Gonna Lead. Followers Gonna Follow.

Back to that 1-to-1. When you have earned a live conversation, and the pressure cooker reaches a breaking point—this is the moment you make your stand. A conversation is when you take ownership of your insecurities.


You have the opportunity to control the discourse—or at least defend yourself before any misconceived perception of you festers into self-destruction. You own the conversation on your terms—not the public’s terms—and not at the whim of the other party.

For example, you’re in an interview, and there’s a phat gap on your resume.

I’m talking about a scary phat gap. Like a “what the hell were you thinking” sized gap. You must have been backpacking Europe. Or chomping mushrooms galavanting around with delinquents.

Okay, I’m done. But you get the picture.

What could the other person possibly be thinking about your gap?

(1) You’re an unhirable failure.
(2) Something is wrong with you.
(3) There’s probably a reason.
(4) Maybe it’s a typo. Career paths must be linear.
(5) I wish I got more sleep last night.
(6) If I smile and nod a lot, they’ll think I read their resume.
(7) Do people still use resumes?

Seriously, how bad can it be?

But, again, the same can hold for other insecurities. Not only gaps in employment.

Think about how your insecurity can be perceived well.
Now think about how your insecurity can be perceived negatively.
Finally, how can you lead the conversation toward a positive focal point?

Answer? Take ownership and address your insecurity on your terms. Don’t wait and wonder. Lead.

Grokkable Damage Control.

A final example, and I’ll pick on myself.

I have had at least ten jobs in as many years. Typical punk-ass millennial. Now that can be perceived very poorly (and if I’m honest, it probably should be).

I can’t lie about the breadth of work and can’t change my past. What should I do?

Well the real story is, some were contract consulting positions, some were full-time. Some were my fault and some companies had big layoffs. It happens in the Wild West of Tech Startup Land.

Look: There are 1001 different ways this conversation can go badly for me if I don’t bring it up. What’s worse is, when I’m asked about my job-hopping in a way that I’m not 100% prepared to conquer, it could throw my confidence off and derail the conversation.

So. I own the damage control on my terms.

“I’ve learned a thing or two working at a handful of tech startups. I’ve been fortunate to lead through a few exits, but I’ve also been on the receiving end of terminations, inability to find product-market fit, and a healthy dose of poor decision-making. I’m happy to go into more detail, but I imagine that you get the gist. You’ve lived it too.

I’ve learned that I’m less interested in the earliest stage companies. Now, I’m looking for a more stable environment where I can roll up my sleeves for several years and lead a product from zero to one to acquisition—which is why I’m excited about what you’re working on. From the looks of where your team is, I bet we can swap war stories and get to work solving the challenges you’re tackling today.

Where are your current go-to-market efforts falling short?”

You must:

(1) Confidently address mistakes.  …a healthy dose of poor decision-making…

(2) Sprinkle in positives.  …I’ve been fortunate to lead through a few exits…

(3) Share that you’ve grown. …I’ve learned that I’m less interested in…

(4) Most importantly, shift the conversation away from your shortcomings and into solution mode. …Where is your current go-to-market effort falling short…

(B) Bonus points if you can share contextual commonality. …I imagine that you get the gist. You’ve lived it too….

If you wait, or play follower in the conversation, you may find yourself on the backfoot. You’re at the mercy of wherever the conversation goes, responding just in the moment.

Maybe your insecurity gnaws at your brain and weasels your conversation apart. Don’t ask that… Please don’t…

So, what’s your own challenging faux pas? Comment below, and I’ll answer for everyone to see—or email me directly, and we’ll navigate a way to take ownership of the situation.

Oh right – that insecurity assassin. Text five 3 zero 5 seven five 5 nine 8 nine. Tell them The Duke sent you.

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