The Entrepreneur Conundrum

Written By: Victoria Frankel

Victoria Frankel | Founder of Validity Science Communications

A few days ago I posted a quote from a client of mine about entrepreneurship and the unseen challenges of founders in the job market. I wish I could say I was surprised by the level of interest and feedback I received, but frankly, I’m not.

I have had many conversations that defy industries, leaders, and experiences. Just from that post alone, I have received a dozen different direct messages in my Linkedin Inbox exemplifying this issue. From solopreneurs to serial CEOs, there is a genuine note of concern with future opportunities. If this too shall pass, what comes next? 

Hence the claim:

“Once you become a CEO, you’ll never get hired for another job.”

What truth is there in that, and why? Are we, as founders, doomed to an irrevocable position of entrepreneurship? For what feels to be the apex of industry leadership, how is it that career sustainability seems to be a leading fear in some of the most brilliant, resilient minds?

Let’s starts this off with a quick disclaimer: there are a number of reasons to start a new job hunt as an entrepreneur and none of it signals failure. Rest easy, Entrepreneurs. You are not Macbeth, relaying the story of your past business ventures as if “… told by an idiot, full of sound and fury, signifying nothing.” Building a business is one of the greatest feats out there. Whether you’re a small solopreneur developing a brand and expanding your small footprint into an echo chamber of industry experts, relaying your differentiating factor, your unique value proposition that makes you worthy of being there – or a profoundly proliferate entrepreneur, building one of many businesses under your belt and making claim to the economic landscape that is your own expert voice… your story is one of passion and meaning.

We are all worthy voices. We all have profound vision. We all signify something, and more often than not – it’s a lot. In fact, there are countless books, novels, directorates, guides, interviews, documentaries, and educational platforms that have emphasized the profound difficulty and excellence of the entrepreneurial journey. When you have entire academic programs around the nation – nay, the globe – dedicated to researching, understanding, expanding, and building upon
entrepreneurial opportunities, you may be wise to view it as the juggernaut force that it is. Foundership is a privilege, though exceptionally laborious.

Moreover, there are countless young minds romanticizing the journey, viewing their own footprints in the sand, daydreaming of their own impact as an entrepreneur across both new and saturated industries.

So why is it that those who – for whatever reason – shift off course and look to make their own impact in other commercial establishments are seen as, well…

A red flag?

“We are all worthy voices. We all have profound vision. We all signify something, and more often than not – it’s a lot.”

The Pro/Con Con

Believe it or not, this is a well-known observation in the business world. I’ve spoken with an arguably concerning amount of entrepreneurs and executives on this specific topic. It is a wide consensus: once you separate yourself from the traditional workforce, it’s arduous to get back in. I won’t say impossible – but close.

We’ll get into the why in a moment, but for the time being let’s just acknowledge the absolute absurdity of that statement. We’re essentially stating that leadership, autonomy, and accountability (all key requirements for entrepreneurship) – oh, and vision – are ringing alarm bells for hiring managers.

Of course, that isn’t the case at all. Why on earth would someone seeking to fulfill essentially a high-level open position disregard the exact attributes they’re looking for? The caveat paves the way into an uncomfortable truth: leadership implies authority issues; autonomy implies playing poorly with others; accountability implies rule breaking; and vision, well, that vision may counter the current vision of the company. Hard pass.

Ultimately, those traits that are prized in entrepreneurship can be unsettling to challenge or even manage. Rather than view entrepreneurship as a skill, we’re white labeling all applicant entrepreneurs as unmanageable and untamable rebels without a cause.

To note: there is an additional component to this perspective.

What on earth does an entrepreneur do?

Identifying key responsibilities and experiences and translating it into other industry roles ultimately becomes a jumbled mess of a job description, making it near impossible for hiring managers to determine if their individual experiences really translate into the role they’re seeking to fill. Not to mention, an entrepreneur on the hunt may be applying for a diverse range of positions, from various director or executive positions in marketing, business development,
technology, innovation, and strategy just to name a few.

It can make it feel near impossible to perfectly fit the wide range of duties an entrepreneur has had in their prior leadership position to the confines of a more clearly defined role.

And for the final nail in the coffin – with no direct superior, who will be your reference? Hiring managers are left taking resumes and curriculum vitae at face value, which rarely goes well. Never mind the impact you have made, the clients you have served, or the professional network you have developed. You’re a wild card, and most companies like a cut-and-dry applicant with a strong history of W-2’s to boot.

I can’t deny that it is natural to do what we humans do best and convert a complex equation into black and white. I also agree that understanding these hurdles and why they exist is essential to breaking them down. No persuasive argument would be as profound without the evaluation of both sides and understanding the evidence – and biases – of the counterargument. And though I deem them wildly out of touch or out of proportion, I do acknowledge the perspective, and may also admit that therein lies some level of truth to the noise.

As an entrepreneur myself, I admit I struggle with authority issues – but I have always felt this was a direct response to poor leaders that deemed respect a consequence of meritocracy, rather than sharing the view that respect should be inherent. I have also found that there are times where I excel when taking decisive action, rather than adhering to an incessant level of meetings and “circle-backs” with a team. And although rule-breaking is given a negative connotation, I believe respectful innovation spurs creativity and can easily trickle down to direct reports when facing business challenges.

Many founders share these views, and this is what makes them (and us) so remarkably formidable.

More organizations these days would benefit from the vision of a disruptor. Organizations have become stale. They function in antiquated ways. Their channels are broken, and they are overdue for a shakeup. And I have worked with some of the most expansive-thinking founders ready to defy the status quo.

So what is my Call-to-Action? Check in with your Entrepreneurial friends and see if they’re doing okay.

Just kidding.

But really, stop viewing entrepreneurship as an end-all and examine it under the same lens we view pressurized charcoal. Although you might think that black lump is only good for setting fire to the whole establishment (yikes), beneath the surface is an unbreakable diamond ready to refract and give your company a shiny new look. Maybe you should stop digging at it already. Haven’t you heard? Intrapreneurs know how to get things done, too.

About the author » Victoria Frankel

With an academic background in cellular and molecular nutritional sciences and entrepreneurial experiences as a scientific writer, communications consultant, and publicist, Victoria has developed an understanding of the internal and external machinations behind the fields of biotechnology, pharmaceuticals, and medical sciences. She is dedicated to making scientific principles more accessible to the public.

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