The Entrepreneurship Penalty — and How to Beat It

Were you among the thousands of us who so fervently escaped corporate during The Great Resignation to launch your own business? 🏃‍♀️💨

You might have discovered that life off the hamster wheel doesn't cut it.

Social media, the news, and the colleague who quit just before you, all promised a blissful pot of gold at the end of the rainbow (true meaning and purpose) that could only be found by working for yourself. 🌈💰

Something they didn't tell you about launching your own business is that you are immediately thrust into wearing ALL. THE. HATS.

Making all the decisions solo is brand new. Having complete autonomy over your schedule is a blessing and a curse. Determining direction and maintaining momentum every single day in an environment with zero structure is challenging.

The worst part of all (for most people) is that chasing sales looms perpetually over your head. If you didn't come from a background in sales, you're naturally averse to the extroversion required, or the concept feels slimy, in general, the task is one you might procrastinate doing at your peril.

Basically, the whole experience can be exhausting.

That hamster wheel, now so far away in your review mirror, starts looking shinier than you remember - and less oppressive. 🤔

So you start poking around in the job market again. The last time you looked for a role, you sent a few resumes, talked to a few connections, landed a few interviews, and had a couple of offers on the table within a few weeks.

In today's market, you send 50+ resumes, may score a phone screen or two, maybe an interview, and get tons of automated rejection emails, if anything at all.

What gives?

You might be falling victim to the "entrepreneurship penalty".

A news reporter from Fortune recently asked my perspective on bias against entrepreneurs who decide to move back into a salaried position.

I candidly shared that in my experience, recruiters do tend to shy away from current entrepreneurs because it can be difficult to evaluate someone with a non-traditional background.

And, entrepreneurs face the stigma that they might balk at being told what to do after running the show on their own for so long.

“It’s really critical for them to be able to explain the elephant in the room,” says Debi Creasman, CEO of recruiting firm Raven Road Partners. “Because the vibe is that someone who’s done an entrepreneurial thing for a good long while is a bit of a maverick and doesn’t really want to fit into a confined structure or be a small piece of the puzzle.”

Buuuut, I also believe that entrepreneurs are an asset to an organization that seeks greater innovation and agility.

Companies “are really struggling to grasp the concept of the new and the next,” so when you hire somebody from an entrepreneurial background, they bring a sense of calm because they’ve lived in chaos for a long time.”

Raven Road Partners can help you beat the bias and land a great role.