Out of the Corporate Prison & Into The Entrepreneurial Straitjacket

Anna Margolis
Transformation Agency
5 min readMay 5, 2017

Let’s imagine for a moment that you’re an extremely high potential corporate misfit, who harbors a BIG vision.

Perhaps you want to buy into an existing brand (as a licensee or franchisee) or to create and innovate an original idea.

In essence, you want to build a business that will act as a vehicle for your passion and purpose in the world and, as such, the closest definition or reality that currently exists for you in the world of business, would be that of an Entrepreneur.

As someone leaving the corporate space, what would you need to get prepared? Initial financial capital aside, you’ll likely need an extraordinarily diverse skill set just to be able to get off the ground and stay ahead of the curve. If it’s a license or franchise, then, at least in the beginning, you’ll likely find yourself doing the work of 4–5 people and learning about things like:

  • Accounting;
  • Tax;
  • CMS (which stands for Client Management Systems);
  • Sales processes;
  • Social Media; and
  • SEO

In the early days, it’s important to be prepared for the business to take up a huge proportion of your attention, as you seek to get your head around everything you need to learn. As you soon discover, even when the clock hits 5pm or 6pm, as an early stage entrepreneur, there is rarely a time when you can completely leave your work behind at the end of the day, at least until you can rest assured that it’s either at, or edging it’s way toward, self-sustainability.

And, as a heads up, you may also want to be prepared (especially if you’re not surrounded by other entrepreneurs in your close circles and networks) for that experience to be more than a little isolating. Very few non-entrepreneurs can begin to understand the responsibility that comes with trying to take an idea or a business from zero to fully functional.

It’s literally the equivalent of having a new-born child. It’s fragile, it’s delicate, it’s precious, it requires a lot of time, energy and attention and it’s inevitably going to be a very high priority in your life.

Now, let’s imagine that after the initial 6–12 months, you’ve built enough momentum to hire someone to support you. Then what?

The same way you would want to ensure that you get a good nanny for your child, one that you can trust with your baby, you naturally want the same thing for your business, especially if someone is going to be spending a lot of time with your baby.

So then you face the quintessential entrepreneurial recruitment challenge.

As a small but growing business owner, paying contractors or staff is a big financial commitment, especially in the earlier stages. Outsourcing is a huge gamble as you may be paying someone else the same or more than you’re paying yourself to help you with things that you can’t do or don’t want to do. And ultimately, you’re hoping that if you’re paying someone $30k+ that they can take a whole load of things off your hands that will allow you to at least earn an additional $60k+ to make it worthwhile.

The problem is, you rarely know if someone’s the right person for you, until you’ve spent 3, 6 or 12 months’ of paying their salary figuring that out.

And what if you’re someone who’s looking to start from scratch and to create a completely new idea? Then what?

Then among other things:

  • You’ll need to be able to articulate your idea;
  • Provide market research to show why other people want it;
  • Be able to demonstrate how it’s sufficiently different from anything else in the marketplace;
  • Have a decent number of people who are willing to pay for it, so that you can show how it will make money; and
  • Then you’ll need to write that all down in a business plan, well enough that it persuades other people to give you money to build it.

Oh, and your chances of success are about 1 in 10 according to current statistics — so you better make sure that you have some kind of fall-back plan, just in case.

Even entrepreneurs who would be considered to have “made it,” by virtue of their financial success, often report that they experience little to no direct correlation between entrepreneurial success and actual happiness.

When a business grows bigger, it seems that there’s even more to manage, control, approve and juggle. The responsibility of carrying the weight of a self-
created top down hierarchy is immense; on the entrepreneurs, on the people who work with them (whose security, is inextricably tied to the healthy functioning of the entrepreneur), on their partners and on their families etc.

So, it would appear, that neither solopreneurship nor entrepreneurship seem to consistently deliver on the dream of freedom or fulfilment.

Which means that we currently find ourselves in an environment where:

  1. Employees (and managers) are largely disengaged;
  2. Solopreneurs are stymied; and
  3. Entrepreneurship is exceptionally tough and largely unfulfilling or unsupported, even for the most talented people.

One thing’s for sure, the way we currently have our business models set up is clearly not honoring the emergent values we hold today. The millennial generation plea was captured beautifully by Gary Hamel on p.31 of What Matters Now:

“[Talking about bureaucracy]…… Though we’re grateful that someone invented this clattering, savage machine a century ago, we’ll also be happy when it’s finally carted off to the scrap yard and replaced with something a bit less menacing.

In our hearts, we know the future cannot be an extrapolation of the past. As the great-grandchildren of the industrial revolution, we have learned, at long last, that the heedless pursuit of more is unsustainable and ultimately unfulfilling. Our planet, our security, our sense of equanimity and our very souls demand something better, something different.”

It seems that we are now at an inflection point, a new epoch in business, where the systems and models we’ve got aren’t working. So if we’re no longer inspired by a mechanistic economy, then perhaps it’s time to revolutionize how we’re doing things.

Ok. So where do we go from here?

According to Gary Hamel,

“The most important question for any organization is this: are we changing as fast as the world around us?”

If we’re serious about a revolution in business, then given how fast the world is changing today, whatever approach we take would need to birth a truly sustainable business model, one that can continue to flex as we grow and develop, in order to stand the test of time.

So how can we learn how we, as human beings, are changing?

How we’re evolving as a species?

How our values, the things that are most important to us, and our resultant behaviors, are changing?

Because it’s only by knowing where we’re going, that we can begin to create our organizations and our businesses to better support and align with that evolutionary imperative.

To get the best long term picture of where humanity is going, we therefore need to look to what we know is happening right now, most effectively and most successfully, out at the farthest reaches of human evolutionary development.

By observing what’s already happening on the emerging evolutionary edge, we can engage in the practice of intentionally bringing more of what we learn about what’s working into our lives and businesses, and begin to engage in the experience of, “Conscious Evolution.”

More to follow in our next blog…..”An Evolutionary Development Perspective”.

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Anna Margolis
Transformation Agency

As a former lawyer, Anna merges material world memories, tales of transformation and embodied experience in articulating the future of collaboration