From Executive to Entrepreneur: 7 Essential Keys To Success

Leaving corporate life can be scary but these questions can help plan a smooth transition.

Linda was excited. “Time for a career change! I’ve got a terrific idea for a service targeted to first-time home buyers and real estate agents. And I’ve got a year’s salary in the bank.

“My friends say, ‘Go for it!’” she continued. “But my business advisor warns, ‘If the real estate market slows down, your idea won’t work.’ How can I forecast the real estate market?”

No crystal balls here.

Did you hear a crashing sound? That was my crystal ball, shattering.

Back to reality.

When you can’t predict events but you need to protect your future, your question shifts from “What will happen?” but “What would I do if X happens?”

Let’s face it: Sometimes we need to carry an umbrella even if the sun is shining and we have an “all clear” forecast.

(1) How well do you know your target market?

Clients who consider starting a business usually worry about getting a business license, finding health insurance, and accumulating capital. Sure, these areas are important. But what you really need are customers.

In my experience, success comes most easily to those who speak the language of their target market and have direct access to potential customers. For example, you could be prominent in the real estate community. Or you might be an accountant or marketing pro with many clients in the real estate field.

(2) What are your red, green and yellow lights?

Once an investor said, “I can’t predict the devaluation of the dollar. But I have identified the maximum tolerable devaluation that I can handle. If the dollar goes below that level, I know what actions I will take.”

You can do the same. Each business (and each job) will have different benchmarks. But you can decide ahead of time when you will pull out, invest more aggressively, or slow down.

(3) What is your Plan B?

What is your most pessimistic scenario? And what will you do?

“I can always go back to my current career” is not a Plan B.

Ideally, I recommend running your Plan B parallel to your new venture, for at least six months to a year. Plan B’s include (but are not limited to) a spouse’s job, second business, or part-time income stream.

(4) Can you test the waters?

Often you can start on a small scale, part-time basis to see if the market is ready for your idea. More importantly, you also decide if you like your new world.

If you’re not competing with your employer, you may be able to get an unpaid leave of absence to test your venture. These sabbaticals are rare, and you have to be careful with the way you phrase your request. But it happens.

(5) Have you cast a wide enough net?

When it’s time for a change, you probably have to consider a move. In my experience, frustrated workers tend to experience physical symptoms. Some even sabotage their own success so they’re forced to find a new career.

Few professionals have just one (and only one) passion. And once you begin exploring, you will find alternative paths to career success and fulfillment.

If you’d like to make decisions guided by intuition, check out this non-woo-woo guide to intuition on Amazon:

Originally published at on April 5, 2021.

Helping entrepreneurs and independent professionals grow their businesses one story at a time.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store