Want to see positive change in your organization? Consider how you tap into your employee’s entrepreneurial  or gig mindset.


You’ve heard or read about “that” brave soul who took a leap of faith, quit his job, and started his own thriving business. Or that digital nomad who ditched her demanding job for a relaxed lifestyle in Bali, Indonesia, and now earns twice what she used to in the corporate world.

People like them are showpieces for the entrepreneurial or gig mindset. They’re the heroes of the weary 9-to-5ers who yearn for autonomy and the opportunity to earn huge.  We love their stories because we worship that kind of mindset shift.  (And we secretly fantasize ourselves in their shoes!)

The entrepreneurial mindset and being your own boss isn’t easy

Swinging from employee to being your own boss is a huge undertaking.  First, you accept that you now won’t be able to get away with anything.  Coasting along (as you would with a regular job) won’t cut it when you’re a freelancer running your own business.  You have the world on your shoulders from Day 1.   And it may seem terrifying at first, but the control you have is liberating.  True, failure can be disastrous. But the opposite can be exhilarating!

The gig mindset takes more than just being responsible.  When you’re on your own, you have to be determined.  You’ve got to have the grit to stay for the long term.  And because you got skin in the game, failure isn’t exactly an option.

Wouldn’t it be nice to have an entrepreneur as an employee?

Technically speaking, entrepreneurs are individuals who start their own business (or several businesses) with their own money.  As such, they take a huge financial risk.  Examples of entrepreneurs range from the likes of Bill Gates, Steve Jobs, and Mark Zuckerberg, to your neighborhood fishmonger, the hole-in-the-wall coffee shop barista, or home-based cupcake baker.

The type of business doesn’t matter.  It could be a small business, large company, scalable startup, or social entrepreneurship.  What all successful entrepreneurs have in common is a passion for what they do, confidence, loads of business sense, a strong drive to learn, and the stamina to do all the extras (the extra mile, the extra service, the extra customer care, and the like).

MaMa’s mindset

The entrepreneurial mindset is a great mindset to have.  If the world was perfect, the ideal employee would be an employee-slash-entrepreneur hybrid. Let me give you an example of this.

MaMa’s Fish House is an upscale restaurant on the island of Maui in Hawaii.  The owners give employees retirement pay, health benefits and the opportunity to start their own businesses to augment their work in the service industry. Turnover is very low.  These are seasoned service experts who love surfing during the day and waiting tables at night.

One employee, Leslie, started her work at MaMa’s by taking customers to their tables. She advanced to hostess service and then moved to the accounting department. The owners recognized her organizational ability and numbers acumen.  Then she started wearing really pretty flowers in her hair to work. She had a new flower every day. The owners loved this and discovered that gardening was her secret passion.  So, they spotted her money to buy enough blooming plants to provide flowers for all the service employees year around. Then the company purchased the flowers from her. Their small investment in perennial blooming plants reaped real rewards. Over the years they have acquired fragile and fresh blooms wholesale with restaurant delivery.

So the owners spotted her the cash and worked with her on the pricing. She now grows flowers for other companies, too.

But her passion and green thumb got tapped again. Now she is in charge of all the gardens on the property with a staff of heavy lifters to move what she wants moved around.

She could not be happier. The owners could not be happier.  Her co-workers could not be happier because others have their side businesses, too. It’s encouraged. Everything is transparent and on the table with employees thinking of constant ways to make MaMa’s more successful.

The Gig Mindset

An often-discussed buzzword, the gig mindset is a metaphor that refers to the new breed of employee – someone who combines an entrepreneurial mindset while behaving like an employee.

Many describe those with a gig mindset as someone undisciplined.  They disrespect tradition and at times, lack respect for the hierarchy.  That couldn’t be good, right?

But then, it probably IS an advantage.  While they are viewed as deviants who would always go against the grain, they are often the ones who can find creative solutions to complex problems or new innovation.  Ideally, you want an employee who, despite being salaried, approach their work with the mentality of a freelancer or entrepreneur.  They are neither defined by roles, hierarchy, nor established procedures.

How to make the entrepreneurial mindset work for you

If you’re thinking, this isn’t possible or sustainable, think again.  Many organizations have encouraged this way of thinking and are now reaping the benefits.  How?  Here’s what they did:

  • They allowed people to move easily from project to project, which entailed changing roles and bosses/project owners quite often;
  • Employees are encouraged to self-manage. They choose where they work (remotely or in the office);
  • Training and mentoring are always provided.

As a result, many of these employees are exceptionally “networked”, active on enterprise social networks, and are often members of external, peer-to-peer networking groups.  In addition, there seems to be a higher degree of TRUST with close colleagues.  This happens because people tend to trust someone based on direct experience with them.  In other words, employees are bound to give their trust based on that leader’s past performance.  And because they know they are trusted, the leaders move mountains to repay this strong gesture.

What is the ultimate benefit for leaders?

Repaying the freedom that comes with the entrepreneurial mindset comes in the form of reciprocity.  It’s a fundamental law of human psychology.  If you do a good deed for someone, they are likely to pay it back. Team members who hold informal power to get things done are virtuosos at this.  It isn’t the negative kind of power (manipulation) at all.  It’s an “I want to do this for you because you’ve done a good job for me.” And when the time comes to repay, everyone is eager to do so.

At this time, when new work protocols and practices are the post-Covid norm , the biggest advantage is that everyone has their eyes on the same goal.  Everyone (or at least the majority) is on board when it comes to experimenting, driving change initiatives, taking risks, and making decisions.

An entrepreneurial mindset is easily a competitive advantage in any industry.  Dig deeper HERE and see how this builds a winning team culture.

Copyright TIGERS Success Series, Inc. by Dianne Crampton

About TIGERS Success Series

TIGERS provides a comprehensive, multi-pronged and robust system for improving your collaborative workforce behavior, collaborative work culture, profitability, project management and team leadership success. We license existing coaches, consultants and HR professionals in the use of these tools.

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