How to Cultivate an Entrepreneurial Mindset


Project leaders can no longer be satisfied with only knowing project planning and implementation, says Jennifer Bridges, PMP. Now they need to think like an entrepreneur, too.

Here’s a screenshot of the whiteboard for your reference!

what is an entrepreneurial mindset and how to cultivate one

In Review – How to Cultivate an Entrepreneurial Mindset

Jennifer noted that the role of a project manager is changing. In the past, a project manager was able to ensconce themselves in the back office and deal primarily with planning and implementation, but now things are different.

Project managers are expected to be on the front lines, supplying strategy and innovation. That means they need to have business acumen and an entrepreneurial mindset in order to align projects with business strategies. But what is an entrepreneurial mindset, anyway?

What Is an Entrepreneurial Mindset?

To begin with, an entrepreneurial mindset is just that, a mindset. A lot of people think of it as a business model, but Jennifer feels that is misguided. What an entrepreneurial mindset does is orient a person towards entrepreneurial thinking, such as seeking opportunities, innovations and new value creations.

Therefore, it’s really a personality type. Jennifer noted that entrepreneurs also have the ability to take calculated risks and accept uncertainty better than most.

How Can You Recognize the Entrepreneurial Mindset?

Are you an entrepreneur at heart? Or, more accurately, do you have the temperament and personality to cultivate an entrepreneurial mindset? Jennifer said to look for these signs indicating an entrepreneurial mindset:

  1. You Take Action: Entrepreneurs don’t wait to be told; they’re true leaders who see an opportunity and act.
  2. You’re Fearless: That doesn’t mean that you’re never scared. It’s important to have some fear because it can be sobering, but it shouldn’t stop you from doing what must be done.
  3. You’re Resourceful: Acting on an opportunity without being stymied by fear is going to take a lot of creativity and deep digging to clear the hurdles.
  4. You Obsess Over Cash Flow: Here’s a practical side of the entrepreneur: your actions always consider the potential return on investment.
  5. You Recover Quickly: There will be mistakes, but an entrepreneur doesn’t feel sorry for themselves. They get up and try again.
  6. You Focus on What Matters: The entrepreneur doesn’t get bogged down in trivial matters, but manages and prioritizes tasks effectively.

What Are the Benefits of an Entrepreneurial Mindset?

An entrepreneurial mindset is one that thinks holistically across both the project and the entire enterprise. They understand business drivers, like what’s impacting the project and how that is affecting the overall business.

Those with entrepreneurial mindsets tend to have the ability to evaluate the situation and take the necessary risks to succeed. And, again, they are able to take action when action is needed. Being able to take action and see opportunities often leads to advancements in one’s career and life.

Entrepreneurs are often thought of as people who can’t work in a structured organization, and therefore start their own business. But this is not always the case. It’s also a misconception that businesses are reluctant to hire original thinkers. In reality, their innovative thinking can often bring great, recognizable benefits.

How to Cultivate an Entrepreneurial Mindset

Okay, having an entrepreneurial mindset is a good thing. How can you work towards having one if you’re not innately entrepreneurial? Jennifer has some suggestions.

  1. Make a Development Plan: What are some of the traits of entrepreneurs you want to cultivate? Plan towards achieving one goal, and create opportunities for yourself. Then systematically move on to another.
  2. Find an Accountability Partner & Mentor: Have a person to hold you accountable, someone who you can check in with, and seek a mentor who can offer guidance.
  3. Set Check Points: Have milestones, so you can keep yourself motivated.
  4. Create a Tracking Template: Apply those milestones to a template, so you have a document to track your progress.
  5. Evaluate Your Progress: Create a process to look back on your progress and note how well you’re doing.
  6. Preview with an Accountability Partner & Mentor: Evaluate yourself, but use your accountability partner and mentor as soundboards for perspective and a more impartial opinion.
  7. Repeat: A good entrepreneur doesn’t sit on their laurels and neither should you. Continue the process indefinitely and watch yourself grow.


Today, we’re talking about one of my favorite topics, how to cultivate an entrepreneurial mindset.

Well, more and more, today, managers are required to be more on the front line of strategy and innovation, wherein project management, as a matter of fact, there are business acumen and strategic alignment are becoming required skills for project managers, whereas, in the past, they were required to be in the back office, and really focus on implementation, planning, and estimating.

But today, companies want an entrepreneurial mindset. Well, I want to start with the definition because that term is kind of thrown around a little bit, and I want to start with clarity of what it is.

So, some people think it’s a business model. Well, it’s not a business model, it’s a state of mind. So, it really orients human conduct towards entrepreneurial activities or outcomes. So, those with an entrepreneurial mindset are drawn to opportunities, innovation, and new value creation.

Some of the characteristics that we commonly think about are people who have the ability to calculate risk, take calculated risk, and accept uncertainty. Well, what are some signs, some ways that you can recognize if you have it? Well, here are…they’re more than these, but here are just a few, okay?

So first of all, you take action. Here’s a contradiction, it seems, but you’re fearless, but you’re scared. So, it’d be crazy not to be scared because there are some things that entrepreneurs do that’s new and never done before, but they take the fear and they do it anyway.

They’re also resourceful. They’re able to find people who can get things done. So, they find where maybe their gaps are and find people to fill them.

They obsess about cash flow because, typically, the opportunities they’re doing, they want to get a return on investment.

They also recover quickly. You may have heard of fail fast and fail often. So, maybe that’s a sign of an entrepreneur, but they’re able to get back on their feet quickly.

And then, they focus on what matters.

So again, they’re more than these, but here are just a few. So, what are the benefits and why do companies really want people to develop an entrepreneurial mindset?

Well, they think holistically across the enterprise or even the project. They also understand the business drivers, what’s impacting the project and how their project can impact the business. They are able to evaluate and take necessary risk and also, again, take action.

Well, if you find that maybe you’re trying to cultivate an entrepreneurial mindset for yourself, then how do you do it? So, I wanted to just share a few steps, a few steps that I use for people I mentor.

First of all, make a development plan. Think about the ones that you want to develop. Create some opportunities around them to develop yourself.

Find an accountability partner, somebody that you can call and you feel comfortable with, checking in that they can hold you accountable.

And also find a mentor. Find an entrepreneurial mentor. They love talking about this stuff. They have a passion for what they do.

So, set some checkpoints, some milestones where you can check your progress along the way and create a tracking template.

So, if these are a few you’re trying to develop, again, use a template to track your progress.

And then evaluate your progress along the checkpoints, and then as you do, review that with your accountability partner and your mentor. Talk through some of the things that maybe you find scary, and talk through those things.

And then, also, it’s a matter of practice. Just rinse and repeat. Just keep doing this until you cultivate one of your own.

And if you need a tool to help you manage your plan, then sign up for our software now at ProjectManager.