May 6, 2024

No Matter What You Do, Think Like an Entrepreneur

If you’re having trouble finding your next gig, or you’re running into unexpected friction or headwinds in your current position, you may be thinking too much like an employee. Consider the advantage of a more entrepreneurial mindset.

As you evolve in and beyond mid-career, your mindset must shift if you’re going to maintain your momentum and get recognized and appreciated for your insight and experience. An entrepreneurial mindset will identify you as a more seasoned, effective, and strategic thinker – if not a leader.

That’s what employers expect of you at this stage. They want you to step up and “wow” them. They want and need a reason why you deserve the position or promotion and the attendant responsibilities.

If you’re older and more experienced, aren’t you supposed to have everything figured out?

What’s the Deal With Entrepreneurial Thinking?

An entrepreneur thinks like an owner. They have a vision for how to create a valuable venture. And they have a plan for how to manifest it. They’re prepared to take full responsibility for bringing their idea to market. They are totally committed to making it work.

Entrepreneurial thinking isn’t magic. A successful entrepreneur does their homework. They do their research, model or prototype their idea, and identify why it can work, should work, or won’t work. They’re not afraid to call out or acknowledge obstacles or risks, and develop strategies, tactics, or scenarios to mitigate them. Smart entrepreneurs are also disciplined. They maintain focus on their goals and are not distracted by other people or other events that will detract from their commitments or their agendas.

An employee doesn’t think like an owner. Their concern is to execute their job to meet their manager’s expectations.

Just look at the language of the corporate performance review process. You can either exceed, meet, or not meet expectations. Even if you exceed expectations, you’re adhering to the playbook set up for you. If you want to take initiative, the only way that initiative will be recognized is if it’s within that box.

How to Shift To an Entrepreneurial Mindset

In mid-career, you’ve reached a higher level of expertise. You can leverage numerous experiences that support your decisions and your professional beliefs. It’s time to put those experiences into motion and use them to take a more critical approach to the work that you do or want to do.

Be Responsive vs. Reactive

Think through your answers and your ideas before sharing them. Take time to consider what’s being asked of you, and why. Don’t ever write an email or a report and send it without letting it sit for at least an hour (email) or a day (report). Let them wait. That extra time will reveal additional insight that underscores your value.

Find the Question, Not the Answer

For most of your career, you’ve been learning how to solve problems. Now, it’s going to be more important to ask the right questions. People make assumptions about what the problem is that they’re trying to solve. With your experience, you may see that they’re actually focusing on the wrong problem. Asking the right question is a way for everyone to discover and agree on the pathway forward.

Identify the Transformation, Not Just the Deliverable

Go deeper. Think about the longer-term, contextual, or cross-functional effects of what you’re working on – or being asked to work on. Unlike others, your experience may help you understand that the outcome of a given project may actually not make much of a difference – or the difference others expect. Look for – and then articulate – what you’re seeing from your “50,000-foot level,” and advocate for an approach that delivers a greater level of value.

Look Beyond Your Lane

If you stay in your lane or your silo, you’re going to miss what’s going on around you that can affect your work. Always know what your counterparts are up to in related areas of the company – or in your industry. If you see or hear about something that could disrupt your goal, project, or mission, get on top of it to avert a negative impact.

Always Be Prepared to Pivot

Entrepreneurs always have a Plan B (and a Plan C). They know that, as Bob Dylan said, life is what happens when you’re otherwise making plans. Always know how you’re going to recover from any unforeseen setback. Adhering to this mindset discipline also means you’ll want to stress-test upcoming milestones to mitigate any surprises.

You’re Ready to Step Up

Shifting to a more entrepreneurial mindset can be scary. You may feel like taking more responsibility for success and failure in your work puts you in the glare of a spotlight.

While change is usually uncomfortable, it will be ultimately more uncomfortable to stay stuck in your employee mindset than it will be to unshackle yourself. Because you do indeed know more, it will get increasingly difficult to defer or suppress what you know is right – or right for you.

Stop thinking as if you are still in an earlier stage of your career. You may not fully appreciate and realize how much you know and how much you’ve grown and learned. Thinking more entrepreneurially may actually come naturally to you if you give it a shot.

Start an Entrepreneurial “Watch List”

To ease into your entrepreneurial mindset, spend a few weeks or a month prototyping a new approach to your work.

Start a daily or weekly journal where you review what’s going on in your job and describe decisions, discussions, or other inflection points where you could have made a more entrepreneurial choice. Track this activity and at the end of your prototyping period, compare how your alternative choices or insights might have affected things differently. If necessary, keep this going for a longer period to get a fuller picture of just how valid your entrepreneurial mindset actually is.

Create an Avatar or Alter Ego

Who’s your favorite or most respected entrepreneur? Another way of getting more comfortable with your entrepreneurial mindset is to imagine what that person would do in your situation. What decisions would they make? How would they execute their plans?

Bring them inside you and carry yourself as you imagine they might do if they were doing your job. Take on their persona and combine it with your own judgment and values and see what that feels like. After a while, you may begin to see a difference in your confidence level and the way you express yourself on the professional questions that are important to you.

You Can’t Go Backwards…

While there may be external factors standing between you and your goals or aspirations, adopting an entrepreneurial mindset will put you in a better frame of mind to deal with these factors and likely overcome them.

Reframe those obstacles as opportunities, and use your new way of thinking to step into this next phase of your life and career.

John is a nationally recognized career coach, author, and speaker who supports mid-career professionals in landing better jobs and building sustainable, purpose-driven careers.

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