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So it happened. You blinked and you’re in the second half of your career. Suddenly, there are fewer rungs on the ladder ahead of you and achieving those milestones is no longer about merit or job performance, but a variety of uncontrollable variables: bureaucracy, nepotism, politics.
There are plenty of entrepreneurial people who get a job and absolutely crush it, move up, achieve goals, and move up again. But inevitably, at some point, they realize the efforts they are putting in no longer translate into that upward mobility. They keep putting in the effort, but they begin to realize they’re hitting a ceiling. Or, in my case, I kept running into organizational chaos during mid-career that forced me to repeatedly reinvent myself until I moved fully to self-employment.
Fortunately for you, you’ve got a lot of professional miles left in the tank. You’ve gained valuable experience and know that your skills would be an asset under the right management — better yet, maybe under your own management.
Could you be an entrepreneur that’s been disguised as a corporate employee? Here are a few telltale signs.
Do you have an innate competitive spirit?
Are you someone who hates to lose? Not for bragging rights or for external validation, but because you know that you are capable of great things and hate to fall short of that high standard? Being competitive is an indicator of someone who is entrepreneurial.
It’s worth mentioning, this competitive spirit shouldn’t be based in fear. Fear leads to a scarcity mindset which can feel limiting and promotes inactivity or indecision. A focus on possibility and opportunity and having the fortitude to tackle competition head on are hallmarks of an abundance mindset – a necessity for having an entrepreneurial competitive spirit.
Related: Here’s how we determined the annual Franchise 500 ranking — and what we learned from the data.
Are you constantly seeking continuous improvement?
Say you’ve spent months working on a big project or initiative and now you’re seeing the fruits of that labor. No matter the results, are you someone who is asking: How can we be more efficient? Can we produce more/better/faster? Are we being intentional and aware of every consideration?
Look, if you’re never satisfied with the status quo and are consistently looking at performance and results with a constructive critical eye, then you’re likely someone who is constantly seeking continuous improvement. This is a key trait of entrepreneurs.
Do you spend personal time laying the groundwork?
As a corporate employee, do you find yourself spending personal time bettering yourself and sharpening skills that could benefit your career even if there’s no exact application? Are you investing in yourself? Earning certifications, building a network, purposefully putting yourself in the way of opportunity?
This type of proactive engagement can take the form of a side hustle or gig work or even simply investing personal time into developing an awareness or understanding of something you deem important. Even without the background, are you willing to take the leap and figure things out as you go? This could be a sign that you are either intentionally or subconsciously laying the groundwork for a future career shift.
Related: Greg Flynn Owns 1,245 Restaurants and Makes $2 Billion A Year. Here’s How He Did It.
Do you often imagine how you might run a larger initiative?
At the end of the day, entrepreneurs are ambitious. Starting a business and creating something out of sheer will and determination is not for the faint of heart. You have to be a person that puts in the work when no one is looking.
Look, no judgement — it’s always nice to receive validation externally, but it’s important for an entrepreneur to keep external validation as a “nice to have” and maintain internal validation as a “need to have.” If you’re someone who considers projects and assignments as exciting opportunities and prepares possible avenues for success – even if you’re not the leader – then you’ve got an innate tendency towards leadership.
Related: See Which Brands Topped Entrepreneur‘s 46th Annual Franchise 500
Are you a continuous learner?
We’ve all heard how valuable it is to be a continuous learner. After all, there’s no other way to stay on top of trends or ahead of the learning curve unless you dedicate yourself to a certain level of cognitive elasticity.
Are you interested in the “how” and “why” of daily tasks? I’m not inventing the wheel here – look no further than the habits outlined by Stephen Covey in The 7 Habits of Highly Effective People — particularly the seventh habit: Sharpen the Saw. This principle emphasizes renewal and the drive to continually change and grow. This ongoing need to develop and sharpen skills is vital for longevity and success in entrepreneurs.
If you’re reading this list and thinking “check, check, check” then you may be someone who should consider digging more deeply into entrepreneurship. These tell tale signs are indicators that you should listen to now. After all, you don’t want to blink again and realize you’ve missed a window of opportunity that could lead to stability and a peace of mind rooted in your own efforts rather than the way the wind is blowing at a company you can’t control.
Related: The One Factor the Top Franchises of 2025 Have in Common
