Skip links

The Challenger Mind of Entrepreneurs: 7 Keys to Success

Entrepreneurs, by nature, are singular risk-takers that see the world through a different lens than most anyone else. These days, there’s a surge in sole proprietorships, ventures, and start-ups with the majority of them touting an “entrepreneur” moniker by the named CEO.

We’re living in the era of entrepreneurship. In fact, there’s an entire magazine dedicated to recognizing, inspiring, and highlighting the entrepreneur within and amongst us. Arguably, with this influx of branded “entrepreneurs” everywhere, it has become overused, watered down, and less impacting, to say the least.
The reality is being a successful entrepreneur is a rarity. With over 70% of first-time business ventures failing, reaching and sustaining success as an entrepreneur is often an achievement lauded by business publications, dissected by clinical minds, and studied by undergrads.

In an earlier blog post, I wrote about the lessons I’ve learned as a solopreneur. While there’s a distinct difference between solopreneurs and entrepreneurs, I drew upon my experiences in working with and for entrepreneurs over several decades. For me, the fundamental definition of what it takes to achieve a successful entrepreneur status is the ability to calculate to what degree risk can be ventured before failure – a point of no return that makes others shudder to approach.

To me, there are seven key elements that embody a successful entrepreneur:
  1. They see things others don’t.
  2. In the Clifton StrengthsFinder, skills akin to strategic thinking are entrepreneurial essentials. Specifically, future-thinking and creative-thinking lead to visionary-thinking. Entrepreneurs innately have the ability to see and create something that was once thought unimaginable. Look at some of the most famous (and successful) entrepreneurs of all time: Steve, Jobs, Walt Disney, Oprah, Benjamin Franklin, and Bill Gates.

  3. They calculate risk-taking.
  4. They are prone to risk-taking, but which risks they act on are largely dependent on data, trends, projected success, along with a good dose of rock-solid gut instinct. They aren’t bridled by wins and losses but focus rather on the next big opportunity. Serial entrepreneurs are even a more elite group where they have proven success that is repeatable.

  5. They don’t go at it alone.
  6. Unlike a solopreneur, an entrepreneur is motivated by founding and building a business. Therefore, they know the importance of finding the right people to surround themselves with who will complement their core competencies. Often, entrepreneurs are better at founding and creating than they are at running and sustaining companies. Look at some of the most notable partners that founded tremendous success: Bill Gates had Paul Allen and Steve Ballmer; Steve Jobs had Steve Wozniak; Larry Page had Sergey Brin.

  7. They are agile with a capital A.
  8. Agility is what moves them. It’s that deep burn from within to make things happen. Working with or for an entrepreneur will challenge you to exercise change agility on a frequent, ongoing basis. The capital A also applies to a Type A personality, while not mutually exclusive to entrepreneurs, many of them possess it.

  9. They have a challenger mind.
  10. I’m convinced that within their minds, there’s a constant battle going on that will challenge your thinking. I’ve encountered some entrepreneurs that are masterful at this, often times, leaving you to question your own thoughts or beliefs. It’s with this rigor that sharper, clearer thinking emerges. I have, on occasion, thought after undergoing such scrutiny and self-reflection on my own convictions that I came through with a much stronger thought process and wondered if this was just one small taste of what entrepreneurs put themselves through daily.

  11. They aim high and wide.
  12. BHAG (big hairy audacious goal) is often a mantra for entrepreneurs. Whether it’s top line or bottom line results, you can count on it being a stretch target.

    Les Brown, an American motivational speaker, author, radio DJ, TV host, and politician, and an entrepreneur in his own right penned the quote,

    “Most people fail in life not because they aim too high and miss, but because they aim too low and miss.”

  13. They have an insatiable thirst for knowledge.
  14. Having an advanced degree from an accredited university doesn’t predetermine your likelihood of becoming a successful entrepreneur. It’s about having an insatiable desire to seek and learn in all forms and formats. The discipline to feed their minds continuously produces a natural increase in dopamine, much like undergoing a rigorous workout regimen.

    Further, I would add that curiosity has wide-ranging benefits to being a successful entrepreneur. I’m certain that the children’s book series, Curious George, was not just about the trials and tribulations of life as a monkey, but more of a parallel to the makings of an entrepreneur. After all, George only fell in the ocean because he was audacious enough to attempt flight without wings.

    Entrepreneurs not only challenge and change the way we do business but also the way we think. I’ve long admired the unique qualities, traits, and strengths that make up a true entrepreneur and their influence in my life continues to be a source of inspiration.

    Your turn

    Do you have any essentials to add to the list as to what makes an entrepreneur successful? Leave them in the comments below!


    Michelle Mariola is founder & director of ISH-Productions, a Chicago-based branding and marketing company whose mission is to help emerging to mid-market companies develop their marketing strategies and brand identities.

Leave a comment