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Entrepreneurship: A Way of Life

Scroll through a handful of public social media profiles today and you’re guaranteed to see “entrepreneur” listed in at least one bio. The 2020’s may be the Age of the Entrepreneur, but the pop culture status of modern entrepreneurs has its origins during the Great Recession (2007-2009) when young millennials entered the labor force. Many millennials adapted to the lack of quality jobs by piecing together a living in the rise of the gig economy. Markets began to stabilize in the 2010’s and some of those individuals were able to transform successful gigs into full-scale businesses with the evolution of new tech. The subsequent expansion of these ventures catapulted entrepreneurial visionaries into roles of leadership with the clout of financial security. Others in this cohort, who waited out the downturn in graduate school or donning a barista’s apron, have often experienced a slower rise to stability.


Recent history has made entrepreneurship an attractive concept, but one could argue that authentic entrepreneurship is far more than a title for a dating profile or a personal YouTube channel. Being an entrepreneur is as much about work accomplished as it is a way of thinking and behaving. So, which traits make someone a promising entrepreneur? And what are the psychological pitfalls for individuals wired to build businesses in pursuit of success?

It’s impossible to talk about entrepreneurship without mentioning risk. Creating or building anything new requires individuals to play in the same sandbox as failure. Risk tolerance is a requirement for any entrepreneur. Strong needs for certainty will plague an entrepreneur and stymie their ability to be agile in a changing market. Make no mistake, risk tolerance is not to be confused with fool-hardy gambling or uninformed reliance on intuition. A novice sees risk-taking as a taunt to the Universe in a bare-fisted contest, but a savvy entrepreneur has done their homework and knows the specificity of their risk. In the end, the entrepreneur must stomach the leap when others stay on the sideline in the shade of certainty.

The engine of risk needs a particular type of fuel to power a person forward into uncertainty. The drive to take chances is most effectively supported by passion. Without getting lost in the weeds about the dopaminergic systems that make this possible, passion is mostly about drive. An entrepreneur needs energy, and lots of it, to chase a specific goal for a long period of time in the face of failure and uncertainty. Passion is a powerful force, and it engenders trust. A founder needs passion to convince investors, buyers, sellers, colleagues, and employees to join a vision. A founder needs passion to keep a complicated and difficult project moving forward. Without it, an entrepreneur will dry up, and so will their dreams.

So, you have drive, you can endure uncertainty, but where are you going? Clarity of vision is imperative in any successful entrepreneurial endeavor. Data capture and exchange is possible in every microfacet of human life today, but understanding what the data illustrates is another skill. Clear vision is a two-fold exercise: Can an individual understand market demands/trends as indicated in the current data AND can they set a course that propels new ventures into prime market positions?


An entrepreneur’s vision is a directional pursuit, not the uncompromising gospel truth. Effective entrepreneurs must possess the capacity for innovation and creativity. Creativity is the ability to derive uncommon connections from otherwise unrelated entities, whereas innovation has to do with the adaptability of systems, protocol, and behaviors when old ways are no longer effective. Entrepreneurs must set a course for growth but be open to new methods and ideas. Said conversely, rigidity and certainty are the enemy of the entrepreneurial mindset. Entrepreneurs need the space to play with ideas in pursuit of ideal solutions.


All the aforementioned traits can land an entrepreneur in a successful venture. One thing remains to ensure an entrepreneur can maintain success over time — resilience. Any new venture comes with guarantees of hardships, situational changes, unpredicted outcomes, and failures. Resilience is absolutely required to help an individual overcome, adapt, and grow. In the mind of a healthy entrepreneur, “failure” is just a snapshot of an unexpected outcome in a moment in time. Failures don’t endure unless effort evaporates. Resilience is the ability to continue to apply effort in moments when it would be easier to quit.


There are a few thinking errors that can hinder entrepreneurs and their success. It is important for anyone in an entrepreneurial endeavor to examine themselves for tendencies that can sabotage their business and their future. Unexamined biases are one of the greatest thinking errors an entrepreneur can have. For an immature entrepreneur, this is often displayed as a naïve certainty that the world is exactly as the founder sees it. One way to combat this tendency is for founders to examine resistance to uncomfortable feedback. Another tactic is to ask oneself what informational or educational gaps exist in one’s conceptual understanding of a situation.


Another very common error for many entrepreneurs is to utilize poor measurement scales. The conditions might be ripe for a product or service, the ability to deliver the product or service might be certain, and the personnel, systems, and methods of delivery may be sterling. If the estimated time to get a return on investment, or the capacity for effort of the people involved is off, a guaranteed win could fizzle. Most entrepreneurs are optimists by nature. This often means they overestimate their capacity to complete tasks in a timely manner. Entrepreneurs are ripe for burn-out. Giving generous timelines and making accommodations for unplanned challenges can help keep an entrepreneur afloat in the face of pressure.

Related to timeline miscalculations, an entrepreneur can fail to realize they are focusing on a fixed point in the future of a business. That future goal could be about earnings or managerial freedom or the size of a company. Either way, working towards a fixed point has a way of killing motivation and is another opportunity for founder burn-out. As an entrepreneur, it’s important to set benchmarks to measure growth, but to recognize that the most joy comes from the work itself. Being content in the making and the doing is the best way to stay engaged, set reasonable expectations, and to celebrate the wins. No serial entrepreneur ever “arrives”; they have already arrived and they keep arriving.


A final common mistake made by budding entrepreneurs is a lack of balance in life. Business is one facet of life, but it isn’t the whole of life. Robust social connections and hobbies outside of work keep an entrepreneur grounded and recharged for the next big project or challenge. Creating and managing a business can be an incredibly taxing endeavor. It’s extremely important to have outlets for fun, rest, and pleasure.


In the end, being an entrepreneur can be an incredibly rewarding experience, but it’s certainly more than a socially acceptable way to describe a person who is unemployed but has big dreams. Building something new is hard work, but creating a business is a great opportunity to learn about oneself and the world. Cultivating traits that lead to success, and understanding pitfalls along the way, is insurance for the future. Hiring a therapist, coach, or mentor can also be a helpful resource in this process.


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