Entrepreneurship vs. Employment: Which Avenue Provides Happiness?

Caitlin Cohen


With social media making it easy to network and gain a large online following, a number of entrepreneurs are making their debut. Many have chosen to pursue  their passions. For example, there are performance artists who travel to work at fun events, vintage collectors who are creating boutiques to sell their finds, yoga instructors, life coaches, bakers and chefs, etc.


Have you ever spoken to or took a minute to read entrepreneurs’ social media posts?  Usually the topic of being your own boss, following your own schedule, and following your heart comes up. These entrepreneurs can turn their passion into a living, which seems like such a more fulfilling way to pay the bills.


So does this mean that entrepreneurs have discovered this life hack to finding a way to make money that isn’t soul-sucking? Are entrepreneurs happier with their day-to-day lives than people who are employed at companies?


After interviewing several people who are employed, own a business, or have experience in both fields, the biggest takeaway from these conversations is that career fulfillment comes from the worker’s perspective. There are ups and downs to every role, but happiness will come from your outlook of your work. It simply depends on the kind of person you are and how you approach work in general.


For example, there are a lot of rose-colored ideas of what it means to be an entrepreneur. Entrepreneurs may get to make their own schedules and not have a corporate contract committing them to a set time period. However, most of their time isn’t committed to themselves.


In order to successfully run a business, an entrepreneur must consistently focus on their business. A lot of their time may go into making their product, networking with potential partners, selling, marketing/advertising, and of course, keeping track of sales and the budget for the business itself.



There’s a big benefit of being able to make those executive decisions and be fully responsible for the improvement of a business. However, it is a lot to balance for just one person and can be quite challenging. It is possible but usually it takes a special and very driven person to successfully grow a business. It takes someone who doesn’t allow failures and the lack of actual leisure time to abandon their business.


That being said, entrepreneurship is a leadership-oriented role that takes a balance of organization and self-confidence. Yet, that doesn’t prevent it from being enjoyable for a person who isn’t intimidated by learning or committing a lot of their time into one area.


For example, Olivia Joy Aley of LiviJoyHoops, makes and sells hula hoops for dancing. Besides making the hoops and running an active (both live and online) business for them, she also has a big role in marketing her shop and staying active in the hula-hoop dance community.


“My working brain is always going. I’m always thinking of ways I could stay present, stay busy, keep growing, and brainstorming fresh ideas. What I do is not just about making hoops. It is also thinking of consistent and successful ways of sharing them,” said Aley.

 With corporate jobs, it doesn’t make anyone who works for someone or a company any less worthy than an entrepreneur. Some people value being able to have a more structured environment that has all the fundamentals figured out and only requires people to fill certain roles to make that business run successfully. Usually, the work itself isn’t what produces the feelings of being fulfilled at a job.


The culture of the company within the team that is working together to the kind of service they are providing to the public can play a huge role.



For example, sometimes it’s the way the company itself makes an impact on the clients who use it. Whether it’s a learning institution, a wellness clinic, or even a coffee shop, what seems to stick the most after someone clocks out are their relationships they may build with the clients they work with. It can take just a simple conversation with a customer about what impact that business has on them.


Lucy Frolova works the front desk at a chiropractic clinic. Frolova has a history of working managing jobs but reports a higher level of fulfillment within her current role.


As Folova explained, “When the clients come to me and tell me that with just one session that they can move their neck around. Or with just a few sessions, that they don’t have back pain anymore.” Hearing these stories about how much the care helps them makes me actually feel like I’m working for something that matters. I feel like I am a part of something that provides people with the help that they are seeking.” 


Even when work can feel daunting or overwhelming, those interactions with the people we work with can make it feel worthwhile. Even in those challenges, we learn a lot about ourselves as individuals and have a major opportunity to grow.


A childcare teacher, who prefers to remain anonymous, shared how her role as a teacher may be a lot of work. However, her pride comes from within the emotional aspect of the job. Knowing that her students trust her and are learning from her is what brings her the most fulfillment in her role.


“I see the impact that I have on their lives each and every day, and I know that they really look for me. Although it drains me emotionally and physically, I love my kids and teaching SO much that my days fly by -- I don’t even have time to think about the stress I’m under, and as someone who loves a challenge, I think it’s exactly what I need,” she said.



“People view being a daycare teacher as a glorified babysitting position, and to that, I say f*** off. It’s very important work, and so rewarding if you’re good at it. I get lots of random drawings and notes and compliments from my students, and it makes my heart melt. Sometimes my kids will look at me in a moment of my frustration and literally have said, “You work so hard, I love you.” I get a lot of ‘I love yous’ throughout my day. It’s awesome to have that impact on little growing souls.”


Our society can create a lot of pressure on individuals to feel like they have to be living extraordinary and Instagram-worthy lives. However, it doesn’t matter if you are your own boss or if you work for someone else, if you love what you do then you will inevitably find fulfillment in your job.


You don’t have to be traveling the world performing on a stage, selling art online, or running a global movement to feel that you are doing something meaningful with your life. If you are feeling tied down to a job that doesn’t fulfill you, that doesn’t mean you are failing at life. It may just be a sign that it may be time to explore options that pursue those core values. You may be surprised what the little things in a job can make a major positive impact on your life outlook.


Author Bio:


Caitlin Cohen is a contributing writer at Highbrow Magazine.


For Highbrow Magazine

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