Which Big Five Traits Make for the Happiest Freelancers?

Freelancing offers a unique lifestyle. For many, it’s an opportunity to escape the rigidity of traditional 9-to-5 jobs, work with people they enjoy, and earn a living on their own terms. It's also much harder than it looks. As a freelancer, you are solely responsible for your success, and there is an endless stream of challenges that come with it, such as maintaining a steady flow of work, managing client relationships, the administration of running a business and making enough money to support yourself.

What makes one freelancer thrive while another struggles? You won't be surprised to learn that personality can play an integral role in determining how well someone adapts to and enjoys the freelancer lifestyle. Specifically, the Big Five personality traits shape how individuals approach their work, engage in professional relationships and pursue opportunities.

What Do We Mean by "Happiest" Freelancers?

Before we dig into the Big Five traits, let's define what we mean by "happiest" freelancers. Happiness, in this context, isn’t just about fleeting feelings of contentment or even a persistent sense of "I love my job!" Instead, it’s a broader measure of well-being, characterized by:

• Loving your work: This means finding fulfillment and satisfaction in the tasks you perform, the way you’re able to perform them, and the schedule you set up for yourself.
• Loving your relationships: This involves building strong connections with clients and collaborators that bring joy into your work-life. It might include having no responsibilities for others if you prefer working entirely on your own.
• Loving your income. Freelancing often comes with a feast-or-famine cycle that can impact income. The 'happiest' freelancers may not be able to break that cycle, but they find ways to gain a sense of financial stability in their work and comfortably meet their personal and professional needs.
• Loving your lifestyle: Freelancing is often sold to people as a way to gain more control over their lives. In reality, you may have to deal with demanding clients, clashing deadlines, and more stress than you would in a traditional job! In spite of these challenges, the 'happiest' freelancers find ways to maintain a sense of balance and well-being in their personal lives.

How Do Big Five Traits Affect Freelancing Happiness?

As mentioned earlier, the Big Five personality traits can significantly impact how an individual experiences and navigates the world – including their work as a freelancer. These five traits are often referred to as OCEAN or CANOE, with each letter representing a different trait:

• Openness: This trait reflects one's willingness to experience new things, think creatively and be open-minded. High scorers are imaginative and innovative, while those lower in this trait prefer routine and practicality.
• Conscientiousness: Indicates how organized, reliable and goal-oriented a person is. High scorers excel in planning and discipline, while those lower in this trait may struggle with consistency and focus.
• Extraversion: Measures sociability, energy and assertiveness. Highly extraverted individuals thrive on interaction and are often seen as enthusiastic and outgoing.
• Agreeableness: Relates to how cooperative, empathetic and compassionate someone is. High-scoring individuals are easy to work with, while lower scorers may prioritize independence or be more skeptical in their relationships.
• Neuroticism: Reflects emotional stability and susceptibility to stress. High Neuroticism is associated with anxiety and emotional reactivity, while low scorers tend to be calm and resilient.

Now that we’ve covered the basics, it’s time to explore which traits are especially beneficial for freelancers.

The Big Five Traits That Create Happy Freelancers

1. Conscientiousness: The Engine of Freelance Success

Conscientiousness is arguably the most important trait for freelancers to cultivate. Freelancing demands self-discipline; after all, there’s no boss watching over your shoulder to ensure deadlines are met or tasks are prioritized. Conscientious freelancers tend to:

• Organize effectively: They set clear schedules, break tasks into manageable chunks and use tools to stay on top of deadlines.
• Follow through on commitments: High reliability builds trust with clients, making it easier to maintain long-term relationships and secure repeat work.
• Maintain consistency: By staying disciplined, they’re less likely to fall into productivity slumps or lose focus on their goals.
• Find comfort in routine: Routine can be a dirty word in the freelancing world,  but for Conscientious individuals, it can provide a sense of control and structure. They have an easier time separating "work" from "play" which stops work becoming a 24/7 preoccupation.

While everyone has a natural level of Conscientiousness, it can be improved over time with goal-setting and repeated practice. Our article How to Become More Conscientious At Work and Beyond has some tips.

2. Openness: The Gateway to Creativity and New Opportunities

Freelancers must be able to think outside the box, get creative with their solutions and adapt quickly to new challenges. That’s where Openness comes in – this trait is strongly related to creativity, curiosity and flexibility. Particularly advantageous in fields like design, writing, tech and marketing, freelancers with this trait are more likely to:

• Adapt to change: The freelancing world is anything but static. AI changes the way we research and write, social media platforms change algorithms, and new tools constantly emerge. Open individuals are likely to embrace these changes and see them as opportunities for growth.
• Explore new trends: As one door closes, another opens. Freelancers who are open to new experiences and ideas are always willing to step through that next door, try something new and take on challenges.
• Find creative solutions: Clients may come to freelancers with unrealistic expectations or vague project briefs, but those high in Openness will likely thrive on the challenge of finding an innovative solution that meets their client's needs.
• Offer unique perspectives: Creativity can be the difference between a freelancer getting passed over for someone else's proposal or landing an exciting project. Openness is closely related to divergent thinking – generating multiple solutions for problems. This comes in handy when pitching ideas or solving complex problems that require innovative approaches.
• Have strong internal motivation. Internal or intrinsic motivation is the drive to do something because you enjoy it, rather than for external rewards. Open, curious individuals tend to have high levels of intrinsic motivation, which can help them stay motivated and engaged in their work.

There's nothing wrong with being a traditionalist, of course. People with low Openness tend to do very well in risk-averse careers and those that require a lot of diligence, caution and Plan-Bs. 

But for many freelancers, a higher level of Openness lets them embrace the excitement and potential that comes with self-employment. Our article Is It Possible to Become More Open Minded? can help set you on the right path.

What About the Other Big Five Traits?

As for the three remaining Big Five traits – Extraversion, Agreeableness and Neuroticism – it really depends on the type of work and individual preferences. Extraverts are going to be more comfortable with the networking and self-promotion necessary for freelancing. Agreeable individuals are likely to seek out opportunities for collaboration, which can help build strong client relationships. But there are plenty of Introverted, lone-wolf freelancers out there who do very well in fields like app development, content writing, data science and so on, so these are not make-or-break traits.

As for Neuroticism, while lower levels tend to be associated with more resilient and happy workers, high Neuroticism doesn't necessarily mean freelancing is not for you. With effective self-care routines and stress-management strategies in place, those with higher levels could also do well as freelancers. In fact, they may do better with an opportunity to create their own schedules and routines rather than being forced into someone else's.

The bottom line is that anyone can succeed inside any type of work structure. But honing your Conscientiousness and Openness levels?  That can help give you the freelancing edge.

How Open and Conscientious are you? Take the Big Five personality test to find out.