Now imagine not having a steady paycheck, having to continuously market yourself, and being 100% responsible for each project’s success.  Both of these scenarios are accurate depictions of what it’s like to be self-employed. It can be equal parts wonderful and frightening. So how do you decide if self-employment is the path for you? This career path isn’t for everyone, but there are certain skill sets and personality traits that predispose some people for entrepreneurial success. Read on for our thoughts on the skills and traits needed to succeed.

"Having a higher-than-average risk tolerance is an asset if you’re considering self-employment"

Experience. Most people striking out on their own will benefit from gaining several years of experience in a more traditional employment setting. Self-employment often means being a jack of all trades – you’ll need to understand at least the basics of core business functions, such as sales and accounting. Working in a more traditional setting can expose you to the various areas of business so you gain some familiarity with what it takes to make a business run smoothly.

Motivation. There’s absolutely no point in starting a business that you don’t feel passionately about. You’ll be putting in long hours, pushing yourself out of your comfort zone and hopefully building something that will be your lifelong career. Figure out what sort of work would motivate you to make those kinds of sacrifices; usually it’s something you enjoy doing so much that it doesn’t even feel like work.

Risk-tolerance. Having a higher-than-average risk tolerance is an asset if you’re considering self-employment. Business can be feast or famine and you’ll need to have the mindset to weather the uncertainty. The good news? With consistent hard work and patience, your efforts will eventually pay off and you’ll be rewarded accordingly.

Creativity. Initially you’ll likely be a one-person team, which means that all brainstorming and problem-solving efforts will fall on you. You’ll need to apply your creativity to your product or deliverable to ensure that your offering has its own unique value proposition in the market. Additionally, as a small business you’ll need to use that same creativity to find ways to leverage your business.

Organization. Without the constructs in place of a typical employment arrangement, you’ll be left to your own devices to manage your time, workload and deliverables. Success in an entrepreneurial environment is very much tied to organization so if you aren’t naturally organized, you’ll need to put some systems in place to structure your projects and hold yourself accountable.

Financial stability. It takes time to build up an entrepreneurial gig, and so financial positioning is key. Having a nest egg, along with the ability to reign in your spending when necessary will provide the space and time you need to create a viable enterprise.



Self-employment will test you in ways you likely haven’t been tested before. If you’re up for a challenge and are at a point in your life where you can afford to take some risks (and reap some great rewards), then self-employment may be the path for you!

Article By

Ashleigh Finley

An ex-shopaholic, she’s now passionate about financial optimization. Her undying wish is that more people can experience financial freedom.

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