Do you have what it takes to become a successful independent worker?

Written by Adam Troudart,

Content Manager at Umbrella @AdamTroudart

The Intuit 2020 trend report has come up with some fascinating findings:

  • The number of contingent workers - freelancers, contractors and other specialties - will increase worldwide, exceeding 40 percent of the U.S. workforce by 2020.

  • Small businesses will develop their own networks of contingent workers.

  • Self-employment and personal and micro-business numbers will increase.

If you’re tired of answering to your boss and seeking real job security, there’s no better time to consider an independent career.

Here are five questions you should ask yourself before you take the plunge and start flying solo:

1. Are you self-aware? To begin with, understanding yourself well will help you predict how you’ll be facing certain scenarios as an independent worker. Ask yourself some core questions:

  • What are you naturally good at?

  • What do you love/hate doing?

  • Do you enjoy explaining your work?

  • What are your weaknesses?

  • Are you a good listener?

  • Are you self-motivated? (More on that in a bit)

For self-assessment, HuffPost provides some self-assessment tools. recommends the Myers-Briggs Personality Type Indicator (MBPI) for personality assessment.

2. Are you self-motivated? It’s one thing to be fired up about an idea or a thought, it’s yet another thing to actually take action and turn it into reality. Being self-motivated means you can get yourself to move from thought to action.

There are many barriers to action. For example - fear of failure, fear of success, thinking a task is too complicated or large to accomplish, and more.

As an independent worker, you are your own boss and you’ll need to come up with ways to stay positive and energetic even when the going gets tough, or procrastinating seems more appealing (ex: 2-hour lunch with friends).

3. Are you a natural problem-solver? According to senior-employee-turned-entrepreneur Susie Moore, “problem-solving is the cornerstone of all good business.”

If you’re the kind of person who loves helping people with your advice, solving problems in creative ways, and people say that you should start your own consulting business - working for yourself may be a better fit for you.

4. Are you self-disciplined? Most independent workers start as a one-person team. This means you’re the CEO, Product Department, Operations Team etc. - all at once!

Now this requires boatloads of self-discipline - you’ll have to manage your time well, set your own framework and get things done within the time you set.

Plus, you’ll need to allocate time and hold yourself accountable when learning networking, prospecting and other essential skills for working independently.

5. Do you feel trapped in a box? Do you find yourself having great ideas, and creating in-depth plans and amazing schemes yet no one at your workplace seems to care enough?

Or maybe you’re that excellent analytics guy, creative sole with a great eye for details, and you just can’t find a job that encompasses your unique set of talents?

If you feel too big to fit into a job description or an office cubicle, maybe it’s time to start a side hustle, and eventually become a fully independent worker.

After all, as proven by the aforementioned study by Intuit, contingent work is gaining massive momentum, and over the next decade, traditional full-time, full-benefit jobs will be harder to find!

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