Should You Feel Challenged By Your Work?

Being self-employed comes with its own set of challenges: establishing your business, carefully keeping track of your taxes and deduction, generating leads, negotiating your own health insurance… The list goes on and on.

However, you may notice your day-to-day workflow falling into an all-too-predictable routine. You feel fortunate to do what you love for a living, but is it stimulating enough? Do you feel challenged – or rather, should you feel challenged?

Being self-employed comes with its own set of challenges: establishing your business, carefully keeping track of your taxes and deduction, generating leads, negotiating your own health insurance… The list goes on and on.

However, you may notice your day-to-day workflow falling into an all-too-predictable routine. You feel fortunate to do what you love for a living, but is it stimulating enough? Do you feel challenged – or rather, should you feel challenged?

Finding your niche is important, whether you’re running a business or juggling clients as a freelancer. But if you’re in a rut of pumping out the same content over, and over, and over again, you won’t be able to grow within your field.

Don’t get me wrong – practice makes perfect. Yet, there’s certainly a point where practice crumbles apart into monotony.

One of the many beauties of self-employment is being your own boss. It’s liberating to work at your own pace and set your own goals.

With no one hovering over your shoulder to raise the bar for you, its your responsibility to keep raising the bar for yourself.

Burnout is not equal to success. It’s a sign that you need a break. Remember: you don’t have to work your fingers to the bone in order to feel accomplished.

Rather than aiming to “be more productive,” guide yourself toward quality over quantity. Continue to build upon your pre-existing skill set.

How to Challenge Yourself When You’re Self-Employed

Be Diverse

Having a niche is important, but variety is the spice of life. Instead of pigeon-holing yourself to the same type of content, expand your reach by creating under diverse circumstances.

Work with an array of clients or change up your format a little…

  • If you’re a writer, play around with different styles and voices in your work. Tackle your niche from different angles. Try short-form writing, long-form writing, and other formats.
  • If you’re an artist, experiment with different mediums and color pallets. Use different supplies, browse the internet to learn new techniques.
  • If you’re a musician, incorporate new instruments and samples into your tracks. Try creating a song in an entirely different genre.
  • If you’re a software engineer, innovate your app development. Try out a new programming language, fiddle around with different frameworks.

“Vibe-Check” Your Work

You may find yourself in a mindless loop of writing, painting, mixing, programming, or packaging up products. You’ve been working in this current position for weeks, months, perhaps years or decades. Understandably, you question whether you’ve finally succumbed to tedium.

Now is the time to reassess your work and reevaluate your creations. Put your content under the microscope without being overly self-critical.

Compile a list of your strengths and weaknesses:

  • What do you like about your work?
  • What aspects of your content appeal to others?
  • What could you improve upon and where would you like to see yourself – skill-wise – in five months from now?

Educate Yourself

Do your research! Watch videos or read blogs by other people within your field to expand your skillset.

Always aim to stay up-to-date on your understanding of the industry. For example:

  • What’s the current economy for freelance writers, artists, etc…?
  • How are other freelancers promoting themselves?
  • What’s the latest software that everyone’s currently using?
  • What’s trending right now?

Connect With Others

Connecting with other creatives in your field gives you the opportunity to talk about your feelings together. You’ll quickly see you’re not alone in your conquest as an independent contractor.

Furthermore, this opens up the opportunity for you to collaborate with like-minded individuals. You could work together on a piece, cross-market and promote each other’s work. This effectively expands both of your audiences.

Perhaps you could even launch a side project as a duo!

Set Realistic Goals For Yourself

Having a goal in mind is a great way to stay motivated. It gives you a tangible target to lock sights on, something to keep working towards.

On the other hand, goals can become toxic if you let them run your life. You may begin holding yourself to unrealistic standards or putting unnecessary pressure on yourself.

When setting goals for yourself, you have to be realistic. It’s healthy to dream big, but goals that feel too distant can become discouraging.

Instead, compile a list of short-term and long-term goals. Your short-term goals can be on a daily, weekly, monthly, or quarterly basis. It’s totally up to you!

Short-term goals should encompass what you’re already on track to accomplish but up the stakes a just a tiny bit.

Long-term goals should encompass where you can actually see yourself in a few months or a year from now, assuming the world doesn’t end and you’re able to keep working optimally.

Again, don’t hold yourself to any quotas or get too down on yourself. Even if you just check off one out of a dozen goals, you’ve still accomplished something.


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