Working as an independent contractor can be an exciting prospect. You gain more control over your work, your schedule, and your finances.

However, there are also a number of stressful aspects to freelance work that many people don’t understand if they haven’t done it. You can be frustrated when you don’t know who to turn to while you’re doing your taxes, scheduling tasks, getting motivated, and obtaining further job training.

Here are four of the greatest challenges that freelancers have to face.

1. Taxes

You might have grown accustomed to seeing taxes disappear from your paycheck when you had a “day job.” But when you’re self-employed, you become responsible for calculating your taxes and paying a portion of them to the IRS on a quarterly basis.

This can be quite the shocker for new freelancers, who are unclear about how much they owe. The percentage can quickly add up, and leave you with an enormous tax payment at the end of the year.

Don’t make this mistake. Contact a CPA to help you out with your taxes during the first year or two, until you hit your stride. You might decide to stick with a CPA because he or she can reduce your risk of getting audited.

2. Scheduling

It’s true that many freelancers enjoy a more flexible schedule than traditional 9-to-5 workers. This freedom comes at a cost, however.

As an independent contractor, you’re usually expected to be the master of your own time. This means that you could find yourself working on holidays and during popular events, such as sports matches and concerts.

Essentially, you will need to meet the demands of your clients. You must be self-directed in your scheduling efforts if you intend to make it as a freelancer.

3. Motivation

Do you remember procrastinating during college and waiting until the last minute to write an essay? The same psychological quandaries can come into play when you have work piling up without a set schedule.

This can be especially challenging when you work from home. You have to be able to separate your work mindset from your leisure mindset.

If you can, work away from home at least occasionally to stay motivated.

4. Career resources

One of the most significant items that freelancers can miss when they go independent is access to continued professional resources. Some independent workers, such as agents and brokers who explore franchising, gain access to important career resources and development tools, which can be a huge boon for people who work in real estate and want to take their career to the next level.

An independent contractor probably can’t thrive in isolation. You mustn’t be afraid to ask for help and reach out to industry organizations and services for assistance. Such contacts can help you avoid major freelance pitfalls.


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