5 Questions to Ask Yourself before You Become a Freelancer

Freelancers are masters of their own destiny. They don’t depend on any single employer for their livelihood. Instead, they diversify their life by creating several different income streams. When one client bails, it’s no big deal. They can be replaced with a new one. Still, freelancing isn’t for everybody. The freelance lifestyle includes challenges that some people can’t handle. Ask yourself these five questions before you become a freelancer. If you’re not a fan of spending time alone, pay close attention to #5…

1. Are you skilled at a certain trade?

To get paid, you must first be useful.

In the gig economy, he (or she) who provides the most value wins.

The most successful freelancers have mastered a marketable skill. Some obvious examples include writing, photography, web design/development, social media management, and SEO.

Reading books is smart, but the knowledge won’t do you any good until you apply it in real life. The same fact is true for taking classes. For every hour you spend learning, spend two hours applying what you learned.

You don’t need to spend thousands of dollars on a college degree. You can teach yourself how to do anything online without spending a dime. For example: websites like Codecademy and the Odin Project will teach you how to code for free.

If you haven’t learned a new skill, don’t quit your day job (yet). Choose a skill that is interesting and easy to sell. Devote at least 1-2 hours to developing that skill everyday. After you’re confident in your ability to deliver results, offer to do a test project for a friend in exchange for a testimonial.

2. Can you easily access the Internet?

A reliable Internet connection is a MUST for this kind of work.

Don’t even think about becoming a freelancer until you have a plan B in place.

If you wake up and discover your cat chewed a cord on your router (bye bye, wi-fi), now what?

I’m privileged here, because there’s two coffee shops and a library within walking distance of my house. If my Internet craps out and I need to finish work for a client, I can still get it done.

Your situation might be totally different. That’s okay. The specifics don’t matter. Just figure out your plan B before you begin to freelance. Failing to do so could cause an immense amount of stress. Don’t risk it!

3. Do you have clearly defined boundaries?

Some freelancers are willing to answer texts, emails, or phone calls from clients at anytime. Good for them! I’d rather eat dirt. You can be productive at home without sacrificing your sanity.

I refuse to work with clients who expect immediate responses, because that’s a huge violation of my boundaries. My life doesn’t revolve around the hustle. Work is just a small part of my life.

In the afternoon, I exercise for 1-2 hours. In the evening, I participate in community theater. (Note: I recently got cast as Macbeth in — you guessed it — “Macbeth.”) After all of that, I like to hang out with my girlfriend.

Am I sacrificing potential clients and income? Sure! I have no aspirations of being a millionaire. As long as I’m setting and negotiating a rate that lets me live comfortably, I’m happy. I limit work to certain hours of the day, because time is worth more than money to me.

You might disagree. There’s nothing wrong with that. We just have different priorities. Determine whether you’re more interested in maximizing your free time or bottom-line. (No, you can’t have it both ways.) Let your decision guide the professional boundaries you put in place.

4. Is it important for you to have good benefits?

I don’t have health insurance. Approximately a hundred people have called me “insane” (but considering I haven’t had to see a doctor in over a decade, it seems like a dumb expense).

I believe in the power of prevention. If you exercise and eat healthy, you can prevent most of the medical conditions that would result in an expensive bill from the hospital. It works for me!

Some people aren’t so lucky. If you’re born with a chronic condition like diabetes or epilepsy, there’s no way to avoid medical expenses. And if you can’t avoid medical expenses, you need health insurance. Period. Full stop.

Sounds familiar? If so, please factor the cost of health insurance into your financial predictions. Self employment provides more freedom than a regular job, but it carries a cost. You’ll miss out on 401K’s, insurance, paid time off, and other benefits provided by traditional employers. Is it worth the sacrifice? (I can’t answer that question for you.)

5. How do you feel about spending a LOT of time alone?

Working at home gets lonely fast.

(Seriously. If I didn’t have a dog to keep me company, I would have lost my mind YEARS ago.)

When I had a regular job, I complained about co-workers who got too chatty. That’s easy to do when you’re trapped in an office with the same people for 40+ hours every week.

Become a freelancer and that problem will cease to exist. You will have literally no one to talk to. Introverts might appreciate the solitude. Extroverts might think: “This sounds like Hell on Earth!”

Both reactions are normal. Either way, accept this reality and decide how you’ll deal with it. Extroverts (and slightly social introverts) might want to find a coffee shop or shared office space to make workdays seem more interesting. (Or you could adopt a pet like me.)

Do you have any advice for people who are “on-the-fence” about becoming a freelancer? Share your thoughts in the comments. If you have a friend who’d appreciate this article, go ahead and pass it along.


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