5 Questions to Ask Yourself Before Starting a Freelance Career

By March 29, 2018Freelance

Taking the leap into a full-time freelance career can be extremely scary. Trust me, I’ve been there. Not only would your income stream no longer be guaranteed, but also your lifestyle must alter drastically. After making the change myself, I’ve come up with a few questions I feel are beneficial to anyone considering becoming a full-time freelancer in their trade:

1. Why are you considering freelancing? List the pros.

This is a good exercise before you make such a big change in your life. The reasons that freelancing is an attractive option vary from person to person. For example, my main motivators were freedom to travel more and to feel fulfillment in the work I was producing. For you, it could be so that you can spend more time at home with your kids (or dog/cat).

2. Why aren’t you getting that (insert answer from #1) from your current job situation?

I believe this to be a good qualifier for whether freelancing would really make you happier than you are currently because it will quickly identify whether your goals are achievable in your current situation or not.

For example, before I made the decision to quit my job and become self-employed, I moved departments and tried to find work within the company that I would feel fulfillment in; as you might have guessed, I was unsuccessful which gave me all the more reason to start my business. In addition to that, there was no real way for me to get approval for the extended travel trips I truly wanted to go on.

3. Are you self-motivated?

If the answer to this is, ‘I’m not sure,’ I wouldn’t shoot down the possibility of succeeding at freelancing right away. You may enjoy coming home from work and vegging on the couch with 0 productivity until 9am tomorrow, but that doesn’t mean you’re not self-motivated. If you’re someone that will meet deadlines consistently, and doesn’t need someone to remind them of projects, I’d say that’s enough to consider yourself as a potential freelancer.

That being said, a sense of motivation is extremely important when you’re your own boss. YOU are the one in charge, YOU are the one setting your own deadlines (that will keep your clients happy), and YOU are the sole person responsible for creating a quality product or service (that also pays the bills). Sound like a lot of work? It is… at times. And it certainly takes a minute to get used to, however, the rewards are well worth it.

4. Where will you work?

It doesn’t matter if right now the answer is ‘Starbucks’ – make sure you’re going to have a place to operate your new business. Although this seems a bit unimportant, I find it is a good place to start before diving into the more stressful topics of money and client acquisition. If you don’t have a place to work at home, check out shared workspaces near you and if their pricing seems reasonable (or ridiculous).

Try to picture your day-to-day as a freelancer – do you need to answer phone calls? Do you need a location to meet with clients physically? Do you need super fast Internet? Make sure to think these things through when you’re considering your answer.

Personally, I’ve only rented a shared workspace for a few months out of the entire time I’ve been freelancing. It varies for everyone, but for me I am perfectly productive sitting in my own apartment/hotel/home (as you may or may not know, I’m also a traveling nomad so my workplace tends to change a lot). No one knows you better than you; so what do you think? Could you be productive straight out of bed without physically going into an office? Or do you feel it’d be necessary to have an office to produce quality work?

5. Can you afford it/are you financially responsible?

While you certainly don’t need to drain your entire savings account, you should have some cash available for up-front business expenses before you start. These will range depending on what type of business you’re in but I suggest making a list of recurring and one-time expenses you foresee if you DO decide to become a freelancer full-time.

Also don’t forget you won’t have any of your job’s benefits anymore (unless you have a spouse with benefits that you can latch onto). This can be a big one as health insurance premiums have skyrocketed in the recent years. If you will be needing to purchase a plan, do a quick google search for plans/pricing and add that to your list of expenses.

I added ‘financially responsible’ to this question because you must have incredible restraint when it comes to saving money for taxes. As a freelancer, you’ll most likely pay into estimated quarterly taxes, so you won’t have to drool over the money for more than a few months, but it still can be tough to not spend.

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