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16 questions to ask as a freelancer-to-be

Leon Cordier

After a global health crisis put a pause on life as we know it and encouraged us to reevaluate things, work dynamics look to be changed for good. Freelancing has gained popularity among many who seek a better life, however, it requires considering some key questions to ask as a freelancer aspirant.Now more people than ever are working remotely, and increasingly, more people are looking at the prospect of being their own boss. When you’re looking to become a solopreneur, meaning someone who sets up their own business, or a freelancer, you’ll be reaping the benefits of working for yourself.You get to work for your own benefit and not someone else’s, you get complete autonomy in deciding how you work, and you get to work on what’s meaningful for you. But, with all these benefits come some very important questions to ask as a freelancer in the making.

16 questions to ask as a freelancer in the making

Here are the 16 questions to ask before considering freelancing:

Can I adapt to changes in working conditions and daily routines?

The change in work conditions is both one of the advantages and disadvantages of working as a freelancer. The freedom from the old routine can feel liberating, but if not properly managed, it can be a curse too.

Do I mind working alone?

Self-employment means working for yourself, and that usually means working on your own. If you’re someone who needs to work with people, you’re going to have to find ways to adjust, such as working in a shared co-working space. Of course, if you run a business, then you’ll have the ability to hire the people you want to create the atmosphere you want.

Can I motivate myself?

Working for yourself means having to self-motivate. When looking at how to be your own boss you need to be disciplined and motivated to do your work. It’s easy to blow off work when you’re working on someone else’s dime, but you can’t afford to do that when it’s your enterprise on the line.

Am I good at organizing my time?

One of the most important solopreneur skills you can have is time management. Since there are no more 9 to 5 occupying your time, you need to set your own schedule. Disciplining yourself by efficiently organizing your time is a surefire way of seeing yourself succeed as a self-employed person. You can try out time tracking tools to help yourself with self-monitoring and adjust accordingly.

Do I like to control my goals, schedules, and finances?

Being in control is one of the perks of being your own boss. But, it comes with a lot of work. You need to be capable of managing all these responsibilities, from setting actionable goals to finding a work rhythm that works for you. Once you do, you’ll be able to reap all the benefits of working for yourself.

Do I prefer to manage myself?

The chances are that you are going to be your business’s only employee. It means always being able to channel your thoughts and your actions into something productive for your business. When you become a freelancer, it means you have to be able to find ways to keep yourself productive.

Do I enjoy flexibility?

Who doesn’t enjoy being flexible with their time? It’s one of the biggest perks of being your own boss. You get to decide when you work, where you work, and how you do it. The flexibility also makes the option of freelancing good for students and full-time workers looking to explore alternatives and earn some extra cash. Just make sure you manage your time wisely when deciding your schedule.

Do I have the necessary skills to become an independent professional?

There are a lot of people who want to break away from the 9 to 5, but not everyone has the skills needed to work on their own. You need to be sure that you really do have the skills to pay the bills.

Do I have a skill that I can sell?

Starting freelancing with no skills is not feasible. Having a marketable skill is the first step to becoming a solopreneur. Finding a skill that you can sell is paramount to standing out in the freelance market and being able to start making money. Discovering your skill and a way to market it will give you a big advantage as a solopreneur getting started. Moreover, the answer to “What is the best freelance job?” is oftentimes what you’re already good at and enjoy doing.

Am I a good negotiator?

When you’re self-employed, you are always your own negotiator. That means knowing the value of your work and what you can get a client to pay. Negotiating isn’t a skill that everyone has naturally, but it’s one that you’re going to have to pick up if you want to make sure you’re paid fairly and on time.

Can I wear many hats?

When you’re your own boss it means you’re HR, the project manager, the social media specialist, and the accountant all rolled into one. It’s a lot to manage for anyone, so be certain that you can handle all these tasks. Doing so is necessary for being successful as a solopreneur.

Am I a good communicator?

Communication is a key skill that any aspiring freelancer should look to master. Being able to effectively communicate your expectations from your relationship with your clients avoids possible miscommunications. So make sure you can communicate both the things that you can offer and what you expect when working with clients.

Am I good at networking and building relationships?

When you’re self-employed, networking is something that you can do to expand your business in many ways. You can get introduced to new ideas and information, find opportunities to collaborate, or even use it as an opportunity to pitch your services or products to professionals. Networking is one of the underrated solopreneur skills that you’ll have to cultivate to be successful.

Am I adept at self-promotion and marketing my skills?

The first step to making money without working a 9 to 5 is learning how to promote yourself. You will have to sell yourself and your services to get people to hire you, so finding what works best for you is important. Is it social media, email marketing, writing a blog, or a combination of methods? Promoting yourself is important for guaranteeing that clients find you and your business grows. You need to learn how to introduce yourself as a freelancer.

Do I have the personality traits necessary to work autonomously?

Being self-employed means being able to work for and by yourself. This is one of the essential questions to ask as a freelancer-to-be, as being able to work autonomously is a key characteristic trait for solo work dynamics.

Am I comfortable with risk and uncertainty?

It’s no secret that working as a freelancer is a bit of a gamble because you’re betting on yourself. You have to be comfortable with facing the uncertainty that comes with it because there are going to be highs and lows. Learning to roll with the punches goes a long way to becoming a successful solopreneur.

Can I be flexible and ready to upskill all the time?

When you’re self-employed, you have to be able to adapt. This means always looking to improve your skill set. You are responsible for keeping your skill set fresh and relevant in the industry that you fall in. So, be sure to find whatever ways you can to improve your craft.

Can I set boundaries and manage expectations?

When you’re working freelance, you are also responsible for your own job description and maintaining the boundaries in your business relationships. You may run into difficult clients and situations that require you to communicate your limitations and negotiate with different expectations.

Do I look for improvement constantly?

The freelancer that looks to improve their operations constantly is the one that tends to be successful. You should always find ways to make your operations more efficient, to see if you are marketing your business the best way and if your skill set is up to par. By constantly improving yourself, you give yourself the best chance to be a successful solopreneur.

One place for all your questions about freelancing as a career

It takes a courageous leap to make the transition to a solo career. We hope you found some answers in this list of questions to ask as a freelancer-to-be. If you’re still in need of support, explore Ruul Blog for all the ins and outs of freelancing and leading an autonomous career. Connect with us on LinkedIn and Instagram, and never miss an update to help you along your journey.


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