6 Questions That Will Determine if You Fail or Succeed as a Freelancer

When I started my solopreneur business, there were many things I didn’t consider and lots of questions I should have ask myself before starting.

Don’t get me wrong, I’m still very happy with my decision to supplement my day job income with my freelancing.

However, I still wasn’t prepared for all the decisions and obstacles that came my way. In the future I plan to be more prepared, which in turn, can help my business become more successful and I’ll avoid making the same mistakes.

Here are 6 vital questions to ask before becoming a your own boss.

1. Can You Handle the Business Side of Business?

Just because I’m a solopreneur and my own boss doesn’t mean I don’t have business related expenses and decisions like a regular business.

Most likely, you’ll find yourself in the same position. Depending on what your freelance business is, you might want to file for a DBA (Doing Business As) with a Tax ID number, or become an LLC and register with the state.

If you plan on the business growing rapidly, you should probably at least start looking around for a lawyer, or a company like Sun Document Filings, that will help you file the proper paperwork should you decide you need to incorporate.

Then there’s other expenses to consider like small business insurance, quarterly taxes, creating invoices, finding clients, scheduling meetings and balancing your deadlines to each client’s requests and needs.

Learning is a never-ending job. You’ll constantly be learning new things, keeping up with trends, and applying what you’ve learned.

For example: I’m a writer, so I have to do a lot of reading and keep up with the latest financial news, new gadgets in technology and new social media services. This the business side of freelancing you need to know before starting your business.

2. Are You Motivated Enough to Push Yourself (and your team)?

As your own boss, you’ll have to make sure you start working on time and stick to your daily routine and be disciplined to get your work done. It’s very easy to lose focus and start doing things like visiting social media sites, chatting with a friend, or watching TV.

Another thing to remember is that while you create your own work hours, you’ll probably end up working well over 8 hours a day. Are you motivated enough to work over 40 hours a week? This is something many freelancers on a regular basis.

You’ll also have to make the tough decisions, taking on new client because you need to pay the bills, instead of just doing pro-bono work that you’re passionate about.

3. How Do You Handle Stress and Deadlines?

As a freelancer, you’ll have multiple clients and work with multiple types of businesses. You’ll need thick skin because you’ll be handling a lot of requests, opinions and clients who won’t mind being brutally honest.

Some clients will never be satisfied and will request an insane amount of additional work. How do you handle this type of thing? Are you easily stressed out at by people and last minute deadlines?

If you get stressed easily, make sure you have a remedy that works. Some preferred methods of handling stress are: drinking hot tea, meditation, getting a massage, or listening to music.

Sometimes the best way to handle a stressful situation is to just take a break. Another great way to release tension and stress is to exercise, so go outside for a walk or a quick jog.

4. Are You Organized Enough?

If you aren’t organized enough, you won’t make it as a freelancer. But thanks to technology, it’s easier than ever to get and stay organized.

There are countless ways going digital can help manage your business, with task management tools, to-do lists, and calendars. Plus, most of them let you sync between your computer and mobile devices so that you can keep track of your work on the go.

These tools don’t work by themselves though! Each day you’ll have to view your list of tasks, assignments and things that need to be done.

Then you put them in order of importance by what deadlines need to be done first. Once you’ve gotten your daily schedule worked out, you’ll need to create weekly and monthly plans.

One of my best productivity tips is to keep good notes. Whether you prefer to use a mobile app, online tools or a regular notepad, if you write everything down, you’ll be much less likely to forget things.

Keeping good notes is important because you want to be sure you do everything your clients ask for. It’s like being a waiter. Ever person’s order is different and customized to their tastes. And in the event you (or they) misunderstand what they ordered, you’ll have written proof of their requests.

5. Do You Know What You’re Worth?

When you’re first starting out, this will take a lot of research and experimenting. But you’ll need to know your worth so you know how much to charge.

Whether you’re an employee who’s starting a side hustle, like I am, or a full-time freelancer, there are simple things you can do to increase your worth in the eyes of clients. Being more valuable, means getting paid more money!

Start by finding out what other freelancers with similar experience charge or check out the Freelance Switch hourly rate calculator to help you know what you have to charge to cover your bills.

Something else important to keep in mind, is that you won’t get the regular bonuses that normally come with a full-time job, like insurance, 401K contributions and paid vacation days.

Of course you can do these things on your own, but it will probably cost you more as a freelancer, so you’ll want to compensate for that when quoting prices.

6. What’s Your Backup Plan?

Notice I didn’t ask, “do you have a backup plan?” — I asked “what is your backup plan?”. Because without a doubt, you’ll need to have at least one (if not several) backup plan when it comes to making money as a freelancer.

Some months will be really good and others will be really slow. It’s that feast or famine thing, and you’ve got to be prepared to handle it. Let’s face it, freelancing is not for everyone.

So if freelancing doesn’t work out for you, you’ll need to have another plan to pay the bills. Obviously you shouldn’t go in with the intent of quitting as soon as the slightest thing goes wrong; you just need to make sure that you have yourself covered financially and emotionally if things get rough.

What are some other questions to ask before starting a business?

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About the author: Carrie Smith is the financial artist and owner of Careful Cents, a site that helps creative freelancers discover the art of making a living. In May 2013 she quit her full-time accounting job to pursue entrepreneurship and blogging. Since then she’s been featured in sites like The Huffington Post, Glamour Magazine, and Kiplinger Finance. In her spare time she enjoys painting, sketching, and making food with her chef husband. You can connect with her in real time on Twitter or Instagram: @carefulcents.

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