Are you ready to be your own boss? Here are 5 questions you need to answer first.

February 15, 2019 | Virtual Agents | Blog


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These five questions should prepare you for life as a freelancer.

Freelancing and self-employment is becoming incredibly popular. In the U.S. alone, more than 33% of people make a living from freelance work, and many pundits predict that this will increase to 50% of the workforce in years to come.

With that in mind, you’re far from alone if you’re giving consideration to saying “goodbye” to fixed hours, bosses and commuting. Instead, you can say “hello” to freedom, flexibility and the ability to work from wherever you like.

However, moving from an employee to a 1099 contractor isn’t a decision you should take lightly. It means becoming a business owner which, like everything in life, has its pros and cons . Life as an independent worker can be liberating, absorbing, and—most importantly for some—lucrative.

Plenty of studies suggest the freelancers can end up earning more than their traditionally-employed counterparts. But there are also considerations regarding job security, guaranteed income, and living without employee benefits.

This article should help you weigh all of that up. It asks some searching questions to help you to uncover your motivations, fears and priorities. After working through it you should feel more certain of your decisions, and prepared to take your first steps in the world of freelance work.

Why are you choosing to work for yourself?

This may sound obvious, but it’s really important to define why you’re deciding to move into freelancing.

There are loads of good reasons why self-employment could prove fantastic for you. For example: having the flexibility to spend time with family, gaining the freedom to work on exciting and varied projects, and building a business that could one day become an asset for you and your loved ones.

But there are bad reasons to start freelancing too. Hating your current job or boss may tempt you to freelance, but it’s perhaps not enough of a reason – in isolation – to impulsively turn your back on all traditional jobs! Similarly, making such a significant life change because you think it may mean less hard work and no more “doing as you’re told,” is not a solid long-term strategy.

The important thing here is not to decide to freelance on a whim. So long as you’re clear of your own motivations and have a vision of the life you want to create, you have a good chance of success.

There’s no need to be a passenger in your working life – you can choose to drive instead.

What are your life goals?

Many people find that they “end up” in careers rather than really choosing them. They look at what jobs are out there and consider whether they could do them or not.

You don’t have to do this, and if you’re embarking on a freelance career you have the perfect opportunity to build a working life that’s more in line with your hopes and dreams. Instead of looking what’s out there, you can instead think about what you’d really LOVE to do and work out a way to get there.

Better still, it doesn’t have to only be one thing. Nowadays, more and more people are building portfolio careers . If you want to spend half of your week doing some solid customer service work from home , and then spend ten hours making artisan jewelry and another ten starting a niche blog, there’s absolutely nothing stopping you.

There’s no need to be a passenger in your working life – you can choose to drive instead.

What’s holding you back?

Of course the reality is that you can’t always just visualize your ideal freelance working life and walk straight into it. There may be a series of things you have to do first. For example:

  • Building a financial safety net to carry you through while you’re “paying your dues” and waiting for your first income.
  • Developing skills in the areas you wish to work in.
  • Arranging family life around your planned working patterns.
  • Taking online courses to get certified or set up a back office to launch your new career

Those are just a few examples, but the important thing is to see the actions you need to take as steps along a path to what you want , rather than obstacles. The approach people take to such things marks out the difference between those who get what they want, and those who look back year after year lamenting the fact that nothing has changed.

You can build a financial safety net by saving, cutting back on things, or working on a side gig. The key point is that you actually have to DO those things!

How prepared are you?

The above step covers how to put yourself in a position to achieve your freelance goals. However, you also need to prepare for what freelancing is actually like.

In some ways, switching to freelance can be quite a shock to the system, especially if you’ve been in the “traditional” workforce for some time. In the early days, that new-found freedom can resemble isolation when you realize that there are no longer colleagues to bond and gossip with. And when it comes to getting things done, nobody’s going to motivate you or make you accountable; If you don’t drive yourself to get stuff done, it won’t get done, and you won’t earn any money.

There are various “rites of passage” for new freelancers: The first time you issue an invoice instead of waiting for a paycheck; The first time you get sick and realize it’s still down to you to work out how the work gets done. But many of them feel fantastic too, such as the first time you take a trip without having to request time-off in advance, or when you decide to spend a summer afternoon in the garden – just because you CAN!

Before you embark on your freelance life, give yourself time to consider the good and the bad. You can be sure it will all feel very different to what you’re used to, and it’s a bit of a roller-coaster sometimes.

How will you stand out?

The freelance world is rather competitive, especially when it comes to online freelancing. You’ll soon realize the workforce is truly global, and there’s some stiff competition out there. Furthermore, some people may live in countries where they don’t need as much to live on as you do.

As such, it’s wise to work out exactly how you’re going to stand out. So, for example, if you’re going to be a virtual PA, what services are you going to offer that are hard for potential clients to find? If you’re starting a niche blog , how will you make sure it’s the VERY best one out there on your chosen topic? If you’re planning to do customer support work, how will you ensure you provide the kind of service that keeps you on the phone?

The point here is that in a crowded marketplace, the best freelancers are those who are conscious of their unique selling points. These can be anything from offering innovative services to working to be the very best in the business. If you want to be a true success, it’s worth working out what YOU intend to do to stand out.

Answering the five questions above should really help prepare you for a life of freelancing. The opportunities are endless but competitive– so don’t miss out! Once you feel ready to embrace the independent contractor lifestyle and if you think a career helping others is right for you, considering joining Liveops Nation and becoming a home-based, independent agent. Learn more.

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Ben Taylor

Ben Taylor is the Founder of, a portal for aspiring freelancers and home workers.

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