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So, You Think You Can Freelance? Questions to Ask Yourself Before Taking the Leap

Becoming your own boss is a big decision.

Westend61 / Getty Images
Westend61 / Getty Images

By Marion McGovern

Becoming a freelancer is a big step. It means creating your own business, being your own boss, becoming an entrepreneur. It is exciting and daunting at the same time. So, before you jump right in, take a breath and ask yourself three questions.

Do I really have a ‘Special Sauce’ that can make money?

No one wants a mediocre expert. If your skills aren’t strong enough to claim mastery, then think no further about it. That said, different fields need different levels of experience. It is unlikely that a recent college graduate could develop a change management strategy for a multinational corporation. However, he/she could be perfect for developing social media campaigns for small companies. So when assessing your skills, be sure to consider the types of assignments you hope to get.

Assuming your skills are marketable, the question then becomes, “Can I make enough money with my special sauce?” The annual earnings you need is a personal question, contingent on your savings, income from other sources and your spending patterns. You need to budget carefully and make some critical assumptions about the income levels you could earn, the time it will take to get up to speed and the downtime between assignments. Digital talent platforms can provide a cushion for rookies; as you launch your consulting practice, you can also drive for Uber or do weekly TaskRabbit gigs to generate income during the slow periods. This ability to be able to depend on side gigs through digital platforms may be contributing to the growth of the professional independent work trend.

One way to deal with the income uncertainty is to set a goal for a 3- or 6-month time period If you get traction in the pilot period, you continue, if not, perhaps you rethink the choice. Similarly, another good idea is to ask trusted colleagues what they might pay for the types of services you could offer. Digital talent sites like Spare Hire or Zintro can offer some ideas about the going rate for projects, but the bid and offer structure means there is a fairly broad range. if you get excited looking at the digital talent sites, because many of the gigs look right up your alley, keep in mind that many of these sites have more shoppers than buyers. In fact, some sites even rate the buyers to indicate which have actually hired people when they posted projects

How do you feel about being alone?

John Donne said “No man is an island”, but he did not know about the freelance lifestyle. As an independent, you are an island because you are totally on your own. You must be able to look to yourself for direction, motivation, reinforcement, and consolation. Professional associations and colleagues can provide some support, but for the most part, it is up to you to create a fulfilling work environment. In many cases you will be working off-site, and not in the client environment, which can add to the isolation. For some, working at the client site can be just as bad, since you may be seen as an outsider.

Some freelancers partner with other independents to get more of a sense of community. Others rent offices at co-working facilities since these offer community as well as office space, administrative support, and technological assistance. However, these services come at a cost so be sure to factor that into your thinking,

Can you make the tough calls?

Many people don’t like confrontation. Freelancing provides a great deal of flexibility and freedom from office politics to a certain extent. But along the way, there can be some confrontations, because you are running your own business, so you are the only one who can make the tough calls,

You may need to tell a client that something they ask you to do is not within the scope of a project. As employees, we are all used to doing whatever the boss says; if you are working on X and are asked to do Y you pivot and do it. As a freelancer, it is not that simple. Your contract for deliverables. If the client asks for something above and beyond those deliverables, you are facing scope creep, and the contract must be renegotiated. That is a difficult conversation to have with a client, but it is an essential one.

Depending on your field, you need to be able to tell a client that he or she is wrong. They may not like that answer, but you need to give it. The consultant who tells a client what he/she wants to hear, rather than bad news will hurt his/her practice in the long run. Remember, you are being paid for your expertise, not your political skills.

Finally, there are the logistical problems, like late payments, expense overcharges or contract problems. Calling a delinquent client is never fun but neither is not getting paid.

If you answer these questions and are still intrigued, go for it. Studies say 28 million people are considering a freelance career. Trust me you won’t be the only one jumping in.

Marion McGovern, author of Thriving in the Gig Economy, is the co-founder and former CEO of M Squared Consulting, one of the first Gig Economy talent intermediaries to thrive before the term was even coined and the founder of Collabrus, a company focused on independent contractor compliance. She is also the author of A New Brand of Expertise: Independent Consultants, Free Agents, and Interim Managers Are Transforming the World of Work.

Originally published at

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