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February 25, 2020

How to gain the confidence to go freelance

Written by Jack Lewis

A big thank you to Blue Cricket’s Tim Bradburn for the following post.

How to gain the confidence to go freelance

If you’re currently considering going freelance, you might be feeling unsure what your next move should be.

If that’s the case, a good way to start is to define the type of business you want to build.


If that word surprises you, don´t be fooled into thinking that freelancing is an alternative type of job.

When you go freelance, you are in fact starting a business.

It may be a one-person business, but its still a business because its success or failure depends entirely on you, its leader.

So in order to lead your business with confidence, it’s important to have a clear understanding of what success looks like to you.

Here are five questions to help you consider this in more detail.

Why freelance?

Freelancing can be amazing, when you do it for the right reasons.

What are your reasons? Have you thought about them in depth?

Is it because you love variety? Freelancing could certainly offer you that, because you tend to work on a wider range of projects as a freelancer than as an employee, and that can really spice up your career.

Or is it because you want the freedom to set your own hours and control your own destiny? Do you want to focus on your craft, rather than climbing up the management ladder? Those are great reasons, as long as you understand that freelancers don’t have the security of employment. If you’re not comfortable with a certain degree of risk you might be better off looking for a job with a company that embraces flexible working instead.

Or maybe you see it as a first step towards building something bigger – a company with employees that you could eventually sell. That’s also a good reason and one that requires a very specific strategy with that end in mind.

Alternatively it could be because your vocation pushes you in that direction. For example it might be harder to find permanent employment doing work that is project-based by nature, like web design or photography. So if you’re passionate about a particular field where most of the opportunities are freelance, this may be the right way to go.

There could be plenty of other reasons. All are valid, as long as they are true for you, right now. You can always adjust them if things change in future.

The important thing is to list them – write them down so you can refer back to them.

Being explicit about your reasons for going freelance provides a solid foundation to build the business you want – one that you continue to feel passionate about from one year to the next.

What fires you up?

Talking of passion, do you know yours?

Steven Kotler is a journalist and entrepreneur who trained his body to beat Lyme disease, which had him virtually bed-ridden for years. Inspired by this experience he set out to “decode the neurobiology of flow – understanding what is going on in the brain and in the body when humans are performing at their best.”

In his book The habit of ferocity, he talks about the importance of “stacking motivations.”

To stack your motivations, write down 25 things that fire your curiosity.

Of these 25 things, how many would be fulfilled by your freelance work?

Ideally you should see more than one, because the level of passion increases when several curiosities intersect.

Running a business can be challenging at times. But when you have a stack of motivations fuelling your passion, this drives you to persevere when the going gets tough.

What are you good at?

Chances are you already have an idea of the service you want to provide.

Have you analysed your strengths in this area?

Sean d´Souza, founder of the business mentoring site, is known for accomplishing more in one day than most people could in a week.

Here’s how…

Instead of trying to iron out his weaknesses, he focuses on what he calls “the weaknesses in my strengths.”

He found that achieving a 10% improvement in his strengths made him much more efficient than a 10% improvement in his weaknesses. By working on strengthening his strengths, he just keeps on getting better, and faster, at what he does.

When you know your strengths you can refine your focus. It helps you find a gap in the market where you´re a good fit, and where you can become an even better fit.

For example, a writer with a background in news could excel by working with clients who need a fast turnaround and by applying the weaknesses in strengths principle to become even faster.

Which ties into the next point – the client need.

Who needs you?

There are few things more draining, or unprofitable, than working with the wrong clients.

Jonathan Glazer became one of the world´s most successful advertising and music video directors before moving on to feature films.

“You are defined as much by the work you turn down as the work you take on,” he said. “When I started directing commercials I decided only to do work which was related to where my head is.”

This is another way of saying that it’s really important to work with clients who need and value your strengths.

When starting out, the temptation is to offer your service to all and sundry in order to build momentum.

This is nearly always a mistake.

Sylvina, a designer, admits that she wasted years of her life trying to tone down her natural quirkiness, adapting to clients who found her style too uncommercial. She eventually concluded that she had been watering down her work. Her portfolio felt lacklustre and although her clients continued working with her, they seemed slightly indifferent. It wasn´t until she started focusing on clients who valued a more edgy look that her career really took off.

That’s why the previous three questions are so useful.

Knowing your reasons, passions and strengths helps you understand who you should be talking to. Rather than going to random networking events, you can pick specific ones that are likely to be filled with people who share your passions and may need your strengths.

Once you find those people you can ask them about their needs. What are they trying to achieve? What worries them? What isn´t working for them right now?

This information will help you refine your offer to address the things they really care about.

If you’re focusing on the right audience, the things they care about should be compatible with the things you care about, leading to a win-win.

Can you afford to be picky?

Following on from the previous point, the answer to this question should be a firm yes!

But how?

How do you avoid the trap of taking on random clients just because you need the money?

The confidence to freelance can be rapidly eroded by monetary woes, particularly if you have mouths to feed. Once you lose confidence, the business can begin to falter because you find yourself making rash moves.

The truth is it’s very difficult to start a business without some cash in reserve.

Entrepreneurial start-ups (think Uber and AirBnB) get going by raising enough seed capital to see them through the initial stages before the business generates revenue.

A freelance business is no different. You need at least some money set aside.

Have you worked out how much you need to live? Do you have any savings or resources you could fall back on if you had no work for six months?

If you don’t, it might be a good idea to get a job, or stay in your existing job, and start freelancing on the side until you build up enough capital to freelance full-time.

Having that safety net will give you an added layer of confidence to get out there and build the business you want, instead of a business shaped by outside forces.

And once you’re able to build the business that you want to build, going freelance could well be one of the best decisions you ever made.

About Jack Lewis

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