4 Reasons Your Freelancing Business Should Not be Built Around a Brand New Skill

Look, I get it. We’ve all heard stories circulating on the internet about people pivoting out of some dull, thankless 9-5 job and into an exciting new freelancing career as a web designer, or a writer, or whatever else sounded interesting to that person. If the stories are to be believed, these skills come easy and clients will be lining up at your door before you can even hang the sign out front. You just have to fake it ‘till you make it.
The problem is that many of those people end up broke, stressed and working harder than any 9-5 job would require, until eventually they run out of emotional and financial currency and return to the 9-5 life. I’m not trying to bring anyone down, this is just the reality of it. Here’s what I think people should do instead.
My personal recommendation is to have two or more years of hands-on professional experience in your chosen field before freelancing. Here are four key reasons for this:
1. Freelancing is Easier With a Personal Network
Freelancing is significantly easier when you already have a network of industry peers and potential prospects. It is a major boost to have colleagues recommending you to others, and to be able to reach out to prospective clients you have prior experience working with.
2. Institutional Knowledge is Hard To Come By
While it’s possible to learn raw skills like WordPress development or graphic design from internet resources, it is really tough to learn how an industry functions without direct, immersive experience. Your chosen field will likely have many industry norms that experienced practitioners will be well-versed in – typical client expectations and needs, how projects are managed, efficient workflows, best practices, tools of the trade, common deliverables and expected formats, roles and responsibilities, industry rules and regulations, and more.
3. Skill Set Matters
Freelancing in almost any field tends to be highly competitive. We’ll sidestep much of this by using the “niche down” approach discussed in other articles and our Freelance Master Class, but the fact remains – If your skill set is entry level, you will struggle to compete.
4. Experience = Value
There are two main ingredients to a freelancer’s offering – consultation and execution. Behind every good website, logo or app is a ton of analysis, planning, strategy and decision-making. Experienced freelancers are capable of contributing to these discussions in meaningful (and therefore valuable) ways. This consultation creates tremendous value for the client, and that value is reflected in the freelancer’s invoice. Inexperienced freelancers tend to be brought in after the decisions have already been made to execute the vision others have developed. Needless to say, executing other people’s vision is far less valuable, and the pool of potential competitors that can accomplish the task is much deeper.
Yes, you CAN launch your freelancing business based on a newly acquired skill. But the key to sustainable freelancing is building a small roster of “A-List” clients that bring you repeat business all year long. Most “A-List” clients are experienced, properly financed, organized, focused on value, and loyal to vendors they trust. And this trust is earned by demonstrating that you understand their needs on a deep level, that you know how to execute, and that you will deliver a quality product with minimal friction or effort on their part. To these highly prized clients, consultation is a luxury good, execution is a commodity.
If you lack the proper experience in your chosen field, your raw skills will be limited, you will lack insight into how best to deliver on the client’s needs and you will make common mistakes that create friction along the way. To put it plainly, you will be in over your head, and A-List clients will know it.

The end result is that “fake it ‘till you make it” freelancers tend to be stuck pursuing less experienced clients who simply don’t know any better. And because of these clients’ own lack of experience, they tend to be focused on all of the wrong things – price, quantity/volume, hours worked, etc. It is inevitable that we will all work with some clients that fall into this category now an then, but it should be the exception, not the rule. Our mental AND financial health depends on it.