Making The Transition
Don't build a freelance business around a brand-new skill.
"Fake it till you make it" is how freelancers end up broke and back at a desk. Experience is the moat.
Brendan Coots
We have all heard the stories: someone pivots out of a dull 9-to-5 into an exciting new freelance career as a designer or writer. The skills come easy, they say, and clients will line up at the door. 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 day job would demand, until they run out of emotional and financial currency and return to the 9-to-5 life. I am not trying to bring anyone down. It is just the reality. Here is what I think you should do instead.
My recommendation is to have two or more years of hands-on professional experience in your field before you freelance in it. Four reasons why:
Freelancing is easier with a personal network. It is a major boost to have former colleagues recommending you, and to be able to reach out to prospects you have already worked with.
Institutional knowledge is hard to come by. You can learn raw skills like WordPress or graphic design online, but you cannot easily learn how an industry actually functions: client expectations, how projects are run, workflows, best practices, common deliverables and formats, and the rules of the road.
Skill set matters. Freelancing is competitive. Niching down helps you sidestep much of it, but the fact remains: if your skills are entry level, you will struggle to compete (and nowhere more brutally than on the gig platforms, where the economics punish inexperience hardest).
Experience equals value. Every good website, logo, or app sits on top of analysis, planning, and strategy. Experienced freelancers contribute to those decisions in valuable ways. Inexperienced ones get brought in afterward, just to execute a vision someone else developed.
Experience leads to better clients
The key to sustainable freelancing is a small roster of A-list clients who bring you repeat business all year. Those clients are experienced, properly financed, organized, focused on value, and loyal to vendors they trust. That trust is earned by showing you understand their needs deeply, know how to execute, and will deliver quality with minimal friction on their end.
To A-list clients, consultation is a luxury good. Execution is a commodity.
If you lack the experience, your raw skills will be limited, you will miss the best way to deliver, and you will make the common mistakes that create friction. You will be in over your head, and A-list clients will know it.
The end result is that fake-it freelancers get stuck chasing inexperienced clients who do not know any better, and who therefore fixate on all the wrong things: price, volume, hours worked. We all take one of those jobs now and then, but it should be the exception, not the rule. Your mental and financial health depend on it.
Frequently asked questions
Can you freelance a skill you just learned?
You can, but it is the path most likely to leave you broke and back at a desk job. Raw skills like WordPress or graphic design are easy to pick up online. What you cannot pick up quickly is how the industry actually runs: client expectations, workflows, and the judgment calls that separate a professional from a beginner. My advice is to get at least two years of hands-on experience in your field first.
Is "fake it till you make it" good freelance advice?
No. It is how a lot of freelancers end up stressed, underpaid, and working harder than any day job would demand. Clients who pay well can tell when you are in over your head, so faking it tends to strand you with the inexperienced clients who fixate on price, volume, and hours. Build on real experience instead, and the better clients follow.
What matters more, raw skill or industry experience?
Industry experience, in most cases. Raw skill gets you in the door, but experienced freelancers get paid to contribute to the analysis, planning, and strategy every project sits on, while beginners get brought in afterward just to execute someone else's vision. To A-list clients, consultation is the luxury good and execution is the commodity. That is where the money and the loyalty live.
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