Freelancing is more popular than ever in 2023 and people have all kinds of impressions, stereotypes, and myths about it.
As I’ve covered myths and impressions already, what’s left is to go through the stereotypes. Some of them are characterizations that you definitely recognize, some are rarer and less obvious, perhaps.
Here are 11 freelancer stereotypes that I recognize from the freelancers from my rather lengthy background as someone who:
- Has hired over a hundred freelancers
- Has coached even more than that freelancers
- Has helped many of them double their rates
- Topped Upwork within 1 year
- Has been writing free guides, tips, and hacks for 4 years
- Has been a solopreneur for 9 years (almost to date at the time of writing this)
- Exercises value-based pricing in all client projects
I’m not saying I’m old, but I am saying there are plenty of experiences, good and bad, that allow me to present the most stereotypical categories of freelancers in every career stage. And some are just ugly!
Therefore, we’re going to take the classic formula, The Good, The Bad, and The Ugly (once again), to group all the 11 stereotypical freelancers. Plus, there’s a little bonus too! Let’s go through them in reverse order so that this little story of freelancer stereotypes can have a happy ending. 😉
Plus plus, there’s a bonus stereotype too!
The holy triage, The Good, The Bad, and The Ugly, works for our purpose of grouping the main freelancer stereotypes.
The Ugly
This is the group of various kinds of freelancers you see everywhere. Unfortunately. Probably it is because so many people are starting up as freelancers in 2023, and in the next couple of years, this group will be even bigger. Nonetheless, this is the group that gives freelancers a bad name mainly because of their lack of freelancing skills.
Those skills develop slowly in some people’s minds.
El Desperado
By ‘desperado’, I don’t mean the criminal notion that the word has in English. I mean what it actually means in Spanish: a desperate person.
Desperado is the most desperate guy who takes any job he can find because he “needs a job!” Any job. Any kind. Because he has no other options. His need for his own survival is so deep that he has no time to think of what his potential clients might want. His services are the opposite of customer-oriented work.
And this is why he gets all the worst clients and must give up soon concluding that freelancers either work for peanuts or get scammed every damn time. The fate of El Desperado is sealed the moment he started freelancing. He hasn’t got the intellect to find resources that would help him become successful, nor does he have any kind of chance of investing money in premium resources, mentoring, or anything like that.
He is stuck from the moment he started. Forever stuck, sadly.
El Desperado is desperately stuck for his whole freelancing career. No way forward.
The Noob
The Noob has no idea about anything. He does not understand why people hire others but, quite comically, has no issues spending all his time trying to find jobs without any success. The lack of success only feeds into more trying, even if completely futile, because he believes that putting enough effort, no matter how brainless, will bear fruit eventually.
This is the guy who screams on the user forums of freelance sites why the freelancing world is so hard or screwed and blames everyone else for his lack of success. He never even tried to learn anything systematically.
He’s also the person sending messages to senior freelancers hoping to get help, but because he’s beyond help (it’s the attitude), nobody wants to start spoonfeeding this guy! If given some free tips or pointers to good resources, he’d probably ask you for more freebies.
The Noob is the type of freelancer who never gets past entry-level opportunities. Going in circles.
The Noob has no idea what he does, how he does it, or why he even tries to do it.
The Future Millionaire
This one is similar to The Noob but is hoping to change his life overnight. The guy who wants it all and wants it fast. He joined a freelance site, so now he’s a freelancer!
I keep telling these guys a little secret: it won’t happen overnight! At this point, The Future Millionaire gets surprised and later, when his first clients don’t actually offer very high pay (if anything at all given the lack of perceived competence), gets so frustrated and starts something else… with the same faulty pattern that doesn’t really get him anywhere except the next little step in his future unimpressive career.
The Future Millionaire wants it all – now!
Le Miserable
This is the type of freelancer whose freelancer profile is below any standards, his communication with others is worse than poor, and he has no skills to mention nor any future as a professional in general. He spams random people on social media with the worst copy-pasted pitch starting with “Hiiiii Sir!!!” hoping to reach someone who could pay him big bucks. Just try long enough and he will get there!
But no. Not this way.
This guy belongs in a safe and certain day job… the classic type of corporate hamster wheel where everything he needs to do is taught to him, and nobody even remembers his name. Unfortunately, he got fired or laid off and thought his new freelance career would save him.
The big difference between Le Miserable and El Desperado is that the latter starts freelancing because he has no choice and the former because he doesn’t know or doesn’t learn how to do anything else. For both, freelancing is the last resort but unfortunately, it won’t work out. They walk the freelancer path from disaster to disaster until the inevitable, miserable end takes them off the market.
Le Miserable **cks up everything unintentionally.
The Wannabe
The Wannabe wants to be a freelancer because everyone else he knows is freelancing. The trend is too big to ignore and he just wants to jump on the bandwagon he sees and hears being so blissful.
But, the approach is what stops The Wannabe from seeing any success. He tries and tries without doing any of the background work needed to lay the basis right. He watches YouTube videos about freelancing every day without learning one damn useful thing from them. He never buys anything that would help him. He never pays anyone for anything either.
The Wannabe has the skills of The Noob (meaning, no skills), but that doesn’t stop him from wanting to be a great rich freelancer one day. He’s slightly more realistic than The Future Millionaire, but equally clueless about how to get things going.
The Wannabe just wants to be a freelancer like everyone else.
The Pretender
The Pretender has no particular skills nor does he even aim to have any. This is appalling to many, but when looking at how he tries to do business, it sadly makes sense. Kind of.
He cannot execute projects on his own, he has to resort to others to get anything done but doesn’t really understand what even that approach takes.
He lacks the management, organizational, and business skills to become a true entrepreneur, so that path is clearly blocked. This leaves him in a limbo where he won’t succeed as an individual freelancer nor can he build an organization that could succeed as a team e.g. a good agency.
All he can do is advertise a nameless “team of freelancers” that always looks much worse than a real company. Unfortunately, as his teammates are similar to him (because nobody else would join his pursuit), the results for the clients they occasionally manage to get are usually worse than those delivered by one really good freelancer. Not speaking of a real multidisciplinary team.
The Pretender wants to run a business but doesn’t know how to… as an individual or as a team.
The Bad (but successful in some sense)
There are a couple of freelancer stereotypes that manage to get somewhere in terms of business, but their approach leaves much to be hoped for.
The Middleman
This is the type that attempts to use his sales skills to make money out of others who do the actual work. Typically, he tries to get projects for $30/h, then hires people for $15/h, therefore, attempts to make profit of $15/h for minimal effort!
The Middleman can’t actually execute anything else than the sales process, but his clients don’t know that, so it’s ok!
He might even screw his supply line by not paying the guy who does the work occasionally or worse, systematically. This variant of The Middleman we can call The ScamLancer without any remorse. Its very apt.
Fortunately, the business is in constant danger because of its nontransparent nature. Clients might realize and call his bluff, his (unpaid) supply chain might cause more trouble than the money is worth, and so on.
The Middleman tries to get others to do all the work.
The BusyLancer
The BusyLancer kind of freelancer is someone who is always busy with work because working for a far too wide clientele. He is good at getting jobs… in fact, too good! But hasn’t yet figured out how to delegate and run projects by hiring and managing others.
Typically, BusyLancers cannot raise their rates very much either as the niche isn’t all that clear yet, the work is bulk stuff by nature, and the cycle never ends. This life is similar to the corporate hamster wheel except for the fact that The BusyLancer takes all the business risk too.
No matter how much he works, he’ll always be on the border of succeeding or failing. There’s no escaping the hamster wheel.
BusyLancer is… busy.
The Good
Well, the above probably gave a quite negative impression. But hey, let’s face it: Many freelancers out there are struggling and the struggle is all too real for most!
But there are good examples too. These are the stereotypes you want to aim for!
The Dominator
The Dominator owns his niche in practice because of a smart business plan and flawless execution (that, of course, has had a lot of trial and error in the process). He doesn’t care much about what other freelancers do or say as he’s beyond their level – and he knows it. And sometimes it shows too! Not always in the best way, but at least his carefully selected clients love his ability to make money for them!
The Dominator is extremely choosy about whom he starts working for as almost every job needs to fit his personal agenda of maintaining the dominating position he’s got so far as well. He might even favor taking client projects that pay a bit less than others if they are a perfect fit for his personal agenda.
Sometimes, his agenda is to pivot his business a little to earn more even if spending less and less time.
This guy is tactical and highly conscious of strategic steps in business development.
The Dominator rules his niche… and constantly develops it further.
The Solopreneur
This guy passed the time-for-money trap a long time ago and does not need to do much to cover his expenses. His value to his client is maxed out which only makes him want more. More scale!
This he gets done by making sellable (mini-)products of his own… most likely educational things for others who were in the same stage as he was 5 years ago. He has a strong brand of his own that brings high-end clients in big numbers which allows the excess funds to be spent on developing other businesses and side hustles or just experimenting crazy things for fun.
The Solopreneur went past The Dominator and scaled things up.
The Entrepreneur (a.k.a. ExLancer)
This is the least freelancer-like stereotype. You could call him an ex-freelancer (ExLancer) too.
The Entrepreneur grew his business organically by freelancing and doing all the hard work himself for years, creating a regular clientele that both benefits and depends on him, hiring many others for executive tasks of all kinds, and building processes for others that allowed him to scale up to running an agency.
The Entrepreneur is purely focused on finding the best kinds of customers and organizing how their needs are met. He’s a full-scale business owner now with all the control over the company’s direction and probably won’t bring in any partners or investors to scale up the business faster because of his personal involvement and background in running a small service-based business.
The Entrepreneur got rid of executive work altogether. He built a company or agency and focuses on running it smoothly.
Bonus category: The Cocopreneur!
Haha, that’s the guy who combines the essential parts of the three last categories, The Dominator, The Solopreneur, and The Entrepreneur. He lives on a tropical island, consumes as many coconuts as his belly can handle, and helps others to reach the same sweet life of total freedom!
This is the guy who didn’t work for peanuts at any stage of the game, not even when starting up.
Yes, I’m describing myself here. Apologies. Not!
The Cocopreneur in his natural habitat.
And you cannot avoid meeting this guy either as long as you’re freelancing online! 😉
(If you’re wondering where I got all these cool photos: They are from Unsplash! Except for the last one, obviously. That one was taken by my Coconut Girl/#freelancerlife partner.)
