I know a lot of freelancers particularly in sales, have to look like they are well off. Well-to-do, and their cars show that they are good at their jobs — selling.
That being said, I’ve never found it wise to be flashy with your money in my line of business (consulting).
The fancier of a car you drive and the more you talk about your vacations and how much money you spent on everything, people get the feeling that you’re being paid A LOT … maybe too much.
WAY too much.
Then they get jealous.
Then it’s a whole awkward $$$ situation.
Then they start making comments like: Well if you can afford a [insert luxury German make here], then SURELY you can afford a $15 meal with us!
It’s uncomfortable, not that I’ve ever experienced it, because I don’t show off at work or brag, but I’m also quite young for a freelancer, so they think I’m making half what the older guys are pulling in.
WHAT IF YOU WORK FOR “THE MAN”?
The funny thing is if you worked for a consulting company, that’s a different story.
People relax because they know you’re on a fixed salary just like they are, and they may think that you earn a lot of dosh, but it isn’t a ridiculous amount.
Or they just assume you are buying on credit or ‘wasting’ your money by spending it on a car or vacations (even if you aren’t and you have the cash).
PEOPLE DON’T CARE IF YOU ARE WORSE OFF THAN THEY ARE
But they sure care when it looks like you can afford to drive a luxury car and take 3-week vacations with your family.
I’ve had plenty of comments about my old beater car, but mostly along the lines of sympathy, even pity because they assume that no one would want to drive that car willingly if they had the money to buy something better.
They don’t care if your car is worse or the same as theirs is, just not if it’s better, even if you made a smart choice to buy a well-made luxury car that you would keep for the next 20 – 30 years while they upgrade their own car every 5 years.
It’s a stronger stigma if you work for yourself.
IT IS BETTER NOT TO SHOW OFF
From my point of view, it is better to be thought of as being moderate, even poor, than to be considered rich.
Showing off too much can cause some nasty green-eyed monsters to surface.
I’m not saying that I drive an old beater on purpose to score sympathy contracts (I’d like to think I’m also good at what I do), but it doesn’t hurt, and it is far better than being envied or to be the cause of workplace jealousy.
Freelancers who drive really flashy cars amongst the “plebians” who cannot afford even half of that payment most of the time, have to fend off a lot of comments about being rich, and they have to try and learn how to deflect the jealousy and take it in stride.
I’m not that great of a liar, so I’d rather just not have to lie or cover things up.
It’s like they think just because you’re a freelancer, working for yourself, self-employed, whatever you want to call it —- you are raking in the dough all the time.
This is true in a lot of cases, but sometimes that isn’t how the cookie crumbles because not all freelancers are raking in money, or working all the time (take my friend’s wife as an example).
It really depends on the industry and who you work with.
Perhaps if I dealt only with C-level executives, I’d have to buy a normal car. Maybe.
Just a girl trying to find a balance between being a Shopaholic and a Saver.
I cleared $60,000 in 18 months earning $65,000 gross/year.
Now I am self-employed, and you can read more about 
Context, context, and context. If you’re dealing with corporate types, you’d better look corporate. When in academia, do as the academics do. The rest of the time, keep your bunny slippers on.
I work in insurance sales and I need to look nice. Not so flashy but nice and I do believe that it leads to confidence on the part of the client.
I wouldn’t think much of a freelancer who dresses as shabbily as me, but it’s a balancing act I think. We don’t get freelancers but ‘roaming’ employees who appear and a professional appearance does make the difference. Only female I’ve encountered recently was suited in black/grey – nothing flashy. If she’d turned up wearing the kinds of shoes shown in this article we would have dismissed her as a flake. Oh, and she stayed in a cheap hotel, but that’s because the company was paying!
I love those shoes! Not that I would actually wear them but they look cute, like something an actress would wear in a 1930s period movie…
The safest road in most industries is to look presentable. When you go out into the world people generally look for people that are presentable. People naturally look for people that are hygienic and when it comes to business they want to talk to people that know what they’re doing.
Even if you’re rich there’s no need to talk endlessly about how nice you have it. Affluent people shouldn’t be ashamed of their wealth but there is such a thing as boasting too much. There is such a thing as class. I pretty much agree with Amy.
I don’t want to look poor though. Looking too frugal can be a turn off as much as someone boasting for an hour about how they made $500k last year. I don’t want people’s pity which is why I’m against looking too frugal.
My step-dad has said if I saved I would always be fine. I feel that people would get less jealous if they saved more and got financially savvy.
Looking presentable and looking expensive are two different things. I prefer the former and think it’s more approachable all round.
But it seems ridiculous to me that anyone should feel they need a particular car or house to suit their position, surely that should be a personal choice and not affect their status. Sadly, it appears it does: my cousin feels she has to drive a certain class of car because she holds a good bank position. Even my husband said he needed a new phone now he’s a CEO because his old one was held together with a rubber band (screen came loose!), though usually he is comfortable about not having fancy cars and stuff. He boasts he has a happy family ;). I drive a tiny, ancient 16 yr old car that practically runs on air and will do so until it dies, even if my husband is a CEO. For my life, I don’t need a fancy car, even though I could afford one!!
I think a free-lancer should look competent before everything else. Look too frugal and people think they’re not getting enough work- they’re incompetent; look to good and it looks as though they don’t need to work. Dress to fit in with clients – if working in their space. Drive a car that’s reliable and reasonably low on petrol consumption.
This is an interesting conversation.
I tend to think more about how people in academia “should” dress, as I’m a phD student. I’ve noticed that there are a few opinions on this:
1) dress sloppily to look like you’re so serious about academics that you can’t pay attention to clothes (my old advisor wore velcro sandals with dress socks and a sweater that was at least 3 sizes too big like every day)
2) dress nice but not *too* nice- just try to look like a normal person
3) dress amazingly well so everyone knows that you’re an academic rockstar
#3 seems pretty rare, but it really only works for those that *are* rockstars in their field. Otherwise you just look like a huge jerk. Ditto #1, you’ll just look like a crazy person unless you actually are a genius. #2 always seems like the safest bet to me. Boring, but being on par with everyone else makes the clothes/car/hair/whatever blend in, so what you do and say can stand out. It’s the same concept as not wearing bright blue eyeshadow to work because it’s distracting.
Of course, it’s not fair at all that this seems to be particularly important for female academics. But so it goes.
I agree with Amy, I like working with people who obviously have their stuff together but aren’t showing off. Confidence is important, so is being pulled together and not looking dischevelled or that you simply don’t care. But you can look really pulled together and successful at various price points. To me, if someone goes overboard with the brand=name flashing or worse, TALKING about how rich/successful they are, they don’t come off confident, but rather insecure, so they probably wouldn’t get my business.
On a personal level, I have found that pretending to be more modest/poor than you are is always a good idea. It’s funny how, even an inkling that you are making more money, or have more wealth, than someone else, can activate the “green-eyed monster” in them – regardless of how hard you’ve worked to get there. I would never pretend to be poor to take advantage of others, but I always prefer to downplay what I have than the other way around.
I wouldn’t be impressed with anyone who came into the office and showed off. I’m on salary and have been involved in the odd conversation or two with people talking about how great commission is…I work with a lot of sales people. Hearing them brag about their big commissions doesn’t make me want to help them. I get the same amount of money whether I put effort into helping them or one of their humbler co-workers. I go for the humble person every time.
As far as dress goes, I kind of expect the dress to coincide with the kind of freelance work they do. If they are auditing our books, I want them to look professional and polished, but if they are going to do design work, a bit of funky in their wardrobe is nice.
It is a delicate balance even working for The Man. I’ve noticed coworkers getting their noses in a twit if they think I have more than they do. I’ve had one go so far as to comment on how I must make more than she does if I can afford x-y-z item. I deflected the comment by saying that I just SPEND less than she does – then pointed out I don’t eat out 2-3 times a day…etc. It was very uncomfortable for everyone involved. Money makes people funny… especially if they think you are getting too big of a piece of the pie. I am more secretive about my success than I ever was about my failures.
I always like working with people who I feel are in my ballpark, which means not particularly flashy OR frugal. A decent car but not necessarily a luxury model, nice clothes but maybe not Louboutins and Chanel from head to toe…people who obviously have their crap together but aren’t showing off. I like dealing with people who are relatable but successful and don’t feel the need to put on airs. Looking polished and confident goes a long way.
To me, a freelancer should always look like they’re doing well, and should look presentable. Looking too flashy is bad, but looking poor is probably also equally bad. Looking poor might make you look like an idiot who shouldn’t be freelancing and looking rich makes people get jealous.
On the other hand, if you’re working in a position that makes a lot of money, say a lawyer, then it’s almost a lose-lose situation. If you don’t look flashy, then people think that you’re not doing well. If you do look flashy, people get jealous.
I do think there is an in-between way rather than flashy or frugal. Just act / look like you live within the means of a middle level employee in the kind of companies you work for.
I have interacted with freelancers and never ever thought of how much money they earn because they look like any regular employed person with the company. So, in my line, a freelancer who behaves like a middle level manager will go unnoticed. You go as a top level manager though, and maybe you will be respected for your views, (because obviously you earned enough and hence have given consulting advice to a no of companies) but the money factor will flash in.
But then I am talking of the India scenario, where age matter A LOT and so does your style. So personally I feel its best to be conservative, professional and middle-level looking until the grey hair and crows feet start showing.