Is this common? I don’t have the same mail carrier each day. My mail box does not have a flag, but I was told if I clip the mail to it, they will collect it. Most do. However, a fairly large amount of the mail carriers who deliver mail on an outgoing day, leave my cards clipped on the box. I keep the stamp side out (visible), but for this picture I switched it to hide the recipient’s address.
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Mail carriers never pick up mail from a home mailbox in Canada EXCEPT if you have a rural box with a flag; in that box, you can receive and send mail.
In urban life, we pop our mail into a neighbourhood mailbox.
Many homes in Canada (like mine) do not have front door drop-off. One goes to the neighbourhood supermailbox (see below) to pick up one’s mail.
Older neighbourhoods will have a postie hoofing it door-to-door, but Canada Post has been downsizing it’s worker volume for about 40 years now. Why pay 10 people to deliver mail, when one can stuff the mail into a row of superboxes? Efficient, yes. But, there are challenges. Like, when the snow plow blocks access (as in the card image below).
And, if you get a parcel that is too large for your little slot, you get a message (as I did today) to travel to the post office that is holding it hostage. 
Sorry for the long message … any Canadians who want to jump in and add or adjust … please do.
Supermailbox Row card from Postal Happy @stinkypaw
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Thaz sounds like the poor parcel is at gunpoint holding its hands up. 
In Germany we always have to take our outgoing mail to the next letterbox or post agency. There is no collecting at home here and there has never been.
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@EVillalba - I have a mailbox similar to yours (on my house, no flag). I just tuck my outgoing mail behind it (I leave the mailbox closed and put the postcards or envelopes between the mailbox and the house siding). My mail carrier always picks it up. I only put mail out like that on nice weather days…if it’s snowy or super cold, rainy or very hot I don’t like to give her any extra work.
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Most USA cluster-boxes (smaller versions of the Canadian supermailbox pictured above) have an outgoing slot.
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That’s not entirely true. Look here:
Mobiler Post-Service: der Postbote mit Zusatzangeboten
Der Mobile Post-Service ist in vielen Regionen unser mobiles Angebot im ländlichen Raum, um Ihnen eine Alternative für den Weg zur nächstgelegenen Filiale zu bieten. Sie können beim Postboten mit Zusatzangeboten Ihre Brief- und Paketmarken kaufen oder ihm Ihre Briefe und Pakete mitgeben.
Google translate says:
Mobile post service: the postman with additional offers
In many regions, the Mobile Post Service is our mobile offer in rural areas to offer you an alternative way to get to the nearest branch. You can buy your postage and parcel stamps from the postman with additional offers or give him your letters and parcels.
You just have to be at home, when the postman comes. 
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And the mail carrier has to have mail for you, for otherwise they do not come to your house. So that is not really an option.
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My outgoing mail gets picked up- I have a box with a flag. But the post office has been short staffed- some days they don’t even come- and I live in a decent sized urban area. I noticed they don’t put the flag down or pick up mail if the flag is up and there is no incoming mail. I figured out that the new guy doesn’t know what the flag means. Many of mail carriers we see filling in on routes are brand new And just might not know what the deal is with your style of mail box. Maybe a little sign might help?
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Yes; our supermailbox has a small out-going box, but larger mail won’t fit through, including some maxicards. 
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Maybe make up a card with an explanatory note that you can give every time a new postie comes along?
They have been hiring new people and a lot of younger individuals may not know that it should be collected.
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I send my mail and collect my mail at the post office where I rent a box. One or two items I may get here at home. Mail theft is taking a huge surge in this country. This is not to say that theft doesn’t occur at the postal branch. But leaving it outside your house in a box anyone could rifle through, well…that is my thought.
In the image it is actually that red box mid way down, which is the outgoing box. I am super lucky as I live in older area of Ottawa, so our mail is brought right up to our house AND I am 2 blocks from a Jean Coutu drugstore with a Canada Post inside! 
I may or may not spend a lot of money there. Haha.
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USPS carriers are supposed to pick up outgoing letters you leave by your box. But as can be seen here it does not work that way in practice. It appears it is not officially mandated and so is at the discretion of the carrier. For a fee you can guarantee a pickup from your house. I believe you apply online. RURAL carriers I believe ARE mandated to collect outgoing letters from homes during the normal delivery.
With mail theft and “Porch Pirates” USPS now suggests you hand it directly to your carrier if you cannot go to a post office.
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We have an older style supermailbox, which has a tiny opening up at the top row.
I have always wondered if they will come by to collect on days I don’t receive. Thank you for answering this question I forgot to ask but have always wished to know!!!
Good thought! I’ve been mulling a mailbox makeover for a while now. Sounds like a plan!
I don’t know how it works in America.
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All of my adult life I lived in apartments and so I mailed my cards at the post office or in a USPS mailbox, because there is nowhere safe to leave cards at an apartment building.
Last year I moved to a new city and in to a house, with our own mailbox! I was excited to be able to finally mail my cards from home. There are two different but regular mail carriers, and occasionally a substitute, and they all picked up my outgoing mail.
Sadly, it only took a few months to realize that my mail was taking twice as long(!) to be delivered when I sent it this way. A few cards went missing too.
Now I make a special trip to one of the post offices that I think offers the quickest mail service. I know it sounds strange, but the mail service in my new city is very inconsistent, and much slower than my former hometown city where I lived for many decades. I am so disappointed.