We've all had it happen. Your opening hand is a one lander and you take a mulligan which results in no lands; you're forced to go to five. You keep an acceptable five but see zero additional lands and a few turns later it's over. Whether it's not drawing your answer on curve or messing up a complicated play sequence, losing some games in Magic is inevitable. Luckily, with respect to casual games of Commander, winning is not all that important!
Not Winning DOES NOT Equal Losing
First, let's talk about the primary difference between competitive Commander and casual. In cEDH, the goal is victory and the tools are anything and everything to achieve that end. For casual Commander, the goal is enjoying the social experience of playing Magic, with winning a tangential goal at best.
Concentrate on changing what counts as a "win." Maybe you want to test the power of a new card, show off a flashy purchase, or demonstrate an obscure rule using old cards; all are valid payoffs that do not hinge solely on the outcome of the game.
Storm Crow is a bad card. The best thing about Storm Crow is that you can pitch it to Force of Will. Storm Crow is without a doubt the worst card you've ever heard of, but, you have heard of it! Clone it, copy it, make as many tokens as possible. Remember, a group of crows is called a "murder" so don't be afraid to remind the other players that if they attack you, you will literally murder them!
Do You Want To Play A Game?
Challenge one of your opponents to a Game of Chaos and see who blinks first. Find the gambler in your group who cannot help themself and enjoy a couple of minutes of intense coin flipping action - win or lose! Make sure you bring a "lucky coin" to show off at the table. There are a large number of cards that say "When you gain life" or "When you lose life" and they trigger each flip; it's entirely possible that, with the right cards in play, everyone is somehow involved in the Game. Build up a mythos by keeping a tally of total wins/losses and victims; if you do it right the other players will line up requesting to be next!
I Have Five, Do I Hear Ten, Five Going Once, Twice
Illicit Auction can create an interesting life mini-game and stealing someone's commander is always a small win. Also, there are some "gotcha" cards like Neheb, the Eternal which generates massive value, and obviously, the Auction can combo with cards like Near-Death Experience and also Triskaidekaphobia. However the most interesting aspect of this card? You can bid more life than you have! As it is not a life payment effect, nothing stops you from bidding arbitrarily large amounts of life. Why would you? Besides negative life shenanigans including Phyrexian Unlife and a "swap life totals" card, the next section has some additional ideas.
Get Really Comfortable With Rule 800.4
From the Magic comprehensive rules, Rule 800.4 et al. describes multiplayer games and what happens when someone loses. There is a huge difference between Oblivion Ring and Banishing Light with regards to losing. Because Oblivion Ring and effects with return triggers go on the stack, if you leave the game the exiled targets will not return to play. However, something you have used Banishing Light on will return. Make sure the other players are aware of exactly how these different mechanics work when it strengthens your position: "Kill me and you won't get back your card" or "Killing me gives them that card back."
Know the rules well to get the most out of losing (or threatening to lose).
The Cheese Stands Alone AKA (Overly)Complicated Ways To Win
A win is a win is a win, or so the saying goes. However, an Epic Win is far better.
If you are an experienced Magic player you know that, most of the time, winning is typically a straightforward deal 20 damage affair. Commander format adds a complication; 40 life is a ton of life. Thus a lot of Commander players look for alternative ways to win such as dealing 21 points of commander damage (somewhat easy) or going for ten poison counters (a lot easier) or doing some form of an infinite combo (easiest by far). However, there are some questionable ways to win which are quite a bit more difficult, so, why bother? For the experience of an Epic Win of course!
Ordinary Wins vs Epic Wins
I assure you that any game in which you take out even a single player with Triskaidekaphobia, or actually kill someone with The Deck of Many Things, or pull off an actual Etrata, the Silencer kill will be a lot more memorable than just attacking for damage or comboing someone out. That game will be more worthy of your time, as even if you do not ultimately win, the memory of an epic game will stick with you no matter the result.
Strixhaven Stadium deserves a caveat. It's somewhat trivial to get a pile of counters on the Stadium by untapping effects, proliferating or one-shotting someone with a pile of tokens with haste. However, it's a monumental task to attack 7 or 8 times while holding off the entire table trying to hit you back and achieving a victory primarily through multiple combat steps.
Magic has a large number of cards that win the game or make a player lose on the spot, each with a different risk/reward ratio. Some extremely competitive cards like Laboratory Maniac have a built-in win condition that is very reliable. Others like Maze's End have a wincon as more of a side effect or afterthought than a primary usage. If you are uncertain of the general power and competitiveness of any given card you can take a look at edrec and see how many decks play that card; you can safely bet if it's being played a lot it's a powerful card.
Once you know your playgroup well enough you can tune a deck to have a wincon that is not too quick, too consistent and, too powerful but also not impossible. Speaking of impossible wincons...
Hedron Alignment is in a category all its own. This card is the absolute king of overly complicated ways to win; its wincon is so complicated that it is impossible to pull off in commander. Many local groups either allow cards that access outside cards (various Wish effects) to retrieve additional copies, or, allow 4 copies of Hedron Alignment in a commander deck. If you read my previous article here you know that Magic has always had the idea of "house rules" as a solution for playgroups that encounter unfun cards or situations; let your players attempt to Align their Hedrons pretty please!
Winning? Losing? Not On My Watch!
Maybe you've come to realize that you just cannot find any value, any redemption or any fun in a loss. Well, don't let ANYONE lose!
Divine Intervention Play dozens of cards that say "Draw [a card]" no one bats an eye but play one card that says "Draw [the game]" and everyone loses their mind! Divine Intervention has layers of diplomatic angles with cards like Despotic Scepter or any proliferate effect. A lot of playgroups could be pleasantly surprised at the impact of a rare card that generates a unique gameplay experience that is not about winning at all!
Then there's Abyssal Persecutor one of the most misunderstood demons in all of Magic's history. For the bargain price of just four mana he prevents your opponents from losing - what a nice guy! Remember what I said about Despotic Scepter and diplomacy? Abyssal Persecutor takes diplomacy to the next level. Just note that rules mastery is important. Still, for only four mana you can prevent a lot of unnecessary losing for a long time!
Losing Is Not That Bad
When you do not build a deck purely for winning it can help give you a new perspective, which, can ultimately help you win future games! Losing helps you find out what moves in game were technically "correct" but actually drew too much hate from your fellow players, and thus, were incorrect. A loss can force you to establish diplomatic inroads for the next game instead of viewing other players only as enemies. Most importantly, once you realize that there is a lot more to Magic than winning, you are free to explore deck building in all its glory, free from the onerous burden of picking only the absolute most efficient cards. Have a little fun and you cannot lose!