When to (and why) Retire in Gloomhaven

Retiring in Gloomhaven was often discussed in my weekly Sunday night game. Sometimes characters were retired quickly and other times we stayed with certain characters for longer. There are quite a few factors in determining the optimal time to retire based upon your own personal preferences and your group preferences.

Should You Retire in Gloomhaven? Yes you should definitely retire in Gloomhaven, but sometimes you might want to play certain classes longer. Retiring allows you to try other characters and also let other people play those characters. Retiring and changing characters is what keeps the game interesting for the long term and it will allow you to play Gloomhaven, and enjoy it, for an extended period of time.

Before I launch into the pros and cons of retiring, I would like to discuss personal quests. Personal quests in Gloomhaven are a bit all over the place. Frequently they are very easy or very hard to complete which means in some cases deciding whether to retire or not is somewhat out of your hands. That being said if you are really committed to retiring, or not retiring you should be able to make it happen.

Why you should retire (in a reasonable amount of time)

One of my favorite parts of Gloomhaven is the amount of characters. I think this adds a lot of interest to the game. I know personally that the amount of characters in the game, the method of unlocking them and trying out new builds and party compositions is what kept me interested for more than 2 years.

Unlock new road and city events

When you retire a character you usually get to choose a new character that hasn’t been used yet. When you do that you get to add city and road events for the retiring character and also for the newly unlocked character. These spice up the game and keep your city and road event decks ever-changing and specific to characters you have used!

Character Diversity

Trying different things is cool! I absolutely loved changing characters. The excitement of opening a new character was something i had never experienced in a board game and it kept me eager to play week after week.

Opening a new mini and discovering what the character looked like and then going over the deck of ability cards was absolutely awesome. Any time there was a retirement we celebrated and I don’t think that any person in my group ever played the same character twice in a row, just due to how exciting it was to try something new.

Even if a character had been played before by another player, it was exciting for me to go and try that character. I really love trying out different builds and trying to create characters that play really different and cool ways. Hopefully I came up with some that not even Isaac Childres, the creator of Gloomhaven, foresaw!

Different Party Compositions

Gloomhaven has 17 different classes, 6 starting and 11 unlockable. If you never retired then you wouldn’t ever change the composition of your party. Certain party compositions are absolutely overpowered and it was really cool to have a retirement and then one of the group bring in a character that completely altered the dynamic of the group.

On the flip side, there were a couple of times where characters were brought in that didn’t work well with our current group and it was a bit anti-climactic. That doesn’t mean the characters were bad, just that certain part combos don’t work as well as others and there are a couple party compositions that are downright boring/under powered.

Give Other Players a Chance to Play The Character

It’s great to have a class that you just love to play. But seriously, there becomes a point when it is time to let that character go, no matter how over powered they are or how much you love them. I’m talking to you lightning bolt class!

For about 1/3 of our campaign one player had a tough personal quest/loved the lightning bolt character a lot. The combination of a tough quest and the lack of drive to finish said quest meant that this player had one character for a very long time! I never did get the chance to play the lightning bolt with that group. Not the end of the world but retiring means everyone can get a chance at playing a really cool character.


For each character that you retire you record their name and information in the town records book. Each time you retire a character you get to start your next character with an extra perk. Needless to say, after you retire a few characters they start with a pretty great modifier deck. because of the way Gloomhaven difficulty scales, this actually helps you be more powerful in relation to your level. I though that was really cool!

Why you might not want to retire (for a little while)


Enhancements are a part of Gloomhaven that I don’t necessarily love. I get the intent behind them but because I always preferred trying a new character it never really made sense to me. Also, compared to item cost and benefit it was very cost prohibitive and only made sense if you planned on playing a character for a long time, or you wanted to enhance the character for the next person. I guess I’m just selfish but when it came down to buying 5 items(or even way more if it was to enhance a level 9 card with a strong ability) or 1 enhancement, I always chose the items.

I did play one character twice: Spellweaver. She was the first character I ever played, and one of the last, and the only character I put an enhancement on.

After all that, if you are planning on playing a character multiple times/an extended period, or you are just a good person, then multiple enhancements can make a character quite powerful so they would be a reason to not retire and just go on raking in that gold and slapping stickers on all of your cards.

Scenario Level

In Gloomhaven you can set your difficulty level by adding or deducting levels to your scenario. This drastically alters the difficulty of the game. Before you get your prosperity high, keeping one character for a long time(aka not retiring) is the only way to get them to a high level. This also allows you to get a great item setup and possibly some enhancements.

When you are setup like that you can push the scenario level up and play some really hard Gloomhaven!

High Level Cards and Builds

High level cards are just the best! I still fondly remember when I first started playing Gloomhaven. I would look at the level 9 cards and dream. Not retiring is a good way to get to those cards sooner. For example, my groups first retirement was a Cragheart at level 4. He never even made it near the higher level cards. If you don’t retire then you can push up into those higher level cards and make those builds sooner.

Favorite Character

Some characters are better than others. And some people just like certain characters and play styles better than others. Either way if you are playing a character that you just absolutely love, no shame in pushing retirement off for a while to really utilize the character and be the best you can be with it. Just remember that when you are playing a character nobody else is, so share the love!

Hopefully all of this helps you in your quest to decide when to retire or not. Truthfully I thought in the beginning I would hate the retirement mechanic. When I first read the rule book I was not overly happy. I can tend to be a min-maxer on occasion, and the thought of starting over again multiple times left me with a bit of bitter taste in my mouth.

Fortunately, retiring is actually awesome and it really helps with long term engagement and allows the game to stay fresh. So go ahead and retire already!

Recent Posts