Hey there,

I've been listening to a lot of inspirational self-help style videos lately that say "Don't just give up on doing things you're bad at, but instead keep trying as long as you have fun with it". Best way to get into that mindset is to start with video games!

So... I am a very dumb person and never really got a handle on strategy games. Thing is though, I really enjoy games with historical settings and LOVE watching strategy game let's plays (especially for grand strategy games, like Europa Universalis). I've always wanted to get into these sorts of games but never really dared to as they looked too complex.

What's a good beginner-level strategy game that is still interesting and will still develop my … 'Strategic mind'? I don't want something braindead that even children could beat, I do want to get challenged. I am willing to read up on every little detail about the game (that's actually the most exciting part to me)!

I don't really care if you recommend a RTS, a 4X or a Grand Strategy game (though I guess turn-based games would be preferred). In fact, I've also loved watching people play simulation games like Rollercoaster Tycoon, or Cities: Skylines! Recommending me anything in that genre is cool with me.

(Just for reference, all I've really played throughout my life is Point and Clicks and games in any of the action genres - FPS, Action-Adventures, etc.)

Master of Orion 2 is a fairly accessible 4x game that may also give you a challenge.

HoMM3's base campaign is very beginner friendly I think. The expansions on the other hand, especially the 2nd one, are a different matter entirely.

The Civilization series on lower difficulties is another possibility.

There is tons of strategy games for beginners available on GOG.
Do you like fantasy games, modern style games, scifi themed games, or oddball grab-bag games?
Here's a bunch of Strategy game recommendations that you might enjoy.

Like Sid Meier's Colonization, it's a historical turn-based Civilization game with low stakes, and most importantly, it's available on GOG.

The Frozen Synapse 1/2 series (also available on GOG) is pretty good, but randomized maps/randomized unit placement can be frustrating, especially on the timed missions.

Jagged Alliance series is also very very good(and available on GOG too). The most user friendly JA game is probably Jagged Alliance 2 Gold. I wouldn't bother with the Jagged Alliance 2 1.13 mod/megapak because it adds lots of enabled by default settings for seasoned veterans of Jagged Alliance 2 that will absolutely wreck a player new to the Jagged Alliance series.

Fantasy wise, there is the Age of Wonders series, Disciples (warning: exceptionally ugly graphics), Fantasy General (very tough game),

scifi: there's the alien invasion/defense XCOMs, X-COMs, UFOs series, Space Rangers HD (which has a crazy amount of game modes....text adventure/realtime with pause RTS/arcade bullet hell/FPS/turn-based space).

Stellaris is pretty customizable in difficulty, Majesty HD is great, Dungeon Keeper series, War for the Overworld, Empire Earth 1, Factorio, Battle Brothers, Theme Park, Fallen Enchantress, Frostpunk, Tropico 3, Warcraft 2 and Master of Magic.

All of which are available on GOG.

My recommendation for turn based is Battle for Wesnoth, simple at first but with lots of replay ability and lots of depth. Can be played with mouse only, can beat AI in various ways, have single and multiplayer and it´s open source.
It has some RPG elements and it makes you feel kind of connected with some units. It´s not available on GOG but can be downloaded directly from the website.
Did I mention is free?

I´ve played cities skylines and it´s very fun and fast to learn, it quickly turn into traffic manager simulator.
Check out Shadow tactics as it can be very fun.

Edit: There´s a old game that I really enjoy: Populous the beginning. I´ve played since it came out on the ps1 and there is a lot of action in the mix you might enjoy. I think is the "strategy" game I had most fun, never boring. Is available only in GOG.
Is a little diferent than most strategy games and may be a great starting point.

If you don't mind a wargame, Order of Battle is a intermediate-complexity one with somewhat modern graphics.

For grand strategy, I've played most that Paradox put out between 2006 and 2013, and I think Europa Universalis 4 is a good one to jump in as it has more intuitive and better-explained mechanics. Hearts of Iron 3 should be avoided because of the micromanagement, but I can recommend Darkest Hour for a more accessible version. Great game with a bunch of awesome mods available, from Fallout to Kaiserreich. If it's daunting, you can always choose a smaller peripheral country like Canada to cut your teeth on.

Someone already mentioned HoMM 3, but the Heroes Chronicles games are even more beginner-friendly, being one of the few strategy games I can think of that were actually designed for beginners, rather than just happening to be easy.

If you're looking at sim games, there are of course the Sim City games (2 and 3 are my favourites), but maybe you want to have an objective instead of an open-ended experience? You've already mentioned Rollercoaster Tycoon, but SimTower and SimAnt are relatively easy while still having clearly outlined campaigns (get a "Tower" rating, chase the human out of the house). I might even go so far as to call SimAnt a beginner RTS of sorts. Of course, open-ended games are arguably beginner friendly since there's nothing than go so wrong that it stops you!

Hah, Disciples has exceptionally ugly graphics? They are very comparable to Diablo... and there are much worse on GOG.com, sadly even some post 2010 games.

A lot of games not tagged as such do have some strategy. The Overlord games come to mind and my beloved Mount & Blade is hardly winnable without any strategy but can be played with no thought of tomorrow too.

Ohh, I just watched a let's play of Master of Orion 2 and it looks fantastic. Right up my alley art design and settings-wise. Feel like I did back when I watched Star Trek for the first time! These games look great, definitely also getting on my wishlist. Really?! Those games looked like the 'final boss' of the strategy genre with sooo much going on.

By the way, I am trying to keep this limited to GOG games! I don't completely disregard Steam and Epic or anything, but I would first like to exhaust the GOG catalog (if possible).

Civilization 4+ and the rebooted X-Com games are my super easy recommendation for entry-level strategy. Not only are they not that hard, but both have easier modes to start out with, and both have easy to understand interfaces. Not a lot of older games can say the same. I don't play much strategy but I love those two series.

The Braveland games are very easy and beginner-friendly turn-based-strategy games.

Edit: My bad. You wrote "I don't want something braindead that even children could beat, I do want to get challenged. I am willing to read up on every little detail about the game (that's actually the most exciting part to me)!". Instead I read: "I do want something braindead...".

In that case Braveland series is far to easy and not the right thing for you.

Whatever game(s) you choose, make sure to also buy Alpha Centauri sooner or later. Maybe not suitable for a beginner, but surely a game you should try once you learn the ropes of the genre.

https://www.gog.com/game/sid_meiers_alpha_centauri

Some recommendations from more left of the field

The Creeper World series and Particle Fleet - https://knucklecracker.com/
Excellent and not very difficult games. Not the usual strategy games, as the enemy is either a liquid or particles. But highly recommended, especially Creeper World 3

Infested Planet - https://www.gog.com/game/infested_planet
more actiony, and it is real time, but need to think about strategy and tactics to win the maps

Oh for sure, I am loving how this looks. This is definitely on my wishlist.