Your warrior or mage can do something else to make money that your thief can't. What if you only let characters who should know lock-picking pick locks? Worried about what you might be missing? Don't be. People complain about it being too easy to make money, but what if you played one character who made money by crafting and selling weapons and armor, another who did the same with potions, and a third who stole what they needed? No one character is likely to suffer from 'too much gold' syndrome if they're only pursuing a single occupation. That being said, instead of trying to do everything with one character, create several characters and make each character different.

Create several characters and be particular about them.

This might seem like a harsh rule, but it can work wonders for making each play-through a unique and interesting experience. A general rule of thumb you should follow is that if it seems even a little out of character for your character to engage in that kind of activity, don't do it. If you're playing a warrior, is there really any reason to go around collecting flowers and butterflies? Would your warrior really do that? (Maybe yours would, but many people know exactly what I'm talking about here.) The same goes for skinning animals, mining ores, chopping wood, crafting weapons and armor, brewing potions, picking locks, and so forth. It's also a good idea to restrict the kinds of things you allow yourself to accumulate and the kinds of activities you allow yourself to engage in. Most of the quests are designed to support your intuitions, even if different people have different takes on things. You might be surprised to discover how often an NPC you considered 'bad' the first time through turns out to be 'good' on a second run. If your instinct is to help every person who asks for it and trust people unquestioningly, the next time you play Skyrim, try making the opposite choices.

You will find that Skyrim's quests are very forgiving from a role-playing perspective so that no matter what choice you make you will be able to justify your actions in a sensible way. You might find that the game is more enjoyable if you play it through a few times and restrict each character to the main quest and one other major faction (plus random adventuring and quest-taking, of course!) You may not clock as many hours with each character, but your experience may be more enjoyable overall for having experienced each story more intensely. There is plenty of content in Skyrim, and there's no reason why you need to experience all of it with a single character.

Don't feel obligated to take every quest, or join every faction.

In regards to your character, though, here are some general tips:

Do they have a tendency to overindulge in drink or sweetrolls?.

Does your character have any weird habits like only eating raw meat or traveling only at night?.

Is there a particular race or type of person that your character doesn't particularly like?.

Other questions can help deepen your experience when you're not busy completing quests:

Does your character accept or reject their destiny as the Dragonborn?.

If your character is of a race other than Nord or Imperial, how does their race affect their opinion of the war?.

Will she earn her gold as a mercenary, or do her best to heal the wounds of civil war?.

If your character hasn't chosen a side, how does she stand to profit from the conflict?.

Should they be working together or fighting furiously for dominance?.

Do the people of Skyrim have the right to govern themselves?.

Do the people of Skyrim need the protection and assistance of Imperial soldiers?.

Does he approve of the Imperial occupation of Skyrim?.

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