Possibilities:
"Poor squiddy, it's my fault he died...I brought him into a situation he didn't have a chance in. Never again!" - Midian decides to renounce the practice of animal companions; at least for the sake of combat. He chooses a PrC that will enhance his wildshapery, like Nature's Guardian, and/or Warshaper. Possibly Master of Many Forms if you don't mind hosing your spellcasting beyond all recognition.
"If only I had more help, squiddy might not have died!" - The path of the summoner is a natural one for druids, with powerful Nature's Ally spells and spontaneous casting. A few levels of feats (Spell Focus: Conjuration, Augment Summons and, optionally, Rapid Spell) can make a druid into a formidable summoning engine. Certain items can also boost this significantly.
"I'll never let a companion die again!" - With a small investment of cross class skill ranks, a druid can take the Spontaneous Healing feat, which allows them to swap prepared spells for Cure spells of equal level, like a good aligned cleric. Other feats to boost healing capacity are also possible, but probably not essential to be a powerful healin' druid.
"I will make sure my next companion is strong enough!" - A one level dip into Beastmaster PrC, combined with the Natural Bond feat, result in a potentially very potent animal companion. Check with the GM to see if that Natural Bond feat will boost your effective druid level for the purposes of companions with negative modifiers, or it may be for naught.
Pitfalls:
Wildshape is most potent from levels 8-12 or so, IMO. It never goes -completely- out of style, but even with Natural Spell it starts to lose its luster when compared to the powerhouse druid spells of levels 6 to 8. In general, the better your items, the worse an option wildshape is. This changes a bit once you get Elemental shapes, but even then they're more useful for utility purposes than for heavy combat.
Animal Companions suffer a similar curve, but start to fall off even earlier. By level 10, without significant investment in items and/or buffs, your companion is basically a few attacks worth of spare damage you won't be taking (unless via area effect). There are techniques and feats that help this...but the fact remains that by the time you're level 15 or so, even a dire bear isn't THAT big a deal in your day to day battles. Not to mention lugging around a large, 1 ton bear has real consquences when you're exploring dungeons and taking ships around.
Conversely, druid spells pretty much bite until spell level 4...then they start to become increasingly good. A powerful high level druid is often hard to tell apart from a wizard...except for better saves, BAB, armor, hit points and they can turn into a dire bear if someone grapples them. Or use Freedom of Movement.
Just some thoughts.