Skyrim’s “Taking Care Of Business” Quest: Complete Walkthrough & Tips For 2026

The Thieves Guild questline in Skyrim isn’t just about stealing, it’s about rebuilding a broken organization from the ground up. “Taking Care of Business” is the cornerstone quest that kickstarts your journey to restore the guild to its former glory. If you’re serious about joining the Thieves Guild and unlocking its exclusive rewards, this quest is non-negotiable. Whether you’re a stealth-focused character or just looking to diversify your playthrough, understanding how to tackle this quest efficiently can save hours of grinding. This guide breaks down everything you need to know: exact requirements, step-by-step walkthroughs, common pitfalls, and pro tips to make the whole process faster and smoother.

What Is ‘Taking Care Of Business’?

‘Taking Care of Business’ is the primary quest that drives the Thieves Guild restoration arc in Skyrim. Issued by Delvin and Vex, the guild’s current leaders, this quest tasks you with completing minor theft jobs across five major holds: Whiterun, Markarth, Riften, Solitude, and Windhelm. Each job strengthens the guild’s influence in that region, gradually restoring its reputation and power.

The quest itself doesn’t have a traditional end point: instead, it feeds into a larger faction progression system. As you complete jobs, the guild regains control of its operations and presence in Skyrim. Once you’ve worked in all five holds, the quest technically completes, but the Thieves Guild questline continues with additional opportunities to further solidify the organization’s dominance.

This is essentially the backbone of the Thieves Guild experience. You’re not just stealing for profit, you’re actively rebuilding a criminal empire.

How To Start The Quest

Meeting Delvin And Vex

Before you can begin ‘Taking Care of Business,’ you need to find and speak with Delvin Mallory and Vex. Both are located in the Thieves Guild headquarters, hidden beneath the Riften Flagon tavern. Getting there requires a bit of exploration or prior knowledge, you can’t just walk in off the street.

To access the guild, enter the Riften Flagon (the tavern in Riften’s marketplace) and head to the back. Brynjolf, a well-known guild member, usually stands near the bar. Talk to him and ask about joining the guild. He’ll either accept you directly or send you to complete a basic stealing task first (depending on your character’s approach). Once you’re accepted, you’ll gain access to the guild headquarters.

Inside the Flagon Cistern (the underground hideout), you’ll meet Delvin and Vex. These two are the ones running the guild in its weakened state. They’ll approach you with the proposition: help them rebuild the guild by completing jobs in multiple holds. That’s when ‘Taking Care of Business’ officially begins.

Quest Requirements And Prerequisites

Technically, there are no hard stat requirements to start this quest, you just need to be a member of the Thieves Guild. But, the jobs you’ll undertake vary in difficulty. A character with low stealth skills might struggle with some assignments, but the game scales difficulty reasonably well, so a level 1 character can theoretically complete every job.

Practically speaking, having some investment in Pickpocket or Lockpicking helps, especially early on. A decent stealth rating (not necessarily maxed out, but decent) makes jobs faster. You’ll also want to carry light armor and avoid heavy, noise-making equipment.

One often-overlooked requirement: you need to be able to fast travel to different holds to reach each job location. If you haven’t discovered the major cities yet, you’ll need to either discover them first or get a follower to escort you. Alternatively, you can use the carriage service at each major city’s stable.

Step-By-Step Quest Walkthrough

Completing Jobs In Each Hold

Each hold (Whiterun, Markarth, Solitude, Windhelm, and Riften) requires one completed job to restore guild influence there. The jobs aren’t particularly complex, but they do vary in scope and challenge.

Whiterun: Delvin or Vex will direct you to steal a specific item from a business owner or notable NPC. A common example is stealing jewelry or valuable items from wealthy merchants. The goal is to pressure the owner into paying the guild for “protection.” Once you’ve stolen the item and it’s registered in the quest log, return to the guild and report success. The job counts as complete regardless of whether the victim knows it was you, stealth is a bonus but not mandatory.

Markarth: Jobs here often involve stealing from The Silver-Blood Inn or similar establishments. Again, you’re targeting valuable goods from NPCs in positions of authority. The hold’s heavy guard presence makes stealth more rewarding, but brute force solutions exist if you’re willing to handle the consequences.

Solitude: The capital’s jobs tend to be slightly more challenging. You might be stealing from nobles or established businesses with better security. But, Solitude is large enough that blending in and moving undetected is feasible with decent stealth.

Windhelm: Jobs here are generally straightforward. Target business owners, steal from them, and report back. The hold’s architecture makes hiding easier than Solitude.

Riften: Since the guild operates primarily from Riften, local jobs may feel more personal. You might be dealing with rival guild members or competing criminal factions. Riften jobs can vary in intensity.

The common thread: complete one job per hold, and each hold’s influence meter increases. You’ll see progress markers on your quest log. There’s no time limit on individual jobs, so take your time and plan your approach.

Rebuilding The Thieves Guild

As you complete jobs across the holds, the Thieves Guild slowly regains power and resources. This isn’t just narrative flavor, guild control directly affects guild vendors, available quests, and faction standing. With each hold “conquered,” the guild grows stronger.

Delvin and Vex will periodically offer you new jobs once you’ve reestablished influence in a hold. These are optional but highly recommended if you want to fully revitalize the guild and access its most valuable perks. The more jobs you complete, the more the guild headquarters transforms. You’ll notice improvements in the Cistern, additional guild members recruiting, and better inventory from guild merchants.

The rebuilding process is gradual. You won’t see dramatic changes after one job, but by the time you’ve worked in all five holds, the shift is noticeable. NPCs comment on the guild’s resurgence, and guards begin to fear the guild again.

The Final Job: Recovering Guild Influence

After completing work in all five holds, Delvin and Vex offer you one final objective: the Bedlam Job and Heist Job, these are large-scale operations designed to fully restore the guild’s legendary status.

The Bedlam Job involves creating chaos and distraction in a target location (typically a major city) while guild members raid a rival operation or steal high-value goods. You’re not necessarily doing the stealing yourself: you’re providing cover or creating the conditions for guild success.

The Heist Job is the true finale, a coordinated effort to pull off an elaborate theft that demands all your skills and planning. This job requires more preparation and coordination than earlier tasks, and it’s where the quest truly “completes” in a meaningful way.

Completion of these jobs unlocks the full Thieves Guild questline ending and ensures maximum faction benefits. But, the quest tracker may still show “Taking Care of Business” as active, this is normal. The quest essentially transitions into a repeatable job system where Delvin and Vex continue offering work.

Thieves Guild Faction Benefits

Rewards And Perks For Completion

Completing ‘Taking Care of Business’ and restoring the guild unlocks significant rewards. The most immediate benefit is faction standing, you’ll gain substantial reputation with the Thieves Guild, unlocking their vendor services, dialogue options, and access to previously restricted areas.

Here’s what you gain:

• Access to guild vendors with improved inventories. Early on, guild merchants have limited stock. As influence grows, they stock rare items, ingredients, and stolen goods you can fence.
• Special guild jobs offering higher payouts than standard radiant quests.
• Safe houses and storage. The Cistern becomes a fully functional base with chests, crafting stations, and alchemy labs.
• Guild member allies. Additional guild members join the cause, appearing in Riften and other holds. Some become followers or quest companions.
• Reputation with other criminals. Restored guild influence affects how other criminal factions perceive you. Some may respect you: others may challenge you.

The most valuable reward for roleplayers and serious thieves: the Thieves Guild Restoration Quest line becomes available. This unlocks additional questlines that push the guild narrative forward and offer bigger, more complex jobs.

Best Thieves Guild Gear And Equipment

While ‘Taking Care of Business’ doesn’t directly award unique items, completing it opens access to guild vendors who stock superior equipment. The guild merchants carry items you won’t find elsewhere.

Recommended gear obtained through guild vendors:

• Thieves Guild Armor Set: Lightweight, quiet, and stylish. It provides no inherent bonuses but is iconic and fits the faction aesthetic. You can obtain full sets (helmet, cuirass, gauntlets, greaves, boots) through vendors.
• Nightingale Armor: Unlocked later in the guild questline, this is the true endgame Thieves Guild armor. It’s light armor with enchantments boosting Illusion magic and Lockpicking, making it ideal for pure stealth builds.
• Transmute Ore Spells and Alteration Books: Guild vendors stock rare spellbooks and crafting materials.
• Lockpicks and Poisons: Essential consumables. Guild vendors sell them in bulk at better prices than general merchants.

For weapons, the guild doesn’t push specific builds, but daggers and bows are thematically appropriate and mechanically efficient for stealth. The guild’s vendor typically carries quality small weapons and bows.

One note: some players consult resources like Game8 for detailed build guides matching their playstyle with faction rewards. Character optimization is personal, so experiment with what fits your approach.

Common Mistakes To Avoid

Not pickpocketing the job item early. Some players try to steal after the quest marker is active, alerting guards. Pro tip: steal the target item before you formally accept the job. Once you have it, the job completes instantly when you check in with Delvin or Vex.

Attacking guards or creating combat. The whole point of guild jobs is stealth. If you go loud and kill guards, the jobs still complete, but you’ll face bounties and lose faction reputation. Guard kills in the wrong town can escalate into full city lockdowns.

Selling stolen goods before securing guild vendor access. Stolen items have reduced value at regular merchants. Until the guild is fully restored, use guild fences (like Thieves Guild vendors) to sell stolen goods for full price. If you sell to the wrong merchant, you lose profit.

Ignoring Riften as a home base. The guild operates from Riften. By the time you’ve completed jobs in other holds, Riften becomes relatively safe. Avoid starting major conflicts there early on, you’ll need it as a rest point.

Forgetting that stealth characters need stamina management. Sprinting and sneaking both drain stamina. If you’re caught mid-heist and need to escape, you might run out of stamina mid-sprint. Keep an eye on your stamina bar and use potions if needed.

Not using followers effectively. While guild jobs are soloable, a follower can create diversions or block guard patrols. Some builds benefit from having a companion: others prefer working alone. Experiment to find your rhythm.

Rushing through jobs without planning. Skyrim’s AI is forgiving, but taking 10 minutes to scout a location beats failing and retrying. Most jobs have multiple entry points and exit routes. Identify escape paths before committing to the theft.

Selling the stolen item to the wrong faction. Some NPCs are faction-aligned. Selling stolen goods to the wrong person can damage relations with that faction. When in doubt, sell to the Thieves Guild or unaligned merchants.

Pro Tips For Efficient Quest Completion

Optimizing Your Stealth And Thievery Skills

Stealth in Skyrim is less about numbers and more about positioning and awareness. You don’t need 100 in Stealth to succeed: 40-50 is functional early on.

Skill investment priorities:

• Pickpocket (30+): Essential for stealing quest items without alarms. Invest perks into increasing success rates and pickpocket capacity.
• Lockpicking (20+): Most jobs require picking locks. Carry plenty of lockpicks, they’re cheap and abundant. The “Wax Key” perk saves lockpicks on easy locks.
• Light Armor or Clothing (optional but useful): Wearing light armor or guild-aligned clothing makes guards less suspicious. Heavy clanking armor broadcasts your presence.

Stealth mechanics refresher: You’re detected when enemies see you (line of sight) or hear you (movement noise). Sneaking reduces movement noise. Standing still in shadows makes you nearly invisible even to nearby enemies. Use terrain and furniture to break line of sight.

Practical approach for each job:

1. Enter the location during off-hours when targets are sleeping or predictably positioned.
2. Identify the target item’s location (usually on a desk, shelf, or in a container).
3. Check for guard rotations, watch for 1-2 minutes to understand patrol patterns.
4. Find a quiet route to the item. This might mean climbing, waiting for guards to move, or using side entrances.
5. Grab the item and exit. Don’t linger.

The goal is in-and-out efficiency. If you’re caught, it’s not a game-over, you can often pay a fine or escape, but it’s slower than staying undetected.

Leveraging Followers And Companions

Followers serve multiple purposes in guild jobs:

• Distraction: Tell a follower to wait in a specific room. Guards may focus on the follower, creating an opening for you to move.
• Extra hands: Some guild jobs benefit from a second thief. Followers can carry stolen goods, reducing your encumbrance.
• Combat backup: If a job goes wrong, a combat-capable follower gives you an exit strategy. This isn’t ideal for pure stealth, but it’s a safety net.

Best follower choices for guild work:

• Brynjolf (after recruiting him): He’s a guild member and understands the work.
• Karliah (obtained during the guild questline): A master thief with stealth skills.
• Any conjuration mage: Summons distract guards and soak up aggro.
• Melee-heavy characters: A warrior follower in a different room can draw guard attention away from your location.

When to use followers and when to solo:

• Use followers if the location is heavily guarded or if you’re early in your stealth skill progression.
• Solo play once you’re confident in your stealth. Solo jobs are faster and grant better stealth experience gains.

Many experienced players eventually ditch followers for guild work, the added mobility and control is worth the slightly higher risk. But early on, having backup removes the learning curve pressure.

Pro optimization tip: Before starting a job, check if guild members are already working in that location. Sometimes Delvin or Vex have guild members conducting reconnaissance. Coordinate with them (or avoid them) to avoid friendly fire or accidental detection.

Resources like RPGSite occasionally publish detailed character build guides that sync thief skills with follower selection, worth reviewing if you’re theory-crafting an optimal playthrough. Also, for modded experiences, Nexus Mods hosts thousands of Thieves Guild overhaul mods that enhance these quest mechanics with quality-of-life improvements, new job types, and expanded guild features.

Conclusion

‘Taking Care of Business’ is the gateway to Skyrim’s Thieves Guild questline and one of the most rewarding faction questlines in the game. It’s not flashy, you won’t fight dragons or command armies, but it offers something equally satisfying: the steady, methodical process of rebuilding a criminal empire through skill and cunning.

The quest structure is simple: work in five holds, complete jobs, restore guild influence. But the execution rewards clever thinking, stealth positioning, and resource management. Whether you’re a hardcore stealth optimizer or a casual player dipping into guild life, there’s value in understanding the mechanics, avoiding common pitfalls, and leveraging the right tools and companions.

The beauty of ‘Taking Care of Business’ is its flexibility. You can run jobs loud and aggressive, relying on followers and combat. You can ghost every location without triggering a single alarm. You can speed-run it in an hour or stretch it across multiple sessions. The quest accommodates different playstyles, making it accessible to the entire gaming audience, from speedrunners to immersion-focused roleplayers.

Start with the basics: meet Delvin and Vex, complete one job per hold, and let the guild restoration flow naturally. As you progress, optimize your approach, refine your stealth technique, and enjoy the satisfaction of watching the Thieves Guild rise from obscurity back to dominance. The rewards, faction standing, vendor access, unique quests, and the legendary Nightingale armor, are well worth the investment.