What to Outsource First in Your Business (and How to Build a Team Around Your Life)

You don't need a full team to stop doing everything yourself.

You need one good hand-off.

When I started this business in 2020, I was working full-time in corporate, teaching my girls at home during the pandemic, and editing podcast episodes on the weekend. Editing took me two to three hours I didn't have. So I set one goal: make enough money to hire someone to edit the podcast.

That single hire gave me my weekends back and left me more time to create content, which was the part that actually grew the business.

Knowing what to outsource first is one of the most common questions I get. And in 2026, the answer has changed. Some of those first hand-offs can go to AI, some still belong with a real human, and some tasks should just be deleted.

Outsourcing is handing a task to a person, an agency, or an AI tool so you can spend your time on the work only you can do.

In this post, I'll walk you through:

• How to know you're ready to outsource
• The time audit that shows you what to hand off
• What to outsource first, in order
• What to give to AI and what to give to a person
• How to hire well, even on a small budget
• The team I built (and the mistakes that taught me the most)

Grab a notebook. You'll want a list by the end of this post.

How to Know You're Ready to Outsource

I get asked this all the time: "How do I know if I'm ready?"

If you're asking, you probably are. Even two focused hours a week is two hours you get back for the work that brings in clients.

Here are the signs I look for:

• You're overwhelmed in one specific area. For me, that was podcast editing.
• Tasks aren't getting done at all. In my early days, my website and my repurposing simply sat there because I didn't have the time.
• You're the bottleneck. Everything has to go through you before it can move.
• You're doing work outside your expertise. I have a technical background and even did coding in college. A website update could still take me two days, and Studio Classica could do it in about ten minutes.
• You can't take a week off. If everything stops when you stop, you need support.

It's going to feel uncomfortable. You'll most likely take this step before you feel 100% ready. (Isn't that true of everything in life?)

The Project Triangle: Time, Cost, and Scope

One idea from my corporate project management days helps here. Every project has three constraints: time, cost, and scope. Change one and the other two move.

When I started, I had 8 to 10 hours a week and a big goal. I couldn't add time. So I cut the scope down to the activities that brought in income, and I paid for help with the rest.

Your takeaway: if your hours are fixed, your choices are to do less or get help.

Start With a Time Audit

Before you hire anyone, find out where your time is going. This is the very first thing I do when I feel overwhelmed.

Step 1: Track everything for one week

Write down every task you do for a full week. Yes, all of them. The tiny ones are usually the ones eating your day.

Step 2: Sort each task into four buckets

About 90% of what you do can be delegated. We aren't there yet in my business, but it's a good goal.

The delete pile is the one people skip. My guess is there are tasks on your list that don't need to happen at all, and those never need to be outsourced. They just need to stop.

I run this audit as part of my quarterly planning, and I still ask myself the same question at the end of every session: "Holly, where do you need help?"

Step 3: Ask what fuels you

Here's the last check before you decide. What do you actually like doing?

The worst thing you can do is hire someone to take over the task that fuels you. If you love writing your emails, keep writing your emails. Outsourcing should make your job more enjoyable and leave you more time for the work you love.

What to Outsource First (in Order)

The first thing to outsource is the repetitive task that eats the most time and that you don't enjoy. For most women I work with, that's content repurposing, podcast or video editing, or admin.

Here's the order I'd follow:

My two smartest early hires

The two best moves I made at the beginning were these:

1. A VA to repurpose content. I hired Kaitlyn, who I'd met through my mastermind. She worked just eight hours a month turning podcast episodes into Pinterest posts, emails, and more.
2. A website designer on retainer. All the hours I spent on small fixes became someone else's job.

Add a podcast editing team to those two, and I'm guessing I saved 10 or more hours a week. In the beginning, most of those tasks simply weren't getting done.

Kaitlyn is a great example of starting small. She was a dental hygienist building a VA agency when we met. We started with simple repurposing tasks, and she grew into our Director of Community Relations.

Outsourcing doesn't have to be permanent

You can hire help for one project or a short season. A launch, a website refresh, or a big client push can all be a one-time hire.

And outsourcing can go beyond your business. If you just need more time, get a sitter. Two hours of focused work with someone watching your kids can free up the rest of your day to be with them. I'd take that over trying to work in pockets of time while they get frustrated with me on my computer. (Speaking from experience here.)

What to Outsource to AI vs a Person

Give AI the drafting, summarizing, and formatting. Give people the judgment, the relationships, and the follow-through. This is the biggest change since I first wrote this post.

Many of the tasks I once hired out can now start with AI, so your first hire might do something different than mine did.

Here's my rule: AI drafts, you direct. Machines don't know about your daughter's dance rehearsal. You do, so that part stays with you.

Here's a real example from my team. We used to write our emails in a Google Doc and then paste them into Kit (formerly ConvertKit). We still write every email in that Google Doc. Now Claude reads the doc, then formats and schedules each email there. The writing stays ours, and the copy-and-paste job is gone.

The AI Bot Squad

Inside Anti-Social School™, we built the AI Bot Squad, a private set of more than a dozen AI assistants. Each one handles a job a marketing team would normally do:

• Betty the Blogger repurposes your podcast and emails into SEO-friendly blog posts.
• Clara the Content Coach turns content chaos into a plan.
• Emma the Email Analyst plugs into Kit (formerly ConvertKit) and tells you what to fix.
• Penny the Pitch Pro writes pitches that get answered.

Every assistant speaks from your Brand Book, so the drafts sound like you. If you want more on doing this well, read How to Use AI in Your Business Without Losing Your Edge.

Your takeaway: try AI on a task first. If it still takes too much of your time to fix the output, that's your cue to hire a person.

How to Hire Your First Team Member

Once you know what to hand off, here's how to find the right person.

Get your house in order, or hire someone who will

My mantra is simple. Either you have clear systems for someone to follow, or your first hire is the person who sets them up. See how simple that makes the decision?

If you love systems like I do, you can write down the steps and hand them off. If you don't, hire for that first.

Learn it, then delegate it

I believe in doing a task yourself first. Learn it, understand it, and then hand it off. Every job on my team is one I understand and could do myself. That makes it much easier to review the work and set clear standards.

Hire for heart, then teach the skills

Your hire might not be the most qualified person on paper. I'd still take someone with heart and dedication and teach them what they need. I felt the same way when I was hiring in corporate.

Here's what I look for:

• Shared values. Ours are family first, belief in our clients, and commitment to our model.
• Passion for the work. Skills can be taught.
• Their own goals. Many of my team members run their own businesses, and I love supporting those women as they grow.

Plan for capacity

When you hire, ask one question: what capacity is this going to create for me?

The return isn't always money, and if it is, it may not show up right away. Creating room to work on your business is what pays off over time. The creative time, the time you spend dreaming about what's next, can't be outsourced.

My favorite book on this is Who Not How by Dan Sullivan and Benjamin Hardy. Instead of asking "How do I do this?", ask "Who can do this?"

Give your hiring a money system

Hiring feels easier when the money already has a place to go. Scott and I split our revenue into buckets every month:

When I started, there wasn't much to reinvest, so my corporate salary helped grow the business. Whatever your numbers look like, the habit is what makes hiring a calm decision.

How to Build a Team Around Your Life

A team doesn't happen all at once. Mine was a very slow build, one piece of support at a time.

Here's roughly how it grew:

The hire that surprised me: an integrator

Once we had a team of six, a new problem showed up. Me.

I was waking up to 17 Slack messages. Something needed a review, someone's password wasn't working, someone had a launch question. Every request came to me.

So I hired an integrator: someone whose job was to manage the team requests, run the project plans, and turn the whiteboards in my office into real work. She managed my capacity too. When I said I had 17 ideas, she could say, "You already told me you have 15. Maybe we should space it out."

That hire let me step into the visionary role and stay there.

Could I have done that work? Yes. But if I want to travel, speak, and be present with my family, someone else needs to do it. Ask yourself the same thing: in a traditional company, what is the CEO doing? What are you doing? Do those two match?

Who's on my team today

Here's who keeps our life-first business running now:

Notice how many of them run their own businesses. You don't need six employees. You need the right support for the job in front of you.

Build your home team, too

Your paid team is one kind of support. You also need a home team: the people you turn to when you start questioning everything.

Mine fill different roles:

• The questioner: my husband, who pushes back in a good way
• The prioritizer: my best friend, who reminds me what matters
• The cheerleaders: business friends from masterminds and trainings

You need someone who supports you no matter what, someone who tells it like it is, and someone who cheers you on. Who fills each role for you?

Your takeaway: start with one hire, build in the order your time audit tells you, and let your life set the pace. If you want to see what that looks like week to week, read How to Run Your Business in Part-Time Hours.

Common Outsourcing Mistakes

A few things trip people up every time:

• Outsourcing a task that should be deleted. Run the audit first.
• Giving away the work you love. If it fuels you, keep it.
• Hiring before you have steps to hand over. Write the process down or hire someone to do it.
• Staying the bottleneck. If every question still comes to you, you need a person in the middle.
• Handing off without reviewing. My goal is that everything gets double-checked, and it shouldn't always be me doing the checking.
• Expecting AI to run on its own. It needs your stories and your final edit.

Here's How to Get Started

1. Track every task you do for one week.
2. Sort each task into Do, Delegate, Delete, or Defer.
3. Delete what you can, right now.
4. Circle the delegated task that takes the most time and that you enjoy the least.
5. Try AI on it first, then decide if you need a person.
6. Write down the steps, then hand it off for one month.
7. Check in at the end of the month and pick your next hand-off.

If you want company while you do this, we map out plans together at the live monthly Planning Party inside Anti-Social School™.

Not Sure What to Hand Off First?

Sometimes the bottleneck is your content. Sometimes it's your email engine, your visibility, or your offers.

Take the 2-minute quiz and I'll send you a personalized plan for your next move. 💛

Prefer to listen first? The Anti-Social Shift is my free private podcast on growing a business without living on social media.

XO, Holly

Frequently Asked Questions

What should I outsource first in my business?

Outsource the repetitive task that eats the most time and that you don't enjoy. For most small business owners, that's content repurposing, podcast or video editing, or admin. To find yours, track every task for one week and sort each into do, delegate, delete, or defer. Delete what you can first. From the delegate pile, choose the task that takes the most time and fuels you the least. For me, the first hand-off was podcast editing, followed by a VA who repurposed content eight hours a month.

How do I know when it's time to outsource?

If you're asking the question, it's probably time. The clearest signs are feeling overwhelmed in one specific area, watching tasks go undone, doing work outside your expertise, or becoming the bottleneck for every decision. You don't need a big budget or a full-time hire to begin. Even two focused hours a week gives you time back for the work that brings in clients. Expect it to feel uncomfortable, and start before you feel 100% ready.

What should I outsource to AI instead of a person?

Give AI the drafting, summarizing, and formatting, and keep people on judgment and relationships. AI works well for first drafts of blog posts and emails, repurposing a podcast episode, turning notes into task lists, and analyzing email results. Keep a person on client conversations, managing your team, quality checks, offer decisions, and your books and taxes. Try AI on a task first. If fixing the output still takes too much of your time, hire a person. Either way, your stories and your final edit stay with you.

Who should I hire first, a VA or an agency?

Start with a VA for repetitive tasks, and bring in a specialist or agency for skilled work like podcast editing or website design. A VA can start with just a few hours a month, which keeps the commitment small. My first VA worked eight hours a month on content repurposing. An agency makes sense when one service has outgrown what you can do well yourself. As you grow, add an operations manager or integrator so that requests stop coming to you.

How do I build a team as a small business owner?

Build your team one hire at a time, in the order your time audit tells you. Start with a small, specific job, like repurposing content for a few hours a month. Write down your steps so the person has something to follow, or make your first hire someone who can set those systems up. Hire for shared values and passion, then teach the skills. Outsourcing can be short term too, so a single project is a fine place to start. As the team grows, add someone who manages the work so you can stay in the visionary role.