What to Outsource First When You’re a Team of One

Quick answer: Outsource the tasks that drain you, the tasks you’re slow at, and the tasks that don’t move your business forward. Automate before you hire a person, since software is the cheapest help available. Then hand off exactly one task, document how you do it, and only add the next once the first is working. The goal isn’t to give away as much as possible—it’s to protect the hours that grow your business and the hours you actually enjoy.

When you run a business by yourself, you’re the founder, the marketer, the bookkeeper, the customer service line, and the person taking out the trash at the end of the night. Doing it all can feel like dedication. Mostly it’s exhausting—and it caps how far you can grow, because there are only so many hours in a week and you’re already spending every one of them.

You tell yourself you’ll delegate once things calm down. Things never calm down.

Decide what to hand off before you hire anyone

Before you spend a dollar or post a job, get clear on what actually belongs on someone else’s plate. Otherwise you’ll hire help and hand over the wrong things.

Run every recurring task in your week through three questions.

Does it drain me?

Some tasks cost far more energy than the time they take. If you dread it, put it off, and feel wiped out afterward, that’s a strong candidate. Energy is a real budget line, even though nothing tracks it.

Am I slow at it?

We all have work that takes us three hours and would take someone else thirty minutes. Bookkeeping, design, editing, tech setup. Being slow at a task usually means it belongs with someone who’s faster.

Does it move the business forward?

Some tasks make you money. Some just keep the lights on. Answering the same question by email for the hundredth time doesn’t grow anything. Meeting a new client, sharpening your offer, and doing the work you were hired for does.

The tasks that drain you, that you’re slow at, or that don’t move the needle are your first candidates. Your goal is to protect your hours for two things: the work that grows the business and the work you actually love. Everything else is up for grabs.

Three places to outsource

Once you know what to hand off, it helps to know where to look. Outsourcing falls into three buckets, and the strongest plans borrow from all three.

1. Your business

Start with automation before you start with people, because software is the cheapest help you’ll ever hire and it never calls in sick.

If you use 17hats, workflows can send the right document or email at each step of your process, invoice reminders can go out on their own, and clients can book straight into your calendar without the back-and-forth. That’s hours a month you’re no longer touching by hand.

When you’re ready for a person: a virtual assistant can field calls and email, a bookkeeper can take your finances off your plate, and a local assistant can handle the in-person work that eats your day—packaging orders, mailing, deliveries, thank-you notes.

One owner might automate their whole booking and payment flow and never think about it again. Another might keep a VA on for five hours a week just to stay on top of the inbox. Both are outsourcing.

2. Your personal life

This is the bucket most people skip, and it’s often the most valuable one. Every hour you don’t spend cleaning, running errands, or grocery shopping is an hour you can put back into your business or your life.

A housekeeper every other week, a sitter so you can work an uninterrupted afternoon, a grocery delivery app, or a house manager for a few hours a week can free up real time. Sometimes the smartest business move is paying someone to clean your kitchen so you can spend that Saturday on your marketing—or with your kids. The work-life ledger has two sides, and buying back personal time counts just as much.

3. Your craft

The hardest things to let go of are the parts of the work you’re known for. Even here, pieces can come off your plate. A photographer can outsource editing. A course creator can hand off video production. A writer can bring in an editor.

The rule of thumb: keep the work clients hired you for, and let go of the steps around it. Handing off those supporting steps frees you to spend more time in the part only you can do—the part clients actually pay you for.

Can you afford it? Here’s the math

There’s a rough calculation that settles most of the hesitation. If an hour of your work earns more than an hour of help costs, paying for that help pays for itself.

Say a bookkeeper costs you $50 an hour and clears five hours off your month—$250. If those five hours help you land even one new client, you’re ahead, and you’ve stopped dreading your books in the bargain.

Some hours never show up on an invoice at all. Time with family, rest, and a clear head are worth paying for too, even when the return is harder to measure. The trade is simple: you swap money for time, then spend that time on what earns more or matters most.

Make sure it actually pays off

Outsourcing only works when the time you free up goes somewhere worthwhile. Handing off a task and filling the gap with more busywork misses the point.

Before you delegate something, decide what you’ll do with the hours it gives back. Maybe you’ll take on one more client. Maybe you’ll finally build the offer you keep putting off. Maybe you’ll be present at dinner. All three count—but pick one on purpose.

Start small: the one-task rule

For one normal week, keep a simple log of where your time goes. A notebook, a spreadsheet, or right inside 17hats if you already use it to run your projects. At the end of the week, look for two things: the tasks that show up over and over, and the ones you dreaded. Where those overlap is where you start.

Then pick one task and hand it off. Just one. Write down how you do it so whoever takes over can match your standard, and let them run with it. Give it a few weeks, see what the freed time is worth, and only then decide what to hand off next.

Starting small keeps your risk low and lets you build trust in the process before you lean on it. The point is momentum. One good handoff makes the next one feel obvious.

The hard part is letting go

If outsourcing is this useful, why do so many owners resist? It usually comes down to two fears.

The first is money, because spending on help feels risky when every dollar counts. The second is control, because no one will ever care about your business the way you do.

Both are understandable, and both will keep you stuck right where you are. The right help is an investment that pays you back in time, and time is the one thing you can pour into growth.

You also don’t have to give up control to begin. Hand off only the tasks that don’t carry your personal stamp. The invoice reminder, the grocery run, and the photo edits can leave your hands without changing a thing about what makes your business yours.

FAQ

What should a small business owner outsource first? Start with tasks that drain your energy, tasks you’re slow at, or tasks that don’t move the business forward. Log one normal week, find where “repeats often” and “I dread it” overlap, and hand off that single task first.

How do I know if I can afford to outsource? Compare what an hour of your work earns to what an hour of help costs. If your hourly value is higher, the help pays for itself—especially if the freed hours go toward landing clients or growing your offer. A $50/hour bookkeeper who clears five hours a month costs $250; one new client usually covers it.

Should I automate or hire a person first? Automate first. Software is the cheapest help you’ll ever hire. Workflows, automatic invoice reminders, and online scheduling can remove hours of manual work each month before you spend anything on a person. Bring in people once the repeatable pieces are already handled.

What tasks should I never outsource? Keep the work clients specifically hired you for—the part that carries your personal stamp. Hand off the supporting steps around it instead: editing, admin, scheduling, follow-up, and repetitive communication.

How do I hand off a task without losing quality? Document your process before you delegate. Write down how you do the task, what “done well” looks like, and any client-facing standards. Hand off one task at a time so you can correct course quickly, and give it a few weeks before judging the result.

Where to start this month

Look at your week, find the task you dread most, and hand it off. Then watch what the extra time does—for your business and for the life you’re building it around.

You became your own boss for a reason, and drowning in admin probably wasn’t it. If your first handoff is the admin itself, 17hats puts contracts, invoicing, scheduling, and follow-up on autopilot so the busywork runs in the background. Try it free for 7 days.

This article is adapted from the August 2026 issue of The Journey, 17hats’ magazine for solo business owners. Read the full issue here.