Had a call the other week with a coach I’m working with to map out a full funnel, and she asked me point-blank: “Do you actually hire people in your business? Like, do you outsource?”

My answer was a hard yes. All the time.

Here’s the thing nobody tells you when you’re building a business. The myth of doing it all yourself isn’t a flex, it’s a fast track to burnout, mediocre output, and resenting the business you built to give yourself freedom in the first place. So if you’ve been white-knuckling every task because hiring feels scary, premature, or financially irresponsible, this one’s for you.

The short version? Knowing when to outsource in your business comes down to one question: is this task worth your time, energy, and skill, or is it stealing from something that actually is?

Let’s dive into that a bit more.

My Rule for When to Outsource

If something is going to take me X hours to do, and I’d genuinely rather be doing literally anything else for those X hours, I outsource it. Period.

If I know I’m not the most skilled person for the job, absolutely, I’m hiring someone who is! I’m not interested in cobbling together something that ends up with a “it’s fine” shoulder shrug. I’d rather save myself the time, the headache, and pay an expert to do it properly, probably quicker, and spend my afternoon reading the latest Carley Fortune release, you know?

It’s the same logic as washing your car. Do you want to spend two hours of your glorious, sunny Saturday scrubbing mud off your bumper, or do you wanna pay $20, drive through the car wash around the corner, and be done in six minutes? I don’t really care about my car’s paint job, but I DO care about my Saturday. So I’ll happily fork over the $20 every single time. Take my money.

That’s the “framework” if you wanna give it a title. Now let’s get into the nuance, because there’s alllllways nuance.

When Should You Actually Outsource in Your Business?

The honest answer to “when should I hire vs. keep holding this” is the same answer to most business questions. The one everyone loves to hate (hehe)

It depends.

Because it always depends. Everything in business is contextual. But a good gut check is if you don’t have the time to do the thing, and you want it done in the next X days, weeks, or months, hire someone. Save yourself the spiral. Enjoy your life instead of grinding yourself into the ground to make “it” happen.

A few things that signal it’s time to outsource in your business:

The task keeps getting bounced to next week. If it’s been on your to-do list for three weeks and you keep finding reasons not to do it, that’s good knowledge! You’re avoiding it for a reason, and the work isn’t getting done.

You’re the bottleneck. If your business can’t move forward until you finish a specific task, and that task isn’t your zone of genius, you’re drowning growth to protect ego or avoid spending money.

The cost of NOT doing it is higher than the cost of hiring. If a $2500 project sitting on your desk is blocking a $45,000 launch, the math isn’t mathing.

What You Should NOT Outsource (At Least Not Yet)

Not everything should be handed off, especially early on. There are pieces of your business that need YOUR fingerprints, your judgment, your voice. Outsourcing them too soon creates a hodgepodge, Frankenstein business that doesn’t feel like yours.

The stuff that’s worth keeping in-house, at least until you’re really established your brand voice and core messaging. You can hire support to amplify it, but the foundation needs to come from you.

High-stakes client relationships. Especially in the early years when reputation IS your marketing.

Strategic decisions about direction, pricing, and positioning. These are CEO calls. You can absolutely get input (more on that in a sec), but the final answer needs to be yours.

Anything you actually love doing. If creating Reels is your favorite part of your week and it lights you up, keep it. Outsourcing isn’t about offloading every task, it’s about offloading the ones that drain you.

The Privilege Part, Because It’s Real

Have to name that the ability to outsource is a privilege. You can’t always just declare you don’t wanna do something and hand it off immediately. Cash flow is real. Hiring before you’re ready creates a different kind of stress. I get it.

But when you CAN outsource, the math almost always works out in favour of buying back your time. And even when you can’t yet, knowing what you’d hand off first means you have a plan for when revenue catches up. That’s a roadmap, not a fantasy.

Start small if you need to. A few hours of virtual assistant support. One project handed to a specialist. A monthly bookkeeper instead of doing your own books at 11pm on a Sunday. Outsourcing isn’t all-or-nothing.

How to Actually Decide What to Outsource First

If you’re staring at your business going “okay but where do I even start,” here’s a quick exercise. Make a list of everything you did last week. Beside each task, write one of three letters.

L = I love this and I’m great at it. Keep.

T = I tolerate this but it has to get done. Consider outsourcing eventually.

H = I hate this OR I’m not good at it (or both). Outsource first.

Start with the H tasks. Those are the ones eating your time and your soul, and they’re usually the easiest wins because you genuinely don’t want to do them anyway. So there’s no guilt, no second-guessing, just straighttttt relief.

What Outsourcing Actually Looks Like

I outsource a LOT. Bookkeeping, certain types of content creation, tech setup, design work, and yes, even strategic support when I need an outside brain on something. I have a business coach. I work with specialists. I am NOT a one-woman show, and pretending otherwise would slow everything down.

What I keep in-house? Client strategy, my voice, the decisions that shape where Tidal & Co. is going. The things only I can do.

Everyone’s split will look different. There’s no universal “outsource these five things and you’ll be free” formula. It’s about knowing your strengths, your time, and what you actually want your week to feel like.

When You’re Too Close to See Clearly

Sometimes the “is this actually worth my time” signal is loud and obvious. Other times you’re too close to it to see clearly, and you need someone outside your business to weigh in. Someone who can look at the pros and cons honestly, who knows your goals, and isn’t going to sugarcoat it because they like you, or worse, want you to like them.

That’s literally what I do for clients. Fractional operations and marketing support for small business owners who want a life-first business. I help you figure out what to keep, what to hand off, and how to build systems that don’t require you to be the bottleneck on every single thing.

Time is my most valuable resource, no doubt about it. If you’ve been running yourself into the ground trying to do everything, that’s your sign. You don’t have to keep doing this alone.

If you want a person to do business therapy with, who’ll lay out all the facts and help you find the answer you probably already knew deep down, you know where to find me. Or if you’re not quite ready for that, hop on the newsletter for bi-weekly(ish) real-talk advice on running a life-first business without losing your weekends.