If you’ve ever caught yourself saying “I’ve always been the one”—the one who handles the emails, manages the calendar, talks to the clients, runs the books—you’re not alone. Most business owners start out doing everything themselves. It’s how small businesses survive their early days.
But here’s the uncomfortable truth: that same “I’ve always been the one” mindset that got you here is now the very thing holding you back.
Delegation isn’t just about offloading tasks. It’s about fundamentally changing how you think about your role in the business. And for most owners who’ve never delegated before, that shift feels harder than any operational challenge they’ve ever faced.
The First Question to Ask Yourself
Before you delegate a single task, you need to answer one question: What am I trying to achieve?
Are you trying to open up opportunity costs? Save time? Get some stuff off your plate so you can breathe? The answer matters because it determines what you should delegate first and how aggressively you should pursue it.
Once you’re clear on the goal, look around at your day. Think about your inbox, your calendar, your document management—all that stuff that takes up hours but doesn’t actually move the needle on your business. That’s where you start.
The question shifts from “what do I need to do?” to “how do I get rid of it?”
Why Control Is the Real Enemy
The hardest thing to turn over isn’t the tasks themselves—it’s the control. The perceived quality lapse. The sense that if you’re not doing it, you won’t see it all, understand it all, or be on top of things.
Here’s what surprised me when I first started delegating: the challenge isn’t keeping up with the stuff anymore. It’s keeping up with the people. That’s a shift in thinking that catches most owners off guard.
Where you used to feel like you were behind and failing yourself, now you might feel like you’re behind and failing everybody else. It sounds worse, but it’s actually progress. Because when you let someone else be accountable for a task—when you let them run it—you can hire people who are better, smarter, and faster at it than you ever were.
The truth is you can get a lot more done, a lot faster, and a lot better. It just doesn’t feel that way when you’re first getting started.
The “I’ve Always Been The One” Trap
It’s always been in my head that I can do my emails. It’s always been in my head that I have to be the one who manages the calendar. I’m the best at talking to the customer. I’m the one who manages the money and the books. I’ve always been the one who handles the website.
I’ve always been the one. I’ve always been the one. I’ve always been the one.
You get used to that identity. And then one day you wake up and realize you’re spending four, five, six hours a day doing stuff that has literally no value to you. At that point, you have to ask yourself: what the heck am I doing?
When you finally push through that control barrier, you can actually start to move forward. Most people don’t understand or don’t realize the amount of time, money, and resources they’re losing on a daily basis—and they don’t even know it.
The $100K Wake-Up Call
I was talking with a client in Louisiana recently. He and his wife had always kept things separate—she had a job outside their business because of cheaper insurance rates. He ran everything inside the business. Common arrangement.
But here’s what he realized: while bringing his wife into the office would cost him $30,000 to $40,000, the truth is he was probably losing $100,000 a year with her not being there.
That’s the shift in thinking you have to make. You have this thought of “I need to be the one that does this” because you get certain benefits from it. But the reality is, if you realign how you’re thinking about what you’re doing, you start looking around the business and seeing all the things that need to shift.
Different people in different spots. Different approaches. And that brings you right back to delegation: how do I offload this stuff as quickly as possible?
When to Start Delegating
I believe delegation is necessary from the very beginning. There are places where you need to spend your time and places where you don’t. There are places where you get a return on investment and places where you don’t.
It doesn’t take long for a business owner to realize they’re wasting two, three, four—sometimes six, seven, eight hours a day—doing non-productive work. Even at just one or two hours a day, you could bring someone in at minimum wage, or get a virtual assistant with more skill sets for less cost, and never look at those tasks again.
Think about it as return on investment. The time you’re not spending on things you’re probably no good at anyway—versus time with clients, time in the community, time being the steward of the business instead of the lawnmower.
If you’re doing more than $100,000 a year in business, you really need to be thinking about how to turn some of these tasks over.
Your People Are Investments, Not Expenses
This is where people get stuck, especially with virtual assistants: they look at staff as expenses. They’re not. They’re investments in time and resources. You should get a return on that investment.
When you look at the people you’re bringing in or the tasks you’re trying to delegate, the reason you’re doing it is because you’re going to get something back. That’s the investment mindset you need.
I talk about activity versus impact in consulting. There’s a lot of activity inside a business, but much of it doesn’t actually have an impact. The stuff that’s just activity—that just needs to get done as a recurring thing—that’s what you want to delegate as quickly as possible.
Where to Start: The First Tasks to Hand Off
If you’ve never delegated anything, start with email and calendar. That’s it. Get your emails turned over to someone and get your calendar turned over. Let them figure out the low, medium, and high priority stuff. Let them manage your day.
From there, think about what else takes up your time: CRM management, proposals and quotes, client onboarding, recurring tasks that need to happen every day, week, or month.
These are all high priority from an owner standpoint, but they’re low return. That’s exactly the stuff you want someone else handling.
The Biggest Mistake in Delegation
The biggest mistake is thinking that control equals quality.
Picture this: you hire a really great executive assistant—someone who’s been doing this for 20 years, who every previous employer thinks is the best thing ever. But somehow she’s “horrible” for you.
Here’s the truth: she’s not horrible for you. You were horrible for her. That need to be right, to be in control—that’s what gets people. When you delegate something, you actually have to let it go.
If you can’t do that, you’re setting yourself up for problems.
The Keys to Successful Delegation
First, hire the right person. Make sure their skills, experience, and personality fit with who you are, who your organization is, and what the role requires.
Second—and this is where most owners fail even when they get the hire right—take the time to train. Don’t assume they should “just know how to do it.” Sit down with them. Show them how you do things. Make sure they understand, and make sure they agree with the expectations.
When expectations are clear, even if they start doing things a little differently than how they were trained, you’ll still get to the same correct outcome.
It’s an investment. Once you train the position once, you shouldn’t have to train it again—if you’ve got the right SOPs, procedures, and tutorials in place.
Managing the Anxiety
As a business owner, you never completely lose the anxiety about how people do things. That’s just reality. But here’s how you manage it: let people operate, and hold them accountable.
There will be times when you feel like someone should be further along, but they still get it done. You start to understand their process, and as long as it works, you’re good.
I can usually tell within a week—two weeks max—if things are going in the right direction. When I see it working, my anxiety backs off pretty quick. But when someone isn’t catching on despite more time and training, that anxiety never stops. And that’s when you have a different decision to make.
The good news? As you delegate more and more, you start checking things off: this is handled, this is handled, this is handled. Of the 25 things your business needs to get done, you go from 25 to 24 to 23. That helps a lot.
Checking In vs. Micromanaging
Checking in is asking “where are we on this?”—understanding the percentage of completion. Micromanaging is “have you done this task? Have you done this task? Have you done this task?”
When you truly delegate, you’re saying: go do this in whatever way you feel most confident. Here’s all the training, funding, skills, knowledge, and resources you need. Get it done.
Your job becomes holding accountability to the result. When you’re doing that, you’re doing it right. But if your job becomes telling them every single step along the way—that’s the very definition of micromanaging. And I don’t know many people who enjoy that process, including the ones doing it.
The Freedom on the Other Side
When delegation goes right, you can literally watch it happen. The facial expression lights up. The shoulders rise. The weight comes off. I’ve seen guys who were weighted down by the world walk in completely different six weeks later—because of what they’ve been able to turn over, the systems they’ve put in place, the investment they’ve made in their people.
They feel different. They look different. They’re talking different. Better in every sense of the word.
Business owners get into business because they want freedom. But you’d be amazed how many find themselves in an even bigger prison than they’ve ever been—prisoner of the business from 6 AM to 9 or 10 at night.
If you can stay out of that trap, if you can figure out how to get return on investment with your people, a lot of things go really well for you really quickly.
Your Quick Win
If you’re a single operator who’s never really delegated anything, start simple: email and calendar. Get those off your plate. Let someone else manage them. Let them figure out priorities and organize your day.
Then figure out where to go from there.
Remember: the goal isn’t to do everything yourself forever. The goal is to create the business and the life you actually wanted when you started. Delegation is how you get there.
Don’t let “I’ve always been the one” become the reason you never become anything more.