181: Why We Struggle to Delegate (and How to Fix It)
Delegating can feel hard in side hustles, especially when control and perfectionism get in the way. Renee Hastings explains why we struggle to delegate, what to hand off first, and how to build trust as you grow.
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Delegating is one of the hardest skills for side hustle owners to master, especially when you care deeply about your business and want everything done right.
Today Renee Hastings shares why fear, perfectionism, and trust issues often stop entrepreneurs from letting go, even when they know it’s holding them back.
You’ll learn:
- What tasks make sense to delegate first
- How to set clear expectations so things don’t fall apart
- Common mistakes that can derail the process
If you’ve ever felt overwhelmed trying to do everything yourself, this conversation will help you start building a side hustle that can actually grow.
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Why Many People Struggle to Delegate in Their Side Hustle
Delegation is one of the most important skills for growing a side hustle, yet it is also one of the hardest for many people to master. If you struggle to delegate, you are not lazy, incapable, or bad at business. In most cases, the challenge is rooted in fear, control, and a deep sense of responsibility for something you built from the ground up.
When you start a side hustle, you do everything yourself. You manage emails, schedule meetings, post on social media, handle admin work, and deliver the actual service or product. At first, this makes sense. But as your side hustle grows, continuing to do everything becomes the very thing that holds it back.
The Real Reasons Delegating Feels So Hard
Perfectionism and the need for control
One of the biggest reasons people struggle to delegate is perfectionism. You know how you want things done. You care about quality. You worry that someone else will not do it as well as you would. So instead of handing it off, you keep doing it yourself. Over time, this leads to long hours, burnout, and slow growth.
Fear of losing control
When you delegate, you are trusting someone else with part of your business. That can feel risky, especially when your income, reputation, and clients are on the line. Many people would rather stay overwhelmed than risk something going wrong.
The Hidden Cost of Doing Everything Yourself
The real cost of not delegating is rarely obvious in the moment. Every hour you spend on low value tasks is an hour you are not spending on growth, strategy, client relationships, or revenue generating work. Over time, this keeps your side hustle stuck at a level it cannot grow beyond.
How to Delegate Effectively Without Losing Control
Focus on outcomes, not just tasks
Instead of simply handing someone work to do, be clear about what success looks like. For example, if you delegate your inbox, the goal is not just replying to emails. The goal is that nothing important gets missed, clients feel supported, and you are no longer overwhelmed by messages.
When people understand the bigger picture, they become problem solvers instead of task doers. This builds trust and leads to better results.
Start with low value tasks
Begin by delegating work that does not directly grow your business. Common examples include scheduling meetings, managing emails, posting on social media, organizing files, booking travel, and handling basic admin tasks.
Your time is best spent on work that only you can do, such as serving clients, creating content, building partnerships, and making strategic decisions.
Building Trust Through Coaching and Check Ins
The first person you hire will not do everything perfectly right away. That is normal. Early on, reviewing work and offering feedback as coaching moments helps build alignment and confidence.
Regular check ins also keep things on track. This might be quick daily messages or a short weekly meeting. The goal is to catch small issues early and stay aligned on expectations.
Delegation Is a Growth Skill, Not a Loss of Control
Letting someone help you is not a weakness. It is a form of smart business building. There are people who enjoy and excel at the tasks you find draining. When they operate in their strengths, your side hustle runs better.
Not every hire will be the right fit, and that is part of the process. Match people to what they naturally do well, and adjust as you learn.
Start Small and Let Your Side Hustle Grow
If you struggle to delegate, start with one task. Get comfortable with the process, build trust, and then gradually hand off more responsibility over time.
Delegation is not about doing less. It is about focusing on what matters most. When you stop trying to do everything yourself, you create space for growth, better opportunities, and a healthier balance in your life.
Learning how to delegate effectively is often the difference between a side hustle that stays small and one that becomes sustainable.
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