
“I only need help with a few tasks here and there—why shouldn’t I just use Fiverr or UpWork for specific projects?”
Sound familiar?
That mindset can make sense, in the short term. If you have a one-off design project, a quick copywriting task, or something else that doesn’t feel ongoing, a freelancer on Fiverr or UpWork seems like a quick, cost-effective solution.
But here’s where things start to break down—especially for leaders juggling a lot.
Maybe the thought of having a consistent person on your team feels like overkill if you only need small tasks handled sporadically. But let’s break this down.
With platforms like Fiverr or UpWork, you’re getting task-specific solutions for individual projects. That’s great for short-term needs, but what happens when you have new, ongoing needs? You’re back to square one, searching for someone new, explaining your business all over again, and hoping for quality results every time. Each project is like a restart.
Why Consistency Beats One-Offs
Now, imagine having someone integrated into your business who knows your systems, your preferences, and your goals. This is where the value of a regular assistant comes in.
Here are a few reasons why consistent support, even for just 5 hours a week, is far more effective than juggling one-off freelancers:
- Mind-Share Matters
A remote Executive Assistant with regular responsibilities is always thinking ahead. They’ve got a consistent pulse on your business and are ready to take action before you even have to ask. You won’t get that kind of forward-thinking from a freelancer who’s popping in and out of projects. With regular assistance, your EA can become proactive, anticipating your needs and saving you from constant firefighting. - Less Repetition, More Efficiency
Every time you hire someone new for a one-off project, you have to explain your systems, preferences, and needs from scratch. That’s time-consuming and inefficient. When you work with someone regularly, that person is already onboarded, familiar with your processes, and knows how to hit the ground running. Less time spent explaining means more time focusing on the big picture. - Building Trust and Dependability
A consistent relationship with an assistant builds trust. You know that they’ll deliver because they’re already part of your team. They’re invested in your success, and as time goes on, they’ll become more reliable and accurate in their work. You won’t need to micromanage, and you can depend on them to handle the routine tasks that free up your time. - Fewer Fires to Put Out
If you’re relying on one-off help, you’re likely still putting out a lot of fires yourself. You hire someone for a quick fix, but they’re not around for the long-term maintenance. A regular assistant can take ownership of ongoing tasks, keeping things in check so small problems don’t become big ones. You stop being the go-to person for every little thing, and that means fewer urgent interruptions in your day. - Integrated, Not Just a Helper
When you hire a regular assistant, they’re not just a helper for small tasks. They become part of your team. They know your goals, your business, and your style. This makes them much more than just a “doer” of random projects—they become a strategic partner who can help you grow and scale.
Ready for Consistency?
One-off projects might get you short-term fixes, but consistent, dedicated assistance will move your business forward in a more powerful way. When you have someone who knows your business inside and out, they don’t just check tasks off a list—they help you create momentum.If you’re feeling stretched too thin, it might be time to stop thinking about “What small tasks do I need help with?” and start thinking about “What regular support can I get to free up my time?”

Micah Foster, Co-Owner
Micah Foster is a partner at Dream Support LLC who has been providing remote executive assistants to busy leaders who need administrative and organizational help for over five years.
He has a passion for creating and maintaining positive and productive work environments and empowering people to reach their full potential.