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Entrepreneurs Hate Asking for Help. Here’s Why.

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At Trusty Oak, we’re all entrepreneurs: from our CEO and founder, Amber Gray, who created our company, to each and every virtual assistant (VA). As VAs, we each operate as independent contractors, and many of us also own other small businesses—from small-batch coffee roasters to pet sitters to off-shore fishing companies. 

That’s how we know personally that entrepreneurs (kinda sorta) hate asking for help. There are so very many reasons for this aversion, and most of us have experienced how it limits our success. Today, let’s look at some of the reasons we entrepreneurs fail to ask for help when we need it most, and the truth behind what’s holding us back.

1. Perception: Asking for Help is Overwhelming 

Let’s start here by acknowledging that asking for help can be overwhelming. Finding the right assistance and then setting yourself up to delegate tasks isn’t a one-step process. For many entrepreneurs, the thought of hiring an assistant is daunting enough to make them stop before they begin. When you don’t even have time to find and train a new assistant, help can feel completely out of reach. 

Reality: You’re already overwhelmed

Although you may not be able to envision taking the time to delegate, you can’t scale your business without this crucial step toward growth. It’s true: choosing a virtual (or in-person) assistant and bringing them on board will take time and effort. But down the road, this investment of time will exponentially improve your business and make your company more successful. 

Related: 13 Tasks Busy Entrepreneurs Should Delegate

2. Perception: It’s Too Vulnerable 

It’s not easy to admit you’re drowning in emails, tasks, and to-do lists. Besides that, bringing someone in to help out involves letting them see the mess: your 2,963 unopened emails, your disorganized Google Drive folders, your bright red past-due Trello notifications. Entrepreneurs have a capable, can-do attitude that can make it a little painful to admit where you’re falling behind. 

Reality: Competent, compassionate help is available

Most individuals who get into assistant work find purpose and fulfillment in watching their clients succeed. While it might be uncomfortable to give someone the behind-the-scenes tour of your company, it’s a sign of strength and leadership to push beyond these feelings and delegate. VAs are on your side and their help will give you the extra time you need to do your best work yet.

3. Perception: “No One Cares as Much as I Do” 

Many solopreneurs operate on a guiding myth: there’s no one who can help me with my business because no one could possibly care as much as I do. When you’ve built a business from the ground up, it’s understandable that you’d have some apprehension about handing over the steering wheel to anyone else. 

Reality: Empowering an assistant makes them care, too

When you work diligently on delegating and instilling trust in an assistant, the right person takes ownership. When you reach the pinnacle of delegation and leadership, you’ll find that empowered employees and assistants begin to care just as much as you do about your company’s success. After all, the more you delegate, the more your company’s future is tied with your assistant’s. 

4. Perception: Help is Expensive $$$ 

Small business owners are geniuses at pinching pennies and running on a lean budget. Hiring a virtual assistant may seem out of your budget—after all, payroll tends to be the highest expense of any company. 

Reality: As-needed, hourly help is affordable

It’s true: hiring an employee is incredibly expensive. But there are other options, such as hourly, as-needed assistance that fits your budget. At Trusty Oak in particular, we give business owners the opportunity to purchase the packages that fit their budget, and as their company grows, they can delegate more. 

Related: Are Virtual Assistants More Affordable Than Traditional Employees? 

5. Perception: “Help” Has Failed in the Past, It Will Again

Maybe you’ve had a past experience where you tried to delegate to an assistant and it went poorly. Maybe you trusted someone and they didn’t deliver, costing you time and money. When this is the case, it can be hard to try again. 

Reality: Delegation doesn’t happen overnight 

It’s understandable when entrepreneurs are hesitant to delegate because of past experiences. But delegation is a process, and it takes time to perfect. Although previous failed attempts may have been frustrating and ineffective, they can also teach you something about what you need in the future: for instance, you may have realized you prefer certain personality traits like humor or poise in an assistant. Take what you learned from the past and bring it forward with you for a better delegation experience today. 

Knock one task off your list right now: ask for help. We promise you’ll thank yourself later.


Emily Fisk

Emily Fisk began her career in marketing after graduating from Boise State University with her B.A. in English, Rhetoric and Composition. Emily started freelancing as a writer and found Trusty Oak in 2016. Emily spent three years as a virtual assistant, helping clients build their digital marketing efforts, while taking on more responsibility as an account manager and marketing manager as Trusty Oak grew. In 2019, Emily took on the role of Marketing Director, and in 2020, she began serving as Trusty Oak's Vice President of Operations. Emily’s passion for clear communication, vibrant teamwork, and helping others find meaningful careers has made her a key part of Trusty Oak’s growth. She gets a kick out bringing Trusty Oak’s story alive and watching clients succeed. Under her leadership, the Trusty Oak marketing team has accomplished large-scale projects and numerous successful campaigns, undertaken new brand identity initiatives and launched innovative content. When she’s not working, Emily loves digging into a good book, cooking a delicious meal, and getting outside with her two daughters and husband. She lives in beautiful Boise, Idaho and is a founding member of a (totally cool, not at all nerdy) writing group.

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