Asking for Help: A Guide for Small Biz Owners

November 4, 2021

If you’re like many Purposeful Hustlers, you’re an independent go-getter who isn’t afraid to roll up your sleeves and do whatever needs to be done. You take pride in your work ethic, and you’re dedicated to following through with your commitments. These are all excellent qualities to have, and they will take you far in your endeavors, BUT your rugged independence could occasionally have negative effects.

Pushing yourself is one thing; pushing yourself to the point of exhaustion is an entirely different story.

Additionally, there are some situations where—even though you may hate to admit it—you’re simply not an expert. You can’t know everything about every topic. If you’re trying to be your own website designer, marketer, IT manager, and accountant (in addition to running your business, founding a program, or whatever your “hustle” might be), you’re bound to run into areas that are simply beyond your expertise.

And that’s okay!

It’s fine to admit when you need help. In fact, it takes a good deal of courage to be vulnerable and humble enough to acknowledge when you’ve reached your limit.

Dare to seek help when:

  •   You’re feeling overwhelmed or stressed.
  •   You’re having trouble keeping track of your various projects.
  •   You’re facing an issue that is beyond your area of expertise.
  •   You’re struggling to focus on your main mission.
  •   Your mental, physical, or emotional health is beginning to suffer.
  •   Your relationships are being negatively affected by your workload.

Even if you know it’s time to ask for assistance, it’s a whole other thing to ask for it. You might feel embarrassed at the prospect of asking for help. You might feel like you’ve failed in some way if you need to turn to others for support. Or, you might assume that others are too busy to help or uninterested in lending support. Alternatively, you may assume that it’s too expensive to hire someone to assist you.

All these roadblocks can prevent you from reaching out and asking for help when you require it. If you’re grappling with some of these roadblocks, try following these four steps:

1. Categorize Your Workload

Before asking for help, it’s a good idea to gain a thorough understanding of your workload and the areas where you need assistance. Make a spreadsheet of every task you’re facing, and think about which tasks are within your wheelhouse—the areas you’re comfortable tackling yourself. Assign these areas a number one. Then, think about the areas that are less comfortable or desirable, but still manageable. Give these tasks a “two.” The remaining items on your list should be areas that are well outside your area of expertise and/or are very undesirable to you. Give these items a “three.”

Then, start thinking about how you can reassign the “threes” (and potentially the “twos”). You could go through your list again and rank everything, according to priority. Tackle the high-priority items first, and leave the other items until later.

Laying out your workload like this can help you start seeing it logically. Once you’ve wrangled your workload, you can move on to step two…

2. Pinpoint Your Ideal Assistant

Looking over your list, which areas could use the most assistance? Do you, for instance, desperately need help building a new website? A freelance web designer is probably your go-to person. Need help building your brand on social media? You may want to seek help from a social media manager. Do not settle for a friend or acquaintance, just because they “might” be able to help. If you want the best possible results, it’s smart to honor people’s skill sets and only ask them for assistance if they are A) comfortable with the task at hand and B) willing to help.

If you already have access to a network of individuals who could assist you (employees, talented friends), it’s time to tap into that network. Remember to ask for help gracefully, and don’t assume that someone has the free time or skill set to assist.

3. Know Your Available Resources

Many resources are available to help small business owners. In fact, we discussed several of these resources in a recent blog post. Small business assistance programs, such as SCORE, can help you connect with individuals who can help with specific needs (think blog-writing, accounting, financial services, etc.).

You could also choose to do your own sleuthing online for a qualified freelancer. Search Upwork for freelance writing assistance, Fiverr for graphic designers or website designers, or Webflow for website design assistance.

4. Do Your Homework

Before you decide to hire someone to assist you, it’s smart to do your homework. Make a list of candidates and evaluate them based on their talent, expertise, and pricing. Most freelancers will have a portfolio of their work, and it’s a good idea to ask them to send it to you (if it isn’t already posted online). If the freelancer does not have a portfolio or cannot point you to any of their past work, that’s a major red flag.

If you’re on the fence about someone, you might ask for two or three personal references. Talking to a past client (whether over the phone or via email) can give you some insight into the freelancer’s capabilities and work ethic.


Asking for help is not a sign of weakness. Smart, effective leaders are often self-aware enough to understand when they need to delegate a task. If you’re feeling overwhelmed or are facing something well outside your area of expertise take a step back, strategize, and begin seeking help. Your Purposeful Hustle will likely benefit from it.

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