5 common side gig challenges & how to solve them

More and more professionals are running side gigs alongside their full–time jobs – and we understand why. Whether you’re offering dog walking services or designing websites, running a side hustle can be a rewarding experience that boosts income and lets you explore your passions. But like any business venture, running a side gig comes with its own challenges: navigating a tight schedule, juggling competing priorities, keeping customers happy, and managing business communications

The sooner a side gig owner understands these challenges, the easier it will be to solve them. With that in mind, let’s take a closer look at the common obstacles side giggers face and identify practical ways to solve them.

Challenge 1: Managing your time while running a side gig

Side gigs rarely have start and stop times. Without a clear separation between your full-time job, side hustle, and personal time, you could easily end up working late into the night, on the weekends, and even during lunch breaks – until you find yourself answering customer queries at the dinner table or ordering supplies in the middle of your workday.

If there are no boundaries in place, it’s easy to mix your work, personal, and side gig time together, which can quickly lead to burnout. Thankfully, there are multiple ways a side gig owner can manage their time better, including:

• Setting up a schedule with time slots dedicated to working on your side gig. This way, you know that your side gig work always gets done, but it won’t distract you from completing tasks at your full-time job or disturb your much-needed personal time with family and friends.
• Group similar tasks into batches and complete them together. Admin tasks like invoicing, ordering supplies, or answering customer calls can be grouped together and allocated blocks of time. This minimizes the need to keep context-switching between different roles and responsibilities, which can slow you down further.
• Use a call management tool to control when side gig customers can reach you. If customer calls interrupt your full-time job or personal time, use tools that let you control when calls come through and how they’re routed.

Challenge 2: Building a professional image for your side gig

When you’re a one-person business, it can be difficult to compete with larger, established organizations. Without a well-recognized presence, customers may hesitate to trust your side gig even if your skills are top-notch.

Although they could second-guess the quality of the services or products your side gig offers, don’t let that stop you. Here’s how you can still make your small side gig look and sound big to win their trust:

• Build an online presence with a consistent brand image across platforms. Create a simple website and social media page that clearly explains your services, pricing, and how to contact you. Maintaining consistency in branding with standardized colors, fonts, and tone will also help you look more professional.
• Display positive reviews from existing customers. Ask satisfied customers for testimonials or short reviews. Showcase these prominently on your website and social media pages; Seeing that others trust and appreciate your work makes prospective clients more likely to choose you too.
• Invest in a business phone system. A virtual business phone system like Grasshopper offers many useful features, such as custom call greetings, call forwarding, and a virtual receptionist, which can make your side gig sound organized and established from the very first customer call. This valuable touch can help your side gig stand out among competitors.

Challenge 3: Acquiring new customers

Most side gigs operate locally and cater to customers within the same region. This structure has led to a heavy reliance on word-of-mouth as their only marketing tactic, which can slow growth and limit customer reach.

No matter how small or localized your side gig may be, it's helpful to actively seek new customers through other creative marketing efforts, such as:

• Offering limited-time promotions or referral discounts. These deals and rewards encourage existing customers to send new customers your way. They also give the referred customer an added reason to give your side gig a chance.
• Network locally. Attend community events, hand out flyers at popular local spots, or join a neighborhood group. Connecting face-to-face allows you to leave a memorable first impression while educating potential customers on what your side gig offers.
• Partner with complementary service providers. For example, a landscaper could team up with a home renovation company; a baker might partner with a wedding planner; and a dog walker can work with a vet clinic. Collaborating with complementary businesses gives you the opportunity to expand your side gig's reach into other customer bases.

Challenge 4: Staying connected with your customers

Customers expect prompt updates and replies, but making sure your side gig is responsive when you need to focus on your full-time job and personal commitments can be difficult. At the same time, you can't keep your customers waiting every time you’re busy, as this could lead to lost business opportunities or damaged trust.

The good news is that you can avoid these consequences while still setting aside time to focus on other priorities. Here’s how:

• Transparently communicate your side gig's working hours. Set expectations early so customers know when they can reach you. This transparency helps avoid frustration on both sides.
• Maintain an easy-to-access customer database. Store customer names, contact details, and job history in a database you can quickly access from anywhere, at any time. This makes follow-ups faster and easier to manage, even when you’re busy and on the go.
• Use automated tools to send confirmations, reminders, and thank you messages. For example, if you miss a call, you can instantly send an automated text letting the caller know you'll respond soon. These automation tools help you keep side gig customers informed while you focus on other tasks.

Challenge 5: Keeping your communication organized

Using your personal phone number for your side gig mixes business calls, texts, and voicemails with personal chats – making it easy to miss a customer conversation or lose important business information. For instance, you might overlook a potential client's inquiry because it got lost in a thread of group chats.

This challenge doesn't just hurt your efficiency; it can make your side gig appear unreliable and cost you valuable business opportunities. Here's how you can solve this issue with Grasshopper’s virtual business phone system:

• Get a dedicated business number for your side gig without buying a second phone. With Grasshopper’s virtual business phone system, you can have a separate number for your side gig on your existing device. This means every customer call or text can come through a dedicated business number while all customer communications are stored on the Grasshopper app, so you don’t need to purchase or carry a second phone. Grasshopper also lets you choose from a local, toll-free, or vanity phone number for your side gig.
• Keep your side gig and personal life separate. Grasshopper consolidates all customer interactions into one business phone app, allowing you to keep your side gig’s communications completely separate from your personal messages. Whether a customer is asking about your availability, confirming an appointment, or requesting a quote, every side gig conversation remains separate and organized.
• Manage all your side gig communications on one easy-to-use app. Every side gig conversation can live on Grasshopper's mobile and desktop apps, allowing you to reach all customers with just one solution. Additionally, Grasshopper offers a unified view of calls, texts, voicemails, and more, so you can access every customer interaction within a single, cohesive interface.

Running a side gig comes with multiple challenges. While each challenge is different, organizing your side gig’s communication makes the biggest impact on how successful and stress-free your venture can be. When communication is well-managed with an easy-to-use business phone system, your side gig appears more credible while saving you time and protecting your freedom.

How your side gig can succeed with a dedicated business phone system

If you're using a personal phone number or free app to run your side gig, you may have already experienced the challenges that arise when business calls and texts get mixed up with your personal conversations.

Here’s how Grasshopper’s virtual business phone system solves the biggest communication challenges faced by side gig owners:

Side gigs with a personal phone number or free app...	Side gigs with Grasshopper’s virtual business phone system...
Look unprofessional and “small” when customers realize their business is using a personal number	Offer a separate, dedicated business phone number with custom greetings to make every interaction sound established and credible
Face privacy and security issues as their personal number is shared publicly	Protects your personal contact details as customers only get access to the business’s phone number
Can’t control when customers contact them; For instance, customer calls could interrupt mealtimes or a family activity	Can set up call schedules to receive customer calls only during business hours, protecting your personal time and freedom
Miss urgent calls or forget to respond to time-sensitive voicemails from customers	Sends automated texts to keep customers informed even when you miss a call, and uses voicemail transcriptions to access the message instantly
Overlook important business texts that could get lost among their personal chats	Stores all business texts on one app, making it easy to find and respond to customer conversations

 

Grasshopper transforms your side gig's communication into a professional, secure, and organized system that scales with you — all on the phone you already carry.

Grasshopper: Designed to tackle common side gig challenges

Grasshopper's virtual business phone system makes it easy to manage your side gig. Whether you're just starting out or looking to take the hustle to the next level, our business phone system will help you connect with customers, look professional, stay organized, and maintain a work-life balance that makes running a side gig effortless.

Ready to give your side gig the virtual business phone system it deserves? Set up Grasshopper in minutes — no extra device needed. Just download the app on your existing phone and start looking like the professional you are.

Start your free trial today.