The holiday shopping season represents one of the biggest revenue opportunities of the year, and Black Friday and Cyber Monday are at its epicenter. While major retailers dominate the headlines, small business owners and side hustlers can carve out their own slice of this lucrative pie with the right strategies.
Whether you’re running an online store, offering services, or managing a side hustle alongside your day job, these actionable tips will help you prepare for and capitalize on the biggest shopping weekend of the year.
Start Planning Now (Yes, Right Now)
The most successful Black Friday and Cyber Monday campaigns don’t happen by accident. Start your planning at least 4-6 weeks in advance. Map out your promotions, inventory needs, marketing calendar, and operational requirements. The businesses that thrive during this period are the ones that treat it like the marathon it is, not a last-minute sprint.
Know Your Numbers Before Setting Discounts
Don’t just throw out random percentage discounts because everyone else is doing 40% off. Calculate your margins carefully. Can you afford that discount and still make a profit? Consider offering strategic deals that move specific inventory, bundle products to increase average order value, or create exclusive packages that feel special without destroying your bottom line. Sometimes a compelling offer isn’t about the biggest discount—it’s about the best perceived value.
Build Your Email List Early
Your email list is gold during BFCM. If you haven’t been building one, start immediately. Offer a small incentive for sign-ups and begin warming up your audience with valuable content before the big sales weekend. Send a series of emails leading up to Black Friday: teasers about upcoming deals, early bird specials for subscribers, and exclusive preview access. Your email list should feel like a VIP club, not just a broadcast channel.
Create Urgency (Authentically)
Urgency works, but it has to be real. Limited inventory, time-bound offers, and flash sales create genuine FOMO. However, artificial scarcity damages trust. If you say there are only 10 items left, there better be only 10 items left. Use countdown timers, clearly communicate when deals expire, and consider structuring offers that change throughout the weekend to keep customers engaged and coming back.
Optimize Your Website for Traffic Spikes
Nothing kills a sale faster than a website that crashes or loads slowly. Test your site’s capacity, optimize images, streamline your checkout process, and ensure your payment systems can handle increased volume. If you’re on a platform like Shopify or WooCommerce, check that your hosting plan can manage traffic surges. A customer who encounters technical difficulties is a customer who shops elsewhere.
Mobile-First Is Non-Negotiable
Over 70% of online shopping traffic comes from mobile devices. If your site isn’t mobile-optimized, you’re leaving money on the table. Test your entire customer journey on a smartphone: browsing, adding to cart, and checking out. Make sure buttons are easy to tap, forms are simple to fill out, and your site loads quickly on cellular data.
Social Media Strategy: Go Beyond Just Posting
Create a content calendar that builds anticipation. Share behind-the-scenes preparation, sneak peeks of deals, user-generated content, and stories that connect emotionally with your audience. Use Instagram Stories, TikTok videos, and Facebook posts strategically. Consider running targeted ads to reach new customers who fit your ideal buyer profile. Don’t just sell—entertain, educate, and engage.
Leverage User-Generated Content and Reviews
Social proof is incredibly powerful during high-stakes shopping periods. Encourage customers to share photos using your products, feature testimonials prominently, and make reviews visible. If you have satisfied customers, ask them for video testimonials or to share their experiences on social media with your branded hashtag. Authentic endorsements from real people trump any sales copy you can write.
Extend Beyond Friday and Monday
Black Friday and Cyber Monday are anchors, but smart businesses turn them into Black Friday weekend or even Cyber Week. Stagger your deals, introduce flash sales at different times, and keep the momentum going. Some customers deliberately wait until the weekend or Tuesday to shop, avoiding the initial rush. Be there when they’re ready to buy.
Prepare for Customer Service Demands
You’ll get more questions, more orders, and inevitably, more issues during BFCM. Set up canned responses for common questions, consider adding temporary help if needed, and be clear about shipping deadlines and return policies. Fast, friendly customer service can turn a one-time buyer into a lifelong customer. Slow or poor service can generate negative reviews that haunt you year-round.
Bundle Products Strategically
Instead of discounting individual items heavily, create bundles that offer value while protecting your margins. “Buy this complete set and save” is often more appealing than “15% off everything.” Bundles also increase your average order value and help move multiple products at once. Think about what naturally goes together or what represents a complete solution for your customer.
Don’t Forget About Existing Customers
Acquiring a new customer costs significantly more than retaining an existing one. Show your loyal customers appreciation with exclusive early access, special discounts, or bonus gifts. A tiered approach—one offer for new customers, something extra for returning customers—builds loyalty and makes people feel valued beyond their wallets.
Plan Your Inventory Carefully
Running out of stock during BFCM is leaving money on the table, but over-ordering leaves you with dead inventory. Analyze last year’s data if you have it, consider industry trends, and make educated projections. If you’re a service-based side hustler, think about your capacity: how many new clients can you realistically take on without compromising quality?
Use Retargeting Ads Wisely
Not everyone who visits your site will buy immediately. Set up retargeting campaigns that follow up with visitors who didn’t convert. Show them the specific products they viewed, remind them of deals they missed, or offer a small additional incentive to complete their purchase. Retargeting is often more cost-effective than cold advertising because you’re reaching warm prospects.
Create a Smooth Post-Purchase Experience
The sale doesn’t end at checkout. Send immediate confirmation emails, provide clear shipping updates, and include tracking information. Consider adding a small surprise—a handwritten thank-you note, a bonus sample, or early access to your next sale. These touches create memorable experiences that generate word-of-mouth marketing and repeat business.
Analyze and Learn for Next Year
After the madness subsides, dive into your analytics. What worked? What didn’t? Which products sold best? Where did traffic come from? What was your conversion rate? Document everything while it’s fresh. These insights are invaluable for planning next year’s campaign and for other sales events throughout the year.
Special Considerations for Side Hustlers
If you’re managing a side hustle alongside a full-time job, time management becomes critical. Automate what you can: email sequences, social media posts, inventory alerts. Set realistic expectations with customers about response times and shipping. Consider taking a day or two off from your main job around BFCM if possible, or line up help from friends or family. Burnout helps no one.
Final Thoughts
Black Friday and Cyber Monday aren’t just for the retail giants. With thoughtful planning, strategic execution, and genuine care for your customers, small business owners and side hustlers can have their most profitable days of the year. The key is to start early, stay organized, and remember that relationships matter more than any single transaction.
Your BFCM success isn’t measured only in immediate sales but in the new customers you’ll serve all year long and the loyal fans you create. Approach these shopping holidays with both ambition and authenticity, and you’ll build something far more valuable than a weekend spike in revenue.
Now get planning—Black Friday will be here before you know it.
Ready to crush your Black Friday and Cyber Monday goals? Start implementing these strategies today and watch your side hustle or small business reach new heights this holiday season.
