Use These Pointers to Earn More This Holiday Season

RSG contributor Jeffrey Fike is here today to help you prepare for the busy holiday season. Just because it’s a busier time of year doesn’t mean you have to stress during your delivery tasks! Follow his tips below to have a smoother holiday overall.

The holidays are quickly approaching, and every year, it seems retailers and restaurants are battling each other even more fiercely for that prized consumer dollar.

As a delivery driver, this can be the most wonderful time of the year, for sure. With more and more retail stores, in addition to most restaurants, offering delivery through app platforms (like Instacart!), it pays to be prepared.

Quick Summary:

  • Rely on recon from the rest of the year to determine the best chances for smooth pickups.
  • Be prepared for waits and traffic; it’s inevitable this time of year.
  • Trust your past knowledge and experiences to know what’s best for you.

Gearing Up for a Busy Season

Being prepared starts with planning, and executing it will take lots of patience. Vehicle traffic may not return to pre-pandemic levels, but will certainly be volumes greater than 2020.

I discussed planning, preparing, patience, and a few other “p words” here in my article about delivery strategies – check it out! Now, more than ever these principles apply.

You might be asking yourself how to plan for an already hectic season. Well, fear not. It is not as terrifying as, say, hacking out a budget with your spouse, getting your kids to eat their vegetables, or even studying for that final exam you’ve been dreading. The basics are easy: gas in tank, air in tires, tools of the trade, room in trunk/backseat to transport items.

Be ready with your supplies, and your plan.

Merriam-Webster defines Reconnaissance as: “a preliminary survey to gain information; especially: an exploratory military survey of enemy territory”. It may seem a bit over the top, but not really if you remove the word “enemy”.

If you’ve been delivering (or even shopping) in your area for a while, you may have unknowingly done some recon on local stores. You know which ones (Target, Walmart, etc) have the best payouts, friendliest staff, easiest in/out access, closest to other hotspots, and fastest delivery pick-ups, etc.

Grocery shopping and delivery requests are increasing. Stores like Target, Walgreens, Rite Aid, and Meijer’s will be seeing record orders this holiday season, and knowing the lay of the land will pay off for diligent drivers.

Other stores like Walmart, Macy’s, and Ulta rely heavily on delivery services for their “last mile” deliveries—getting packaged orders from the store to customer, and this will only increase as the holiday season progresses. Again, knowing where and when to be there (or not) can pay huge dividends.

Rely on Recon for Smoother Deliveries

Not unlike traditional Black Friday shopping, delivery driving during the holiday season is a game that will be won with patience, and those who know when to wait it out or when to cut and run. This is where your personal recon will come in handy.

Is it possible to avoid all the crowds during the holidays, or never have a long wait to pick up your delivery? Of course not! But having some guidelines in place and following your own well-thought-out strategy based on past experiences (as a consumer or as a driver) should help to minimize those unfortunate but somewhat inevitable incidents.

Such recon has led me personally to decline all orders from certain merchant(s) who consistently make delivery drivers wait, even during slow times. I recheck every few months, and it’s still the same.

Back to the holidays at hand. Think back a few years: which stores did a great job of holiday staffing and traffic management in-store, and which didn’t? Which stores have you been consistently happy with the service you’ve received, year-round, including the holidays? Surely, it’s not a 100% correlation, but generally, companies that emphasize customer service over the years will develop competent management and capable staff, even the holiday temps.

Related content: Learn ways to earn big with Instacart this holiday season!

If you keep your own local recon top of mind, you can probably steer clear of some – but not all – long waits and frustrating encounters. Remember to consistently communicate with your customers if there is an issue, and don’t be afraid to politely ask employees for assistance in-store or when picking up if you have a question.

There will certainly be twists in the road, but using your experience-based knowledge and planning can help keep your averages, ratings, and earnings high, and stress lower.

Just remember that everyone is busy during the holidays, and everyone has their own drama. Taking the time to patiently execute your well-prepared plan based on your own local recon can be rewarding, not just for you, but your customers as well.

Takeaways for Delivery Drivers

If you’re finding holiday time to be too stressful to do others’ shopping, you can consider picking up a gig with Uber or Lyft. Or, keep your bandwidth open to both delivery and rideshare possibilities. It’s sure to be a profitable time of year for everyone, no matter their preference.

The idea of patience and recon comes in handy for rideshare as well. You know if driving downtown is worthwhile, or if the suburbs are more profitable. And don’t forget holiday travelers who need your help with airport pickups!

Don’t forget that packages need to be delivered around the holidays too. Learn about becoming a UPS personal vehicle driver for the holidays:


What pointers do you have for delivering and driving around the holidays? Share in the comments below!

-Jeffrey @ RSG