How to Survive a Mid-Winter Sales Rut (Ask Jeb)

Caroline is dealing with a dilemma so many sales professionals face this time of year: How do you shake off a mid-winter rut and regain your momentum when it’s cold, dark, and everyone else seems to be dragging too?

On this Ask Jeb episode, I offer practical, real-world strategies to help you thaw out from the winter freeze. Whether you’re fighting the gloom of early sunsets, the aftereffects of holiday downtime, or the struggle to get your customers back in “buying mode,” these tips will help you power through and regain your momentum.

Surround Yourself with Positive Inputs

When you’re in a mid-winter sales rut—especially in cold, gray weather—your environment can either lift you up or drag you down. The content you consume and the people you interact with have a direct impact on your attitude.

Limit Negativity
Skip cable news and doom scrolling. It’s toxic and drains energy. Steer clear of co-workers who only want to complain. Instead, find colleagues or mentors who keep the conversation upbeat and productive.

Engage in “Automobile University”
Turn windshield time into learning time. Load up on podcasts, audiobooks, or uplifting content. If you’re on the road for field sales, use that dead time to sharpen your skills or motivation.

Pro Tip: Tune in to the Sales Gravy Podcast (yes, shameless plug!) or revisit classic audio programs by Zig Ziglar, Brian Tracy, or Jim Rohn for a quick confidence boost.

Create a “Win” File
Save glowing emails, client testimonials, or kudos from your boss in one place. On days when you feel like a zero, open that folder and remember your wins. Believing in yourself often wavers most when external results are slow. A targeted self-esteem boost can snap you out of that funk.

Read (or Listen) Your Way Out of the Slump

When you can’t rely on external circumstances (like sunny weather or a jam-packed pipeline) to motivate you, it’s time to feed your mind intentionally.

Pick Up a Book
I once pulled myself out of a rut by alternating 10 minutes of prospecting with 10 minutes of reading No Bull Selling by Hank Trisler. That pattern helped him stay focused and eventually led him to top-performer status in his region.

Audio Allies
If reading a physical book doesn’t fit your schedule, try audiobooks. Caroline mentioned she’s listening to The AI Edge on Audible. Whether you dive into James Clear’s Atomic Habits or any other self-improvement or sales guide, consistent listening can reset your mindset.

Revisit (or Set) Your Goals and Business Plan

Aimlessness often fuels a sales rut. Getting clear on why you’re putting in the work refocuses your daily efforts.

Craft a Personal Business Plan
Break your annual quota or goals into quarterly, monthly, and weekly targets. Then, identify the daily actions that lead to those targets. Write them down, review them often, and adjust as needed.

Check In with Your Plan

If you’ve already set goals: Take them out of the drawer and ask, “Am I doing what I said I would do each day?” If you haven’t set goals yet: It’s never too late to start. Use the lull to plan out the rest of your year.

Try the “BTN” (Better Than Nothing) Approach
On a recent Money Monday episode, we introduced the concept of doing something—even if it’s small—to maintain momentum. One call, one follow-up, or one networking email is better than none at all. Doing a little bit every day builds massive momentum over time. Even if you’re not closing big deals right now, small actions (e.g., 15 minutes of prospecting, 10 minutes of follow-ups) add up.

“Eat the Frog” Early in the Day

The Eat the Frog concept (mentioned in Fanatical Prospecting) is about tackling the hardest or most dreaded tasks first. If winter weather and post-holiday inertia already have you feeling sluggish, don’t let procrastination compound the problem.

Schedule Tough Calls in the Morning
If you tend to stall on prospecting, block out time when you’re freshest. Once you conquer the hardest thing on your list, everything else feels easier.

Celebrate Small Victories
Even if you only manage a handful of calls, pat yourself on the back. Remind yourself that a day with 5 calls beats a day with none.

Lean into Action and Let Momentum Build

Motion begets emotion—meaning the more you do, the more you feel like doing. Conversely, idle time often magnifies a slump.

The Power of Micro-Commitments
Promise yourself you’ll make 5 dials or send 3 targeted emails before checking social media. Then, if you’re up for more, keep going. These little commitments help you sidestep analysis paralysis.

Reap the “Sales Endorphins”
Keith Lubner, calls it “sales endorphins.” Each positive action—be it a successful call, a good conversation, or a micro-goal achieved—releases a jolt of motivation.

You Control the Thaw

Mid-winter, post-holiday ruts can feel like trudging through snow drifts in frigid temps. The key is recognizing that you have the power to pull out of this sales rut. Surround yourself with positivity, draw on small wins, and “eat the frog” before your day disappears under a cozy blanket of procrastination.

Whether you rely on motivational audio, daily micro-commitments, or a well-curated folder of glowing testimonials, do what it takes to spark the engine. And if you find yourself at the end of the day, worn down and tempted to punch out early—make one more call. That simple action can ignite momentum and get your motor running.

---

Got a burning sales question? Head to salesgravy.com/ask. Our producers will reach out to get you scheduled on an upcoming Ask Jeb show where we tackle your biggest sales and leadership challenges.