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 NegativitySkip 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” FileSave 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 BookI 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 AlliesIf 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 PlanBreak 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) ApproachOn 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