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10 Unconventional Moves I’m Making to Win in 2026
Published 4 days ago • 3 min read
10 Unconventional Moves I’m Making to Win in 2026
If you have been around Sales Players for any length of time, you know that December is my reset window. It is when I look at what worked, what fell flat, and what I need to change if I want next year to look meaningfully better than the last.
The last couple of years have been a grind. Layoffs, budget freezes, deals slipping, and pipelines that felt shakier than they used to. A lot of momentum across tech sales has felt fragile.
That is exactly why I am being far more intentional about how I approach 2026.
Instead of chasing louder tactics, I am committing to ten moves that might sound counterintuitive, but have quietly had the biggest impact on my clarity, my pipeline, and my energy.
Here they are.
1. Travel more
The biggest boosts in clarity I get always come after stepping out of my routine. A few real trips reset my thinking and sharpen my priorities. In 2026 I want at least two meaningful personal trips and more in-person time with teammates, customers, and partners. Real relationships are built face to face.
2. Read fewer sales books
I still care about getting better at selling. But I am shifting more of my reading toward fiction, history, and general literature. It has already made me a better communicator and a sharper thinker. Buyers connect with people who have perspective, not walking sales manuals.
3. Walk more
Walking has become one of my best creative tools. Most of my strongest ideas come after a long walk. The more I move, the clearer I think. In 2026 I am making walking a non-negotiable part of my week.
4. Write more
Writing sharpens thinking. It forces clarity. I am committing to writing more, even when no one else sees it. Briefs, summaries, reflections, notes. The better I write, the better I sell.
5. Reconnect with old relationships
Every major opportunity in my career traces back to a real relationship. In 2026 I am reaching back out to old colleagues, partners, and friends. Not for transactions, but to rebuild meaningful connections. The best opportunities tend to follow naturally.
Recent picture of my wife (Michelle) and I near Portland, OR.
6. Lower my outreach volume
Yep, you read that right. Lower.
I am cutting noise and doubling down on relevance. Fewer generic emails. Fewer drive-by voicemails. More thoughtful targeting. More meaningful messaging. Fewer interruptions and more conversations that actually matter.
7. Give more without expecting anything
Add value. Share ideas. Make introductions. Help people. No ledger. No mental scorekeeping. Just give. It always comes back in ways you cannot predict.
8. Go deeper on my buyer’s world
I am shifting time away from generic sales content and into industry-specific learning. More trade publications. More podcasts from my buyers’ perspective. Better understanding creates better conversations.
9. Post less on social
I only want to share things that are actually useful. Not content for the sake of activity. Fewer posts. Higher quality. More signal, less noise.
10. Be more stoic
Sales is strikes and gutters. Some years will feel electric. Some will feel flat.
The only winning move is to keep rolling the ball down the lane. Control what you can. Let go of what you cannot. Keep showing up.
These ten shifts are not flashy. They are not hacks. They are not trends.
They are the foundation I am building my next year on.
And if you are feeling tired of noise, burnout, and constant pivots, you might find that the quiet, steady path is the one that finally compounds.
Here's to a big 2026!
-Jesse
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Sales Players is on a mission to reach 1,000 reps, founders, and operators in tech with FREE weekly content that explores the mindset, skills, trends, and tools used by the industry's top players to win at the game of tech sales.
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