The Sales Struggles No One Talks About—And How to Conquer Them in a Risk-Averse, Volatile Market

Sales is not for the faint of heart.

We are living through one of the most volatile markets of our lifetime. Buyers are spooked. Budgets are tight. And even when you secure executive alignment, that “yes” often turns into a long, painful purgatory filled with endless reviews, escalations, and worst of all—silence.

But these are not just market problems. These are human problems. They’re your problems and mine.

Over the last two decades, I’ve seen a lot of change—product shifts, territory shakeups, org redesigns, reorgs of the reorgs. I’ve been lied to, counted out, fired, promoted, ghosted, and celebrated.

And through all of it, I’ve seen what separates the good from the great.

Let me break down what salespeople are struggling with right now, and more importantly—how we rise.

THE 6 BIGGEST STRUGGLES IN SALES RIGHT NOW1. Market Volatility and Risk-Averse Buyers

The buying cycle has changed. It’s not about how great your product is—it’s about how big the risk feels.

I’ve seen deals vaporize in Q4 because a new CFO walked in and hit the brakes. I’ve had procurement insult me on a Zoom call in front of my leadership team. I’ve been told “we’re just not going to make any big moves this year” after years of nurturing a relationship.

Buyers aren’t afraid of missing out anymore—they’re afraid of messing up.

That means:

You must de-risk the decision.You must help them sell internally.You must show how others like them won by making the move.

You don’t overcome hesitation with hype. You overcome it with proof, partnership, and patience.

2. Cutting Through the Noise

Your prospects are bombarded with a thousand messages a day. Why should yours be the one that gets a response?

Early in my tech career, I decided to try something different. I reached out to 500 people at one of my target accounts. 200 accepted. Over 100 took meetings. It led to a 9-figure deal. Not because I had a magic pitch—but because I created value, nurtured curiosity, and kept showing up.

Here’s what works:

Personalize with insight. Use their own words, news, and mission. Keep it short. No one reads walls of text. Make it about them, not your product.

You aren’t just another vendor. You’re the trusted advisor they didn’t know they needed—yet.

3. Time Management and Pipeline Pressure

We’re in meetings all day. We’re reactive. We check every ping and inbox like it’s urgent. Then we wonder why we didn’t prospect, why pipeline’s thin, or why it feels like we’re always behind.

I used to glorify burnout. I wore it like a badge. But the truth? It’s not sustainable.

What changed everything for me:

Blocking time every morning to touch every key deal. Protecting calendar space like a lion guards its territory. Ruthless discipline around non-negotiables.

Before inbox zero, Slack messages, or internal drama, I move the ball downfield on what will actually impact revenue.

4. Navigating AI and Tech Overload

We’re in a weird place: told to adopt AI, tools, and tech—but also to keep it personal. And a lot of reps are frozen between the two.

Let me be clear: AI doesn’t replace the human touch—it enhances it.

Use AI to:

Summarize meetings.Suggest next steps.Automate follow-up.Surface warm leads from marketing data.

But only you can build trust. Only you can sell change.

Sales is a human sport with digital steroids. Use both.

5. Burnout, Fatigue, and the Mask We Wear

I’ve had to pump myself up like Rocky in the mirror, only to get soul-crushed two hours later in a negotiation. I’ve been insulted on calls, misrepresented, even robbed of the credit on my own deals. I’ve smiled through tears. I’ve led calls after being handed devastating personal news.

And yet, we show up. Again. And again.

Because the show must go on.

What’s helped me:

Theme songs that fuel me. For me, “The Show Must Go On” by Queen became my anthem. Journaling daily to process emotions and stay grounded. Reframing each day as an opportunity to serve—not just sell.

Burnout thrives in isolation. But resilience is built in repetition.

6. Rejection, Ghosting & the Emotional Toll of Sales

Let’s be real. Sales messes with your head. You can do everything right and still lose. You can get all the signals and still get ghosted.

What separates the elite?

Mental agility. Grit. The ability to take one more step when the others quit.

I’ve been rejected hundreds of times. Deals have fallen apart inches from the finish line. But I’ve also gotten massive wins because I didn’t give up after being told “no.”

One of my proudest wins came when a CIO publicly dressed me down, only for us to close a transformational deal six months later—because I kept showing up with value.

7 PRACTICAL WAYS TO WIN RIGHT NOW

Here’s what I coach my team (and myself) to do every single day:

Lead with curiosity and value. Show up asking, “How can I help?” not “What can I sell?” Use probability to your advantage. Reach out to 10x the people you think you need. Track everything. Know your metrics. Gamify the process. Personalize outreach. Don’t mass-blast—craft value in every touch. Engage on LinkedIn. Comment, post, interact. Be seen before you’re heard. Focus on plays that get everyone paid. Align with your team’s incentives. Repeat. Daily. Water your garden every day. Deals grow where momentum flows. THIS IS OUR MOMENT

You weren’t called to this profession to go through the motions. You were called to serve, to solve, and to inspire.

And if you’re struggling right now, I want you to hear this loud and clear:

You’re not broken. The game is just hard.

But you have what it takes. You’ve got the stories, the grit, and the scars to prove it. So get up. Show up. Serve your customer. Solve their problem. And win your day.

Because in sales—and in life—the show must go on.

What are YOU struggling with right now? Comment below. Let’s help each other get better.

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