How to Keep Going When You’re Not Winning

I know what you're thinking. Another "keep trucking along" post.

But I wanted to provide a tangible path to keep you going when things aren't panning out.

Something you can legit pickup and put into action tomorrow.

Hear me out.

At my previous company, we went through an acquisition, and I had the chance to meet a counterpart from another division.

I recall they were running a similar sales function—but at 10x the scale.

On paper, they were absolutely crushing it. Bigger deals, higher quota attainment, and impressive revenue numbers.

Right away, I felt doubt creeping in. Was their approach simply better than ours?

But instead of succumbing to that feeling, I decided to dig deeper.

We went step by step through their day-to-day operations, comparing them to ours.

And that’s when I realized: while they’re ahead in outcomes, we’re miles ahead in culture, efficiency, and process.

Everything I showed my counterpart—our dashboards, call coaching sessions, even small tech enhancements—left him amazed. For me, these weren’t groundbreaking. They were the basics, the minimum standard our team has been committed to from day one.

How could a team with 10x our size and 100x our lead volume not have this setup?

The deeper I dug, the clearer it became. For example our reps were making twice the dials.

They were juggling multiple aspects of the sale while closing half their deals.

My counterpart didn’t even know their conversion rates.

The doubt vanished, replaced by something surprising: pride.

Yes, their numbers are bigger right now, but our foundation is stronger. And while we’re not seeing the results yet, I could feel the momentum.

We’re building something sustainable, and once the gaps are closed, we will be well on our way.

In this case, I got lucky—faith and validation were spoon-fed to me. But it made me wonder: how do we keep going when that validation isn’t there?

Most of the time, we’re working in the dark, taking losses without clear evidence that we’re on the right track.

So how do we persist?

It Boils Down to Trust

Not blind trust that everything will work out perfectly. But trust in your process—that you’re committed to improving, celebrating progress, and sticking to a high standard.

Ask yourself:

? Are you truly giving it your all?

? Are you disciplined enough to stay consistent with your process?

? Are you proud of the effort you’re putting in?

If the answer is yes to any of those questions, then that trust should bring you peace of mind.

This isn’t just about resilience or working harder. Those are table stakes. It’s about silencing the doubt that you’re heading in the wrong direction.

Of course, if you take an honest look at your path and realize, “I’m not doing this the right way,” then by all means, adjust course.

But for most of you reading this, I’m willing to bet you are working hard. You are trying to go about it the right way. And you’re just not seeing the results yet.

Anything worth accomplishing—anything meaningful to you—will come with moments of doubt and frustration.

In other words, there will be a ton of “suck” to deal with.

But trust in your process, take pride in your progress, and know that it’s only a matter of time.

Take a look at this guide to boost your morale this week, and remember: you’re building something that matters.