📣 SixthMan Playbook: Mindset Matters, Milestones Matter More

Hey LinkedIn crew,

This month’s edition of the SixthMan Playbook leans into something a bit more reflective. It’s about mindset, progress, and a powerful shift in how we measure both.

Let’s talk about a concept that’s been shaping the way I think about work and life: “The Gap and The Gain” by Dan Sullivan.

The Way We Usually Measure Progress

If your career has included roles in project management, operations, or strategy, you know the drill. It’s about setting goals, defining outcomes, measuring KPIs, and pushing toward a result. That’s how businesses grow, how systems get built, and how momentum gets managed.

Naturally, we track progress two ways. We look at how far we’ve come, but we also keep a close eye on how far we still have to go. Both feel essential.

But the mindset Sullivan introduces throws that balance into question. He suggests we stop measuring against the future ideal and start measuring against where we began. That’s the gain. And it’s a game changer.

Why “The Gain” Hits Different

Measuring backwards sounds counterintuitive at first. Especially in high performance environments where forward motion is everything. But when you focus on the gain, the ground already covered, you unlock something else entirely. You get confidence. You get clarity. You realise how much progress you’ve made, even if the original plan shifted along the way.

In that rearview mirror you often see things you didn’t even expect to accomplish. Surprises that showed up through good decisions, strong teams, and sustained effort. And the value of that reflection outweighs another look at the mountain still to climb.

What It Means for Operators and Leaders

In my work as a fractional COO, I walk into fast moving businesses all the time. There’s usually a sense that “we should be further along.” That urgency is often well placed. But it can also overshadow the progress already made.

Here’s what I ask clients instead:

• Where were you ninety days ago, or even a year ago?
• What’s easier today than it was last quarter?
• What decisions feel clearer? What systems are in place now that weren’t before?

By shifting focus to the gain, the mindset in the room changes. Teams feel energised. Founders stop carrying so much self-imposed pressure. And everyone realises, they’re not behind. They’re building.

Use This at Work

Whether you’re running ops, growing a team, or leading change, this mindset has practical use. Here are a few places to apply it:

• Start quarterly reviews by celebrating wins before diving into challenges
• Use it in retros to highlight unexpected gains alongside the goals that were missed
• Bring it into team 1:1s as a reminder that even small wins compound

The future still matters. But looking back might just be the best way to build the energy needed to keep going.

Let’s Make It a Conversation

Have you used this mindset in your own work or leadership style? Has it helped or challenged you?

I’d love to hear your take. Whether it’s professional or personal, this kind of reflection often unlocks ideas we don’t get to talk about enough.

Comment below or message me. Always happy to swap stories.

A Personal Gain That’s Hard to Describe

On May 23 at 10pm, my wife Haley and I welcomed our first son 'Charlie Rae' into the world.

And honestly… there are no words that can fully capture that feeling. The connection, the emotion, the gratitude, it’s beyond anything I’ve ever experienced.

I watched a TED Talk recently where Sam Altman, the CEO of OpenAI, said something that really stuck with me: “I don’t know what the meaning of life is, but I bet it has something to do with babies.”

Couldn’t agree more.

This month, my version of “The Gain” includes that little man. And everything else feels different in the best way.

If you’re running a business that feels stuck in the gap,or if you just want a sounding board, reach out. That’s why SixthMan exists. To bring structure, clarity, and momentum when it matters most.

Until next time,

Ben Chambers

Founder | SixthMan Consulting

Strategic Operations. Fractional Leadership. Full Court Results.