You've already said no to most things.

So why does the wagon still feel impossible to pull?

The Pumpkin Patch Moment

I have this photo of my daughter at a pumpkin patch.

She's maybe three years old, determinedly pulling a wagon with a few pumpkins in it. Her whole body is leaning into it. She's making progress, but you can see the effort in every muscle.

The thing is, she already chose carefully.

There were thousands of pumpkins in that field. Literally thousands. And she walked past most of them. She focused. She prioritized. She picked only the ones that really mattered to her.

And still, the wagon was almost too heavy to pull.

That’s every product leader I coach.

You’ve already said no to 90% of things.

You've cut scope, prioritized ruthlessly, focused on what matters…

And you're still exhausted.

The Myth of "Just Focus More"

Every productivity framework says:

"Do less. Focus on what matters most."

You did.

But even just a few critical initiatives can be too heavy when you're the only one pulling.

The problem isn't how many pumpkins are in your wagon.

It’s that you're pulling it alone.

What's Actually in Your Wagon

Let me guess what you're carrying right now:

Strategic weight

• Long-term vision only you can articulate
• Market positioning only you understand
• Company direction only you can connect to daily work

Decision weight

• Priority calls that need your judgment
• Trade-offs that require your context
• Approvals that can't happen without you

Relationship weight

• Stakeholder management that depends on your credibility
• Cross-functional alignment that needs your diplomacy
• Executive updates that require your translation

People weight

• Team development that needs your experience
• Performance issues that need your authority
• Hiring decisions that need your vision

You've already cut the nice-to-haves.

These are the essentials.

And they're still too heavy.

The Real Problem: You're the Bottleneck

The issue isn't your workload.

You’ve built a system where everything depends on you.

You join meetings because "they won't have the context."

You review significant decisions because "they might miss the bigger picture."

You manage conflicts because "they don't understand the history."

You've become the Context Keeper.

The more successful you get, the heavier the wagon gets.

More success = more strategic initiatives = more decisions = more stakeholders = more context to keep = heavier wagon.

You can't focus your way out of that.

You can't time-manage your way out of that.

And working harder doesn’t solve it.

When You’re Overwhelmed… Ask:

"How much of my week is spent doing work that only I can truly do?"

For most leaders? It's ~20%.

The rest is work someone else could do. If they had:

• The strategic context you've been keeping
• The decision-making frameworks you use instinctively
• The confidence that comes from real authority
• The relationships you've built over time

But they don't have those things.

Because you've never built the systems to give it to them.

The Uncomfortable Truth

You're exhausted not because you're doing too much.

You're exhausted because you're doing too much alone.

And the worst part?

You're training your organization that strategic work only happens through you.

Every time you attend that meeting, "just to provide context"…

You're teaching them they can't think strategically without you.

Every time you make that decision, "because they need more experience first"…

You're blocking them from building that experience.

Every time you “step in to handle it"…

You're making yourself indispensable in the worst possible way.

From Solo Pulling to Strategic Multiplication

Right now you:

Pick the pumpkins (decisions). Load the wagon (execution). Plot the route (strategy). Pull the wagon (delivery). Unload it (communication).

You're doing 100% of the work across 100% of the process.

Strategic multiplication looks like this:

They load the wagon

"Take these three initiatives and create project plans."

They're doing execution work, but you're still carrying all the strategic weight.

They help choose pumpkins

"We need to solve for customer retention. Here are five possible approaches. Analyze and recommend."

Now they're building judgment, but you're still the safety net.

They own their wagon

"You own the mobile experience. Make the decisions you need to make. Keep me posted on major changes."

They're carrying full strategic weight in their domain.

They even teach you better ways to pull

"Your system for prioritizing features just solved a problem I've been struggling with. Walk me through how you think about this."

They're making you smarter.

That’s when leadership begins to scale.

Put This Into Action Pick one pumpkin you keep carrying: one recurring decision or responsibility that always needs you. Don't delegate the task. Delegate the context. Ask yourself: What would someone need to know to make this call without me? What framework do I use that I never explained? What authority or trust are they missing? Build the system to transfer that. Don’t just delegate the task, but provide the capability to own it fully.

You don't need a lighter wagon.

You need more people who can pull.

And the only way to get there is to stop pulling alone.

Key Takeaways

✅ Focus isn’t the fix.

You can’t prioritize harder your way out of exhaustion. The problem isn’t how much you’re doing, it’s that you’re doing it alone.

✅ The bottleneck isn’t your workload.

It’s the system where every decision, relationship, and piece of context depends on you.

✅ You’ve become the Context Keeper.

The more successful you are, the heavier the wagon gets, because success multiplies context.

✅ Stop delegating tasks. Start delegating context.

If you only hand off tasks, you stay the thinker and they stay the doers. Transfer your judgment, frameworks, and trust instead.

✅ Build pullers, not lighter wagons.

The goal isn’t to do less. It’s to create more people with the context, frameworks, authority, and confidence to share the strategic weight with you.

---

What if you didn’t have to pull alone?

Even the best coaching can’t replace a table of peers who actually get it.

That’s why I’m quietly forming small, invitation-only mastermind groups for product leaders who are scaling inside complex, high-stakes environments.

6–8 people.

Real accountability.

Conversations that don’t start with backstory.

These aren’t networking circles. They’re rooms for leaders who want to think deeply, share openly, and grow alongside peers who get it.

If you’ve ever wished for a table where you don’t have to translate your world before getting to the good part… this is that table.

I’m still shaping the first cohorts.

If you want a seat at this table, reply to this email with MASTERMIND and I’ll add you to the early-access list.

​

Keep reading: More on scaling yourself, not your stress:

Scale Your Impact: 5-Level Delegation Framework

Don't delegate more. Delegate better.

Why your team feels chaotic (even when you're shipping)

Transform chaos into coordinated progress.

5 questions that reveal what's killing your team's momentum

Is your rhythm working?

---

If this story resonated, consider this your nudge:

Find your table. Build your circle. Invite others to pull with you.

Leadership’s not meant to be a solo sport.

Until next time!

Andrea

Andrea Michalek - @ThatAndreaM ​Say hi 👋 on Twitter, Bluesky, or LinkedIn ☎️ Book a 1:1 call with me

​

P.S. Small rooms. Big growth. See if you fit → reply “MASTERMIND.”

P.P.S. I’d appreciate it if you forward this newsletter on to others you think might enjoy it. Thanks!

Join Leadership Advantage