You’re reading The Messy Middle: weekly deep dives on leadership, startups, identity, politics, and how to make high stakes decisions that are intentional and in-line with your values.
🎯 The Wrong Constraint
This weekend, I facilitated an entrepreneurial workshop on digital channel strategy. In the session's pre-work, I asked everyone one simple question: Where do you think your biggest opportunity for growth is right now?
Almost every founder gave some version of the same answer: "I need to get in front of more people." And yet, as we started mapping where their time was actually going, a different picture emerged. Most of their energy wasn't being spent creating more opportunities to be discovered. It was being spent refining what happened after someone had already found them: tweaking their website, rewriting copy, adjusting pricing, redesigning pages, polishing messaging, or trying to squeeze a little more performance out of systems that weren't the thing limiting their growth in the first place.
It reminded me of almost every business I've ever worked with, including my own. We often assume we know what the problem is. More often than not, we've simply become very good at solving the wrong one.
🧩 What We're Really Solving For
One of the easiest traps to fall into, whether you’re building a business or leading a team, is becoming incredibly good at solving the wrong problem.
We spend months refining our offer, optimizing our website, tweaking our messaging, polishing presentations, rewriting resumes, or searching for the perfect productivity system because those things feel tangible. We can point to them, measure them, and cross them off a list.
But the work that’s easiest to measure isn’t always the work that’s limiting your growth.
If nobody knows your business exists, improving your conversion rate probably isn’t your biggest opportunity. If you’re not getting interviews, rewriting your resume for the fifteenth time probably isn’t the answer either. And if your team isn’t aligned, another beautifully designed presentation probably won’t fix it. In each case, we’ve mistaken the symptom for the constraint.
We optimize what’s visible before we’ve identified what’s actually holding us back. We keep improving the system without first asking whether we’re fixing the right part of it.
Because once you’ve identified the real constraint, the work often becomes harder, not easier. It asks you to stop investing in what’s familiar and start investing in what matters. It asks you to let go of work that feels productive so you can make room for work that’s actually strategic. And that’s uncomfortable because the payoff is rarely immediate.
🔍 A Pattern I Keep Seeing
The more I thought about it, the more I realized this is one of the most common leadership mistakes I see, and that's why I was so struck by what one of the workshop participants texted me after the session:
"A lot of hard work…but good work to do.”
The best leaders don’t just solve problems well; they spend an enormous amount of time making sure they’re solving the right problem, and that is way harder than it looks.
Leadership isn't about working harder, it’s having the discipline to pause long enough to ask a different question before rushing toward a solution. It's about asking, What’s the real constraint here? Sometimes it’s visibility, sometimes it’s trust, sometimes it’s an uncomfortable conversation you’ve been avoiding, and sometimes it’s a decision you’ve been putting off because solving everything around it feels safer than solving the thing itself.
Whatever it is, that’s usually where the real work lives.
And, as client reminded me this weekend, it’s almost always a lot of hard work…but good work to do.
What’s the constraint you’re trying to solve right now? And are you certain it’s the one that’s actually holding you back?
🥨 Snacks
❤️ Wholesome: Marcello Hernandez debuted a new character on SNL, and the story behind it will melt you.
📚 Job Market: Why are executive communications roles paying upwards of $1M comp packages?
🍿 Recently Watched: My friend & colleague's DisruptHR Talk on how your best leaders are burning out, and you just can't see it yet.
☕ Hosting 8/20: I'm co-hosting a free Kismet Coffee Hour on August 20th for senior leaders. How do you build trust when even leaders don't know what's coming next? Think peer office hours, not another LinkedIn pep talk. Join us →
See you in next week's mess,
Arshiya
