Diary of a Leader: Why Project Delivery Stress Still Hits Leaders Hard
- Lindsay Sheldrake
- May 27
- 4 min read
Welcome to "Diary of a Leader" - Real Stories, Leadership Lessons, and Personal Growth
Ah, leadership. It’s messy, rewarding, and full of lessons you can only learn by doing.
Welcome to Diary of a Leader—a behind-the-scenes look at what it really takes to lead high-performing teams and deliver results in project-based businesses.
Whether you’re scaling operations or managing creative chaos, this space is for leaders who want to grow with clarity, confidence, and impact.
The Invisible Weight Leaders Carry on Every Project
If you lead a design firm, creative studio, or project-driven team, you’ve probably felt it—that pressure that creeps in near the finish line, even when everything seems on track.
As a Fractional COO and project leadership partner, I see this moment all the time: the scope was defined, the plan was solid, the team was engaged—and still, leaders find themselves stepping in late to hold the final piece together.
At first, it feels like commitment. Like leadership. And in many ways, it is.
But when this becomes the pattern, it’s often a sign of something deeper: an over-reliance on ourselves at critical moments, rather than building the conditions for shared ownership and trust.
That’s the tension—between leading by doing and leading by design.
Let’s unpack how that showed up for me, and the lesson I wish I had considered sooner.
When Project Delivery Stress Persists—Even With a Good Plan
This wasn’t our first complex project. We’ve tackled plenty of custom finishes, tight timelines, and moments of real project delivery stress over the years. And this time, we were ready.
It was a finish we didn’t typically use—something out of the ordinary. We anticipated uncertainty in both execution and cost. So we did what experienced leaders are supposed to do: we built time for testing, created buffers, and ran tight planning and initiation phases.
The irony? We still ended up working overtime the night before the install. At 10pm, it was me and our Production Manager, still in the shop, finishing the last piece.
The project technically went well. The outcome was strong. But I couldn’t shake the feeling that something didn’t add up.
The Lessons Experience Builds (and Sometimes Misses)
Truth is, we got good at planning the hard way.
Years ago, we made the classic mistake: overconfidence in the early stages, then racing through execution. The result? High stress, creeping budgets, and burnout all around.
That pattern—relying on adrenaline to save the day—was a major source of project delivery stress and taught us a lot... We learned to value preparation, contingency time, and decision-making frameworks. And over time, our team got better. More consistent. More reliable.
But this project revealed something else: even with the right systems, leadership pressure doesn’t always disappear. Sometimes it just shifts.
What Happened This Time—and Why It Still Fell Short
We weren’t improvising. We had scoped carefully. We communicated well. The team performed.
And yet, there we were: just two leaders, after hours, doing what needed to get done. Why?
Were we the only ones who could finish it? No.
Was it because we miscalculated something? Maybe.
Did we step in because we didn’t want to burden the team? Possibly.
Looking back, I can’t pinpoint one definitive reason. But what I do know is this: when you lead project delivery, project delivery stress hits differently. You feel the weight in a way no one else does.
There’s no one else to hand it off to.
The project ends with you.
The Leadership Lesson: Accountability with Perspective
Being accountable doesn’t mean doing everything yourself.
But it does mean owning the outcome—especially when things go sideways.
And sometimes, even with great systems and a strong team, leaders still find themselves in the trenches. Not because they have to, but because they care that much.
That said, doing it all isn’t sustainable. And it’s not always strategic.
In hindsight, this wasn’t a failure in planning. It was a reminder that great project leadership is about more than getting to the finish line. It’s about knowing when to delegate, when to protect your team, and when to step in—not out of guilt, but out of thoughtful intent.
Accountability is essential. But it works best when paired with trust, boundaries, and a team that knows you believe in their capability—even when the pressure is high.
Wrapping Up (Because Time is Precious)
The success of a project often rests on a leader’s shoulders. That’s part of the job.
But how we carry that responsibility—that’s where leadership grows.
So if you find yourself doing the final push alone, ask why. Reflect on what it means. And adjust not just your process, but your perspective.
But what I do know is this: when you lead project delivery, project delivery stress hits differently. You feel the weight in a way no one else does.
Want support building project systems that protect your team and bottom line?
Book a free consultation to explore how I can support project-based businesses to scale without losing their edge.
Related Reads from Diary of a Leader
Stay tuned for more lessons on project delivery, operational clarity, and leadership in action—because building great teams and delivering exceptional work isn’t about doing it all. It’s about doing what matters, exceptionally well.
