No One Taught Me How to Delegate and It Nearly Broke Me

I used to think delegation was a luxury.

Something you did once your systems were perfect, your team was seasoned, and your workload was manageable. Until then? You rolled up your sleeves, stayed late, and carried the weight yourself. That’s what responsible leaders did—or so I believed.

That mindset nearly burned me out.

When I became head of a 360-student K–8 school with limited resources, I walked into an environment defined by scarcity. No admissions director. No marketing team. No instructional specialists. An overextended administrative team. A board that expected rapid academic improvement after years of stagnation.

And me—trying to hold it all together.

Is Decision Making Tiring You Out?

If you lead people, there’s a good chance you’ve had this experience:

You start your day with good energy. Your mind feels clear. You’re making smart calls, moving things forward, and communicating with confidence.

But by mid-afternoon?

Every question feels heavier.
Every choice takes longer.

Productivity solutions for busy entrepreneurs

In my last post, I presented common productivity challenges that entrepreneurs face, such as the need to wear multiple hats, navigate a constantly evolving market landscape, and manage limited resources effectively. We also discussed how the inherent risks and pressures associated with entrepreneurship, including financial constraints and the fear of failure, can further impede productivity by causing stress and anxiety. As a result, entrepreneurs often find themselves caught in a cycle of juggling competing priorities, battling distractions, and struggling to maintain momentum towards their goals.

Despite these challenges, however, many entrepreneurs can overcome productivity hurdles through resilience, resourcefulness, and a willingness to adopt effective strategies and tools to optimize their time and energy.

Common productivity challenges of busy entrepreneurs

Entrepreneurs and founders often find themselves grappling with productivity challenges that stem from the unique demands and uncertainties of building and managing their own businesses. From the early stages of conceptualizing a startup to the ongoing responsibilities of overseeing day-to-day operations and driving growth, entrepreneurs face a multitude of roles, tasks, and decisions that can overwhelm even the most ambitious and high-performing individuals.

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