This piece of wisdom is something I’ve been sharing for decades: Do the most important thing first. Not the easiest. Not the most urgent. The hardest. If you know you must make a difficult phone call with an unhappy client, the natural tendency is to put it off until the end of the day or end of the week. You tell yourself you’re getting ready or researching for it, when you know deep down, you’re delaying the potential unpleasantness. The truth is, delaying leads to negative mental energy and stress. It just doesn’t make it easier, nor does it remove emotional pressure by doing the lighter things first. Get the hardest tasks out of the way first. PERIOD. Then enjoy the rest of your day accomplishing the easier stuff.
One of the people I’ve enjoyed learning from over my career is Earl Nightingale, who famously told a story about Ivy Lee’s “$25,000 idea” (sometimes quoted as $50,000) in his talks. It’s a legendary story in the world of productivity and business consulting. It goes like this:
In the early 1900s, Charles M. Schwab, president of Bethlehem Steel (one of the largest steel companies in the U.S. at the time), met with Ivy Lee, a productivity consultant and pioneer of public relations. Ivy Lee told Mr. Schwab that he could dramatically increase his company’s efficiency with a simple method — and he would share it for free. But, he added:
“Try it for a few weeks, and if it works, send me a check for what you think it was worth.”
Mr. Schwab agreed. A few weeks later, he was so impressed with the results that he sent Ivy Lee a check for $25,000 — the equivalent of more than $500,000 today, depending on the estimate — and the idea has since been called the $25,000 or $50,000 idea, depending on the source. The method Mr. Lee gave to Mr. Schwab was simple. If you’ve followed my teachings at all, you know that I propose simple is not always easy.
Here’s what’s involved:
At the end of each workday, write down the six most important tasks to accomplish the next day.
Prioritize them in order of true importance.
The next day, start with the first task. Work on it until it is finished before moving on.
Approach the rest of your list the same way.
At the end of the day, move unfinished items to a new list of six for the next day.
Repeat daily.
While simple does not always mean easy, what’s simple is often powerful. What’s practiced becomes priceless. Although this thinking has been around for some time, it works. One might say, because it’s been around for so long, we know it works! Why?
It focuses your mind on what matters most.
It reduces decision fatigue – you already know where to begin.
It builds momentum by creating daily wins.
It multiplies results through sustained, focused action.
This idea earned Ivy Lee a $25,000 check in 1918 — because it helped a great company become greater. In truth, its real value is revealed not in dollars, but in what it produces: clarity, momentum, and mastery. This isn’t just about productivity—it’s about leadership. It’s about discipline. And it’s about understanding that ‘discipline is not a dirty word’ - another thing I’ve taught for years.
Today, with so many issues and difficulties colliding transparently around us, we can easily confuse what we have to do with what is happening ‘over there’ or ‘right here’. Defining the scope of our attention to the matters we are charged with, and then approaching them in order of difficulty, can both help us toward completion and help us to separate the ‘noise’ from the real deal.
Why We Avoid the Hard Things
Most people get pre-programmed to think that by disciplining themselves to do difficult work, they must necessarily be giving up something more enjoyable or something better expediently achieved. They focus on the easier, preferred thing—the fun activity they’re missing out on, rather than the positive results they’ll achieve if they do the work.
This is backward thinking. Instead of dreading that difficult conversation or challenging project, focus on the outcome. By tackling the most important - albeit hardest thing first, you’re making an investment in your life. You’re getting closer to your ultimate desired outcomes. You’ll have a sense of satisfaction and accomplishment as you work toward your goal, as well!
When we postpone difficult tasks, they don’t disappear—they compound. That difficult phone call becomes a source of anxiety every time you think about it. The challenging project proposal creates mental clutter that impacts your focus on other work. The hard conversation with an employee becomes a weight you carry into every interaction with your team. Procrastination removes the luster of anything done in place of the thing that should be done.
Research in psychology confirms what many of us know intuitively: unfinished business creates what’s called the “Zeigarnik effect”—our brains keep interrupted or incomplete tasks more accessible in our memory than completed ones. When we avoid hard things, we’re literally keeping them at the front of our minds, creating unnecessary stress.
The Business Impact
In business, this principle creates a ripple effect. When you tackle the most challenging client issue first thing in the morning, you approach the rest of your day from a position of strength. When you have that difficult performance conversation with an employee early in the week, you both have time to process and move forward productively.
Too many leaders procrastinate on hard decisions—delaying layoffs, avoiding difficult strategic pivots, postponing uncomfortable conversations with investors. Every day they wait, the situation gets worse, not better. The hardest thing doesn’t become easier by waiting; it becomes harder.
Here’s how to implement this in your daily leadership:
Morning Priorities: Before you check email, before you grab coffee, identify the one thing you’re dreading most about your day. Do that first.
Weekly Planning: On Sunday evening or Monday morning, identify the most challenging task of the week. Schedule it for early in the week when your energy is highest.
Difficult Conversations: Stop scheduling them for Friday afternoons or end-of-day slots. Have them Tuesday morning. Give everyone time to process and move forward.
Strategic Decisions: The big, scary decisions that could change your business trajectory? Don’t wait for the “right moment.” The right moment is now.
The Freedom in Discipline
My nearly five decades of business has revealed this truth: Doing the hardest thing first is actually liberating. It’s not about sacrifice—it’s about freedom. Freedom from the mental burden of avoidance. Freedom from the anxiety of procrastination. Freedom to enjoy the rest of your day knowing you’ve already conquered your biggest challenge.
Self-discipline isn’t something to be feared or struggled with. You get to see who you really are and how much you really want something by how disciplined you’re prepared to be. As leaders, we’re being watched. Our teams see how we handle difficult situations. When we model the behavior of tackling hard things head-on, we give our people permission to do the same. We create a culture where challenges are met with action, not avoidance.
The most successful people—whether they’re running billion-dollar companies or just starting their first business—have learned this fundamental truth: The things you’re avoiding are often the very things that will move you forward the fastest. So tomorrow morning, before you do anything else, ask yourself: What’s the hardest thing you need to do today? Then do that first. Your future self will thank you for it.
Discipline has been a guiding principle in my life, and the ability to decide to do things deliberately that will assure reaching a determined outcome has been a key strength. It can be yours too. You often regret the hard work you didn’t do. You never regret the hard work you did.