John D. Rockefeller founded the Standard Oil Company in 1870 and is widely considered one of the most successful and wealthiest individuals capitalism has ever produced. At its peak, Standard Oil controlled nearly 90% of the U.S. oil refining industry, seemingly single-handedly leading to the creation and enforcement of antitrust laws in the United States.

There’s a story about Rockefeller in which his workers would observe him at work or, from their perspective, not at work. From what they could tell, the dude never did anything. He sat there alone, quiet, never loading the trains, drilling the wells, or lugging the barrels around. It was beyond them how a man like this got wealthy.

But this backbreaking work wasn’t Rockefeller’s job. His job was to make decisions and to do that, he needed quiet time alone. Just a man and his thoughts. Author Morgan Housel wrote, “Rockefeller’s product – his deliverable – wasn’t what he did with this hands or even his words. It was what he figured out inside his head. So that’s where he spent most of his time and energy.”

Although rare at the time, nearly 80% of us now spend our 40+ hours per week as decision-makers—managers, service providers, officials, and professionals (https://collabfund.com/blog/lazy-work-good-work/).

Like Rockefeller, as you move up the business hierarchy, your job will involve less and less doing.

You’ll focus on more cognitive tasks like decision-making, leading, setting the strategy and vision, understanding markets, and representing the company—things that can‘t easily be measured or tracked, like pulling a level or loading a train. 

A mentor of mine once told me that “not all roles are created equal…” and that “The role you fill determines the results that you receive.”

We can argue the merits of a CEO making 344 times more than the average employee, and, sidebar: if you ever attend a Coleman family event, we spend an odd amount of time debating this one. But I digress..

The fact of the matter is that our results at work now often do depend on our ability to focus on JD Rockefeller-like tasks, and these tasks require a lot of time and energy. And in order to do that, we need to be able to delegate some of the tasks we currently do on a day to day basis.

Why We Don’t (?), Won’t (?), Can’t (?) Delegate 

My brother-in-law is the founder and CEO of his own company (shoutout Cariloop). Last weekend, we were talking about a pretty big transformation he had as a leader. A few years back, he was considering stepping down from the role of Top Dawg. He started working with an executive coach who pointed out that he wasn't necessarily acting as a CEO. He was still working so much IN the business, which was exhausting, inefficient, and ultimately ineffective. There's a point of diminishing returns for a founder to "do all the things." 

So he started restructuring the business so that he could actually do the role of the CEO – focus on decision-making, strategy, team development, and leading – and get out from being in the business to working on the business.

The results were sobering. Not only did his energy and own performance improve, but so did the effectiveness of his team. An already good culture got better, and importantly, the business grew.

I highlight all of this because I do a lot of workshops with new managers, and over and over, they say their biggest challenge is delegating. They want to learn to delegate so that they can focus on these sorts of leadership tasks, but for some reason, they get stuck. 

At first, I thought it was strange that so many people struggled with this. From my vantage point, the shit wasn't that complicated. You simply: 

1. Decide on what needs to be done
2. Assign it to somebody 
3. Make sure they understand what it is that needs to be done..
4. Make sure they have the resources to do it
5. Follow-up 
6. Botta bing botta boom, we're out here delegating

But after working with and being exposed to hundreds of managers and leaders, I started to understand that there's something deeper going on. It's not really a matter of how to delegate.

That's right, we're bringing back, once again, a little splash of psychology here at Take Care. I've found that there are three forms of psychological resistance that keep people stuck. 

1. The Control Freak

This typically shows up for the founders and leaders in growth companies. They've had to do everything for so long to help the business grow, but now they're the reason growth is stuck. At some point, these people become the bottleneck.

They believe that everything can only be done by them; nobody else knows what they know or can do what they can do. They "can just do it real quick" or "will be faster if I do it" but disregard the penalty of "doing it" at all.

This is the dieter of the delegating world. Cutting calories in the short term but eventually burning out, regaining the weight, and watching the cycle continue. 

2. The Dependency Complex:Some managers secretly like being depended upon. It makes them feel valuable and important. They think, "If they do that, then what will I do?"

Of course, the answer is that they'll do what our boy JD does: spend that time and energy on strategy, leading, mentoring, training, making decisions, and the like. But it's part of their identity. 

This person can be the most stifled from growth because it's a hard truth to admit to yourself. In my experience with these types of managers, they become highly defensive if you suggest taking things off their plate. They start to catastrophize and spiral because it's hitting their ego HARD. They think: 

"I must not be that important.."

"I must be replaceable.."

"I'm not as special and indispensable as I thought.."

And that's a hard-hitting experience to sit with. But if they could just see it as an elevation of a role instead of a replacement, they'd be so much more effective. 

3. Most common and most difficult to break, the Everything is Important folks. I recently hosted a workshop, and I walked people through an exercise to see what tasks were urgent, which tasks were important, which were neither, and which were both.

Every single person put every single task in the Highly Urgent / Highly Important quadrant. In reality, if everything is urgent and important, then by definition, nothing is urgent and important. No task is elevated above the rest.

When people feel this way, it becomes nearly impossible to escape the rat race because the house is always on fire. You never feel like you have the time and energy to step back, reflect, and plan.

The great Stephen Covey wrote about this in The 7 Habits of Highly Effective People. His manager rushed into his office, telling him to drop everything. This new thing is the number one priority! Covey calmly stands up, walks over to the chalkboard, and says, "Alright, Bob, these are my top three priorities. Which one would you like me to cross off in order to add this new priority?"

Bob looks at the board, looks at Covey, and says, "Never mind. You focus on those tasks."

This final group needs to have the courage to lead upwards. They need discernment to select what needs to be focused on and what doesn't. And they need the acceptance to go home at night, have a nice glass of red, and not answer emails all night long (and to live with the consequences). 

The irony here is that those who operate this way often aren't penalized the way we think. They're not fired, demoted, or paraded through the streets in their skivvies with an angry crowd throwing plums at them. They're actually respected, catered to, and get reputations as high performers.

The 3 Delegating Principles (Google a Process)

So, if we can agree that this isn't an issue of process but of principle, what can we do? In reality, delegating isn't an issue of know-how but the byproduct of a shift in our psychology. You can google a process for delegating, but if you really want to start acting like our guy JD, then here are three tools to try:

Tool #1: Embrace The Inherently Limiting Nature of Life 

There's a great book called Four Thousand Weeks by Oliver Burkeman. In it, Burkeman talks about the cultural ethos of capitalism that you can and should do it all. If you're not, it's because you're flawed or not properly managing your time.

But life and work have limits to them.

So, the first step to being effective at work and, frankly, being happy in life is to face the fact that we can't do it all. Burkeman writes beautifully, "It's the only way for a finite human being to live fully, to relate to other people as full-fledged humans, and to experience the world as it truly is. What's really morbid, from this perspective, is what most of us do, most of the time, instead of confronting our finitude, which is to indulge in avoidance and denial. Rather than taking ownership of our lives, we seek out distractions, or lose ourselves in busyness and the daily grind, so as to try to forget our real predicament."

Deciding what NOT to do is often more important than deciding what to do. Your task is to organize your days with the understanding that you won't have time for everything you want to do and for damn sure what others want to put on your to-do list. And practice being at peace with that.

Decide with some intention what you won't do. That means most tasks must either be deleted or delegated. Learn to say no. Learn to be Covey at the chalkboard. Learn to sit in a room quietly while everyone else is running around loading the trains and drilling the wells.

Tool #2: Confident Detachment 

In every workshop, I put people through an exercise designed to get them to articulate their values and who they want to be as a human being. What do they want their legacy to be? What character traits do they want to be associated with? What achievements do they want to be remembered for?

And never do I hear things like:

"Danny took on the largest load at work."

"Nobody completed tasks like Danny."

"Danny could wear many hats in the business."

"Danny made so much money."

They also don't articulate that they want to be stressed, urgent, productive, or responsive.

No, it's deeper, more aspirational traits like courage, altruism, vitality, presence, honesty, etc. By the end of the workshop, I want them to have a clear picture of who they are at their best, and their homework is to start practicing those things. These things need to be exercised like getting a nice pump in the gym.

Confident Detachment is the concept I leave them with. I want them to confidently act out those traits, and then detachfrom the outcome. For example, if courage or honesty is your word, then tell your boss you can't take on anything else at the moment and see what happens.

If you want to lead and inspire others, give them a chance to do the work and detach, whether it's precisely how you would do it or not.

Tool #3: Patience 

And finally, have patience with yourself. Have patience with your team. This may seem like a silly tool, but hang with me. If delegating isn't a process issue, then it's not a quick fix. 

That means it'll take time. It'll take small, incremental changes. And hardest of all, it will feel like the wrong approach. It's going to "feel wrong" because 1) Patience is "passive," and we hate passive virtues in the West. Most of us can't stand waiting in line at the grocery store, yet we're rolling out a new way of doing things that can take months or years to catch on. And 2) everybody else will be in a hurry. Nobody else will be giving things time to develop. You'll naturally feel out of place like you're getting left behind or doing something wrong.

You're not.

Look, you may think these things are nonsense. You can certainly continue to bang your head against the wall, filling out surveys for leadership training like mine, saying you "need help delegating."

Or you can make the choice to stop running on the hamster wheel and instead, as the great Daenerys Targaryen once said, "Break the wheel."

Make tough decisions about what you won't do.

Embrace the fact that everything won't get done. And certainly won't get done by you.

Trust others to do good work on tasks you need help with.

And over time, you'll find yourself sitting in a room, thinking, spending your days making decisions, leading your people, and have some extra energy to do things that make life worth living.

Just like JD. 

(Perhaps, minus the whole monopoly thing)