A typical scenario: you are having an internal monologue, a somewhat self-depreciating talk, which includes the word “should”.

“I should go to that [insert social activity] tonight.”

“I should get my paperwork together for my taxes.”

“I should put myself out as a speaker for [insert big conference].”

Sounds familiar, isn’t it? To me, “should”s are a sign. They say to me that I actually don’t want to do that thing. And they come in 3 kinds:

The first is things other people want me to do.  For people-pleasers like me, it can be terrifying to disappoint others. A big part of untangling that miasma is knowing what you actually do and don’t want. Literally ask yourself “Do I want to do this?” and realize you have a choice.

But wait, what about all of the life’s little necessary annoyances? These are the second kind of shoulds – things you wish you wanted to do. In a moment of angst, I ask myself if that activity ties back to some broader arc of who I am and where I want to go. That arc for “I should do the paperwork for my taxes” is I am a CEO that has a stable financial base. Getting my paperwork done is evidence that it’s true. Thinking of it that way ninja mind tricks you and makes the task more tolerable.

If I’m unable convince myself that I do want to do it as part of the bigger arc, I admit that I’m not going to do it and move on.

The last kind of “should”s is things that you want to do but they scare the shit out of you. This is where the opportunities to push yourself lie. This kind of should, however, obscures the goal of the task. Focusing on the outcome you’re seeking reveals other paths that are more appealing. So ok, speaking at a conference gives you a panic attack. Can you gain professional influence in another way? Perhaps reaching out to a podcast host and seeing if they want to interview you gets you to the same place with less anxiety.

On your journey from someone who is doing everything (the jack-of-all-trades entrepreneur working out of her garage) to a leader, one of the most important things you need to learn, is to delegate.

For many this is hard – in two ways:

First, the notion that you give up control over how things are done (and later, as your organization grows, which things are done) is a tough nut to swallow. You get increasingly removed from the day-to-day of your business. You need to trust people that they do their job well. You need to be okay that people do things differently than you.

Secondly, the act of delegating (well) is something which needs thought and skill. One of Steve Jobs’ lieutenants said about Steve:

“Steve was the best delegator I ever met. He was so clear about what he wanted that it gave you great freedom.”

This single sentence sums up what great delegation is all about: becoming incredibly clear about the goals, the ability to clearly communicate and creating the space for the team to execute.

You cannot do everything yourself — you need to learn the art of delegation. And becoming not just good but great at delegation holds the key to successfully scaling your business.

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