Do You Resist Projects That Are Easy?

Charlie Gilkey
2 min readNov 2, 2021

A lot of people struggle not because they can’t imagine how what they’re struggling with could be easy, but because they’re uncomfortable with it being easy.

So I ask: what’s wrong with something being easy? (Notice your own honest reaction to the question.)

Every day, I invite my clients and audience to embrace ease.

What if you could lead in a way that was natural and easy for you?

What if you could create your best work in a way that is easy for you?

What if growing your business could be fun and easy?

Different contexts, same point.

You might think they struggle with imagining how it can be easy or even the actions they’d need to take to get there. Most of the time, those aren’t the barriers.

The barrier is allowing their work and life to be easy.

Between cultural stories that place value on hard work and personal stories that they have to be better than everyone around them, the powerhouses I work with (many of whom are women) have deep existential tension with something being easy.

And yet, they’re exhausted and in perpetual negotiation with burnout, resentment, and overwhelm.

I wish I say that I don’t get it, but I do.

It’s come up for me for a handful of days during this Ship30for30 challenge. Some topics are easier for me to write about than others. It’s…



Charlie Gilkey

Author of Team Habits - - and the best-selling Start Finishing. Executive coach, investor, and philospher.