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 easier for me to write these essays in the evening than during an already compressed day.

Each time I write about something that’s easier for me, at a time that’s easier for me, my inner critic starts taunting me. It’s adamant that my writing would be better, I’d be improving my craft more, I’d get more followers and likes, or whatever else would poke into the insecurities I have for the day.

But I didn’t choose to do this project because I wanted shipping to be hard. I chose it so I could play with how it could be easy.

Well, did you get into whatever you’re struggling with because you wanted it to be hard?

This post is part of a series of “atomic essays” published on Twitter. The previous post from this series is about unleashing your potential in a new job.



Charlie Gilkey

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