There’s a lot of talk about the idea of “hell yes or hell no,” which I think originally came from Mark Manson. When it was first explained to me by one of my mentors, Rich Litvin, he said “there’s no such thing as hell maybe Kendra, that’s just hell,” and I remember laughing out loud because ain’t that the truth! But there is an extra piece I want to add to this.

Hell Maybe & Hell No For Now

Some parts of this practice I really love—taking a piece of paper, drawing a line down the middle, and adding everything in your life to the Hell Yes or Hell No column. You can free up an enormous amount of energy by simply being honest about what is a no….for now. I’m the kind of person who always has a billion ideas and projects that I can get excited and distracted by, and it’s a great practice for me to ask, ‘is this a hell yes, right now?’

It’s less about do I really love this idea and more about looking at the ecosystem of my life as a whole. I could be super excited about something, then look at what it’s really going to take and ask, does this support how I want to feel right now? Does this support me being with my children and family in the way I want to? It might be a great idea……but not right now. There is so much freedom in telling the truth, and auditing and clearing out the mental/emotional space in our lives.

And there’s another layer I personally use on a regular basis in my life: I have found so much value, and also creativity, in asking ‘what would make this a hell yes?’

About four years ago a colleague of mine who I admire deeply reached out to me with an offer that I wasn’t a hell yes to, but I also didn’t feel a full no to. I had a very visceral response to the proposal, and while everything looked good on paper, I knew myself well enough to know that if my body wasn’t behind it, I would come to regret my decision. Every time I imagined saying yes to the offering, I felt heavy, resentful and tired, and every time I imagined saying no, I felt so much grief and loss. I was deeply conflicted.

As I sat with this dilemma, I realized that instead of assuming it was a no simply because it wasn’t a yes, that I could get creative and see if I could make it a hell yes. So I sat down and free-wrote a full page answering the question: What would make this a Hell Yes for me?. I discovered that I wasn’t confused or conflicted; I actually already knew so much about what I wanted in this dynamic!

Sharing what I wanted and what I had to offer felt scary, vulnerable and exhilarating. I sent an email saying, “Thank you, this is an amazing offer! Here’s what I love about it and here are all the other ways I know I can serve you in this role.” I got a call back 3 hours later and a voicemail that said, “Kendra your email stopped me in my tracks, we need to talk.” When we spoke I laid out everything I had written in more detail, in such a way that he was the one who brought up paying me for this role, which was something I knew I needed in order for this to be a Hell Yes for me, but that I probably wouldn’t have gotten if I had lead with the money conversation.

The only reason the conversation even happened was that I didn’t stop at Hell Yes or Hell No – I went further and asked myself ‘what would make it a hell yes?’. Not, what do I want that I think they will say yes to? Or what can I ask for, within reason? But what would make this a hell yes for me? What would make my heart leap? What would make my body sing?

Because I’d already sat with what I most deeply wanted when we spoke he saw that what I was offering was not a volunteer position, but a paid role. And because I’d already thought about it, I knew what my number was. Then we had a very open negotiation about money and numbers, came to an agreement and it allowed me to step into the role with joy and excitement. That collaboration has changed my life, but I don’t think it would have if I had tried to choose between my initial hell yes or hell no.

The value of Hell Yes or Hell No is not wasting energy in the Maybe Zone. But the power of asking ‘What would make this a Hell Yes?’ is in giving ourselves permission to create outside of whatever we believe is being offered.

Take some time with an area of your life that you’ve been struggling to make a decision in and rather than assuming there’s only this or that, yes or no, in or out – ask yourself: What would make this a Hell yes for me? And share with me what happens!

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