In her book Better Than Before, Gretchen Rubin discusses 21 strategies for habit change including the strategy of pairing. In this strategy, you tie two tasks together in your mind, so that one starts to seem incomplete without doing the other. This strategy can work well when you’re seeking to form a new habit that isn’t fully established yet, because you’re pairing it with something you won’t forget to do, like brush your teeth or eat breakfast.

Today I realized that I have started using this strategy to make my daily writing into more of a habit. Before I committed to this experiment of writing daily, I might have had the intention to write or reflect but not the time set aside to do so. To borrow another Gretchen Rubin line, “something that can happen at any time often happens at no time.” It just wasn’t a habit, so I didn’t know when/where/how/why to create space for it.

Over the past week or so though, I’ve been pairing my daily writing with my morning routine. It’s becoming a loop where one task is tied to the next: first I record in my daily logbook (a la Austin Kleon), then I meditate, then I sit down at my computer and write my reflection. Because the tasks are paired (or getting there), I don’t have to think about it or decide when might be best or hem or haw. I just have to do the next step in the process.

I’ve tried to use this strategy before and it hasn’t worked as well, but now I wonder if it’s just because the pairing needs some tweaking. Can I use this to be more consistent about taking my vitamins? About calling my grandma? About going for runs more often? Time will tell, but for this particular habit it’s working like a charm.

Yesterday I had the last group session for the first round of my group program, The Foundery. This was my very first time ever running anything like this, and it was incredibly special that these three wonderful entrepreneurs took a chance on me in a brand-new program that spanned six months.

Leading up to yesterday, I’d had a lot of resistance and sadness about the program drawing to an end. The women taking part had also all expressed interested in continuing our work together in some way, shape, or form, so I’d put together some “alumni” packages for them to choose from. I felt myself not wanting to let it go, hoping that they’d want to continue because the dynamic we’d built together had been so wonderful. 

But a couple weeks ago I read Priya Parker’s wonderful book, The Art of Gathering, which changed my mind. In her chapter on ending a gathering, she references our very human tendency to avoid or prolong endings. We don’t want to face the end, so we “promise to sustain what is better to be surrendered”. But she argues that endings are important to any gathering, they’re what tie the experience together, close the loop, and leave people feeling as though they can integrate the gathering for themselves.

So I decided to really and truly end at the ending. I made personalized cards for each of them, I designed a little reflection activity with some help from my friend Or, and I baked cupcakes with sprinkles on top. At the end of our session, we went outside on the patio and enjoyed a toast and a moment to reflect together before parting ways.

I made it clear that it was an ending, but that that wasn’t a bad thing. I wasn’t afraid of the ending. Instead I tried to express in every way I could that beautiful quote from Winnie the Pooh: “How lucky I am to have something that makes saying goodbye so hard.”

Today is Tuesday, which means that I should technically be sharing a new podcast episode this morning. But I don’t have one to share today, because I didn’t record one this week. Without having consciously decided to, I have clearly decided that my podcast needs to be an every-other-week type of affair. That’s the rhythm that I’m being drawn towards, and the one that I’m naturally falling into as the weeks go by. It’s not the rhythm that I had planned for or “committed to” in my mind, but it’s what I have already been actually doing. Whenever I’m taking action without conscious choice, it’s usually a clear sign that my intuition knows something I don’t. 

The reason that I am okay with this pace changing is because I’m taking my own advice and letting my “Why” cast the deciding vote. Your “Why” is always the truest, deepest reason that you started doing something in the first place. It’s answering Seth Godin’s favourite questions: Who is it for? What is it for? and committing to the answers.

Nobody is buying anything on my podcast, but my Why is super clear: to explore new ideas for myself, to expand on conversations and concepts I’ve been encountering in my life, and less importantly, to share my thoughts with others.

Letting your Why decide means that when you’re faced with making a decision about how to move forward with any project or new idea, you make your core Why the most important factor. So even though I could tell you hundreds of reasons to keep my podcast to a weekly schedule – It will look more professional! People expect it! That’s what the big-time podcasters do! – in actuality the only reason that should carry any heft for me is my Why. As Simon Sinek says, “People don’t buy WHAT you do. They buy WHY you do it.” 

So in this case, changing my podcast schedule doesn’t have any negative impact on my Why. I’ll still be exploring and expanding on ideas and sharing them with others – and in fact, I’m doing much more of that through this new week-daily blogging. When I let my Why be in the driver’s seat, decisions are clearer and easier and less overwhelming. There are always going to be tons of reasons “to be or not to be”, to do or not to do something, but I find that when my Why is my guide, it never steers me wrong.