There can be no more waiting

notes on turning our "somedays" into "todays"

For almost 15 years I didn’t take any real time off from work. 

I would travel, but I’d still be handling emails and other administrative tasks almost every day. I’d go on long-distance hikes, but in each and every trail town I’d have to find the library and use their computer to manage my Patreon community, periodically release new podcast episodes, and make sure that things were running smoothly in my quasi-absence. There were a couple long weekends over the years when I’d go somewhere without my laptop, and yet even then I’d still always be checking on things from my phone. 

In her book Do Nothing, Celeste Headlee calls this “polluted time,” where there is never full delineation between working and not working, and it took me 15 years—right up until last summer—to reach my complete and total breaking point with just how polluted my time had become.

And so in July of 2020 I started a two-month sabbatical. 

For 62 straight days, I did not work. 

I didn’t write, didn’t record new podcast episodes, didn’t facilitate any live groups or gatherings. I lightly checked my email once or twice per week, but I responded to very few messages, and I mostly stayed off social media. I rested, hiked, and read lots of books in my hammock. I was living frugally in my van at the time, not earning income and instead relying on savings, and trying to make the best out of the fact that pretty much everything one needs access to while living in such a tiny van (wifi at the library, showering at the gym, etc) was closed due to the pandemic. 

I showered just once a week at a friend’s house, parking my van in the woods and mountains on the days in between, and each morning I’d wake up and experience the wild feeling that there was absolutely nothing I had to do that day. One of the benefits of having been very public about taking two months off work was that no one expected anything from me. No one was waiting on me to email them back or to do, well, anything at all. 

So for the first time in 15 years I could just… be.


In the weeks leading up to my sabbatical I was privately struggling with a fear that I felt like I couldn’t share with anyone else: the fear that my time as a self-employed creative had some to an end, that I had nothing else to do or make or give, and that I’d somehow have to start over again on a whole new path of employment.

I was just so tired. Tired of feeling like I was constantly “on”, tired of the pressure to turn my life into “content”, tired of the financial fears I’d had in the prior year and a half since my divorce. More than anything though, I was tired of what I saw as my own failure to balance work and rest, and it took me almost half of my sabbatical to finally realize that what I was really exhausted by was hustle culture itself. 

But all I knew on that last day of June, the day before my sabbatical, was that I was weary and worn down, and when I logged out of my work email, my Patreon account, my email newsletter list, and the backend of my website there was a small part of me that wondered if I’d ever log back in. 

How could I keep doing this work if it had left me feeling so depleted? 

This is not a problem that you need to solve today, I wrote in my journal on that first morning off. You are allowed to put this mental load down for a while.

And so I did—I deleted every single work-related app and endeavored to make my phone as boring as possible. For weeks I’d find myself reaching for it, my chest tight with a sudden sense of panic about what might be happening in my inbox or elsewhere, the fear that by taking time off I was becoming irrelevant and would never be able to find my way back to my work if I decided that I did indeed want to keep doing it, but as time went by I got better and better at putting the phone down and gently talking myself through those frenzied episodes. 

In short, things changed—or rather, I changed—and by August I realized that my thoughts of work had become optimistic instead of dejected. And from there a new truth emerged: I did not want to quit my business, not at all actually, but I needed to run it in a completely different way.


What would have to be true in order for this to feel awesome for you?

That is one of my favorite journaling prompts, as well as a conversational launch pad that serves me well whenever a loved one and I seem to want opposing things and are trying to feel our way into some kind of loving compromise.

What would have to be true in order for going back to your business to feel awesome for you?

I wrote that at the top of a blank piece of paper in mid-August, and for the next few days I kept returning to it, listing everything I really wanted, all the things that I felt needed to change, without censoring myself. It didn’t matter if one of my desires seemed unrealistic—this wasn’t the “how” part of the planning process—and allowing myself to admit what I truly wanted in an unfiltered way was a gift that I was no longer willing to withhold from myself. 

When the list was done I closed my journal and went back to my life, letting the ideas settle and marinate, trusting my subconscious to process what needed to be processed for a while. And then a few weeks later, right toward the end of August when I was gearing up to go back to work, I pulled out the list and read over my own words, letting myself be filled up by the descriptions of all the new boundaries I was craving, the shape I wanted the business to take, the values-led changes I wanted to make to my funding model, and more. 

“If these things can’t be true,” I said to myself, “then I will be willing to walk away from this. But I will never know until I try.”

And so I got started, mapping out a new Sunday - Thursday work schedule that would allow me to both host workshops and gatherings on Sundays (for folks who work more traditional hours) and to have two full days off each week, on Friday and Saturday—something I had never explicitly had during my many years of polluted time. To create a visual representation of this boundary I took out my planner and drew a black dashed line around each Friday and Saturday of the coming two months, and I promised myself that I would not schedule a single call on either of those days, especially Fridays, because I knew how prone I was to pressure myself to be available during times when the majority of other folks are working. I checked the original list in my journal again, and saw the notes of changes I wanted to make to my social media use. Most importantly was the fact that as soon as I started using Instagram regularly again I would commit to social-media-free Saturdays. One day completely off social media each week and two days off from work—it was a start, and over the next few weeks the other pieces and boundaries fell into place.

Except no, that’s not true. The pieces didn’t fall into place as if by magic, I had to be the one to put them there. The change in my funding model, a new home for my writing (this newsletter!), a clearer understanding of what I would and wouldn’t talk about publicly, shorter podcast episodes, new types of live gatherings—those changes didn’t just happen, I am the one who worked to make them happen. I committed to my vision, which required saying (first to myself and then to others): “This is what I am and am not willing to offer. These are my boundaries, and it is important that they are respected.” 


For almost the entire time that I’ve been self-employed I told myself that I would rest… later. 

Once my income hit a certain point, then I could rest. Once my podcast or my Instagram or my writing reached a certain number of people, then I could rest. But constantly putting off your wants and needs for some murky time in the future is a dangerous trap. There will always be a benchmark of success that’s just out of reach, and if we make our rest, nourishment, pleasure, and peace conditional upon it, we will forever be left empty and exhausted. 

Without realizing it, my entire life had become a series of “somedays”. I would rest… someday. I would have boundaries… someday. I would prioritize myself… someday.

But at a certain point, if we truly want things to change, our somedays need to become todays


Is this an odd thing to be writing about on Valentine’s Day? Maybe. 

But maybe not, because what if the most romantic thing we can do is allow ourselves to meet even our most inconvenient needs?

Rest is how I romance myself. Boundaries, self-respect, guilt-free time for the activities and relationships that leave me feeling seen and delighted, god are those things sexy.

Because the truth, as blunt as it might sound, is that we have no idea how many more days we will each get to spend on this earth. It is a complete unknown. And so there cannot be any more waiting—we are allowed to prioritize ourselves right now. 

And to me that feels like the most romantic thing of all.

This newsletter (and the Real Talk Radio podcast!) are freely available thanks to the 400+ people in my Patreon community. If you’d like to join us, which gives you access to my popular end-of-month journaling & reflection circles (and so much more!) click here to see our sliding scale pricing. I would love to have you come and check us out for the next few months!