So this happened a couple of weeks ago:
It was pretty upsetting, not gonna lie. In an attempt to get to what really happened, I wrote the below as a form of self-inquiry.
So you had some kind of meltdown. Can you tell us what happened?
It’s hard to say. I think the main thing is that I had too much time on my hands.
Isn’t that a good thing?
In theory, yes. In practice, no. My main client has been out of the office a lot lately and that is often triggering for me.
Why would your client being out of town be triggering for you?
I have a bunch of clients that I work with off and on, but I have one that provides most of my income. So it’s a pretty important client, and it’s important to me to do a good job for them. However it’s not like a full time job in that I’m not in touch with them alllll the time, so during times like last week, when my main contact is gone for a while, it can be difficult for me to stay focused and on track. And when I don’t feel like I’m focused and on track, that puts me on a shaky foundation. And when my foundation is shaky, that’s when things start to unravel.
But don’t you have stuff that you do in your life other than work? Like don’t you have a stable foundation?
I do! I have a supportive network of friends and family that I am in touch with all the time. I have a dog to take care of. I have a steady meditation practice, and I make sure to get some form of exercise every single day. There are many routines and supportive structures built into my life that keep me going, one of which is writing this newsletter.
So then what was it about last week that sent you over the edge?
Time. Just too much time. When my client was gone it meant that a lot of projects weren’t moving forward. I had other stuff I could work on, I always do, but without deadlines, it’s just too easy to not do anything.
But aren’t you a professional? Isn’t this what you do?
Do you think this behavior is tied to money and hustle culture?
Oh absolutely. There is some part of me that is intractable when it comes to money. Like I don’t need to be productive all the time, but being a self-employed person, I find that if I don’t earn some money every weekday, I start to get into trouble, mentally.
Have you done any work to address this?
What, you mean like reframing my beliefs around productivity and self-worth? I have.
So you haven’t worked through all of this?
Not to sound like a total cynic, but do we ever really fully work through anything? Plus, how am I gonna get around the fact that a good life (at least the way that I’ve defined it) ain’t cheap? To quote a wise man, “This is America.”
Moving on, what specifically about all that time did you in?
Well, I think it comes back to a few things, but one of life’s most unfortunate realities is that the more time you think you have, the more you tend to squander it. Here’s what usually happens when I have too much time on my hands:
I make all kinds of grandiose plans for what I’m going to do with all the free time; stuff like finishing abandoned (and grandiose) projects or starting ambitious (and grandiose) new ones
I spend a lot of time daydreaming about said projects and don’t follow through
I also don’t make progress on the projects I already have in progress
Without any deadlines or accountability I end up getting nothing done
I become aware that this is the case and begin feeling like I’m squandering the day
I become angry at myself
My brain enters a long slow spiral into alternating thoughts of shame and recrimination
The tension ratchets up
I can’t get anything done
The tension ratchets up some more
I can’t get anything done
The tension makes the weather in my mind unbearably stormy and I eventually have to shut down the computer if not my whole ass brain
I have gotten nothing done
I resent myself for being like this and resolve to start again tomorrow
Repeat until I manage to break the cycle, which can take days
Oh no. I’m sorry.
Thanks. I should know better by now.
Well I think you do know better by now, from what it sounds like.
I do. But there’s knowing what to do and there’s actually doing it and those are two separate things.
Why is it so hard to do the right thing?
Humans are strange animals. But also I think we’re way more social than we are consciously aware of. One of the hardest parts of being a self-employed person is self-management. It’s hard to stay focused all the time when there’s no one holding you accountable but yourself. There have been lots of studies that show that we are more likely to follow through with something when we have a supportive structure in place to help us get there.
Can you give us an example of how you’ve found this to be true in your life?
Sure. I discovered a few years ago that my meditation practice was an incredibly positive force in my life. It helped me with so many things, but most critically, it helped me detach from a lot of my own shit and see the bigger (and truer) picture that there is way more going on than what is visible to the everyday eye.
Anyway, I knew that meditating was good for me but I also knew that, left to my own devices, I would not do it consistently. So I joined a group of meditators who met regularly, and that helped me stay engaged. I have found that it’s easier to do things when it’s not just about me.
Do you think everyone is like this?
To some degree, yes. I think a lot of people who are entrepreneurs or artists or whatever have a strong vision that leads them to start new projects/companies/etc., but staying engaged is the hardest part, especially in the early days, where you don’t have a ton of momentum, and when it might just be you who is the engine behind it. People need people. We’re wired for connection.
Do you believe that you can be successful as a self-employed person?
I do. I mean, I am. For the better part of the last 10 years, I have proven to myself that I can support myself without having a full time job.
Great! That’s great, isn’t it?
It is! I am proud of myself.
I’m sensing a “but” here.
But it’s hard. I think if you want to do this long term, you have to have a lot of support and mental health practices in place to stay motivated.
Do you ever think you should get another full time job so that other people/an external structure will serve that function?
I think it all the goddamn time.
So why don’t you?
I might. But I have a hard time working on things I don’t care about, so if I am going to get a full time job, it will have to be with a company that is doing something I think is meaningful, and with other people who share that desire.
Do you think having meaningful work is necessary for a good life?
I do, yes. But I think meaningful work can look like a lot of different things. Yes, it could mean saving the whales or the babies or whatever your cause of choice is. But it could also mean being really good at something that is satisfying to you, and seeing that those efforts are valued.
Ah, so this is all a conversation about meaning and purpose.
I think so.
Are you putting a lot of pressure on yourself to view your work as meaningful?
Sometimes. But I have always had this desire. I figure if I’m spending a third of my life earning a living, it’s worth considering whether what I’m doing has value beyond generating a wage. I’ve done plenty of jobs just because they paid well (or because they paid at all), but that’s not a great way to live. As the writer Annie Dillard famously said, “the way we spend our days is the way we spend our lives,” and I agree.
So let’s bring this back to where we started. Are you OK?
Yes! I’m doing much better.
How did you break the cycle you described?
I gave myself a bit of a reset, which is why I haven’t been writing as often. And I made a real effort to be as nice to myself as I could while I recalibrated. Which was not easy.
What has your reset entailed?
A drastic paring down of everything I was doing to only what was necessary to keep my life going. Spending less time on my phone/laptop. Staring off into space more often. Excusing myself from projects that aren’t in line with what I’m doing here on earth.
What are you doing here on earth?
Wow, you’re really trying to press me on this meaning thing, aren’t you?
Is there a better question?
I’ve written about this before, but I do think my mission is to help people feel better. To help them see that a good life is about much more than a shiny, materially successful life. To help them be present for what is, essentially, a fucking miracle every day. Which is that we exist against all odds.
And how, exactly, are you doing that?
Well, this newsletter is a start. But maybe we can talk about that another time...
On to some things I found worth sharing this week.
“One of the more tragic errors of our time is our ready conflation of what is iconic with what is well branded. In an effort at bypassing the difficult work of becoming someone, many of today’s would-be writers, artists, and thinkers opt to present themselves as walking pitch decks, glomming onto a marketable persona and riding it as hard and far as they can. Our moment’s lack of nuance is frequently bemoaned, but what strikes me as the far greater omission is the lack of real mess and breadth: the modern individual’s resistance to any inconsistency that can’t be readily assimilated into her personal brand. The artist is rebranded a “creator”; the goal is to “make things” to “put out there.” It sometimes feels we have forgotten the value of remaining open—of receiving, rather than curating, experience.”
The opening words of this recent review of Rachel Kushner’s new essay collection by Jennifer Montalbo Schaffer may or may not have inspired this week’s issue. Shit is messy around here.
Everything is always changing!
It’s Not Just Me
“Everywhere you look, people are either hitting deadlines or avoiding them by reading about how other people hit deadlines. This may seem like a sly way of marrying procrastination with productivity (you’re biding your time learning how to better manage your time), but, no matter what, it’s an exhausting treadmill of guilt and ostentation, virtue signalling, and abject despair at falling behind.”
For a more thorough examination of the psychology of deadlines, Rachel Syme’s recent essay in the New Yorker is a great read.
“If you just see the good or pleasant part of an activity and avoid the pain, or avoid piercing cold or suffocating heat, then you are limiting yourself, not letting the force go from one end to the other.”
- Kobun Chino Otogawa in Embracing Mind
Speaking of Zen!
Tomorrow night at 7:30 PT I am giving an “Intro to Zen” talk at Angel City Zen Center, and everyone is welcome. The format is 30 minutes of meditation, and then an hour for the talk and discussion. If you’re here in LA, you can come sit with us in person, or you can join us from anywhere on Zoom. Details here.
Surely there’s a metaphor in here.
That’s all for me this week. Hope you’re out there enjoying the long summer days.
p.s. Thanks to Foster superstars Stephanie Ross, Rhishi Pethe, Dan Hunt, and Joel Christiansen for proving feedback on this week’s essay.
p.p.s. This happened on Friday. Would never have predicted my foray into the tattoo world would happen well into my fifth decade here but ¯\_(ツ)_/¯
p.p.p.s. Thanks for being here! Share this if you know someone who needs to stop torturing themselves about deadlines, productivity, etc.
I spent a long time building a company. I loved and hated it. It was hard and that’s part of what I loved about it. Then the company was acquired. That was exciting for the obvious reasons (financial stability, validation) but there was something I never expected: a moment came where it was clear I wasn’t needed anymore. All of a sudden my work wasn’t valued. No one said it, but it was clear that I could leave anytime and they would be ok with that. Nothing hurt more than that. I’ve since taken a new job and I tell people the number one thing that’s been so wonderful is feeling valued. People genuinely come to me for what I bring to the table and are thankful I’m here as a resource. I never in my life realized how important feeling valued at work is. I totally get where you’re coming from on that.
I love the questions. What a fearless, insightful interviewer.