For as long as I could remember, I prided myself on the ability to always have something to work on, to fill my time.
Waiting for an event to start? No worries I can cram in some writing at a coffee shop.
Some plans got cancelled? I can work on my blog or tweak my landing page.
The culture of productivity is deeply ingrained in me. I remember as a kid, a contractor once came by to give my mom a roof quote. Upon seeing my sisters and I quietly working on our homework, they exclaimed “Wow, so studious!” I felt proud, like we were representing our family. This is the way.
So yeah, I’ve been keeping this shit up for a long time.
To work less is antithetical to my nature.
But lately, something has come to a head.
I started feeling more burnt out at the end of the day. I’d work my full time job and then go straight to working on my creative endeavors. I’d end the day with eye strain, stress, a frazzled brain, and often asking: “Why did I do that to myself?”
To rub salt in the wound, I wasn’t making good progress on the side hustles I was spending so much time on.
Frustrated, I journaled about the ways I could improve my work output.
None of the ideas landed because they were all based on this:
Do more.
Then a haunting question entered my brain, one I’ve been resisting…
“What if I worked less?”
The rest follows the journey of my mind, negotiating with myself for more rest time – but also more time for my creative efforts. If you’re a full-time worker with a creative passion or side hustle, I think you can relate. Especially if you’ve been at it for a while and want to shake up your routine.
Trapped in a vicious cycle
For the longest time, I’ve wanted to be a morning person. That means waking up at 5 or 6AM so that I have a solid 3 hours of creative “me time” before my job starts. I’d be able to pull this off from time to time, but it largely eludes me.
Here’s the cycle I’ve put myself in:
- Finish day job
- Start working on creative side hustles. Poor boundaries with how long I work and the time I take leads to…
- Burn out by end of the night, and so I…
- Rebel by committing “revenge nighttime procrastination” – bingeing shows, eating late, doom scrolling. That the leads to…
- Waking up later than I want, and feeling guilty
- I spend the rest of the day feeling behind on everything, leading back to working too long into the night.
- Cycle repeats
This cycle puts me in a state of feeling behind, and the need to catch up. When your hobby is content, it’s always endless.
Redesigning my schedule
I looked at my weekly schedule to find opportunities.
1 idea stood out: pick 1 day during the week to fully rest after work. No writing, no screen time, just socializing and working out.
Wednesday felt like the best day because it was the middle of the week. It also happened to be when I most consistently play pickleball and work out. My energy is usually a depleted after all that exercise, so might as well rest!
Then I looked at the weekend. I knew that I don’t usually don’t work after Fridays anyway. At the end of the work week, I want to chill. It’s an automatic rest day I haven’t really recognized.
Alright…so that’s realistically 2 days of the week where I can commit to relaxing after work.
I wondered what it’d be like to not grind after work FOR THE ENTIRE WEEK.
I caught myself writing these words, and mid sentence I had to stop myself:
“Dream life: I don’t work on anything after 5pm. “
That’s my dream, people!
I didn’t know it was that serious of a problem until seeing my own writing.
Billions of people rest after work.
What the fuck is wrong with me?
(Now, I’ll acknowledge that I’m not yet married, with no kids, have a job offering good work-life balance, and I do love writing. The privilege and amount of free time kinda got me here.)
I started to rethink my strategy.
If I only rest after work, then I’m forced to do all my creative work during the day—and realistically, during the mornings before work. Is that doable?
With the goal of rest and decrease stress during the workweek, here’s my mental accounting:
- 10 hours a week felt good as a starting point. 2 hrs/day on weekdays felt doable.
- 20 hours a week didn’t feel good, because that’s a part time job.
- If I ever wanted to, flexing up to 15 hours (5 hours split across Saturday and Sunday) felt good.
*New schedule* I’ll contain my creative hours to 10-15 hours a week.
Now we’re getting somewhere…but the good feelings didn’t last long.
The more I thought about my 10 hours of creativity a week, the more anxious I got.
Before having even begun, I already started making excuses:
If I really needed to publish something next day, then I should make an exception.
I’ll surely fall behind my competition working so much less.
Will I really be able to accomplish my big goals with this amount time?
Death by a thousand productive cuts is how I got here.
How do I change my conditioning?
Negotiating with myself for rest
Something about staring at my nighttime spending jarred me.
My attention was so fixated on the “morning” track because that’s when I expected to work.
I never put rest first.
It was eye-opening to see that even when striving for rest, I was anchored to the idea of productivity.
Because I’ve spent a whole lifetime habituated to the feeling of being productive, I knew that my practice was in the opposite direction—concentrate on rest.
Instead of having 2 competing goals, I’ll focus on rest first.
#1 goal: Rest, destress
#2 goal: Honor my creativity; be intentional and less distracted
I I hit 10 hrs a week, great.
If not, it’s okay.
Because my main goal is to rest, to play, to not be stuck at the computer all day.
My practice is to do this for at least 1 month to allow a new habit to build. It feels freeing, just to give myself a mandate to rest, and the option to work 10-15 hours a week if I feel like it.
So…what’s next?
I’m still excited to work on this newsletter, Instagram content and money coaching offerings.
But to be honest, I’m not sure what this will look like on 10-15 hours a week.
I might be forced to be less distracted and more focused – there’s the possibility my work output can INCREASE.
Or, I might end up producing less.
The biggest unlock for me is that any of those possibilities are okay.
Because I’m learning how to rest.
Those who are pursuing the FIRE journey may also relate to this—don’t defer your life until hitting your magic financial number.
3 additional insights about rest
Other than redesigning my schedule, these 3 other reflections helped me emotionally lock in to this new habit of rest.
Insight 1: who’s the man I want to be?
One of my dear friends remarked of her ex: “I just remembered seeing his back so much, because he was always faced away working on his computer…”
Someday, my wife and kids might resent me for this very same thing. I don’t want to be that caricature of a man, chained to his desk, and his kids having a memory of his back facing them, pecking away at the computer.
The way in which I work – which affects my stress and mood in the present – may prevent me from meeting the love of my life. #OpportunityCost
Insight 2: Parkinson’s Law
Insight 2: Parkinson’s Law
I am so susceptible to Parkinson’s Law, which is the tendency to spend whatever time is allotted to finish a task.
Given 3 months? Take 3 months, perhaps procrastinating until the end. Due at the end of the week? It’s done by by the end of the week.
I can be more productive working less.
It’s not that I need to work more.
It’s not that I’m a super productive person.
It’s that I need to be more intentional and focused when I do work.
If I’m already not hitting my goals by being so distracted, that’s coming from the current system of how I’m doing things, including my current work even if it feels productive in the moment.
Insight 3: Actually enjoy rest
I want to have a better relationship to rest. Not treat it as a second-class citizen anymore. When I “rebel” against the productive narrative, I end up resting as a reaction—not treating it as a whole in of itself. It would be a lot nicer to just allow myself to rest when I can and fully enjoy it.
You mentioned FIRE?
In the Financial Independence; Retire Early community, the tide has recently turned to focus on living a good life, now.
It’s not just about grinding away and being miserable until hitting your magic financial number, as I wrote about in this FIRE article.
My mistake was thinking that “someday,” after I’m successful with my creative side hustles (e.g. covering my living expenses), then I’d be truly independent. Then I can choose my work and rest hours. But before then, pack it all in.
Ideas can be prisons.
Each of us holds the key to unlocking the stranglehold of limiting beliefs.
I can have my “dream life now” by working less, instead of deferring the idea of a “good life” to some fuzzy someday. Even if it’s something that feels so…ordinary as my daily and weekly schedule.
This is now my work; to work at rest.