Everyday I have ideas for projects I want to pursue or articles I want to write for my blog.  Some of these ideas have stayed in the back of my mind for months, and I’ve either never gotten around to completing them, or (for most) even starting them.  Writing an article for my blog always seems like it will be a lot of work, work that doesn’t have a straightforward payoff, and work that nobody is expecting me to do except for myself.  My blog was updated sporadically at first.  I would go months without writing, which would lead to me feeling guilty about not writing, causing me to put more pressure on myself to write really good articles.  This pressure would build up to the point where I would eventually trash partially or fully completed articles because I felt they weren’t as good as I needed them to be.

The sporadic updates of my blog. A black square means I posted something on that day, grey means I didn't.

The sporadic updates of my blog. A black square means I posted something on that day, grey means I didn’t.

Things changed when Ryan and I started the Paleomodern Polymaths podcast, which I regularly release once a week.  My blog started gaining more consistent and reoccurring popularity, particularly around the episodes.  This made me more comfortable updating my website, and allowed me to put less pressure on myself to make perfect content.  I started writing more, trying more new and different things, improving, and began feeling a genuine sense of fulfillment and enjoyment around working on my blog.  Around the same time my blog took a dramatic, and unanticipated (but not unappreciated) jump in popularity.  I went from being lucky to break 100 page views in a month to breaking 1000 in December, which was partially due to one of my posts trending on stumbleUpon, something that was and is far outside of my control.  Diving deeper than just the numbers, I noticed the more I put out, the more often people would find, explore, and actually read or listen to the articles and podcasts on my website.  I went from one or two people asking about my blog every month, to regularly getting recognized in public by people with whom I hadn’t connected with in years (or sometimes ever), who had read, listened to, or enjoyed something on my website.

January came and went, and I wrote more than ever before, but still maintained a desire to produce more and to grow my web traffic.  Recently I’ve been very influenced by Sam Hyde of Million Dollar Extreme, and Ryan Holiday, both of whom are absolute masters of their craft, and are unexplainably prolific.  They put out so much incredible content every week, that it’s hard for me to even keep up with reading and watching it all (and I rarely do).  As an attempt to explain to myself how they do it, I came across the idea that really prolific and consistent artists often use deadlines to get accomplish more.  I’m a firm believer in Parkinson’s law, which, as explained by Tim Ferriss in The Four Hour Work Week, “dictates that a task will swell in (perceived) importance and complexity in relation to the time allotted for it’s completion.  It is the magic of the imminent deadline.”  The podcast came out every week because I gave myself a deadline to put it out every week, and its quality only got better as I got used to actually working on it, putting it out, getting feedback, and repeating, instead of being a perfectionist and mulling ideas and first drafts in my head for months, hoping it would lead to the right blog post.  From a combination of the ideas I mentioned above, I decided to make a solopreneur mini-course as an attempt to be a more prolific artist.  As silly and arbitrary as this might sound, I also set a stretch goal around the results of the experiment; 1000 page views in the month of February.  I wasn’t sure if it would be possible, but I gave it a shot following the one-pager I outline below.

Solopreneurship Mini-Course #4: Using Deadlines to Consistently Output More

Before the Month (or other time period you are planning on being prolific over) begins:

Get a calendar and mark off what you want to release on the corresponding days.  These are your deadlines.  It’s important to be specific about what you’re releasing (e.g. Episode 10 of Paleomodern Polymaths, a College Article), so that you are clear about what you want to output, without being overly specific (e.g. A podcast episode where I ask Raymond about overcoming his fear to ask Andrea out, an article titled ‘What To Do When You’re in Class’), so that your constraints aren’t too narrow and you are free to be creative within a limited space.  This also allows you to complete tasks even when factors that are outside of your control are present (Ryan deleting his podcast audio, forgetting the most impactful scenes of Knight of Cups, etc…).

An additional tip is to have deadlines for similar objectives occur regularly, like releasing a podcast every Thursday, a college article every other Monday, etc…

Setting up the deadlines

Setting up the deadlines

At the Start of the Month:

Put the calendar on your wall, where you, and others will be able to clearly see it.

During the Month:

Cross off tasks when they have been completed, and again when they have been delivered (in my case posted to my blog or sent to my e-mail list).  Also cross the days off as they pass.  Use different colors or shapes to cross off the different days, so you can clearly keep track of your progress.

Using the calendar, notice I'm getting ahead on a few projects because I see the whole month, instead of just the next blog post

Using the calendar, notice I’m getting ahead on a few projects because I see the whole month, instead of just the next blog post

The Day you Have a Deadline:

For simplicity, it’s important to ensure that every day’s deadline occurs at same time.  My deadlines are 5pm of the day I have marked on the calendar, because refusing to work after 5pm made me feel more free when I was in college.  Staying up late to work is stupid.  The whole point of deadlines is to use them as a tool, not a prison.  The deadlines are rigid, when you hit the deadline you need to deliver your work no matter what state it is in.  Imagine you are in a college course that often gives partial credit, but does not accept late work.  You need to turn something in, and understand that after the deadline passes, it is in it’s final state and out of your hands.  If the deadline has no stakes and is not rigid, it isn’t real, you won’t follow it, and this course will not work.  You need to have skin in the game.

The end result, finished early

The end result, I finished early

Now, I’ll review the mini-course.  I followed the one-pager above for the month of February, where I planned on releasing 2.25 blog posts a week for the entire month including: four podcast episodes, two solopreneur mini-course articles, two college articles, and one personal article.  Up until this point, I’d never released more than 6 posts a month, and I’d averaged 1.75 posts a month since starting the blog, so this was certainly an ambitious goal.  Following the calendar, I did exactly what I set out to.  I never missed a single deadline and I never put out any incomplete pieces of work.  In the first week I cut it close a few times (I posted a few final drafts at 4pm), but pretty quickly I started to get on top of my game, and I wanted to finish articles early to avoid the stress of an impending deadline, so I decided to finish a podcast episode a day or two early, and schedule it to be automatically posted at the deadline.  There was something incredibly satisfying about crossing the tasks off my calendar.  I could see myself progressing, and would receive a small rush of dopamine and publicly visible satisfaction for my work (this is why the calendar is posted where others might see it).  It was even more satisfying to cross items off much earlier than the anticipated deadline.  If I finished something an hour early I would be relieved it got out, a day early I would feel responsible and free, a week early and I would feel like an efficient content producing machine.  When I pushed things out ahead of schedule I would feel not only as though the blog was my job, but that I was killing it at my job.  I felt like a high performer again, a feeling that drove me to achieve much of what I achieved in college.

After front-loading a project I started to experience a runaway positive feedback loop; finishing a task early would give me more time to finish the next task, which would then make me feel good about my work, causing me to want to do more work, and finish the next task even further ahead of schedule.  At one point I looked at my calendar and saw that I only had a few tasks left, which motivated me to finish the work for the entire month early, so I could have everything on my calendar crossed off and I could close the book on the month of February.  Viewing productivity as simply completing the tasks one sets out to complete in the time they want to complete it, this course was extremely successful at making me productive, more so than anything else I’ve ever tried for the blog (so far).

What about my biggest fears?  If I write too much won’t I run out of my reservoir of writing ability and energy (or maybe even things to say), and as a result will the quality of my work fall?  Going into the experiment I was concerned that I would put out some lower quality pieces of work simply because I was producing more work.  I thought maybe I’ll release something I’m not proud of and that will motivate me to work harder so that it doesn’t happen again in the future, which would be a built-in motivation mechanism for the deadline system.  This is a good time to explain that February was probably the busiest month of my post-college life, outside of the website.  I traveled to Dallas and Palo Alto for the first 9 days or so of February, during which I had absolutely no quiet time to work on creative projects.  I went to Phoenix two or three times to visit friends, and I have an on/off work philosophy, which means I work when I’m at work, and with friends I am simply with friends (not working).  I also discovered early on that I would be moving to Dallas, so I went through the entire moving process, including packing all of my belongings, tying up most of the loose ends I had in Tucson (I still have a few left), and driving to Dallas before March 1st.  I also continued to work to prepare for the accelerator I was moving to Dallas to participate in.  I thought Pryzm’s acceptance into the program implied that my lens would be manufactured sooner than I’d previously anticipated, so I wanted to accelerate the progress of my design.  Normally all of that would be an excuse to push all of my blog goals back a month, but I actually found myself working harder, and producing better work than I ever had before (for the blog).  I started to view crossing items off my calendar as a game, which made it fun to chip away at my goals whenever I had a few spare minutes (I wrote the StumbleUpon article at Chris’ house the day I got off the airplane, and wrote 3 college articles on the flight home from San Jose).  I was writing more frequently, which gave me more experience writing, and allowed me to improve as a writer.  As obvious as this sounds (I practiced writing more, which made me a better writer, which led me to write better articles), I legitimately thought my work would be worse if I put it out more frequently.  I fell victim to this perfectionist delusion that we have the perfect ideas deep down in our heads, and if only we could find the perfect mood, environment, headspace, and block of uninterrupted time it would simply flow out of us.  This mini-course helped me realize how delusional these thoughts were and are.  You get better at everything through practice, so forcing myself to practice more, especially in a way in which I receive feedback, (like publicly posting articles and sharing them to my friends on Facebook) should (and will) make me a better blogger, podcaster, and writer.

I started to feel the effects of this practice early on, and by the end of the month I was able to edit and post podcast episodes in half the time it had taken me a week before, and my writing was clearly improving, to the point where my friends were reaching out to me to tell me my that “my new stuff was getting better”, a compliment I value much more highly than “you are a good writer” (or another ‘fixed mindset’ piece of feedback).  In the end that’s really all I hope to experience with my creative projects, continuous improvement, not a delusion of a project suddenly (or ever) becoming “good” or “perfect”.  The theme of my website and my life is learning, and if you aren’t making progress you aren’t learning.  This experiment put me in the exact place I want to be with my website, a clear idea of how to improve (publish more), and some objective feedback that shows that I’m improving.  I achieved both of these through this course, making it undoubtedly a success.  In short, using a calendar with deadlines caused me to complete more tasks than I had before, put me wildly ahead of what I thought I could accomplish and when I could finish it by, improved the quality of my work, reframed deadlines from intimidating and anxiety inducing to a fun game-like challenge, and demonstrated to me an effective learning method.  Will I continue to use it in the future?  I’m buying a new whiteboard today so I can plan out the rest of April.

Also, I received more traffic in February than I ever had before (or since) on the website, by a significant margin, despite the fact that I had absolutely no unexpected traffic spikes.  Instead, it was all pure organic traffic, from people intentionally clicking on and reading my articles.

Objective results

Objective results