The Digital Contrarian™

Ryan Levesque

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The Digital Contrarian™

Ryan Levesque

Issue #079

| The Digital Contrarian™

The Tension Between “Resistance” & Productive Procrastination…

The Tension Between "Resistance", Productive Procrastination & How to Know When It's Time to Ship...

Ryan Levesque

10 min read

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It’s that time of year isn’t it?
 
You know, that time where you look back at the last 12 months and reflect upon all the things you didn’t get done…
 
(Please don’t tell me I’m the only one.)
 
Now, for me?
 
The biggest “thing” I didn’t manage to get done this year – has been getting my upcoming book, Return to Real, over the finish line.
 
Originally, my goal was publish in time for a Fall 2025 release.
 
(Let’s just say, that proved to be a bit… ambitious.)
 
My amended goal has shifted to a Spring 2026 release.
 
But if I am to be honest…
 
This book is a project I’ve found myself procrastinating on for the last few months.
 
In fact, I haven’t made much “tangible” progress since finishing the first draft of my manuscript earlier this year.
 
Now, it’s not for a lack of caring…
 
Instead, in many ways, it comes from a place of caring too much…
 
(More on that in a moment…)
* * *
Now, on the one hand…
 
I’ve had my hands full in the second half of this year…
 
September and October were nearly all-consuming between coaching two soccer teams and the high school application process for my son, including touring and interviewing at a dozen schools – not to mention a busy harvest season on our farm – as well as hosting two (2) in-person masterminds (and three client VIP Days) here at our home in Vermont.
November and December, I spent more than half the time traveling – including trips to Mexico (Tony & Dean’s Zenith Group MM), two weeks in Austin (FRDL, Lifestyle Investor, Tiger21, Prime Elite), as well as a trip to Hilton Head, SC (BBW) to deliver keynotes, interviews, fireside chats and several private sessions…
And on top of all that, in the middle of it all…
 
We somehow managed to start a new business with our brand new Return to Real Agency – wherein we’ve already started building Strategic Content Ecosystems for our first dozen “Category of One” clients – which is taking off like a rocket ship.
NOTE: While our January 2026 Agency Client Cohort is 100% FULL, we’re opening spots for February 2026. If you’d like to apply for one of the few spots we have remaining, please complete this application here. I will be reviewing applications this coming week. We have plans that currently start at $2500/month (but that price will be increasing…)
So it’s not like I’ve been sitting on my hands…
 
And (if you continue to indulge my string of excuses…) much of the work I’ve been doing (e.g. the dozen or so keynotes and interviews I’ve done in the last few months) has helped me further refine my core Return to Real thesis, supporting evidence, and ultimately what to include (and trim) from the content of the book.
 
But all that said…
 
At some point, you just need to sit down and write the damn thing.
 
(Or in my case, ruthlessly edit – and finalize – the manuscript.)
* * *
As Antoine de Saint-Exupéry (author of The Little Prince) famously wrote:
 
“Perfection is achieved, not when there is nothing more to add, but when there is nothing left to take away.”
 
And while perfection has never been my goal, I do have a big vision for what I’d like to accomplish with this book, as I continue to chisel away at the manuscript.
 
And as we explored back in [Issue #060]: Inside a Room with 40+ Million-Copy Bestselling Authors – in the words of James Clear, author of Atomic Habits, who – with 25 Million Copies Sold –  knows a thing or two about books:
“There are many things in life where good enough is good enough. Writing a book is not one of those things.”
Which brings me to the focus of today’s issue…

1 | The Power of Productive Procrastination

One of the things we do as a family each night, is watch a TED Talk together before bed…
 
We rotate each day, where each member of the family gets a chance to choose a talk on a topic they’re interested in. 
 
After the talk, we then have a brief discussion – each sharing our biggest insight and a question that’s emerged from the talk.
 
One of the presentations, we recently watched together was a TED Talk Adam Grant delivered in 2016 titled, “The Surprising Habits of Original Thinkers” with over 23 million views.
In it, Grant explores how the most creative, original thinkers have a very specific relationship with procrastination:
 
Grant’s core argument is that “productive procrastination” isn’t a form of laziness. Instead, it’s a very critical process of “idea incubation”.
 
The most original thinkers are often quick to start but slow to finish, and that lag time is where the magic happens.
 
When you begin a project (so it’s “active” in the back of your mind) and then step away long enough to let it simmer, your brain has room to make the nonlinear connections it can’t make when you’re rushing to lock in an answer.
 
In other words:
 
Procrastination is a vice for productivity, but – when done in moderation – it can be a virtue for creativity.
 
(Reassuring, no doubt, for those of us *ahem* who are “quick to start, but slow to finish”…)
 
But the question is this:
 
How do you balance this “productive procrastination” with the need to eventually ship?

2 | The Truth About Creative Work & Windows...

Whether we like to admit it or not:
 
Every creative endeavor has a window for release – from starting a business to publishing a book…
Windows open…
 
And… windows close.
 
And if you miss your window…
 
Chances are, the window will never open again.
 
(Painful, but true.)
 
Now, it’s not to say that a new window for something different won’t open up…
 
But the window for this thing….
 
The thing you’ve been working on…
 
The thing you’ve been obsessing over…
 
The thing at the center of your “productive procrastination”…
 
Will not be open forever.
 
Market conditions change….
 
And creative energy eventually wanes….
 
Which brings us to the question every entrepreneur and creator must eventually ask, which is…

3 | How Do You Know When It's Time to Ship?

In Adam Grant’s TED Talk around creativity and the power of productive procrastination…
 
Grant layers on a second, equally useful distinction:
 
“Originals” as he calls them, aren’t fearless or effortlessly confident.
 
They feel doubt like everyone else, but they’re better at keeping doubt pointed at the idea instead of at themselves.
 
Self-doubt (“I’m crap”) shuts you down, whereas idea-doubt (“this manuscript isn’t there yet”) energizes you to test, refine, and iterate.
 
Pair that with one more truth:
 
Originals are often more afraid of failing to try than they are of failing outright – so they speak up, ship drafts, run experiments, and generate a lot of bad ideas in order to uncover a few great ones.
 
Something we explored in detail back in [Issue #027:] Building Your Strategic Content Ecosystem if you’re interested in diving deeper into this topic…
 
So how do you know when it’s time to ship?
 
Well, I believe the answer is this…

4 | When "Resistance" Rears its Ugly Head...

Here’s what I’ve come to believe – and this is where the work of Steven Pressfield has been a gut-check voice for me.
Adam Grant may give us permission to incubate… to stay “quick to start, slow to finish” long enough for the idea to ripen.
 
But Pressfield reminds us there’s a thin line where incubation quietly turns into avoidance.
 
In The War of Art, Steven Pressfield names that force Resistance – the shapeshifting inner opponent that will use anything (perfectionism, fear, “I’m not ready,” “I just need one more pass”) to keep you from finishing.
 
The Resistance is lurking at every corner – whispering sweet, soothing songs in your ear, convincing you you’re not yet ready…
* * *
So how DO you know when it’s time to ship?
 
Well, here’s a simple litmus test I use:
 
Is my procrastination truly producing new insight… OR is it simply producing new excuses?
 
(Like all the “reasons” I mentioned earlier for why I’ve been too busy to finish my book these last few months…)
 
If the delay is helping you see the work with fresh eyes – clarifying your argument, sharpening the structure, making the piece truer – that’s Grant’s “productive procrastination” doing its job.
 
BUT…
 
If the delay is mostly you rearranging commas, re-reading the same section for the 37th time, or “getting ready to get ready”… that’s no longer incubation. That’s the Resistance rearing its ugly head.
 
Which leads to a simple rule of thumb:
 
  • If your next step requires real-world feedback – which it often does, ship. (The market, the reader, the audience is a better editor than your inner voice; this is the whole “message should come from your market, not from your mind” central to the Ask Method.)
 
  • If you can state the premise clearly, and the remaining work is mostly refinement, ship. (Refinement has no natural finish line; this is the whole “art is never finished, only abandoned” idea attributed to the great Leonardo da Vinci.)
 
  • If your “idea doubt” has quietly become “self doubt,” ship. (Because the only antidote is motion; this is the whole “motion breeds clarity, confidence, and conviction” that we’ve explored together in many past issues of this newsletter…)
 
IMHO – Pressfield’s blunt rally cry for moments like this is perfect:
 
“Remember one rule of thumb: the more scared we are of a work or calling, the more sure we can be that we have to do it.”
 
In other words, the closer you get to the finish line, the louder the voice of the Resistance becomes.
* * *
Consider this your “pep talk” going into the holiday week next week…
 
As you make your plans for the next year…
 
As you set your goals…
 
As you decide where to redouble your efforts…
 
That thing you’ve been “productively procrastinating” over…
 
Your window for release may be closing faster than you think.
 
So my call to arms for you is this:
 
Now is the time…
 
Get your butt in gear.
 
And ship.
* * *
Have a very Merry Christmas…
 
A very happy Hanukkah…
 
A very blessed Kwanzaa…
 
And on this Winter Solstice…
 
The shortest day of the year in the Northern Hemisphere…
 
May the rebirth of the sun fill you with joy and light.
 
For even the darkest of nights ends with a new dawn.
* * *
Okay, I’ll leave you with that for today….
 
Remember to hug the ones you love…
 
And until next week…
 
Ryan :-)
 
P.S. One last thing for today…
 
I wanted to give you a heads up that I’ll be hosting a LIVE Town Hall event on January 8th, my first of the New Year.
 
I’ll be sharing my Biggest Predictions for 2026.
 
Including a theme I see emerging that I’m calling “The Great Bifurcation” – a force that I believe will shape everything over the next twelve months.
The event will be free to attend, but will be limited to the first 300 to join – and I do expect it to fill up.
 
If you’d like to get on the priority notification list to reserve one of these spots, SHOOT ME AN EMAIL with the word Predictions…
 
This is one you will not want to miss.

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The Great Sea Change diagram from Return to Real