The Digital Contrarian™

Ryan Levesque

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The Digital Contrarian™

Ryan Levesque

Issue #051

| The Digital Contrarian™

Setbacks & Breakthroughs

Setbacks & Breakthroughs: Why Feeling Stuck Means You Are On the Brink...

Ryan Levesque

11 min read

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This mighty sugar maple predates the American Civil War.
 
Crazy, right?
 
Planted on our farm over 200 years ago, this tree recently endured a fierce ice storm that broke its massive trunk, leaving behind the stark standing snag and fallen segment pictured here.
 
(This thing is massive. I mean, look how small I appear next to it.)
 
I felt a pang of sadness, realizing this majestic tree is now closer to its end than its beginning. But reflecting on its resilience – and recent challenges in my own life – led me to explore the nature of setbacks and breakthroughs this week.
 
And it raised a powerful question:
 
What if our greatest setbacks are actually seeds for our most meaningful breakthroughs?

1 | When Nature Laughs at Your Plans (And What to Do When It Does)

There’s nothing quite as humbling as farming.
 
You can have detailed plans, schedules, and preparations, but if the weather doesn’t cooperate, you’re completely at its mercy. Farming is a powerful reminder that we control far less than we like to believe.
 
Take our recent experience:
 
We’ve endured 11 straight weekends of relentless rain here in Vermont.
 
And with each passing weekend, I’ve felt further and further behind on establishing our production garden this season.
 
But then, this past Sunday, we had our first sunny weekend day in nearly three months – and Tylene and I and the boys (along with Blue) took full advantage.
If you look closely, you’ll see tiny little Blue in my lap. Move over “Toddlers & Tiaras” – introducing “Tractors & Chihuahas” – TLC’s next big hit :-)
Then, this past week brought a much-needed three-day stretch of sunshine, allowing us to:
 
  • Plant 200 feet of alliums (onions, shallots, and chives)…
  • Plant 200 feet of cucurbits (summer squash, zucchini, delicata, butternut, and spaghetti squash)…
  • Plant 100 feet of brassicas (broccoli, cabbage, and kohlrabi)…
  • Sow 100 feet of carrots…
  • Install 500 feet of electric netting to protect our greens that have been getting nibbled by the deer and rabbits…
Left: Music garlic; Middle: Chives, flowering; Right: One of our summer squash transplants from the greenhouse into the garden during our sunny stretch this week.
In other words, after weeks and weeks of being stalled – the burst of sunshine brought with it an explosion of breakthroughs on the farm.
* * *
Early in life, I was introduced to the work of Mihaly Csikszentmihalyi, particularly his concept of “flow” – and the idea that the secret to life is to…
 
Detach yourself from the outcome and focus deeply on the process.
* * *
Farming embodies this principle perfectly.
 
Because like entrepreneurship, farming requires an immutable faith that the next sunny day – (i.e. your next breakthrough) – is just around the corner.
Our one-eyed barn cat, Carlito, enjoying a few moments of sunshine in between rain showers while napping on our compost station.
And one contrarian observation I’ve made in both my own life and in the lives of my  private clients (as their strategic advisor and confidant) is the following:
Breakthroughs often tend to cluster after prolonged setbacks.
Knowing that every breakthrough first germinates from the seed of a setback has helped me learn to take setbacks in stride.
 
(And sometimes, when I’m particularly mindful, I welcome my next setback – because I’ve learned that hidden inside the most frustrating delays is often the beginning of something new and special…)
 
But that raises a deeper question:
 
What does it actually look like to find a breakthrough inside the setback itself? And is it really possible to use adversity as fuel in the moment – not just in hindsight?
 
Question for Reflection (1 of 3)
“What’s one small action you can take today to be ready when your next breakthrough opportunity presents itself?”

2 | The Injury That Gave Me My Garden Back

There’s something about minor injuries that forces a reset.
 
Last week, I strained my calf playing pickleball – Grade 1.
(I can walk, but I can’t put fast, intense pressure on that leg.)
 
It came at a frustrating time, because one of my goals this summer is to hit an official 4.0 rating at my local club (I’m close).
 
In fact, I’d just declared that goal to an accountability group I’m part of – and now, it’s likely going to have to wait.
 
Normally, I play pickleball in the morning several times a week after dropping the boys off at school. But suddenly, those 90-minute sessions were wiped off my calendar.
 
And right at the same time, the weather finally shifted from rain to sunshine.
 
So instead of having to choose between two opposing commitments – train on the court indoors or spend that time outside on the farm – the choice was made for me.
 
And in that open space, something shifted.
 
With the rain finally gone and my leg out of commission, the garden became the obvious place to be.
A row of Passat Cabbage Patch Kids making their way into the world :-)
Until then, there hadn’t been much to do outside – so my early mornings went to the court or the gym. But now, the decision was made for me.
 
And with the shift in weather – it couldn’t have come at a better time, because it meant I could be productive on the farm while also giving my calf time to heal.
 
What looked like a limitation turned out to be a blessing in disguise, because that’s the thing about setbacks:
Setbacks in one area often create space
for breakthroughs elsewhere in life.
But the most surprising breakthrough wasn’t physical at all. It came in a place I’ve been struggling with for months…
 
Question for Reflection (2 of 3)
“What part of your life or work has been quietly calling for attention – but which keeps getting pushed aside?”

3 | When the Breakthrough Shows Up on the Page

For months, I’d been circling the same creative block.
 
And a few weeks ago, my forthcoming book – The Return to Real  – the one I’ve been writing, reworking, and wrestling with – was starting to feel more like resistance than flow.
 
I had moments of progress, but they came in fits and starts.
 
I’d write a section, only to scrap it the next morning. A structure would feel solid… until it didn’t.
 
The reality was that I was stuck.
 
And no amount of outlining, white-boarding, or walking around the pasture seemed to change that.
 
But then – almost without warning – something shifted.
 
These last few weeks, writing The Digital Contrarian each week has acted as a kind of forcing function. And within that rhythm, things started to click.
 
[Issue #046]: Brace for Impact – gave words to the 3 Converging Forces Reshaping Our World As We Know It…
 
[Issue #049]: Why Oxytocin = The New Dopamine – gave us the science behind why so many of us are feeling what we’re feeling right now…
 
One insight led to another.
 
Then this week came a conversation with Jon Berghoff…
 
A call with Cary Jack…
 
And finally, a live session I hosted with Simon Bowen for my private clients and members of my Strategic Advisory Group Mastermind that gave me language – and a visual model – for something I’d been trying to articulate for months.
Suddenly, all the threads began weaving together. The philosophical, the practical, the personal.
 
I could see the book again – not as a loose set of ideas, but as a unified thesis with a clear path forward.
 
The breakthrough wasn’t loud or dramatic.
 
It didn’t come with a spark of genius or a burst of energy.
 
It came from consistency. From structure. From surrendering the need to force it.
Sometimes breakthroughs simply come from showing up, steadily.
Which brings me to an invitation:
 
In a few weeks, I’ll be ready to share the updated (draft) Table of Contents from my forthcoming book.
 
It’s changed significantly since I first asked for feedback a few months ago.
 
And I’d love your input again – because the way this book is shaping up has been influenced by many of the insights, stories, and reflections you’ve shared in response to these newsletters.
 
So if you’re interested, please keep your eyes peeled for that.
 
(And BTW – If you’ve responded to one of my emails over the last few weeks and you haven’t heard from me, I am still catching up on replies. I love receiving your messages. It just takes me time to reply. Thank you for your patience :-)
* * *
Before we go any further, let me first share the unexpected lesson this breakthrough revealed…
 
Because here’s strange thing about breakthroughs:
 
Even when they happen, they rarely arrive alone.
 
Often, they bring a trail of scientific breadcrumbs in their wake – insights that help explain why adversity seems to work this way in the first place.
 
Question for Reflection (3 of 3)
“Where in your life are you pushing for progress, when what you may need most is simply to keep showing up?”

4 | The Science Behind Why Setbacks Work

Earlier, I mentioned Mihaly Csikszentmihalyi’s concept of flow – the idea that fulfillment often comes not from chasing outcomes, but from immersing ourselves in process.
 
But what does the rest of the literature say about the relationship between setbacks and breakthroughs?
 
As it turns out, quite a bit.
 
In 2010, a team of researchers led by Dr. Mark Seery published a study in the Journal of Personality and Social Psychology that examined how people respond to adversity. What they found was fascinating:
 
Individuals who had faced some adversity in life – not none, not overwhelming amounts, but moderate, manageable levels – demonstrated greater resilience, better stress tolerance, and higher overall well-being than those who had faced either extreme.
 
In other words: As we explored in [Issue #035]: Why Struggle is the Solution – some struggle makes you stronger – but too much can break you, and none at all can leave you fragile.
 
The question of course is: What’s the “right” amount?
* * *
This supports a phenomenon known in psychology as post-traumatic growth – a concept developed by Richard Tedeschi and Lawrence Calhoun.
 
Their research shows that many people don’t just bounce back from adversity. They bounce forward.
 
They develop deeper empathy. Stronger relationships. Clearer priorities. More durable inner frameworks.
 
And then there’s what neuroscientists are finding in the field of creativity:
 
Periods of frustration and “creative block” often precede moments of insight.
 
In fact, some researchers argue that the brain requires downtime, ambiguity, and even a sense of failure to reorganize its ideas into a breakthrough pattern.
 
Which, if you zoom out, sounds a lot like… farming.
One of our randall lineback heifers, Athena, whom I’ve written about before – watching me closely as I prepare to move her fence.
You don’t get growth without some kind of friction. Seeds need pressure. Roots need resistance. And sometimes, the best thing you can do is give it time.
 
But if all this is true – if setbacks really are necessary for growth – then it raises an even harder question:
 
What do we do when the setback feels like too much? Or worse when it asks us to walk away from something we’ve built?
 
Because after all, like with LEGO…
Sometimes we need to break what we’ve
built – to build something better.
Nathan Sawaya’s iconic sculpture “Yellow”, which we had an opportunity to see as a family in person at the Perot Museum of Nature and Science in Dallas, TX – where this photo was taken.
* * *
As I wrap this up, I keep coming back to that tree.
 
That 200-year-old maple has seen more seasons, more storms, more quiet recoveries than any of us ever will.
 
And while it’s nearing the end of its life, it’s still standing.
 
And there’s something about that.
 
Because setbacks are often like that, too.
 
They look like breaks.
 
But often, they’re actually an opening to what’s next.
 
So if you’re in the middle of one right now – whether it’s a delay, a derailment, or just a weird liminal space – I hope this week’s newsletter offers a helpful, albeit contrarian perspective to consider.
 
Because while setbacks don’t always feel fun when you’re in them….
 
They often mean that breakthrough you’re looking for, is right around the corner.
* * *
Okay, I’ll leave you with that for now.
 
Remember to hug the ones you love.
 
And until next week,
 
Ryan :-)
 
P.S. One last thing for today…
 
My friend Derek Coburn (pictured with me below) just released a brand new book called Let’s Retire Retirement, which I think is worth checking out. In fact…
In many ways, Derek’s message echoes the core of what we’ve been exploring in this newsletter:
 
That what looks like an end might actually be an opening.
 
Whether you’re in your 30s or your 60s, this book will challenge how you think about life’s next chapter – and what it means to build a life worth living now, not someday.
 
Here’s the link to grab a copy of the book: Let’s Retire Retirement
I highly recommend checking in out.
 
In the meantime, I hope you have a great rest of your week.

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The Great Sea Change diagram from Return to Real