RSPA Recommended Read: The Obstacle Is the Way

“RSPA Recommended Read” is a series of articles in which RSPA staff members share details from books we think would be helpful to leaders and aspiring leaders at VAR, ISV, and vendor member organizations.

By: Jim Roddy, President & CEO at the RSPA  

Bob Dukiet, my basketball coach at Gannon University, was no eloquent stoic like Marcus Aurelius, but they shared a spirit.

Aurelius wrote, “Our actions may be impeded, but there can be no impeding our intentions or dispositions because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting.

“The impediment to action advances action. What stands in the way becomes the way,” the Roman Emperor penned in his journal.

“EXCUSES ARE FOR DOGS,” Dukiet scribbled on his white board in the Gannon basketball office.

Author Ryan Holiday blends classic stoicism with modern day realities in The Obstacle Is The Way: The Timeless Art of Turning Trials into Triumph, one of my highest rated leadership books of all time.

Let’s dive into some key passages from the book to see what insight it offers to VAR and ISV leaders today:

  1. Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?
  1. The world is constantly testing us. It asks: Are you worthy? Will you stand up and show us what you’re made of?
  1. We blame our bosses, the economy, our politicians, other people, or we write ourselves off as failures or our goals as impossible. When really only one thing is at fault: our attitude and approach.
  1. Not: “This is not so bad.” But: “I can make this good.”
  1. Obstacles are not only to be expected but embraced. These obstacles are actually opportunities to test ourselves, to try new things, and, ultimately, to triumph.
  1. While others are excited or afraid, we will remain calm and imperturbable. This will be an incredible advantage for us in the fight against obstacles.
  1. John D. Rockefeller had sangfroid: unflappable coolness under pressure. He could keep his head while he was losing his shirt.
  1. Nelson Mandela and Malcolm X turned prison into the workshop where they transformed themselves and the schoolhouse where they began to transform others. We face things that are not nearly as intimidating, and then we promptly decide we’re screwed.
  1. Does getting upset provide you with more options?
  1. To argue, to complain, or worse, to just give up, these are choices. Choices that more often than not, do nothing to get us across the finish line.
  1. Most people start from disadvantage (often with no idea they are doing so) and do just fine.
  1. Those who survive, survive because they took things day by day – that’s the real secret. Focus on the moment, not the monsters that may or may not be up ahead.
  1. The struggle against an obstacle inevitably propels the fighter to a new level of functioning.
  1. It’s a huge step forward to realize that the worst thing to happen is never the event, but the event and losing your head. Because then you’ll have two problems (one of them unnecessary).
  1. Action is the solution and the cure to our predicaments.
  1. By all means, vent. Exhale. Take stock. Just don’t take too long. Because you have to get back to work.

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  1. How do people become great at things? They start. Anywhere. Anyhow. They don’t care if the conditions are perfect or if they’re being slighted.
  1. If we are to overcome our obstacles, this is the message to broadcast – internally and externally: We will not be stopped by failure, we will not be rushed or distracted by external noise. We will chisel and peg away at the obstacle until it is gone. Resistance is futile.
  1. In 1878, Thomas Edison wasn’t the only person experimenting with incandescent lights. But he was the only man willing to test 6,000 different filaments. Genius often really is just persistence in disguise.
  1. Consider this mindset: Never in a hurry, never worried, never desperate, never stopping short,
  1. Doing new things invariably means obstacles. A new path is, by definition, uncleared. Only with persistence and time can we cut away debris and remove impediments.
  1. Each project matters, and the only degrading part is giving less than one is capable of giving.
  1. To whatever we face, our job is to respond with: hard work, honesty, and helping others as best we can.
  1. Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages. They can be gifts. These things force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest.
  1. True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition. See which lasts longer under the hardest of obstacles.
  1. Acknowledge the pain but trod onward in your task.
  1. The Inner Citadel: That fortress inside of us that no external adversity can ever break down. We are not born with such a structure; it must be built and actively reinforced.
  1. The only guarantee ever is that things will go wrong. The only thing we can use to mitigate this is anticipation. Like runners who train on hills or at altitude so they can beat the runners who expected the course would be flat. You’re always fighting uphill. Get used to it and train accordingly.
  1. As the Haitian proverb puts it: Behind mountains are more mountains. One does not overcome an obstacle to enter the land of no obstacles.
  1. No matter how many times we are thrown back, we alone retain the power to decide to go once more.
  1. See things for what they are. Do what we can. Endure and bear what we must. What blocked the path now is a path. What once impeded action advances action. The Obstacle Is the Way.

RSPA Recommended Read Rating: 10/10

Like Coach Dukiet, I have a note on my office white board that’s been there for years, and it aligns with Obstacle Is the Way thinking: “I did not come back from hell with empty hands.” (The quote is attributed to French author André Malraux.)

You might know me as the RSPA CEO, the high-energy guy on the RetailNOW stage, the award-winning podcast host, the two-time author, or the guy with 7,000+ LinkedIn followers. But did you know:

  • My first job out of college – my dream job working for a pro basketball team – the franchise and league collapsed less than three months after my graduation.
  • When I was self-employed back in the day, my average gross income was about $11,000 per year.
  • And there was no big payoff at the end. I didn’t sell my business; I shut it down.
  • My first ever hire (a sales rep) never sold anything but he did convince me to give him a $500 advance on his pay – then I never saw him again.
  • My second year as President for a technology publisher coincided with the Great Recession of 2008-09. Our revenue declined sharply, we amassed significant debt, instituted three rounds of layoffs, and the surviving employees received a cut in pay and benefits.
  • In 2019, my job as a VAR/ISV Business Advisor came to an abrupt end when I was among hundreds laid off.
  • Once I was promoted into a VP role, pointed the department in a positive direction in just months, and then was inexplicably demoted to my old role.

Did I enjoy any of that in the moment? Heck no.

But did those experiences turn out to be, in the words of national champion college basketball coach Tony Bennett, a “painful gift”? Undoubtedly.

What scarred me in the past shapes my thinking and behavior today – and I’m not the only one.

Longtime retail IT solution providers will recall their arduous transitions from mechanical cash registers to ECRs (electronic cash registers) to POS systems.

They remember when tablets started displacing POS systems, when payments guys started stealing deals, and when giants gobbled up their ISVs.

They also recall the elimination of protected territories and the bumpy conversion from break/fix to the as-a-Service recurring revenue business model.

Those experiences have afforded them confidence that they can convert the threat of margin-obliterating, VC-backed, 800-number, one-size-fits-all POS providers who don’t have a channel into an opportunity.

They understand, as Holiday wrote, “Obstacles are actually opportunities to test ourselves, to try new things, and, ultimately, to triumph.”

Those high-initiative solution providers have faced daunting obstacles head on, got punched in the nose, lost a tooth or two (and some hair for sure), but ultimately survived and thrived.

One of the most rewarding current activities I engage in at RSPA is working with VP of Education Kathy Meader on our Leading Conversations Bootcamps. The goal of each bootcamp is to help retail IT channel professionals build the confidence, presence, and skills needed to actively participate in and lead conversations, whether at industry conferences, customer meetings, or within their own organizations.

How do we achieve that? Through obstacles that push participants outside their comfort zone.

They prepare outlines for each discussion and are offered constructive criticism on what they submitted. They are put on the spot to speak in front of the group, and afterward we share a candid assessment of where they met the standard and where they can improve.

On top of that, they watch recordings of themselves speaking. Every participant cringes when they learn that’s part of the deal.

And these are small groups – 5 to 10 participants – so there’s nowhere to hide. Everybody gets multiple turns in the hot seat.

Those who make it through all the bootcamp sessions achieve genuine confidence and genuine skills.

As Holiday said, “The struggle against an obstacle inevitably propels the fighter to a new level of functioning. … Action is the solution and the cure to our predicaments.”

In one of my first public speaking presentations, I opened my mouth without researching the group I was speaking to and unintentionally offended them so badly that I should have seriously considered never speaking into a microphone again.

But knowing “excuses are for dogs” and I should “acknowledge the pain but trod onward in my task,” I chose instead to double down on pre-presentation preparation and still do that to this day – about 34 years after feeling I ruined the Northwestern High School basketball banquet.

“Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?”

Choose wisely and choose bravely. Your customers, your partners, your team, and the RSPA community are counting on you to “stand up and show us what you’re made of.”

Purchase your copy of The Obstacle Is the Way here.

Be sure to register today for the retail IT channel’s #1 trade show, education conference, and networking event: RetailNOW 2026, July 26-28 at Caesars Forum in Las Vegas


Jim Roddy is the President and CEO of the Retail Solutions Providers Association (RSPA). He has been active in the retail IT channel since 1998, including 11 years as the President of Business Solutions Magazine, six years as an RSPA board member, one term as RSPA Chairman of the Board, and several years as a business coach for VARs, ISVs, and MSPs. Jim has been recognized as one of the world’sTop Retail Experts by RETHINK Retail and is regularly requested to speak at industry conferences on SMB best practices. He is author of two books – The Walk-On Method To Career & Business Success  and  Hire Like You Just Beat Cancer – and is host of the award-winning  RSPA Trusted Advisor podcast. For more information, contact JRoddy@GoRSPA.org.