The Grit Factor Podcast w/ Karl Jacobi | Episode 28: Twenty Years of IT. One Deliberate Step Backward with Chris Farr

Episode 28: Twenty Years of IT. One Deliberate Step Backward with Chris Farr

May 12, 2026 / 57:01/E28

Episode Summary

Most people spend their careers chasing the seat at the table. Chris Farr had it. Vice President of Technology at a credit union in southwest Georgia, twenty years building his expertise from the ground floor up through the era of mainframes and dumb terminals, through the rollout of online banking when half the membership still preferred the phone teller, through compliance frameworks and security protocols that come with the weight of managing other people's money. He earned that seat. And then he walked away from it.

Not because of a crisis. Not because he got pushed out. Because he looked at the landscape, saw that the MSP world would let him do more for more people, and decided that the discomfort of starting over at the bottom of a new learning curve was worth more than the comfort of staying at the top of one he had already conquered. That decision cost him his confidence for a stretch. It cost him long nights on weekends relearning things he thought he already knew. It humbled him in rooms where he had expected to be the expert, and dropped him back into the experience of being a green technician figuring out systems he had never seen before.

Almost a decade later, Chris is VP of Operations at Envision, one of the most trusted MSPs in the southeast, serving clients across multiple industries as a true technology partner rather than a vendor. He is also a published author, with a book called Built in the Trenches, and someone who has become increasingly focused on cybersecurity education for small businesses who wrongly assume they are too small to be a target.

This is not a comeback story. It is something rarer. It is the story of a man who chose voluntary discomfort at the peak of his career because he knew comfort was the enemy of growth. This episode is for any leader who has been quietly wondering whether the seat they are sitting in is still the right one.

In This Episode, You'll Discover:

What VP of Technology at a credit union actually looked like day to day, how Chris helped drag an entire industry from mainframes and green screen terminals into the era of home banking, and what a winning week felt like when members could transact without standing in a drive-through line
Why Chris made the deliberate move from a single-client corporate IT role into the multi-client MSP world in 2016, what drew him to the variety and challenge of serving multiple industries simultaneously, and what nobody told him about how humbling the first twelve months would be
The specific moment when Chris realized his confidence had cracked, standing in front of a client whose whole site was down, second-guessing whether he actually knew what he thought he knew, and what he told himself to keep moving forward
Why the MSP model, at its best, functions less like a vendor and more like a fractional CTO partnership, giving small and medium businesses the strategic technology leadership they need without the overhead of a full-time executive hire
The platinum rule Chris drills into every technician on his team: not the golden rule of treating people the way you want to be treated, but treating them the way they want to be treated, and why that distinction is the difference between a forgiven mistake and a lost client
Why cybersecurity is the season Chris is most focused on right now, how small businesses massively underestimate their exposure, and the specific problem of cybersecurity insurance forms written in language most business owners cannot actually interpret
The radical responsibility mindset Chris is actively building, the shift from knee-jerk dismissal of a struggling employee or client relationship toward asking what he could have done differently, and how that reframe changes everything downstream
How to distinguish between pushing through and pivoting, the framework Chris uses when everything is falling apart around a decision that made sense on a whiteboard, and when it is time to take it back to the drawing board

Key Takeaways:

Voluntary Discomfort Is a Career Strategy. Chris was not forced out. He chose the bottom of the curve over the top of a comfortable one. That choice cost him confidence in the short term and built capability in the long term. Most people wait for forced change. Chris engineered it. That is a different kind of grit.
You Think You Know Until the Client's Site Is Down. Confidence built in one environment does not automatically transfer. When the pressure is real and the system is unfamiliar, you find out quickly where the gaps are. Chris's answer was not to fake it. It was nights and weekends resharpening what had gone dull. The foundation was still there. It just needed work.
The Platinum Rule Beats the Golden Rule. Treat people the way they want to be treated, not the way you want to be treated. In tech support this means no jargon to someone who does not need jargon. It means making them feel heard before you make them feel fixed. When they know you genuinely care about their problem, they will forgive the technical slip. They will not forgive feeling dismissed.
You Are Too Small for the News. You Are Not Too Small for a Cyber Attack. A small law firm or medical practice may never make headlines when compromised. But the reputational damage in a small community is catastrophic in a different way. You still have to see those people at church. The question is not whether you are big enough to be a target. The question is whether you have the right locks on the door.
Radical Responsibility Is Not Just for Founders. Chris is building this as a daily practice. When a client relationship sours or an employee struggles, the first question is not what is wrong with them. It is what could I have done differently. Even if you were not the primary cause, you were in the room. That means you had a hand in it. Claiming that is not weakness. It is leadership.
The Right Person, Wrong Seat Problem Costs Everyone. An analytical employee doing creative work is not a bad employee. They are a misaligned one. Moving them costs nothing. Losing them costs months of replacement. The culture fit is the hard-to-teach part. The skills are transferable. Always try the seat change first.
Your Job Security Ends Where the Customer's Happiness Ends. This is the Sam Walton quote Chris keeps on his office wall. Not as a motivational poster. As a daily operating principle. Every hire, every decision, every interaction runs through this filter. If what you are doing is not serving the person who trusts you with their technology, you are not doing your job. Everything else is secondary.
Push Through When the Goal Is Right. Pivot When the Path Is Wrong. Chris's framework is clean. If the destination is correct and the team is committed, grip it and grind it through. If the execution is revealing that the plan itself was flawed, you have to have enough clarity to call it before it gets worse. Grit is not stubbornness. It is knowing which one you are in.

Timestamps:

[00:00] Karl introduces Chris Farr: twenty years in IT, VP of Technology at a credit union, VP of Operations at Envision MSP, published author, cybersecurity advocate, Leesburg Georgia
[03:00] What the credit union IT world actually looked like: mainframes, dumb terminals, green screen prompts, and dragging an industry into online banking
[07:00] What a winning week felt like: members transacting without lines, employees set up for success, and the technology quietly doing its job in the background
[11:00] The 2016 pivot: why Chris left a role he had mastered for a world that required him to start over, and what drew him to the multi-client MSP model
[15:00] What the MSP model actually is, how it differs from break-fix IT, and why the best version of it looks like a fractional CTO partnership rather than a vendor relationship
[20:00] Karl's ad break: The Grit Code Exposed at https://gritcodeexposed.com
[21:00] The platinum rule: teaching every technician to communicate the way the client needs, not the way the technician prefers
[25:00] The first twelve months: imposter syndrome, second-guessing every decision, nights and weekends resharpening skills he thought he already had
[30:00] The specific moment confidence cracked: a client site down, unfamiliar systems, and realizing he was effectively starting over as a green technician in that context
[34:00] What shifted first: the mindset before the tactics, and why you cannot get the systems right without getting the head right first
[38:00] Clarity and accountability in leadership: how Chris learned early from great leaders that you do not need all the answers, you need to own your part when things go wrong
[42:00] What successful transition looks like from the inside: looking back and knowing you left the place better than you found it
[46:00] What Chris had to let go from his corporate IT identity to become the leader he is now
[49:00] Karl's ad break: The Grit Code Exposed at https://gritcodeexposed.com
[50:00] Right person, wrong seat: the employee who was analytical doing creative work, the realignment, and the transformation in the first week
[55:00] What Chris is most fired up about today: empowering communities through technology and watching the next generation of leaders develop inside Envision
[59:00] Cybersecurity as the defining season: why small businesses are massively underestimating their exposure and the insurance form problem nobody talks about
[01:04:00] Where to find Chris, the LinkedIn page, and the book Built in the Trenches
[01:06:00] Grit defined: sticking with it thick or thin, keep on keeping on
[01:08:00] Subtraction: removing the knee-jerk reaction to dismiss struggling employees or clients, replacing it with radical responsibility
[01:10:00] The directive: your job security is only as strong as the customer is happy, from Sam Walton's autobiography
[01:12:00] Matthew Hasler's question from the previous episode: how do you distinguish between pushing through with grit versus knowing when to pivot?
[01:14:00] Chris's question for the next guest: when everything is falling apart around you, how do you keep your team motivated and marching forward?
[01:16:00] Karl's close