Set Up to Fail

Last week, I was sitting with my parents at my son's basketball game, and the subject of track, specifically the pole vault, came up.

My mom interjected, “Did you know your grandmother was a pole-vaulter?”

“Nope, sure didn’t.”

My grandmother was a true gem.

She once painted a friend's toilet gold as a joke. Making it an actual throne.

A real spitfire, who was as funny and fiery as she was driven.

My mom went on to share that her instructor, also a woman, had a doctorate in physical education and brought pole-vaulting to the girls.

No wonder my grandmother was pole-vaulting in the late 1920s. It was acceptable for her teacher to encourage her to do so, and of course, she was probably game to try it.

What is amazing is that pole vault didn't become an Olympic sport for women until 2000.

My grandmother, whether through her makeup or by circumstance, didn't adhere to gender roles.

In the early 1950s, she was working off the family farm at night, developing film and printing pictures.

It was at this job that she heard the news one night.

Her house, where her husband and four sons were sleeping, caught fire.

In the blink of an eye, she was a 37-year-old widow, mother to 1, my uncle, her only surviving son.

Instead of working off the farm to help her family's farm make ends meet, she picked up the pieces and took over running it. Oh, and she gave birth to my mom about 9 months later!

This was in 1951.

My grandmother, by her own volition or by circumstance, wouldn't let herself fail.

She did what she had to do whenever it came her way.

She did not know or adhere to gender roles. She was a school bus driver, a town mayor, ran a mechanic's garage with my step-grandfather, and was the town seamstress and furniture refinisher.

So often, we are set up to fail based on others' perceptions. Other people decide what we can and can’t do.

For decades and generations, organizations have decided who can and cannot promote or serve roles based on degrees or external qualities.

People have been set up to fail merely because they have been pigeon-holed.

But that is only part of the story.

My grandmother bucked the trend a century ago. By doing this, she ingrained it in my mother, and I hope to instill it in my children as well.

The shortcut is only the other option until it becomes the way. How does it become the way?  

When people are willing to try. To give someone without a degree a chance at a job or position.  

When people stop seeing through biased lenses.

When merit means more than any other qualifier.

When people are willing to do the work, and the work matters.

Thats when the shortcut or other option becomes the way, because sometimes that is the only option.

The Things We Hide - Moment

Growing up on a farm taught me endless lessons. Some were wildly valuable, others might have held me back.

One attribute was both. It was valuable, but became restrictive.

In any given day growing up, I could cover all these professional skills—Carpenter, welder, plumber, electrician, veterinarian, general laborer, financial planner, and IT.

The ability to do all at a passable level was essential to get through the day. Being a Swiss Army Knife was the greatest limitation for so many years of my life.

I could do a little bit of everything, but I never focused on mastery.

I still fight it some days.

Farmer, author, content creator, financial planner, mechanic, landscaper, carpenter, and marketer all made the list this week alone.

I think it is part of life to be multi-disciplined, but if we rely on it, we will be “set up to fail.”

Being pretty good at a lot of things will hold you back more than going all in and becoming a master at something.

It follows this adage: be the sharpest knife in the kitchen rather than all the utensils in the drawer.

John Maxwell taught me the lesson, and John Ruhlin helped me understand and apply it.

We each have things we excel at; some are classically educated, others are because we had the drive and desire to express.

Choosing to develop and get better at what we already excel at moves us from being good to world-class.

People seek out world-class.

World-class is impactful. Being average is being set up to fail.

Podcast

Barbara Wittman had about as untraditional a path to becoming an IT executive as any. Her career started in Germany, close to the Alps, in a bike shop.

She learned to weld, fabricate, and repair. This set her on her path, but didn't limit it.

In a culture and time when most women chose nursing as a profession, she made a much different choice that fit her unique interests and skill sets.

Eventually, Barbara found herself helping a major international technology company integrate their processes and software into manufacturing facilities. Her experience working with her hands gave her the leg up in implementation that other executives couldn't comprehend or communicate.

Her Swiss-Army knife ability allowed her to hone her unique talent and become a sought-after digital implementation specialist.

Not having an engineering degree was her greatest skill, because she saw what others couldn’t.

Here are three key focus points from my conversation with Barbara that we all need to focus on so we don’t set ourselves or others up to fail.

1. No Growth Path = Unrealized Potential
   When companies don’t intentionally create space for personal development, they quietly limit their people. Not because employees lack ability—but because no one is helping them stretch it. Talent stalls when growth isn’t invited.
   

2. Knowledge Without Inner Growth Breaks Under Pressure
   Skills matter, but they aren’t enough. A workforce trained in what to do—without developing self-awareness, resilience, and adaptability—will struggle the moment conditions change. Competence alone doesn’t carry you through uncertainty.
   

3. Lack of Empowerment Leads to Stagnation
   When people aren’t empowered to grow personally and professionally, momentum slows. Innovation fades. Organizations don’t usually fail in a moment—they harden over time. Growth always starts with people, and when it stops there, everything else eventually follows.

The reality is that so many organizations are cutting funding for employee development, from self-development to technical development.

Educational and developmental programs are often the first to get cut by earnings and budget-centric organizations.

Which, itself, is a self-defeating prophecy. Stop feeding the cow, and eventually she stops making milk. Sure, you don’t have the expense of feeding the cow, but pretty soon you won't have milk to sell, and the cow will be dead!

You gotta feed your cows, and the better job you do at it, the more milk and healthier your cows and bank account will be.

But it's not easy. It takes work and investment, but the pay-off is worth it.

An Option for You, the 2026 IDL Roundtable

2026 marks year six of the IDL Roundtable Community. When I started it, the goal was simple: create a way to serve people beyond the podcast—something more personal, more intentional.

Six years later, it’s grown into a complete 36-week framework, and honestly, I’ve been just as shaped by the journey as the people walking through it with me.

Last year, I made two critical shifts. First, I introduced a shorter on-ramp—a 12-week Awaken the Leader Within experience that parallels the chapters of The Things We Hide. Second, I kept the full-year cohort for those ready to go deeper and stay longer.

The next cohorts begin the week of January 26th. Due to some travel, I have the first week of February, it starts the week of February 9th.

If you’re at a place where you’re ready to stop hiding from yourself and start leading yourself, I’d love for you to consider joining us.

I would love to chat with you about this being an option for you to Awaken - Grow - Lead in 2026.

Did you catch this podcast? If not, listen to it here.