An Interview on Long-Term Success, with Rick Meekins

Certainty Is Often the First Mistake

“Give up. Find somebody to blame and you’re fine.”

That was my joking answer when Rick Meekins asked what we should do when things don’t go the way we expected.

Of course, that is exactly what many of us are tempted to do.

We try something. It doesn’t work. We get frustrated. We blame ourselves, someone else, the market, the team, the customer, or the timing. Then we either double down harder or walk away too soon.

But the problem is not that the first attempt failed. The problem is that we let unexpected results block us because we were so certain, so sure we knew what to do and how it would work.

Simple, Complicated, or Complex?

Why are we so sure?

One of the ideas Rick and I explored on The Relentless Pursuit of Winning podcast is that we often treat complex problems as if they are simple ones.

A simple problem is one where the answer is known and repeatable. If you follow the recipe, you get the result. Boiling water, sending an invoice, or following a checklist can often fall into this category.

A complicated problem has more steps and may require expertise, but it is still mostly predictable. Building a bridge, setting up a technology system, or designing a financial model may be complicated. You need knowledge, experience, and precision, but experts can usually map the path.

A complex problem is different. In a complex situation, the outcome cannot be fully predicted in advance. The system changes as you act. People respond in unexpected ways. Markets shift. Teams resist. Customers say one thing and do another. What worked yesterday may not work tomorrow.

That is real life. That is business. That is leadership.

And yet the human brain naturally wants to simplify. It wants certainty. It wants the shortcut, the expert, the formula, the one right answer.

That instinct is what gets in our way.

Why Certainty Blocks Learning

As I said in the interview, “Nobody has a solution to a complex issue.”

There is no shortcut, expert, formula, or right answer.

That does not mean expertise is useless. It means expertise helps you avoid foolish mistakes, but it does not remove the need to test, observe, and adapt.

In simple problems, good decision-making means following the known answer.

In complicated problems, good decision-making means getting the right expertise and executing carefully.

In complex problems, good decision-making means running small experiments, reading the feedback, and adjusting quickly.

That’s the gift Rick gives to his clients. When Rick works with a leader, here is how he prepares them for complexity, “We’re going to take an iterative process. We’re not going to go all the way. We’re going to take stages and see how it goes. We’re going to learn from that. We’re going to adjust and keep moving forward.”

That is exactly the mindset complex situations require.

Tiny Experiments Turn Failure into Feedback

This is where tiny experiments become so powerful.

A tiny experiment asks: What is the smallest action we can take that will teach us something useful?

That question changes everything.

When we judge an unexpected result as failure, our survival brain often takes over. We get defensive. We look for someone to blame. We protect our ego. We may quit too soon, or we may keep pushing the same approach because admitting it is not working feels too painful.

But when we treat our actions as an experiment and the result as feedback, we stay resourceful. We can ask better questions:

• What did we learn?
• What surprised us?
• What should we try next?
• Was the idea wrong, or was the execution weak?
• Did we misunderstand the customer, the team, or the environment?

As Rick said, “If we’re curious, we can be more objective with the outcomes and make appropriate adjustments, rather than relying on confirmation bias.”

That is the heart of relentlessly pursuing winning.

The Real Relentless Pursuit

The relentless pursuit of winning is not about pretending we know the answer. It is about staying engaged long enough to learn our way forward.

For me, this connects directly to my mission. I want people, especially students and educators, to learn the skills that lead to successful, fulfilling lives. That means learning how to regulate ourselves, think clearly under stress, work with others, handle conflict, and adapt when reality refuses to follow our plan.

These concepts are foundational to business success.

But what makes this conversation with Rick so meaningful is we were not just talking about business strategy. We were talking about how people actually grow, lead, recover, adjust, and keep moving. In life, at work, in society, in relationships. Everywhere.

Why Listen to the Full Interview?

Certainty feels powerful, but in complex situations it often blinds us.

Tiny experiments, curiosity, and feedback help us see.

And seeing clearly is how we keep moving toward the win.

In the full episode of The Relentless Pursuit of Winning, Rick and I go deeper into the survival brain versus the resourceful brain, why curiosity changes the way we lead, how conflict styles shape outcomes, and why resilience is not just “pushing through,” but learning how to respond when the first attempt does not work.

If you are building a business, leading a team, working in education, or trying to create meaningful change, I think you will find the conversation useful. It offers a practical way to think about uncertainty, setbacks, conflict, and progress.