About The Leadership Progress Cycle

Have you spent time feeling stuck or blocked? Have you had times when what you really wanted seemed far away and your options limited?

I have.

And I've found a way to get past stuck. I've learned that barriers come from competing commitments and found a pattern for finding breakthrough solutions. The Leadership Progress Cycle is that pattern.

This is how I found it.

In late 1999, I felt stuck. I worked in a gray cubicle at a tech writing job I did not love. I saw much better prospects if I became a software engineer, but I couldn't afford more schooling. I faced a paradox in the opposing pull of two necessary things: Obligation and Aspiration. I was obliged to support my young family and I aspired to a new career.

So I began experimenting with solutions that honored both my obligation and my aspiration. I bought books, began a self study program, and completed two technical certifications. In Aug 2005, I was hired as a software engineer.

After several years as an engineer and then a product manager, I saw that I could have more impact as an entrepreneur. But in this new goal, I faced the classic founder's paradox: A successful business plan requires funding and funding depends on a proven business plan.

So I began experimenting with business plans and funding possibilities. I built apps and actually incorporated 3 different companies, none of which survived. Finally, in Dec 2014, I had a chance to became a co-founder at Niche Academy—an angel funded training platform for libraries and non-profits.

Niche Academy became a profitable company, training thousands of engaged learners around the world.

I saw the greatest impact came from training leaders but I noticed something missing.  In all of the leadership training available, no one was teaching leaders how paradoxes lead to hidden solutions. Despite the disruption and seemingly impossible barriers facing leaders everywhere, no one was clearly teaching a process for finding breakthrough solutions.

So in Jun 2025 I created The Leadership Progress Cycle. My new book, Tension—Mastering the Superpower of Paradox-Aware Leadership, is set for release in Jan 2026. 

As I’ve faced my own barriers, led my teams past blockages, and then trained leaders across hundreds of organizations, I’ve discovered a simple and repeatable pattern for overcoming them. In a nutshell, it has four steps:

1

Get clear about what you’re really trying to accomplish. As yourself: What's the thing that stirs my soul enough to justify the work? While it may be true that no single goal is truly out of reach, you can’t pursue all goals at the same time.

2

Get clear about the real barriers. Some barriers that seem the biggest turn out to be illusions—especially the ones that involve a conflict between two necessary opposites. Risk and Security... Bold Action and Caution... The tension between those opposites is called paradox and it's actually a catalyst for breakthrough innovation.

3

Experiment. You’ll never have the solution at the start. The faster and the cheaper your experiments, the more of them you can run and the sooner you'll find your solution.

4

Measure the results of your experiments. Measuring keeps you honest and shows how close you’re getting. What you learn from your experiments will, in turn, refine your goals. 

That pattern is what I call The Leadership Progress Cycle.

It’s how I became a software engineer without ever enrolling in a computer science class. It’s how Jeromy Wilson and I created a profitable SaaS company in a small and resource-constrained market. It’s how I wrote a book while working a full-time job. It’s how I launched a company called The Leadership Progress Cycle without outside investment.

The Leadership Progress Cycle is what I offer now to you.

If you have constraints, limits, or barriers that, for now, seem insurmountable...

You can overcome them. 

I can show you how.

Jared Oates

Creator | The Leadership Progress Cycle