Meet Jon Douglas | Sr. IT PM / Entrepreneur / Hooman

We had the good fortune of connecting with Jon Douglas and we’ve shared our conversation below.

Hi Jon, what role has risk played in your life or career?
I don’t glamorize risk, I manage it. As a former Sr. IT Project Manager, risk was never a surprise guest; it was a standing agenda item. Every project I led had a risk register, owners, triggers, and mitigation/contingency plans. I run my life the same way I run programs: everything starts with a clear objective, a plan, and a set of “what-ifs” mapped to specific responses. Measured risk is the cost of progress; unmanaged risk is just gambling.

Planning is what turns uncertainty into something workable. I front-load effort: define scope, surface assumptions, stress-test timelines, and pre-decide what we’ll do if X or Y happens. That’s how you make risk either safe—or at least visible, accounted for, and within scope. Dwight Eisenhower said it well: “Plans are worthless, but planning is everything.” The plan may change, but the discipline of planning gives you options when reality does.

In my career and life, that mindset has let me take bolder steps, because I’m not leaping blind. I’m moving forward with eyes open, contingencies in place, and the humility to adapt when conditions change. That’s the role risk plays for me: it’s a catalyst for momentum when it’s identified, quantified, and actively managed.

Can you give our readers an introduction to your business? Maybe you can share a bit about what you do and what sets you apart from others?
I run a simple business with an ambitious mission: teach people the money game they were never taught. Broke by Design is a blueprint for getting out of the rat race; not with hype, but with a system.

What sets Broke by Design apart: it treats the rat race like the game Mouse Trap. You already know the board; you’ve lived on it. I map the traps, show how they’re built, how to spot the triggers, and how to avoid them. Then I hand you better plays. Once you’ve mastered the mechanics, you design your own system and step off the board entirely. The book walks you through building a personal exit plan—and executing it.

The brand has two pieces:
• The book, Broke by Design: Reclaiming Your Mind, Time, and Wealth, which exposes the traps (debt, insurance, fees, taxes, lifestyle-creep, learned helplessness) and gives a method for exit—earn, automate, invest, protect, and reclaim your time and humanity.
• A companion project, MoneyKat, a gamified finance app that turns the playbook into daily actions—track net worth, budget by category, set goals, and earn “wins” for real behaviors. I want money skills to feel learnable, not intimidating. I’m going for Duolingo for personal finances and wealth building.

Nothing worth it is easy. A few years ago, I took my life into my own hands and put myself through “money college.” I read 30+ money books, built a plan that fit my reality, and then did the boring, consistent things that compound. Today I’m retired at 39, living simply, and building tools and stories so others can do the same because watching people I care about struggle through life just because they don’t know money is painful to me.

Getting here wasn’t easy. I left a high-paying career, upended my life, moved to Mexico, rebuilt my life around sustainable freedom, and ignored a lot of noise. I overcame it the same way I ran projects: plan, test, iterate, and remove blockers one by one. Diligence is key and having everything on a list that is prioritized, sized, and sorted makes it manageable because you only have to do the one item on the top of the list and not stress about the rest.

Key lessons:
• You can’t manage what you can’t measure. Track everything!
• Planning is Key: Document your targets, risks, and contingencies—then work the plan.
• Simplicity scales. Fewer points of failure, fewer rules, more repetition. KISS.
• Invest in yourself first: skills, health, and systems have the best long-term ROI.
• Protect your time: Boundaries, automation, and the right tools change the game.

What I want the world to know: you’re not “bad with money”—you were never taught it. And the system isn’t broken. It’s working exactly as it is meant to, at your expense. To leave the rat race you have to make your own system. Broke by Design exists to shorten the learning curve and hand you a plan you can actually execute.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
The Desert Botanical Garden, the Phoenix Zoo, Papago Park, Tempe Beach Park and Tempe Town Lake. On a hot day, go tubing down the Salt River near Saguaro and see the horses. Road-trip the Frank Lloyd Wright sites across Arizona or chase some of the state’s dozen or so waterfalls or numerous castles.

Who else deserves some credit and recognition?
Here’s my shoutout:

First, to my dad. He didn’t have much, but he gave me everything he could: Time, belief, and the kind of steady encouragement that keeps you going when plans fall apart. Because of his combat injury in Vietnam, I was able to access government support that made college possible for me; without that, I don’t know that I would’ve finished.

Second, to Nadine—thank you for the thoughtful feedback on my book and for recommending me to Shoutout AZ. You’ve been a generous mirror and amplifier.