12 Questions That Can Transform Your Career, and Life, with Ryan Yockey
In a world that celebrates relentless hustle, many people assume their careers falter because they’re not working hard enough. But according to entrepreneur and engineering leader Ryan Yockey, that’s rarely the real problem.
“Most careers don’t break from lack of effort,” Yockey says. “They break from asking the wrong questions.”
Yockey is the founder of Growth Code, a system that helps founders scale their audience, income, and impact without burning out. After scaling multiple companies past $1 billion as a VP of Engineering, he now works directly with founders to help them build leverage into their businesses.
In this episode of Time Billionaires, he shared how asking better questions transformed his career and how it can do the same for others.
Why Root Cause Thinking Matters
At the core of Yockey’s philosophy is a simple but powerful practice: getting close to the real problem.
“People get really high-level in their assumptions of what they’re trying to solve,” he explains. “But the root of fixing something is to go deeper, get close to the problem, and solve that first.”
This mindset has shaped both his leadership career and his personal life. For Yockey, clarity starts with asking the right questions early, and often.
Start With the Real Problem
One of Yockey’s biggest lessons is the power of starting with the problem statement. Instead of jumping into solutions or experiments, he encourages leaders to simplify the issue first and ask:
What is really wrong here?
Are we the right people to solve it?
How quickly can we solve it?
This structured thinking mirrors the way many high-performing teams approach strategy: identifying the core problem first and ensuring everything downstream connects directly to it. Without that clarity, efforts quickly become scattered and misaligned.
From Metrics to Mission
During his time at The Farmer’s Dog, Yockey found that teams often focused too heavily on metrics like retention or conversion rates, without connecting those numbers to a deeper mission.
“The real goal was to make dogs healthier,” he explains. “If we do what’s right, deliver great food on time, keep dogs and owners happy, the metrics follow.”
That mission-first mindset has guided his career. For him, chasing numbers or titles rarely leads to fulfillment. Aligning with meaningful goals does.
Time, Presence, and Routines That Work
For Yockey, success isn’t just professional, it’s personal. As a founder and father of three, he prioritizes being fully present with his family. His daily structure includes:
Early morning workouts as a mental reset
Daily journaling and to-do planning
Identifying five impactful daily priorities
Using the Pomodoro technique to stay focused
“I really don’t think you need to work that much or that hard,” he says. “If you’re efficient with your time, you can create space for what matters most.”
His approach to time blocking and intentional routines allows him to work with focus and live with presence.
Teaching Presence in a Digital World
Yockey is also intentional about how he approaches technology at home.
“You’re not obligated to share everything about yourself online,” he says. “There’s a lot of negative out there… How do we teach kids what’s enough and what’s comfortable?”
He and his wife have chosen to delay their children’s exposure to social media for as long as possible. When the time does come, their goal is to teach intentional use , focusing on trusted communities, shared interests, and values over endless comparison.
12 Career Questions to Ask Yourself
One of the most memorable moments of the conversation came when Yockey shared the 12 questions that changed his career , a framework he credits with helping him make pivotal decisions at key inflection points:
Would I hire myself for this role again?
What would I do differently if I didn’t care what anybody thought?
If I left today, what would I regret not building?
Am I doing this because I want to or because I’m supposed to?
What’s one thing I’m scared to admit but know is true?
Is this role helping me grow or just keeping me busy?
What am I tolerating right now that I shouldn’t be?
When’s the last time I felt proud of my work?
Do I actually want my boss’s job?
If this company shut down tomorrow, what would I do next?
Would I take this meeting if it cost me $1,000?
Am I playing not to lose or playing to win?
These questions serve as a career compass, revealing misalignments between what people want and what they’re tolerating.
Don’t Sit on the Bench: Core Principles in Action
This part of the conversation also surfaced one of Time Billionaires host Rebecca Shaddix’s guiding philosophies: don’t sit on the bench.
Rebecca shared that this principle first emerged when she recognized the difference between being busy and being impactful in her own career. At a pivotal moment, she realized that the work she was doing wasn’t aligned with her core values; it was keeping her in the game, but not actually in play.
Rebecca’s four core principles are:
Make decisions from a place of empowerment, not fear
Don’t sit on the bench
Make decisions from internal fulfillment, not external validation
Take up space
Yockey connected with this deeply, describing his own turning point: moving from senior leadership to launching Growth Code. When opportunities and timing aligned, he made the leap not because it felt comfortable, but because staying still no longer made sense.
“I felt like I’d been ready to do what I’m doing now for a long time,” he recalls. “I didn’t want to sit on the bench anymore.”
Clarity comes from repeatedly asking the right questions and having the courage to act on the answers.
Key Takeaways
Better questions lead to better decisions. Start with the real problem before taking action.
Mission comes before metrics. Sustainable impact follows meaningful goals.
Intentional routines protect what matters. Time blocking creates space for both focus and family.
Digital intentionality matters. Modeling healthy online behavior is a powerful form of leadership.
The right questions can change a career. Use them as a compass when making pivotal decisions.
Listen to the Full Episode
🎧 Time Billionaires, “12 Questions That Changed My Career with Ryan Yockey”
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