Most entrepreneurs are wired to move forward. Finish one project. Hit the next goal. Start the next thing. David Schaub is no different. But once a year, he forces himself to slow down and reflect before charging ahead.
In this solo episode of the Western New York Entrepreneur Podcast, David walks through the exact questions he asks himself every year to reflect, recalibrate, and intentionally design the year ahead Yearly Planning Podcast Episode….
This process is not about productivity hacks or setting vague goals. It is about asking better questions.
Reflection Comes Before Planning
David starts every year by looking backward before looking forward.
“I naturally want to skip reflection and go right to what’s next. But when I actually slow down and reflect, I realize how much happened in just one year.”
He reviews his entire Google Calendar from January through December. Vacations. Work trips. Wins. Losses. Hard conversations. Missed opportunities.
Reflection allows him to celebrate what went well and also acknowledge what did not.
“Sometimes you need to celebrate. Sometimes you need to mourn. And sometimes you need to forgive yourself.”
Without this step, planning becomes disconnected from reality.
The Categories That Matter Most
Instead of focusing only on business goals, David reflects across multiple areas of life:
- Marriage and relationships
- Kids, family, and friendships
- Health, energy, and mental clarity
- Finances both personal and business
- Professional and business life
- Growth and learning
- Spiritual alignment
- Fun, adventure, and travel
“You cannot fix nine areas at once. But you can identify the one or two that need attention right now.”
This helps him understand what season he is in and what actually deserves focus.
Asking the Hard Questions
David does not shy away from uncomfortable questions.
“What have I been saying for years that I would fix but still haven’t?”
For him, one year that meant finally investing in the right CPA after realizing cheap advice was costing far more in taxes.
“I saved money on invoices but lost way more in missed strategy.”
These questions force honesty and clarity.
Business Reflection Without Ego
David also reflects deeply on how he shows up as a business owner.
“Am I being a CEO or am I just self employed?”
He looks at where he is stuck in the weeds, what drains his energy, and what should finally be delegated.
Burnout often comes from ignoring these answers.
Growth Is Not Always About Business
One year, David realized his biggest growth opportunity was not professional at all.
“I hired a legacy coach. We did not talk about business. We talked about being a husband and a father.”
That clarity reshaped how he structured his time, boundaries, and priorities.
Why the Next 90 Days Matter Most
While David reflects on three and ten year visions, he believes the next 90 days are where change actually happens.
“Momentum beats perfection.”
He narrows his focus to what can realistically be moved forward in the next quarter and schedules it instead of hoping it happens.
Designing a Year That Fits Your Life
David emphasizes that planning must align with your current season.
“What worked before kids may not work now. And that is okay.”
Instead of forcing unrealistic expectations, he plans around what is feasible and meaningful.
The Question That Ties It All Together
David ends with a powerful prompt.
“If nothing changed over the next year, how would you feel?”
That question alone creates urgency and clarity.
Key Takeaways
- Reflection must come before planning
- Goals without context create frustration
- You cannot fix everything at once
- The right questions reveal what truly matters
- Planning should match your season of life
- The next 90 days matter more than distant goals
- Intentional years do not happen by accident
📩 Want the free yearly planning packet
Email: david@wnyentrepreneur.com