Jen Ottovegio Coaching

November 3, 2025

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Rethink How You Plan

If you’re anything like me (and most of my clients), your brain loves a good plan. You set the goal, build the to-do list, maybe even color-code it.

But sometimes the plan still doesn’t work. Something unexpected gets in the way — a missed detail, a human emotion, a blind spot.

What if better planning isn’t about adding more detail… but about asking a different question entirely?

That’s where Inversion Thinking comes in.

Inversion Thinking: A Mental Reframe

Instead of asking, “How do I make this work?”

Ask, “How could I ensure this goes poorly?”

Then build your plan so it doesn’t.

This simple mindset shift can make your decisions stronger, your goals more realistic, and your energy way more protected.

It’s a tool I teach clients to use for both business strategy and everyday life — and once you start, you’ll never unsee it.

Here’s how to do it.

Flip It → Fix It → Fine-Tune It

1. Flip It. Start with your goal, then ask the opposite. “What would make this fail?” You’re not being negative — you’re being proactive.
2. Fix It. Turn what could go wrong into small, protective habits or rules of thumb. These are your guardrails — the things that keep you aligned.
3. Fine-Tune It. Check in regularly. Ask what’s working, what’s not, and where things need adjusting. That reflection keeps you on track.

Five Real-Life Examples

🧑‍🍼 The Overwhelmed Parent

Instead of: “How can I have calmer mornings?” Flip it: “What makes mornings chaotic?” Answer: Rushing, missing shoes, skipped breakfast. Guardrails: Pack bags + outfits the night before. 10-minute buffer built in. No phone until we’re out the door.

🎬 The Productivity-Seeking Team Leader

Instead of: “How can we make meetings productive?” Flip it: “What makes meetings pointless?” Answer: No agenda, no outcomes, same topics every week. Guardrails: Only meet if there’s a decision to make. End with “who’s doing what by when.”

🎨 The Stumped Creative

Instead of: “How can I be more consistent?” Flip it: “What makes me lose momentum?” Answer: Unrealistic goals, waiting for motivation, no accountability. Guardrails: Design a tiny daily habit (10 minutes counts). Share progress weekly with an accountability-buddy.

🤖 The Exhausted Professional

Instead of: “How can I protect my energy?” Flip it: “What drains it fastest?” Answer: Saying yes too fast, guilt, over-explaining. Guardrails: Practice saying “Let me check my schedule and get back to you.” Reserve one night home each week with zero plans.

📈 The Entrepreneur

Instead of: “How can I grow sustainably?” Flip it: “What would guarantee burnout?” Answer: Overcommitting, skipping rest, chasing every opportunity. Guardrails: No calls on Fridays. Decide on one new initiative per quarter. Get “Rest” blocked on the calendar for when you know you will need it.

Try It This Week

Pick one thing that matters right now — a goal, a project, a relationship. Ask:

1. What could make this fall apart?
2. What guardrails could keep it on track?
3. When will I check in to see if it’s working?

It’s not about perfection — it’s about designing on purpose.

👉 Read the full blog post for more examples and context: Inversion Thinking: How to Flip Your Perspective and Make Better Decisions

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Schedule This Work. Monthly. In a Group.

Want to put this into practice? We’ll be using parts of this framework during The Monthly Reset Ritual — Wednesday at 1pm PT (it's virtual + open to all). $5-15 suggested contribution.

You’ll leave with your own guardrails, reflection plan, and renewed clarity for the month ahead.

👉 Register here

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💙 jen

P.S. My Fall Into Focus program is booked! My badass clients are off to the races and making some big moves. It's honestly amazing to witness.

If you are not a client, but are really craving some 1:1 support... I always welcome off-cycle folks that are highly motivated to make a change. Read more about my coaching and schedule a free 30-minute call to learn more. I'd love to chat.