For those considering an investment decision —
and haven't made it yet.

The Overthinking Tax™

by Jack Trama

Every opportunity has a cost — especially the ones not taken.

There's a point where research stops helping. Where more information doesn't make the decision clearer—it just makes it harder to pull the trigger.

Most people don't notice when they cross that line. The research continues. The comparisons multiply. The search goes on for something that will make it feel safe to move.

But that feeling doesn't come from more data. It comes from making the decision.

The gap between those two truths can cost months. And in that time, confidence fades. Momentum dies. What started as opportunity becomes something to avoid.

The Overthinking Tax™ shows how to recognize that line before crossing it—and what to do when you're already on the wrong side of it.

The book reveals:

When due diligence becomes expensive delay
Why "just one more thing to verify" often means something else
What really separates people who move from people who wait
How to build the muscle that makes future decisions easier

Inside:

The moment analysis stops being useful (and how to spot it)
What "I need to be more sure" actually signals
Why waiting erodes the very thing needed to act
A practical framework for knowing when enough is enough

This isn't about ignoring legitimate concerns or rushing past real risks.

It's about developing the judgment to know when you have what you need—and the confidence to act on it.

Because every day spent researching is a day not building.

And that gap gets expensive fast.

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What This Book Shows

Why waiting to feel ready costs more than most think—and how to stop paying for it.

Why waiting to feel ready costs more than you realize—and how to stop paying for it.

WHY DECISIONS STALL

The comfort of "not yet" feels harmless. Reasons like "I need more time" or "I'll start after..." sound legit. But weeks turn into months. Deciding ends the loop.

WHAT DELAY REALLY COSTS

Every day of hesitation has a price. Time gone. Confidence drained. The ability to trust judgment, weakened. Making the call stops it all.

HOW TO MOVE FORWARD

Frameworks for recognizing when enough is enough—and acting on it. Movement doesn't come from perfect timing. It starts with a decision.

Read It Anywhere.

Start Deciding Differently.

More information isn't the answer — making the decision is. This book helps stop overthinking and start acting on opportunities that already make sense.

Instant Access on Any Device
Read it on your phone, tablet, or laptop — no waiting, no shipping.
Built for Busy Thinkers
Short chapters. True stories. Straight talk that gets you unstuck fast.
A Framework You’ll Keep Coming Back To
Every page helps you see decisions differently — and act sooner, with less hesitation.

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Bonus Tools

Frameworks and checklists that help you decide faster and stop second-guessing yourself.

Insider News

Exclusive updates, behind-the-scenes insights, and launch-day previews from Jack.

Community

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About The Author

Jack Trama

For more than twenty years, Jack has sat across from people standing at the edge of major decisions—moments when the next move isn’t about knowing more, but about acting on what’s already clear.

His work spans coaching, strategy, and sales leadership, but the thread has never changed: guiding people through the hesitation that stalls their progress.

The Overthinking Tax™ grew out of those conversations. It’s about the hidden cost of waiting, the weight of almost deciding, and the freedom that comes once you finally move.

If You’ve Ever Second-Guessed a Big Decision, This Book’s for You.

Most people don't realize how much hesitation costs — time, confidence, and missed opportunities. The Overthinking Tax™ is for those done analyzing every opportunity and finally ready to act. It names what's been holding things back, and shows a clearer way to move forward.

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What People Are Saying About The Overthinking Tax™

From those who recognized the cost of waiting—and chose to move anyway.

The nudge I didn’t know I needed.
I'd been stuck on a business investment for a year—researching, comparing options, waiting for the 'right time. This book made me realize there isn't one. After finishing The Overthinking Tax, I finally took action on something I'd been putting off.

Michelle M., Entreprenuer

Made me stop waiting for ‘the right time.’
This book is direct truth that hits when you need it. I'd been avoiding a business opportunity for nearly a year, and this book helped me finally act. Within a week of finishing it, I finally made the decision I'd been delaying for too long.

Scott H., Sales Professional

Exactly the push I didn’t know I needed.

Every chapter felt like a conversation I should've had months ago. Simple truths, told clearly. It doesn't try to motivate you—it makes you honest with yourself.

Jaime J., Business Owner

Finally made sense of why I keep waiting

Every other book tells you what to do, but this one explains why you're not doing it yet. Jack puts words to that stuck feeling better than anything I've read. It's truth that just makes sense.

Rick G., Executive

Inside The Overthinking Tax™

How decisions actually get made—and why doing is harder than knowing.

Introduction

Some people make decisions. Others don't. This book shows why—and how to become someone who does.

PART I — THE PATTERNS

CH 1: Research Cycle

Research is useful up to a point. After that, it only delays the decision. This chapter draws the line.

CH 2: The Review Loop

Checking the same facts doesn’t create new answers. It only adds doubt. This chapter is about trusting what’s already known and breaking the loop.

CH 3: The Time Trap

The perfect time never comes. This chapter is about deciding now, not after one more busy month passes.

PART II — STORIES THAT STALL

CH 4: Still Thinking It Through

Thinking helps at first, then just repeats itself. This chapter marks the shift from “sorting it out” to “this is the answer.”

CH 5: Not Financially Ready

Sometimes the numbers work, but fear says they don’t. This chapter separates real money limits from excuses that keep a decision on hold.

CH 6: Need Partner's Support

Partners can sense when a decision isn’t clear. Asking for support too early turns the talk into a sales pitch. This chapter starts with clarity alone, then a clear, direct conversation.

CH 7: Too Risky After Last Time

One bad outcome can shadow every new opportunity. This chapter separates a past hit from the decision that’s on the table now.

PART III — SEEING WHAT'S TRUE

CH 8: Comparison Game

Constant comparison feels productive, but it’s delay. This chapter is about choosing one option and letting the others go.

CH 9: The Overthinking Tax

Every day undecided has a cost in time, energy, confidence. Deciding is what ends that cost.

CH 10: Fear's Disguise

Fear turns a clear choice into a problem and adds doubt. This chapter is about spotting that shift early and letting the decision stand.

PART IV — THE WAY FORWARD

CH 11: Use What You Know

Most key facts are on the table already. This chapter turns that knowledge into a clear call instead of another search for more.

CH 12: Start Small

Big change begins with one move that can be made today. This chapter builds that first step and keeps the focus there.

CH 13: Progress Over Perfect

Perfect never lands. This chapter trades perfection for steady movement and shows how small wins stack into real change.

CH 14: The Moment Of Decision

At some point, the decision is the next step. This chapter is where fence-sitting ends and the move gets made.