Try Before You Leap Guide

Tiny Projects for Big Transitions
A practical, step-by-step guide to help you move from stuck and uncertain to unstuck and in motion—through small, low-risk experiments that create real-world insight and momentum.
 
Feeling stuck at a career crossroads?
You're not alone—and you're not doing it wrong.
I created Try Before You Leap because it’s the guide I wish I’d had during my own career pivot. And after working with hundreds of clients, I’ve learned that the biggest thing keeping us stuck is feeling overwhelmed by all the possible directions, and not knowing where to begin. This guide helps you break through overthinking and analysis paralysis by taking action.
 
Clarity comes through doing
Instead of making big, risky changes based on guesswork, or not taking action at all, this guide walks you through designing tiny, low-pressure experiments—so you can test ideas in the real world, gather insight, and build momentum.
 
Whether you're considering a career shift, starting a side project, or exploring a creative path, this guide will help you:
 
Build confidence through small, doable actions
Discover what fits you—through real-world insight, not just overthinking
Explore possibilities with less pressure and more curiosity
Start making aligned decisions—without needing all the answers first
 
This season of transition, as uncomfortable as it is, might be the gift that points you towards discovering your own unique voice, connecting with what brings you meaning and finding your song in life.
 
TBYL isn't for everyone - but it is for you if:
 
You're dreaming of a new direction
You're craving a creative venture or side hustle
You're exploring the idea of starting your own business
 
And right now, you're stuck in your head - overwhelmed by too many ideas, unsure where to begin, and overthinking every option until you end up doing... nothing.
 
This is not a personality test. Or a 5-year plan.
This is a way to get unstuck by doing, not just thinking.
We get stuck when we try to think our way into knowing what can only be discovered through action. The pressure to be certain before we act can keep us frozen—or worse, walking the wrong path.
 
The key is to start.
Start small.
Start messy.
Start curious.
 
“The Transition Projects were the catalyst for me. Through the connections, experiences and opportunities that arose I have transitioned from an established and celebrated career in teaching and leadership into a full-time self-employed garden designer, project manager and business owner—all in under a year. The process has really helped me to learn to trust in setting your compass in your chosen direction and then stepping forwards with optimism and courage.”
—Hannah Phillips