Your Career Field Guide
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Most career advice is written by people who’ve never been laid off, never worked a loading dock, and never had to figure out how to pay rent while finishing a degree, but that’s my story.
I’m Justin Gillebo. I went from loading trucks at UPS for $12 an hour to managing billion-dollar supply chain operations at Starbucks, Microsoft, and Amazon. I did this without family connections, without a strong network, and without a college-educated family to guide me.
Here is what I learned: Most people are pedaling their career with one leg.
People spend decades focused on improving their performance and becoming the linchpin in an organization, but don’t see the freight train around the corner. Whether it’s layoffs, a reorg, or a bad boss, people quickly experience what I call Career Fragility.
You can be excellent at your role and still be blindsided because you built your career on a single leg. The fix is to think of your work as a Career Bicycle where both pedals are required, one for the performance that gets you paid today and one that provides the career resiliency that you will need tomorrow.
Career Field Guide is where I teach you to use both.
Where Are You Right Now?
I Just Got Laid Off (or I’m Worried I’m Next)
Why Resumes Don’t Get You Hired - Your resume is a screening tool, not a selling tool. Here’s what actually gets you in the door.
8 Steps to Prepare for Your Job Interview - The system I used to land roles at Amazon, Microsoft, and Starbucks.
Performance Is No Longer Protection - How AI, Wall Street, and layoffs rewired the rules of career safety
I’m Employed, but Not Making Progress
Build a Network That Brings Jobs to You - A simple 30-minute-a-week system that builds relationships and visibility without feeling like “networking.”
5 Worst Career Habits Smart Professionals Still Do - The invisible patterns that stall careers, even for high performers.
The Most Embarrassing Mistake I Made at Microsoft - What an awkward moment taught me about presence, perception, and giving yourself grace.
I’m Looking to Level Up
Learning Speed as a Career Advantage - Three ways to learn faster when the world keeps changing around you.
5 Career Moves That Look Risky But Aren’t (And 1 That Is) - What I learned about calculated risk vs. reckless gambling at Amazon, Microsoft, and Starbucks.
7 Career Lessons I Learned the Hard Way So You Don’t Have To - The mistakes that cost me years, and how to avoid them.
I Don’t Know What I Want Next
Thinking About Your Career - A 4-step framework to figure out “what do I want to do next?” when the path isn’t obvious.
Stop Picking Surfboards. Start Riding Waves - What Sears, Walmart, and Amazon teach us about spotting career-defining industry waves.
Stop Networking. Start Being Useful. - How Gary Vee’s 51/49 principle took me from factory floor to Fortune 500, and how it can work for you.
Get The Playbook
Every week, I send one idea to help you build a career that is both successful and resilient by sharing practical strategies from factory floors, business dinners, and boardrooms.
You will get strategies that actually work and are informed by my role as a Principal Researcher at Zero100 where I advise COOs and Chief Supply Chain Officers on navigating the challenges and opportunities presented by AI and the Digital Revolution. I hope you’ll join me.
Rooting for you,
Justin