19 Rejections Taught Me How to Finally Win
21 final rounds. 19 rejections. Here's what finally changed.
I want to tell you about an email I got that changed everything.
It was my 19th rejection after a final-round interview. Not 19 applications. 19 times I made it all the way to the end, only to lose out at the finish line.
This particular rejection came after four rounds of interviews and a take-home presentation I spent an entire Saturday working on while trying to figure out how to be a good new dad at the same time.
The recruiter on the phone said what they almost all said:
“Gerome, we loved you, the team was impressed...but we’ve decided to go with a candidate who has more direct experience in the retail industry.”
When I pushed for real feedback, something I could actually use, the response frustrated me even more:
“There was nothing wrong. Keep doing what you’re doing. This was the most competitive interview market we’ve ever experienced, and you were in our top two.”
After the phone call, I felt completely stuck.
I was doing everything right. I was getting so close. But my past experiences kept telling a different story than the one I needed them to tell. The gap felt impossible to cross.
Have you ever felt that same frustration? That gap between what you know you can do and what your resume says you’ve done?
You’re in exactly the right place.
I figured out how to cross that gap. I’m going to show you how to do it too.
Who Is This Guy?
Fair question. I’ve been on your side of the screen, reading articles and thinking, “Why should I care what this person is saying?”
So let me tell you my story. It’s not linear.
I started out studying Mechanical Engineering. Not because I loved it, but because I was told I had to choose a “prestigious” path like engineering, medicine, or law. I didn’t go to a top-tier school, but I learned early on how to sell my experience.
For example, I talked my way into a highly competitive internship at General Electric by highlighting the skills I gained working as a cashier at Babies R Us and flipping cars on the side. Hondas, Acuras, whatever I could buy cheap, fix up, and sell for profit. Something most people would completely overlook.
That internship opened my eyes to Financial Services. I heard other interns talk about six-figure salaries and bonuses after graduation. I decided to pivot. Right after undergrad, I got a Master’s in Mathematical Finance from Boston University, thinking it was my golden ticket to a top paying job.
Reality hit hard. As a Master’s student with zero corporate experience, I competed against experienced MBAs for every role. I eventually landed an unpaid internship at Merrill Lynch, just to get a foot in the door within Financial Services in New York.
My first real job wasn’t glamorous Wall Street. It was a middle-office support role at The Royal Bank of Scotland in Connecticut. A nearly three-hour commute each way from Queens, NY. The salary? $50K. Nowhere near the engineering salaries I’d heard about, and definitely not the six figures I thought my finance degree would get me.
But I had a goal: Investment Banking.
I networked my way into a better analytical role at RBS, but when I kept hitting the Investment Banking wall at RBS, I knew I needed a different approach. So I pivoted again. This time to Risk Consulting at KPMG, specifically to build my client-facing skills.
fter a year, I took my shot. I cold-emailed a boutique, Hispanic-owned Investment Bank on Wall Street and told them my winding story. Ten minutes later, I was on a call with the recruiter. Three weeks later, I got the offer. I finally landed that Investment Banking Analyst role, even though it meant taking a step back in both salary and title despite having three years of experience under my belt.
The Twist
Here’s what nobody tells you about “dream jobs.”
After a year in Investment Banking, I realized that dream wasn’t really my dream. I was just chasing money, not passion.
So I left to start my own footwear brand. It was a huge leap. Honestly, it didn’t take off like I’d hoped. But the experience was invaluable. Those were some of the best 2 years of my life.
After working on that brand, I knew I needed stronger business and leadership skills. I also needed a way to package all my experience together so I could tell my story better. So I aimed for a top MBA.
I talked to students at top schools and realized my profile was missing a key piece: strategy experience. Before even applying to business school, I pivoted again. I convinced a Director of Strategy at a hospital to hire me as a Strategy Analyst, despite having zero healthcare experience.
Armed with that strategy experience, I applied to business schools myself. No application consultants, no services. Just my story and a lot of hard work. I got into Kellogg at Northwestern University, a top-5 MBA program.
During my MBA, I followed the crowd. The majority of people in business school aim for Consulting at a top firm because of the salary potential. It’s hard to ignore $200K to $300K compensation packages.
Post-MBA, I went into Strategy consulting. Learned a lot about strategy, leading teams, becoming a better manager and leader, solving problems. But the hours were intense.
Life moves forward and happens. My wife and I were starting our family planning journey. I had to leave the 70-hour work weeks behind. I left a lot of money on the table.
Another pivot: back to a strategy role at a digital healthcare startup. Way better hours and work-life balance, but the work was definitely not something I enjoyed.
The Biggest Realization
With our baby on the way, I understood I’d spent years following the crowd and playing it safe instead of pursuing my real passion: the fashion and apparel industry.
So during one of the toughest job markets in recent memory, I decided to make the leap.
It took a year and a half.
I interviewed everywhere. NFL. Amazon Fashion. LVMH. Foot Locker. Some of the biggest brands in the world.
The result? I went through the entire interview process for 21 different companies and got 19 rejections.
21 final rounds. 19 “no’s.”
The feedback was always the same: “We loved you...but we chose someone with direct industry experience.”
That painful process taught me more about interviewing, storytelling, and selling myself than anything else in my career. It forced me to perfect my approach.
And finally, it paid off.
I landed my current Strategy role at a major fashion and apparel company. An industry and role I’m truly happy and passionate about for the first time in a very, very long time.
Why Did This Guy Jump Around So Much In His Career?
Valid question.
The truth is, I didn’t have the guidance, career foresight, network, connections, or mentorship that many people in these high-profile fields have.
There was no one in my family or neighborhood I could ask, “Hey, how do I get a job like yours?”
I had to learn by trial and error. By trying as many stretch opportunities as possible.
So why am I telling you all this?
My journey is proof that these pivots are possible. This path of constant trial and error, from engineering to finance to entrepreneurship to a top MBA and countless rejections. It gave me the exact strategies you need to overcome these same challenges.
What I’m sharing here isn’t textbook theory. It’s built on the real-world tactics I used to convince hiring managers, time and again, that my diverse background was an asset, not a liability.
It’s about turning your unique story into your greatest strength.
I know the self-doubt that creeps in at night. I’ve lost sleep feeling like I didn’t belong. I know the frustration of being overlooked.
But I also know the incredible thrill of finally breaking through and looking back at your journey with pride.
In the posts ahead, I’m going to share everything I learned. The frameworks, the mindset shifts, and the practical techniques to help you navigate your interviews with confidence and land your next great role, no matter how big the leap seems.
I’m excited to guide you.
Let’s get started.
Next up: Who is this for? (And more importantly, is it for you?)
Here is the complete career playbook for anyone who is pivoting roles, industries, about to graduate, stuck in their current path, not sure what to do next, etc.
The Complete Interview Playbook for Career Changers: Every Strategy, Every Framework, All in One Place
If you’re reading this, you’re probably not the “perfect” candidate.