I Almost Quit… More Times Than I Can Count. Here’s Why I Never Did.

There’s a moment in almost every career when you feel like throwing in the towel.

Some people only face it once or twice. I’ve faced it dozens of times.

Moments where I was convinced I was done. Moments when the emotional weight was heavy enough to make me actually draft a resignation letter — or in one case, write it out entirely.

And yet… I never sent it.

I never walked away.

That choice — to stay in the fight when everything in me screamed “quit” — has made all the difference in my life and career.

The First Time I Almost Walked Away

It was my very first call center sales job.

Training was brutal. The pace was relentless. The expectations were sky-high. Of 12 people in the class, 2 graduated!

I sat there wondering if I even belonged.

I didn’t know the lingo. I didn’t know the shortcuts. Every call felt like walking into a fight I was unprepared for.

I remember sitting in my car during lunch one day, staring at the steering wheel, thinking:

“Maybe I’m just not cut out for sales.”

I could have driven away and never come back. Nobody would have blamed me.

But I didn’t.

I walked back into that building, picked up the headset, and made another call.

Within months, I wasn’t just surviving — I was thriving. That first job became my foundation. It taught me the fundamentals: persistence, active listening, and how to adapt on the fly. Skills I still use every single day.

The Letter I Never Sent

Years later, I was in my first management role — a sales manager with a growing team. On paper, I’d “made it.”

In reality, I was in one of the most toxic environments I’d ever seen.

I wasn’t just competing with other managers — I was being targeted by them. Some were actively monitoring my team’s calls, looking for mistakes to get my people written up. Others were blatantly cheating to hit their numbers. There were politics, favoritism, and invisible knives everywhere.

I was exhausted.

One night, I sat at my computer and wrote my resignation letter. Every word felt like a release. I saved it to my drafts folder, ready to send.

But something in me hesitated.

Instead of sending it, I decided to double down. I fought for my team. I learned how to navigate office politics without losing my integrity.

And here’s the twist — that same year, my team and I won one of the company’s top awards. It was the first of 14 times in my career that I’ve won the highest recognition in a company.

Early Days at Microsoft

When I joined Microsoft, I was thrilled — but I also almost quit multiple times in those early days.

I came from environments where the rules were clear, the scoreboard was simple, and the playbook was straightforward. At Microsoft, the learning curve was vertical.

It was hard to stand out. Hard to find my rhythm. Hard to drown out the noise.

I questioned if I’d made the right choice.

But every time I considered walking away, I asked myself:

“What if the breakthrough is just on the other side of this wall?”

I stayed. And because I stayed, everything changed.

The Wins That Never Would Have Happened if I Quit

If I had walked away at any of those moments, I wouldn’t have:

Published 6 books — sharing the mindsets, strategies, and stories I’ve lived.Developed a Moneyball-style sales engine that’s been taught to sellers in 11 countries.Generated over $1 billion in revenue through relationship-driven selling.Been featured on over 300 podcasts around the world.Built a career I love, with relationships that have changed my life.Won the biggest award in the company 14 times.The Truth About Quitting

I’d love to say I stayed because of unwavering self-belief. But that’s not always true.

Sometimes I stayed out of sheer stubbornness. Sometimes to prove people wrong. Sometimes because I had already invested too much to walk away.

Here’s what I’ve learned:

The reason you stay doesn’t have to be noble. It just has to keep you in the fight.

Once you push through that low point, the view changes. The skills you gain, the confidence you build, the resilience you develop — they become your armor for the rest of your career.

The Power of Staying in the Fight

Looking back, every time I almost quit became a turning point:

That call center job taught me persistence.That toxic management role taught me leadership under fire.Those early Microsoft struggles taught me patience and the value of the long game.

If I had quit, I wouldn’t have the career, the lessons, or the battle scars that make me a better leader today.

So if you’re in that place right now — staring at a resignation letter or replaying “I can’t do this anymore” in your head — take a breath.

The moment you want to quit the most is often the moment right before everything changes.

Your Turn

I’ve almost quit more times than I can count. But I never have. And that’s why I’m here.

Now I want to hear from you:

When was a meaningful time you almost quit… but didn’t?

What happened next?

Your story might be exactly what someone else needs to hear today.

#Perseverance #CareerGrowth #Leadership #Motivation #SuccessMindset #SalesLeadership #Resilience #Inspiration #NeverGiveUp