15 Ah-ha Moments That Inspired Entirely New Career Paths


At some point in our careers, we all question whether or not the course we’re on is right for us.

Some of us just push on, sticking with what social norms have taught us. Others find a way to start over; we become inspired to do something different (sometimes much different!) than what was always expected of us.

To learn more about the inspiring moments that led to a different career path, we asked members of the Young Entrepreneur Council (YEC) this question:

When did you know the 9-to-5 grind wasn’t for you… and what was your “Ah-ha” moment that led you to seek out something different?

Here’s what they said:

When the Grind Wasn’t About What Was Right for the Client

I never had a “normal” job until after I sold my first company and became an executive at a huge insurance brokerage firm. That’s when I learned that what mattered was appearance inside of the company, instead of what was right for the customer. No matter what I did, it didn’t change that basic fact. So I left and started another company… and I couldn’t be happier with the choice!

Bob Morrell, Riskonnect

When I Realized Monday Was My Favorite Day

Ask most people what their favorite day is and they might answer Friday, Sunday or Hump Day. For me, it’s Monday. I love coming back after a weekend of rest and starting a week of nonstop, relentless work. It’s the oxygen for my lungs. There is nothing that will stop me, bursting right past the 9-to-5 hours. Every job I ever took started before 9 and never ended. 9-to-5 is not in my vocabulary.

Joe Apfelbaum, Ajax Union

When I Noticed I’d Been Fired or Had Quit From Every Job

Every single job I’ve had has resulted in me either telling them what I don’t think they’re doing correctly and getting fired. Or telling them what I don’t think they’re doing correctly and them not paying attention to me, which lead to me getting frustrated and quitting. I just realized I couldn’t hold down a real job!

Liam Martin, Staff.com

When I Realized My Wanderlust Was Important

All it took was one spring break trip and I was done for. I went to Mexico with some college buddies, and we all went around talking about the kind of lives we wanted over the next five years. I couldn’t help but notice all of my answers kept mentioning freedom. I knew it then: I wanted a career that allowed me to be free, travel and explore. It’s the opposite of a 9-to-5 in every way.

Rob Fulton, Audio Luminaries

When I Was Trapped in the Real Life Office Space Film

After a few months in the corporate world, I looked around and realized I was living in the real life Office Space. I had five bosses, a tiny cubicle and couldn’t even answer what I did exactly. My best friend worked in an office building next door, and after a few months of shared misery, we decided to start our own business and create a place that was the opposite of our corporate world experience.

Omar Soliman, College Hunks Hauling Junk

When the Bureaucracy and Lack of Meritocracy Became too Much

The Nine-to-Five (or 5-to-9 in my case), I ran into as a junior officer in the Army was constrained by the bureaucracy (and lack of meritocracy) to make decisions that could save the millions of dollars and thousands of hours. Junior leaders/innovators in the startup world make decisions and lead change at the lowest level. This drove me away from bureaucracy and into the ultimate meritocracy of startups.

Patrick Henshaw, Strap

When I Wanted to Create Something I Hadn’t Seen Yet

I’ve always believed that starting a business is more about having an original idea than possessing an entrepreneurial spirt. I never thought I’d be a business owner, but I realized the only way I could make the things I wanted to make, the way I wanted to make them, would be to set up something on my own. It simplified the process — eliminating the layers and process that were getting in the way originally.

Keith Cartwright, Union Made Creative

When Seeing Missed Opportunity Drove Me Crazy

Being frustrated at a corporate job is not what will drive your success as an entrepreneur. I didn’t leave the corporate world out of frustration. I left because seeing missed opportunity and problems that could be solved kept me up at night.

Rob Nelson, Grow

When I Was in a Cubicle on a Gorgeous Friday Afternoon

My “ah-ha” moment arrived when I was still in college doing an internship at a large telecom company. It was a beautiful Friday afternoon, and I was stuck in a cubicle; at that moment, I realized I was willing to work long hours but preferred them to be on a schedule that I could choose.

– Jay Johnson, Small Lot MN

When I Started a Business as a Teenager

I learned this lesson in my adolescence. I grew up in a house that bordered a golf club and quickly realized there was a small fortune to be made finding and re-selling golf balls. I would spend hours scouring the wooded areas for balls, cleaning them off and selling them back to golfers. I quickly fell in love with the idea that the more time you put in, the more you get out.

George Loucas, BAKED FX

When I Wanted to Do More

At 16, I worked at a prestigious fashion showroom, and I remember thinking: I’d rather work 16-hour days if we were busy, but I hate sitting around if there’s nothing to do. I wanted to do more. Everyone else was just happy to make money doing nothing. In every other 9-to-5 I had I saw the same thing: people happy just wasting their time. I knew life was too short to waste, and that wasn’t for me.

Alexis Wolfer, The Beauty Bean

When the More Money I Made, the Less Happy I Was

I spent years climbing the corporate ladder as a developer turned manager. As a manager I realized how little freedom I had. The big “ah-ha” moment came when I was ordered by HR to give a developer on my team a written warning (for making a coding mistake). He was a great developer, and I didn’t agree with the warning but didn’t have a choice. He actually cried when I told him. That was the moment.

Ruben Gamez, Bidsketch

When I Paid Over $200,000 to Become a Specialized Cog

Four years of medical school convinced me to run my own business. In medicine, I felt no sense of progress; when you’re done with one patient, there’s another waiting to be seen. In medicine, I couldn’t build anything; I had to follow protocol — it’s the job. There was no progress in using our tools. The progress is only in building them. I found freedom in entrepreneurship.

James Console, Antlion Audio

When I Was Excited by Entrepreneurship at Age Nine

I’ve wanted to be an entrepreneur since I was nine and watched my brother start and grow a company. Being in his office was much cooler than going to our parents’ offices for “bring your child to work day.” Though both of my parents were satisfied with their careers, their jobs were just that: jobs. I knew I wanted more; I wanted passion and a lifestyle. I wanted to be an entrepreneur.

Catherine Cook, MeetMe

When I Realized My Need for Impact and Identity

I wasn’t able to see my impact after a day at a 9-to-5 job. I wanted to have a career where every project, spreadsheet, powerpoint and day helped build something that hadn’t been done before. So, I decided to take matters into my own hands and create a company where I could go in every morning knowing that I would be making a difference.

Abby Ross, ThinkCERCA




Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.



This entry was posted in Career Advice and tagged , , , . Bookmark the permalink.