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The Worst Job I Ever Had

Mona Bushnell
Mona Bushnell

Find out the advice these 13 successful people would give their younger selves.

There's a tendency to look at successful people, in any field, and think, "Wow, they're lucky." But how much of that "luck" is really hard work, determination and resilience?

In honor of the idea that some people end up in their dream jobs out of sheer luck, we rounded up 13 "lucky" people who say they have their ultimate dream jobs. We asked them what they do for a living now, what their worst jobs ever were, and the advice they'd give their younger selves if they could.

As it turns out, a lot of CEOs and business owners started out their careers doing things like scrubbing toilets, working in fast food restaurants, and even donning character costumes and dancing on the street. While the stories, paths to success and even definitions of dream jobs vary widely among our respondents, there are some common takeaways.

When describing their worst jobs ever, for example, nearly every person we heard from also took the time to point out positive things they learned at those challenging jobs. Even when the jobs included abuse from bosses or gross tasks in unpleasant circumstances, our dream job-havers were sure to point out a silver lining. Most respondents also mentioned the importance of having a positive outlook, building resilience, staying focused on goals and, of course, being persistent.

Here's how our lucky 13 dream job-havers found their success, and how they survived the worst jobs of their lives.

Immigrant factory worker turned star attorney

Currently serving as director and immigration group lead attorney at Fennemore Craig, Margo Chernysheva is the type of woman other people aspire to emulate. She has an impressive career and loves working her dream job, helping people and changing the world, but her path to the top of her field was far from easy.

"When I first immigrated to the United States, I did a subcontracting job tying, closing and cutting strings left on just-made, new-sewed clothes for a factory," Chernysheva told us. "I would sit for hours at night after English school with all these large bags of clothes. I really needed this work, and I was paid $20 per large bag in which there were many pieces of clothes. ... By the time I was done with three bags, I could not feel my fingers or my back. But it paid for a week of food for our family, and so I had to do it."

After leaving her job in the factory, Chernysheva went on to work 12-hour shifts, for minimum wage, as a dental assistant.

After years of hard work, Chernysheva's dedication paid off.

"I am living my American dream," she said. "I am an immigrant who came from nothing and did a lot in my life to achieve where I am in life. When I first came to this country, I was not sure if I would ever succeed, and so, on that airplane between D.C. and LA, I was the last person I wanted to be. Twenty years later, I was on the same flight, and I did not want to be anyone else but me on that airplane."

A CEO who started at the bottom – literally

Paige Arnof-Fenn, the CEO and founder of marketing firm Mavens & Moguls, jokes that she "started at the bottom," and she did … marketing toilet paper. She says of her time in the TP business, "those are focus groups I would not recommend," but thanks to her sense of humor and drive, Arnof-Fenn was eventually able to build her own marketing firm and create the career of her dreams.

She has lots of advice for people who are still finding their way, including being flexible and unafraid of failure and detours. "[Career] really is a marathon, not a sprint, so do not set arbitrary goals like being named '30 under 30' or '40 under 40,' because it may take you longer than Mark Zuckerberg to hit your stride and that's OK. Most people take many detours on their career path before finding their true calling. Don't be disappointed if you get to 40 and are still exploring, because the journey really is a great adventure, so enjoy it!"

Arnof-Fenn is also a big believer in being a lifelong learner and redefining your vision of success as your life goals change.

Pool cleaner to CEO and author

Joe De Sena is a bestselling author as well as the CEO and founder of Spartan, a company that hosts intense obstacle course races all over the world. Today, De Sena is living the dream. "Every single day, I wake up excited and motivated to work. This is a feeling I never had before launching Spartan. It is unbelievably rewarding when you wake up every day motivated to not only succeed, but [also] inspire other people to face challenges and succeed."

De Sena's success, like many entrepreneurs', was hard-won. In fact, he used to spend his days cleaning other people's pools.

"For over a decade, I spent every single day cleaning out swimming pools. I started it as a child, and even though it grew into a full-fledged business, you couldn't pay me to go back and clean out pools … especially because they were usually filled with black water and loaded with creatures."

As for his advice to his younger, pool-skimming self, "I would tell myself to stop complaining. I'd look myself in the eyes and say, 'Do the work, do it well, and although you don't see the light at the end of the tunnel … it always comes.'"

Conveyor belt counter to actuary and professor

Dr. Mark Farrell loves his job. "As an actuarial science university professor, I get to research and help solve interesting problems as well as working with and teaching some of the brightest minds." Long before he landed his position at Queen's University Belfast, Farrell toiled in a building products factory. "My main role was to stand at a conveyor belt and screw the tops onto various bottles as they made their way to me on the belt. All day long, eight hours a day, for six months, screwing bottle tops! I used to count the bottles and see how far I got to try and relieve the boredom. One day I got to 5,000, yet the day hadn't even finished!"

Eventually Farrell decided bottle capping wasn't for him, but he learned a lot during his months in the factory. He says if he could go back in time and give his younger self advice, he'd say, "Don't let others manage your career. Generally, no one will care as much about your success as much as you do. It's all too easy to take a back seat and be reactive instead of proactive in terms of choices that will affect our careers in the long term ... We often don't realize just how much power we have in different situations and that, instead of accepting the status quo, we can take the career bull by the horns and drive our career in the direction that makes most sense for us."

Sumo chicken boxing rings to executive coaching

You read that right – Toku McCree started out his working life in a very unusual way.

"I once ran a sumo chicken boxing ring for various fairs in Nashville, Tennessee. My job was to convince people to dress up in chicken costumes in the hot sun, put on giant boxing gloves and go at it in an inflatable ring. The job itself was actually pretty cool, but my boss was unreliable, paid us late and didn't really train us on how to do the job. But it was great experience learning how to sell."

McCree continued to collect eclectic work and life experiences, including living in a Zen monastery and touring with a Top 40 rock band. In fact, he held more than 30 jobs before his 30th birthday, but eventually he became his own boss and his old selling skills came in handy. Now, McCree runs Samurai Coaching Dojo, where he helps other entrepreneurs and coaches realize their dreams, and he loves it.

His advice to his younger self is focused on patience and enjoying the journey: "You'll get there. It takes time, but you have to just keep the faith and keep trying things out. What you learn along the way will really help you when you find what you want to do." 

Dirty fast food to clean laundry

Brie Young is a great example of someone who found her dream job in an unexpected place. For her, the perfect job is all about quality of life and everyday enjoyment, and she finds that in her job doing laundry for users of Laundry Source

"While [doing laundry] doesn't sound like the type of glamorous job most people probably talk about when they describe their dream job, it is amazing," Young said. "I love how flexible it is, how you get to make your own hours, helping people, and honestly just making things clean."

She also loves the way her job helps her clients. "It is absolutely amazing to find a stain a client might not be able to get out themselves and to find a way to get it out for them – to see new mothers longing to spend every moment with their child while they are still little and be able to give them even just a few hours."

Young didn't always like her job. Like many young people, she put in time as a fast-food worker, and she hated it. Everything from the gusts of freezing cold air through the drive-thru window to the crackling headsets was a daily challenge. "It was a rough time … I can't even imagine going back to where I was then."

Things are easier now that she can set her own hours and do something she enjoys, and her advice to her past self is to be patient and persevere. "I'd tell myself to just keep working till [I] found the job that fit."

From overworked accountant to independent blogger

Logan Allec owns and operates the personal finance blog Money Done Right, but before he became his own boss, he spent years as an overworked CPA.

"Right out of college, I got a job as an entry-level tax accountant," he told us. "The hours were unbearably long – 50- and 60- hour weeks were the norm, and there were even a few 100-hour weeks in there during busy season. One time I worked 36 hours straight to get a job done!"

Despite the unpleasant workload, like many of the successful people who reached out to us, Allec found a silver lining, which for him was clocking plenty of overtime and using that money to pay down college debts and start investing. That simple act of getting his finances in order ended up propelling him toward his eventual path as a personal finance blogger.

His advice "to those who may feel they're stuck in a tough job situation is that just because you chose to pursue a certain career path when you were in college doesn't mean that that is what you have to do the rest of your life. For example, I'm a licensed CPA … I worked in the industry for nearly a decade. And even after all that effort to pursue my Plan A, I left that potentially lucrative career path to become a blogger, of all things … Life just might surprise you – but you have to be open to surprises."

Company president who used to assemble boxes

The president of Medicare Portal, John Norce, looks every bit the part of the successful businessman he is. Even better, he loves what he does. "I enjoy being an entrepreneur and facing the daily challenge of building a business from the ground up. There is no aspect I do not enjoy, and there is no task or job I won't do."  

Like most people, though, Norce started in a much less glamorous position. "[The] worst job I ever had was putting together freight boxes at a freight-forwarding company on the campus of JFK Airport … I never complained, as it paid well and I needed the money to pay for college. I learned so many life lessons from this experience, and today I [use] this experience … to make sure I develop a healthy, productive and fun work culture."

His advice to his younger self, and to others just starting out, is to try everything, whether you try it through volunteer opportunities, groups at work or community organizations. He also believes in reading, being a lifelong learner and never giving up. "To be successful in life, one must develop mental toughness to get through life's adversity and challenges. Adversity or bad jobs build character, and strong character is at the core of all successful people." 

From working in the kitchen to owning two law firms

Russell Knight, who today owns and operates two law firms, had a doozy of a worst-job story, but he still eventually made it to his dream job.

"The worst job I ever had was in college at a fast-food Italian restaurant. I was literally the only college kid working in the kitchen. Everyone else was on work release from prison. That meant that they were nearing the end of their prison term, so they were released during the day to work and they would go back to a prison or halfway house at night. … They were all desperate for overtime … so the pace of work was incredibly fast and hard. It was 100-plus degrees in the kitchen, and we were always on our feet and always moving for eight-plus hours a day." 

While that experience might have crushed some people's spirits, Knight used it as motivation. He said he knew that doing back-breaking work in a high-stress environment, for very little pay, was probably as bad as it was going to get, so there was nowhere to go but up. Now he enjoys his life working in an air-conditioned office, operating two law firms, and helping his clients while making a great living.

Toilet cleaner to CEO

Daniel Steinfeld, the CEO of On The Block Realty, credits his success largely to his positive outlook, which he kept intact even through some tough jobs, including one at a chicken wing joint where his main tasks were cleaning dishes and bathrooms, as well as putting up with his boss's unpleasant sense of humor.

"It's not that the job toughened me up," he said. "I didn't feel like a victim ... but if it did anything, it showed me I could find the positive in even the seemingly worst of situations. I made friends with the kitchen staff, we made up songs to actually make the nasty work fun, and I used the somewhat demeaning banter from the boss to talk up the regulars."

That ability to make the most out of any situation helped carry Steinfeld through many other jobs, from boring auditing positions to mundane client work, and now he tries to pass the lessons he's learned to his staff. "The 'make the most of it' and 'find the positive' mentality has served me well throughout my career. … Not every job is rainbows and sunshine on the surface, but it is always what you make it. " 

From loading trucks to climbing mountains – with an MIT degree

Steve Silberberg took a circuitous route to his dream job. He said his worst job ever was loading mattresses into trucks in the middle of a scorching summer, for a measly $3 an hour, in 1979. That job was short-lived, Silberberg said, and he eventually went on to higher education, even earning a master's degree from MIT. That wasn't the climax of his story, though: Silberberg didn't want to stick with his technical expertise, so he started his own business.

"I love what I do now," he said. "I started a business that takes people on backpacking adventure vacations to get fit and lose fat. It's called Fitpacking. I spend all day in the wilderness climbing towering mountains, gazing upon bright stars at night and walking among wildlife during the day."

That said, Silberberg would do things a little differently if he could. "If I could go back in time, I'd tell myself to stay with tech jobs until I made my fortune."

Cheesy villain to author and leader

For six short months, Michael O'Brien was famous, in the worst way possible for a teenager. He played Mr. Munch, the villain who stole Chuck E. Cheese's pizza, at his local Chuck E. Cheese. Still, his time as a costumed character was informative. "I learned humility, because it wasn't the coolest job in the world – especially with the girls. I discovered the importance of having a villain to create drama in any good story, and I also learned that the belief that 'there's no bad pizza' is a myth."  

Nowadays, O'Brien is busy working in his dream job as chief shift officer at Peloton Coaching and Consulting, which he jokes is a "much more fulfilling job than playing Mr. Munch." He also wrote a successful memoir, Shift, about his close brush with death during a cycling accident, and his subsequent recovery and rediscovery of life, values, and the power of mindset.

His advice to anyone struggling in their jobs is to take a moment and breathe. "We all spend too much time on the hamster wheel with our head down, grinding away. It's essential to look up and breathe to ensure that we are headed in the right direction, because if you don't know where you are going, you may not like where you end up." 

Bartender and gross-task accomplisher to creative entrepreneur

These days, Sally McAdam, director of Hand Over Your Fairy Cakes, can be found working from her Glasgow home, where she manages her three employees and dreams up stylish and unique accessories, clothing, and stationery for her successful business.

However, at one time, you could have found McAdam pouring drinks at a local pub and intermittently doing unpleasant tasks like cleaning up vomit and mopping bathrooms.

"In some ways it was excellent, as the hours were flexible, the people I worked with were a lot of fun, and I enjoyed serving drinks," she said of her toughest job. "However, if customers became drunk and aggressive, it was a pretty scary experience, as I was frequently in the bar on my own on weeknights." Plus, there was always the gross-out factor. "Once I found someone's underwear in the toilet and had to fish it out."

If McAdam could go back in time and give her younger self advice, she'd say, "Value your own work and time." She says she'd also advise herself to be less afraid of turning down tasks and saying no.

"I used to sell my products for far less than they were worth, sometimes even less than the cost to make them, and would frequently agree to projects and events that I knew would not be good use of my time, mostly because I didn't want to let people down. I've learned to put myself and my business higher up my list of priorities, and I am much better at saying no when I need to."

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Mona Bushnell
Mona Bushnell Staff
I'm a Staff Writer for and Business News Daily.