Rich Girl, Poor Girl, Competing on the Career Path

This is a true story. One girl, whom we’ll call Rich Girl, was born to a 1%-er wealthy family. Another girl, whom we’ll call Poor Girl, was born to a family of very limited means that afforded her no free rides in support of her education.

I’ll start with the conclusion: Rich Girl is now relatively poor and struggling to live according to her expectations. Poor Girl is now quite wealthy, and will have the option to retire within her 40’s, with a lovely house paid off, and lots in the bank. She has exceeded her expectations.

I have been a friendly observer of the careers of both and I’m unable to ignore how markedly their stories, when placed in parallel, would create a picture-perfect Aesop fable, if only they were to have been born turtles or rabbits instead of humans.

Where did Rich Girl go wrong?

Rich Girl chose to stop working while raising kids, though she participated on the board of a charity group during that time. When she chose to return to the workforce, she explained to an interviewer that her charity work was just like sales as they had to set and attain a specific dollar-based goal. She was surprised and indignant when the interviewer rejected her, saying she didn’t have experience to compete for a professional sales manager role after being out of the workforce for a decade.

So where’s her fault in that? In the ten years following the dot-com boom and bust, the salesperson’s job transformed from ‘keep calling, and try taking them out to lunch again” to a complex maze of decisions based on data insight tools and predictive software in order to optimize sales achieved vs. effort and cost invested to achieve them.

The world of sales had markedly changed. To assert in an interview that “I’m sure I can pick it up” is an insult to every other sales professional who had remained in the workforce for those ten years and who had stayed up until midnight each night massaging metrics and wrestling analytics reports, while juggling kids, family, and everything else life throws as you. The ignorance it took to utter those words undressed her professional naivete and old-school sense of entitlement.

Rich Girl’s Next Move

She secured a job with a charity organization. The pay was lower than what she sought, but there was great work-life balance (with the ability to leave at 4:00 p.m. some days to see her kids’ sports matches). She was given that job because there was a degree of alignment between her charity-based activities over the last decade and the skills this employer needed. In that job she was to be a central networking cog, providing a golden opportunity to get to know hundreds of high-influencers. Had she stayed, that job could have served as a means of establishing a fresh and powerful network of people who could catapult her upward in her career, once she’d invested several years to demonstrate her competence.

Unfortunately, she left that job within months of taking it. She got a call from a company that had received her resume several months earlier. The job paid $15,000 more than her existing non-profit organization job. Soon after taking the new job, the extra $15k seemed worth little when she realized everything else in her life had to go out the window. The new company was like a jail cell to her. They tracked the activities of sales people down to the minute, from her hours at her desk to her hours on the road. Her sales calls were pre-scheduled and there was no opportunity to leave early to pick up her kids or see their afterschool games. She hated it and went on an aggressive job search, hoping to prove true the old adage “3rd time’s a charm.” She started sending out her resume again and reached out to friends for help with finding opportunities.

One friend gave her a magical gift. She gave her the direct phone number of a sales director who was briefed and ready to talk. Rich Girl spoke with the executive and then let the conversations die; she was offered a job, but she wouldn’t take it. She explained “They wanted me to sell door-to-door. There is no way I’d ever do that.”

But the friend who’d referred her said “but I connected you with an executive who knows your experience and if she sees you investing time to understand the market and the clientele, she’s in the position to give you an area director role in the future. But you’d just need to start out showing her you’ll put in the time to really get to know this product and this market.” No way, said Rich Girl still, though she very much wanted the the area director role. After that, Rich Girl’s career went through a lot of bumps. She earned herself an extensive period of unemployment, and lots of trial-and-error gigs. Her income since has not exceeded either of the first two roles.

Where’s the fault in that?

I think you’re probably with me here. There were a lot of mistakes in Rich Girl’s choices. The umbrella theme, however, is a bit like the story of the tortoise and the hair. You’ve got to think more about the long game vs. the sprint.

A strong desire for immediate success is great. But sometimes plugging along without control over the outcome is what you need to do to build in-demand skills and earn the trust of experienced leaders. Showing up day after day, even if it’s for a door-to-door gig, makes you someone special to an employer. Many job tasks can seem below you. But year-on-year you realize that every bit of miserable hands-on experience improves your intuition and your credibility. You’ve touched the actual product in the warehouse, you have handled difficult customers and found a way to win them over. You know the core of the business.

When you take a job, it’s not about that job, it’s about the skills, experience and network you build to get you the next job. And for someone who’s hopped off the job path for a decade, to win a gainful opportunity, you are going to have to be flexible, willing, and full of faith about the future. You don’t know what you don’t know until you do the job for a while. You’re going to have to give up the thought of “a great job today” but rather seek “a strong leader for whom I can prove I might be great tomorrow.”

In addition, Rich Girl was cutting off her nose despite her face by revealing, to employers and to the friend who referred her, that she believed an employer had a duty to overlook her shortcomings and risk factors, but that she was not beholden to make a compromise in return. Businesses seek people who advocate for the business, getting their own needs met while ensuring any decision is good for the business. So her mindset alone was like writing at the top of her resume “I’m likely to be high-maintenance and I may not always make choices that benefit the company.”

And another huge mistake Rich Girl made was asking for help from friends, then throwing their efforts in the garbage. Rich Girl broadcast a call for help and her friend stopped her busy (gainful) activities to make a phone call. The friend put her own reputation on the line, saying to her sales executive contact: “If you interview my friend, Rich Girl, it’ll be worth your time; she’s eager and hungry for opportunities to learn and grow.” Well, Rich Girl made a liar out of her friend. For the foreseeable future, the friend and anyone else in that social circle is not going to respond when Rich Girl cries wolf.

A Heartbreaking Story Called Reality

It’s heartbreaking, yes. But it’s just reality. Life is about choices and consequences for those choices. One of the biggest mistakes Rich Girl made was ten years prior, by not understanding that career decisions are never light switches that can be flipped on and off. Career decisions are like forks on a railway. The train is moving fast. Once it veers left or right, it can’t easily turn around and the landscape is going to change before it gets the chance.

So it’s sweet when someone wants to stay home with the kids. And I fully respect that choice. But I don’t respect entitled whines about how unfair it is that after X years in the workforce, one is dropped to a lower rung on the career ladder just for taking a decade off. The workforce isn’t waiting around for you to say “I’m back!” The business world is moving forward every minute and the best jobs are constantly being eyed by—and vied for—by better and better candidates. It is vital to understand that in many industries and professions, when you step away, you will need to be very flexible and creative if and when you choose to step back in.

Anecdotally, a related harsh reality is that, in life, mastering the science of contraception is as important as mastering the art of career management. The world must be peopled—it’s true. But you shouldn’t ‘people it’ until you’ve got key career cred under your belt. It’s sweet to imagine that employers should give limitless flexibility to all employees, but the bottom line is the first ten years of your career are the ‘maximum give, minimal take’ years. It’s hard to build the traction, the momentum and the reputation you need to succeed if you have kids too early. After the first decade you can start making demands in your interviews like “I don’t want to travel,” or “I have to be home by X for my kids.” But until then, cross your legs or use a condom.

Poor Girl’s Career Story

It’s the uncannily perfect mirror-image drawn by Poor Girl’s tale that compelled me to write this article. Take a look at what doing the right things, for the right reasons, even when nobody’s watching (or paying you jack) can bring you.

After college, Poor Girl wanted to go into sales but didn’t have a job lead, nor any sort of highfalutin network of parents’ friends to help springboard her into a great first opportunity.

What did she do?

She took hold of a diamond in the rough, with no knowledge of what it was worth, and made her own success. She put on a hair net and served up food samples at a food club warehouse. While her friends may have been traveling to exciting cities, or dressing up for evening art shows for their corporate jobs, Poor Girl humbly and dutifully served up meat samples to passing strangers.

And she did not mentally check out as she served them. She used every minute to study and learn. She studied what drove people to stop and try samples. She studied what questions people asked. She studied the layout of the store, and what visually attracted buyers’ eyes. She observed the behaviors of shoppers in morning, vs. night, in busy times vs. a lull. She modified what she offered, and how she offered it. She talked at length with shoppers: do you stock up with a lot of meat all at once? Or do you like to come back often in search of new varieties?

Careers: You've got to pucker up with some unglamorous tasks to get needed experience.And she didn’t do this just one day, for a lark, running home to exclaim to her friends how awful and nasty it was. No, she humbly returned day after day, energetically enticing shoppers to purchase her food brand. And like a fairytale ending, she is now the owner of an indisputably successful sales business. She works—A LOT—but because she invested many years carefully building a reputation, a pipeline of loyal clients, a company, she enjoys more than just money today, she enjoys immense security for the future as well as a lot of flexibility in terms of how she runs her life. She can retire early, but if she chooses not to, she’s earned herself levers of control over how much she works, how much she plays, how much time she spends with her kids, and more.

This story is too ridiculously perfect. But it’s true. And it’s a lesson for me, and for every person who seeks to change their career path, or re-enter an industry, or find their first job. If we release from our attachment to the outcomes, and rather focus on the day-to-day inputs, we will slowly but surely amass a mountain of experience that will propel us to where we want to be, some day off in the future. Decoding business to manage your life therein.

Mary Heckert is a corporate communications consultant who blogs for, a collection of straight-talking explanations of how businesses and careers really work.