On Millennials, Power, Entitlement, and My Own Path to Career Success

A response to Paulette Perhach’s request for Millennial career advice

Nicole Dieker
The Billfold
Published in
7 min readFeb 29, 2016

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Photo credit: David Pursehouse, CC BY 2.0.

The year after my college graduation—which was the year I moved to Minneapolis because I had received an unpaid internship that disappeared after I arrived (the theater director for whom I was supposed to work had to take a leave of absence), and then became the year that I worked as a telemarketer and, when I needed more money, quit telemarketing and started temping at an insurance company—was by far the worst year of my life.

Catastrophically.

It wasn’t just the money factor; I made $9 an hour plus commission at the telemarketing agency and $13 an hour at the insurance company, but I was already pretty used to feeling constantly broke as a college student, in the definition of “broke” that means “ramen and thrift stores” and also means “having parents who will pay to fly you home for Christmas.” I had yet to pick up any financial vices, simply because I did not have the money for them.

I paid for everything in cash, because my parents had taught me that credit cards were bad and I had not yet encountered a financial emergency that would cause me to reconsider that assumption. I packed my lunch every day and wore the same five “office outfits” every week. At one point my temp boss gave me a pink cable-knit sweater that “didn’t fit her” and I was too embarrassed and/or proud to wear it to work.

So I wasn’t digging myself into a hole, financially. I wasn’t digging myself into a hole career-wise, either. There were definite hints that, if I was interested in turning my insurance job into a permanent position, my temp boss would be more than happy to bring me on.

But I was miserable. The definition of miserable that means “come home after work and cry because your life has no resemblance to who you are.”

If I had made enough money to go out and make friends, or buy healthier and more nutritious food, or wear a pair of pants that didn’t stink like sour polyester by the end of every day, I might have felt a little less miserable. But there was something else going on here, and it had to do with the fact that—even though my temp boss wanted to hire me permanently because I showed up on time and stuffed envelopes in a windowless room all day without causing trouble—more than one person said I did not fit in at the insurance agency.

When someone says that you do not fit in to a job that you perform primarily by yourself in a windowless room, they’re saying you do not fit in to you. The discrepancy between who I was and what I was doing, even though I was trying my best to have a good attitude about it, was so strong that everyone around me saw it.

And I had no capacity—financially, socially, or professionally—to change that.

So I was miserable.

That was when the adults a generation or two ahead of me, the people whom I thought were part of my support team, started calling me entitled. I had a job. I was one of the lucky ones. I should stop complaining.

I didn’t feel lucky, and I didn’t feel like I wanted to stop complaining—or, at least, I didn’t feel like I wanted to stop here, in the windowless room with the stacks of envelopes, and say “this is my life now.” I did some research, came to the conclusion that everyone who had a job I wanted also had a master’s degree, and went to graduate school.

Graduate school, as I’ve mentioned previously on The Billfold, taught me how to function in a professional environment. I was told, in these exact words, “you need to learn how to play the game,” and I did.

That, by the way, is far better guidance for a 25-year-old than saying “you are entitled and presumptuous,” even though in many ways it means the same thing. In my subsequent jobs, the discrepancy between who I was and what I was doing was still present but it was both less visible and less relevant, because what I was really doing was playing the game. I was figuring out how to be successful within a company, which is completely different than figuring out how to do the tasks of a specific job.

I still packed my lunch every day, but my clothes got better. My finances were in order and my 403(b) was filling up with cash. My social life improved, even though I still felt awkward in nearly every social situation because there was still that hidden discrepancy between who I was and what I was doing.

And, because of that, eventually I quit. The job, the company, and—in many ways—the game itself. I took the lessons I learned about how to succeed in a professional environment and started to build the set of skills that would allow me to be hired for who I really was.

At this point I went back into what you might consider “broke life;” I slept on the floor of a group house share for a year, and then spent two years living in that microapartment where I washed my dishes in a bucket. But even though I was both broke and in debt, I knew that I was building a different kind of value. I was building a career where people would say “I want to work with Nicole Dieker;” turning who I was into a fundamental part of what I was doing and what people would pay me to do.

So that’s how I got out of what, back when I graduated from college, seemed like my own powerless situation—even though it took me almost 10 years and a pile of debt to do it. Paulette, you might consider this “how I built my Suck It Skills,” and you’d be right. I do feel like the layer of “how to play the game” is just as important as “how to build the skills,” because that’s how you push through those entitled Millennial assumptions and get to the real work that needs to be done.

It may also be that many Millennials need that decade—the one you and I both took to get our lives and our skills sorted—before they’ll start seeing career success. This is ridiculously unfortunate, because it seems like such a waste of both talent and life. I don’t believe that it’s presumptuous to want a job that both provides financial security and helps you build a career, and I hate the idea that we have to spend ten years scrambling around and sleeping on the floor to get there.

(Also, I loathe the idea that if you’re not grateful for your $10-an-hour job and your floor futon, you’re an entitled Millennial. Like talia jane, I have gone to bed hungry and slept with all my clothes on under a pile of blankets because there was no heat. You shouldn’t have to do that as the first step towards “making it.” Nobody should have to do that, especially if they have a full-time job.)

Now I have to list all of the “if anything had been differents:”

  • If I had health issues
  • If I had significant caretaking responsibilities
  • If I did not grow up middle class (and white)
  • If I was not quick to learn and retain information
  • If I hadn’t had a computer in the house since I was in elementary school
  • If the internet hadn’t accelerated the growth of freelancing and freelance writing opportunities
  • If my particular style of interacting with the world (specifically, combining personal stories with a strong liberal arts background, an epic knowledge of pop culture, a bit of humor, and a willingness to be transparent) had not suddenly become very valuable

And so on. Building my skills and learning how to play the game was important, but I also got very lucky, and it was a different kind of luck than “you’re lucky to have any job!” response I got back in 2004, because this time I actually feel the luck like a tangible presence, the mortar holding all of my skills bricks together.

Paulette, you asked us what advice we’d give to people who want to dig themselves out of a hole and pursue their dream jobs, and I guess I’d give some combination of “learn how to play the game” and “build the skills that are closest to who you are,” which also implies that the people reading this advice associate who they are with what they do, which is not always the case. (It is very much the case for me.)

But I’d also note that the rules and the game are constantly changing, and it may be harder for people to find paths that lead towards winning conditions. It’s not lost on me that talia jane earned less as a customer support worker in 2016 than I did as a telemarketer in 2004, and she’s paying twice as much as I did in rent. Could I recreate my career path today, if I were a recent college graduate with no money and only a smattering of work-related skills?

So I don’t know. I’ve told my story, shared what worked for me, and now I guess I have to pass the baton to the next person, who can add their story—and their advice—to yours and mine.

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Nicole Dieker
The Billfold

Freelance writer at Vox, Bankrate, Haven Life, & more. Author of The Biographies of Ordinary People.