an open letter to and from Gen Y


After pouring over Gen Y articles across a variety of mainstream media websites, I found one popular generational cliché: soccer participation awards are credited for the sense of entitlement and over-confidence within our generation.

On behalf of Gen Y, I would like to say that we have always understood that stacks of participation certificates are meaningless.

The truth of the perceived entitlement is much deeper and more complex than a red ribbon presented at field day.

I believe the issue of privilege is rooted in the good intentions of our baby boomer parents and our faithful execution of the things we were told to do. From a very young age, we were told that we were smart and capable of doing anything we wanted. We can make a difference!, we were told. On the surface, this pep talk was empowering, yet the subtle (or sometimes obvious) assumption was that our talents and natural gifts would allow us to achieve our heart’s desire. Along with this “follow your heart” compass, we were given a traditional roadmap to “be the best” by relying on our talents and smarts.

Though participation awards did flow freely, the real attention and approval we craved came from our natural abilities and quantifiable successes. Standardized test scores ranked us against our peers, expectations to be “well rounded” pushed us into dozens of after-school activities on top of honors classes, and through most of it, our natural intelligence and aptitude took us quite far.

We heard the message “work hard,” but hard work alone wasn’t what got us awards and accolades. At the end of the day, our output was measured more than our input. This allowed many, but not all, of us to apply ourselves as little as possible to get the greatest outcome as possible.

This doesn’t mean we are a lazy or entitled generation. It means that this reward-style, taught to us by generations before us, shaped behavioral patterns that sought out the easiest course of action for the most reward. “Work smarter, not harder,” might be a more apt description of our generation than anything else.

Because of our high-performance childhood, expectations increased year after year. Top college admissions criteria seemed to shift from excellence to perfection.

When natural intelligence was not enough to ensure success, pressure mounted. Test anxiety sent some, including myself, to the counseling office. Terrified to fail, others in our generation sought short cuts to bolster their natural abilities. Adderall became a common last-minute test preparation solution.

After following all of the prescribed “steps to success” throughout our education, we entered the workforce expecting to claim the fruits of our labors; not because we felt we deserved it, but because we were told that we did.

However, post-college we faced the most bleak economic landscape in recent history – often with crippling student loan debt. Trained to be high-value workers who made a difference and received lucrative salaries (in order to pay off that student loan debt), we faced layoffs, downsizing, and dead ends. Many of us were unable to find jobs. Those of us who did enter the workforce often discovered that the corporate world didn’t provide the meaning or work-life balance we sought. Career security was scarce.

Throughout our lives we followed the prescribed roadmap to success, only to face an economic climate where it no longer applied.

Thankfully, all is not lost. In order to now fulfill our lofty and optimistic vision of work and life, we must learn to develop a new set of skills. We need to take more risks, learn to fail, and persevere no matter what life throws at us. We must realize that our talents alone will not lead to enduring success in today’s shifting workforce. With humble hearts we must re-commit to our original aim. But this time we must be willing to do whatever it takes – as long as it takes.

“Work smarter, not harder” can no longer be a guise for doing a little – or a lot – of work and getting frustrated with the results. We cannot expect that things will continue to flow easily to us just because we are talented.

The good news is that there are many of us out there already taking risks, failing, and persevering. There are people doing whatever it takes, as long as it takes. There are Millennials starting their own ventures, or shifting corporate cultures to include our values. We can learn from these peers and apply these concepts in our own lives.

We must recognize the span of our careers will unfold for decades to come. Just because we were told that success would come from following the rules doesn’t mean we should still play by them. If we can apply our knowledge and gifts with consistent effort and humble endurance, we will see the promises we were sold come to pass.

We must be willing to try, fail, and begin again.

This Post Has 33 Comments

  1. Esmé

    Jess, as a fellow Gen-Yer (oof, can’t we have a better title than that?), I really loved this post. Totally agree about the combination of “learn the system,” aka SAT prep courses and teaching-to-the-AP-exam (did the latter, not the former), and the oh-crap-what-do-we-do-now economic climate. I also believe that our generation is increasingly turning toward the purposeful work that Laura Simms talks about. So thank you for writing this. I’m going to share it with my audience in next Saturday’s links round-up.

    1. Jess Lively

      Thank you for sharing! Yes, I agree too, our generation is figuring things out and finding out new ways to do purposeful work.

      We might have simply needed to take a while and figure out how to do it with a new set of skills, since the ones we were taught often no longer apply. : )

      1. Esmé

        What? You mean my incredible skills of cramming everything right before an exam, getting an A, and then forgetting it all right afterward is no longer applicable to my life? (shakes fist at heavens)

        I have a quick question, while I “have” you – what do you think about Alt Summit for introverts? I attended an online Alt Summit class about business cards and got completely freaked out, envisioning myself hiding in a corner while everyone else passed out their business-cards-enclosing-GPS-systems-that-take-you-to-their-bakery/discotheque/ballet studio.

        1. Jess Lively

          Hah! Your fist shaking visual is wonderful.

          I love Alt, and even as an Extrovert, it can be overwhelming after three full days. I’d suggest rooming with someone you know (internet, or in real life) so that you have a friend.

          If your gut tells you to go, don’t let the ‘hugeness’ of it scare you. And yes, the cards can sometimes be crazy (awesome). But I have a simple card and don’t feel bad that it doesn’t include a sewing kit.

  2. Lauren Linster

    “Just because we were told success would come from following the rules doesn’t mean we should still play by them.” I’m struggling with this every day as I trudge through my mediocre jobs (yes, plural) and 12 hour work days trying to figure out what to do differently and why the job thing isn’t working out like we were all promised. Fantastic article, Jen. I think it’s time to just reinvent. I guess I always knew this but after reading your article it’s clearer- why play by the same rules when it’s a different time?

    1. Jess Lively

      Well said, Lauren.

      I’m glad you like the topic, and even more importantly, I’m happy to hear you are thinking about reinventing and trying new things (that we may not have learned before) to get where you want to go! Bravo!

  3. Megan Berry

    it seems the job market tries to crush my spirit daily. the timeliness of this piece could not have been better. thank you.

    1. Jess Lively

      I’m happy to hear that this has come at a good time for you! Remember: do whatever it takes, as long as it takes. You are talented, now just keep going!

  4. Katie

    Love this! I graduated at the worst part of the recession and it was tough. Thank you for perfectly describing the misconception of our generation and the new challenges we face. I have since started my own business and although it will be a long road ahead I am loving the time freedom and ownership I have.

    1. Jess Lively

      I commend you for graduating during such a difficult time! I graduated 1 year before the melt-down, I cannot imagine what it would have been like to come out during 2008/9.

      Congratulations on forging your own path through perseverance!

  5. Heather

    Love this! Struggling with watching people come out of college and expecting not only their dream jobs but also an executive’s salary out of the gate. I luckily had the buffer of grad school to shield me from the scariness of graduating in 2008 but now I’m taking a different path than I ever imagined in 7 years of undergrad/graduate experience! Working smarter often means putting in lots of hours to become an expert, not assuming that your degree makes you one.

  6. Caroline Leemis

    Great article, Jess. Having graduated in 2009 and doing everything “right” through school (being active in community service and leadership positions, having a good internship in my field, graduating with honors), hitting road block after road block and hearing “no” so many times in the job hunt had me up in arms as to why it was so hard to get a good start to my career. For anyone still struggling with that, or trying to just make it through the day with a difficult and unchallenging job, there is hope. It does take perseverance and thinking outside the box. My first few years out of school contained lousy bosses, boring days with hardly anything to do at work because my boss wouldn’t let me work on anything outside of my job description, and a lot of empty promises. You have to think outside the box and expand your skill set in different ways – for me it was through blogging and trying to keep up with my degree field in other ways. Find something outside of work that gets you excited about life, learn about and read anything you can get your hands on to develop yourself – you just have to take the first steps and do SOMETHING. You can’t just sit back and hope that IT finds you.

    Several frustrating days and a setback with a layoff later, I now own my own business and couldn’t be more satisfied with my work. Sure, some days are still rough, but I know I’m making more of a difference now. With all these challenges that Millennials have been facing, it’ll be interesting to see how companies change over time. I know there’s going to be a rise in innovative ventures with employee cultures that embrace the Gen Y values, yet those more traditional businesses may suffer greatly because they didn’t take the time to consider what contributions our generations has to offer…by the time they do, a lot of us will be on to big and better things.

    Thanks again for the article,

    Caroline Leemis

    1. Jess Lively

      These are great insights, thank you for sharing your experience, Caroline! It sounds like you’ve been through just about every scenario our generation has faced so far. I am happy to see you have found a way to get what you wanted most out of your career. : )

  7. EmSewCrazy

    AMEN! Keep trying and think outside the box. Sometimes I get pressured to go back to “real” college and follow the traditional path but then I read something like this that reminds me how fruitless that path would be for MY life.

  8. Virginia

    Brava, particularly to the sentences you bolded. I’d like to see this post get picked up by a major news source!

    1. Jess Lively

      Thank you! I am thinking about sharing it on The Huffington Post, I’m glad you feel like it might be worthy of the feature!

      1. Erin Haslag

        Yes! Do! This is a fantastic letter that succinctly encompasses so many of the Gen Y experiences. So many gems and wonderful pieces of advice. It sounds like the start of a great commencement speech, as well!

  9. Sage Grayson

    Well said! I am impressed every day by what young people are doing and the obstacles they’re overcoming.

    1. Jess Lively

      So true, Sage! I think it might have taken a while to get our bearings during the recession. But we are starting to get our legs underneath us and finding out what we really want to do now that everything is different than it was before the recession.

  10. Sophie

    Perfectly put. I always felt bothered by the labels generation x put on generation y, but could never quite put my finger on where that was coming from. Now I’m thinking back on my past and realizing you’re right. (though my development in that regard came from school teachers saying those things instead of my absent parents)

    1. Jess Lively

      So interesting! I have never really studied whether the Gen Y labels were coming from Gen X or Baby Boomers. I assumed there was a mix of both. You feel that it’s more on the Gen X side than the Baby Boomer side?

  11. Brittany

    Thank you for writing this – it is a completely relevant (and spot on) assessment of our generation and the reality of coming of age today.

    My husband and I (31 & 27) have been discussing this topic in depth lately and the struggle of letting go of the dreams you set for yourself (You can be anything you put your mind to!) and the reality of life (rent, bills, 401K’s).

    It’s not to say that you cannot achieve anything you put your mind to. It’s just that we are groomed our whole lives to think we are capable of huge dreams (which we are) but aren’t prepared to handle the sacrifices that come with these dreams.

    I know that I, for one, have been struggling with this most of my professional life. Is this what I want to do? Do I want to settle for an office job? Is it worth the sacrifices to chase my dream? Am I even capable of achieving my dream? What is more important – professional fulfillment or personal fulfillment? Can I achieve both?

    So thank you for reminding me I’m not alone. Now, if only I could figure out a way to do it all!


    1. Jess Lively

      Thank you for sharing, Brittany. You cannot do it all. But you can prioritize what is most important and leave the rest.

  12. anne @ wit wisdom and food

    As a member of Gen X that manages a large group of Gen Y I think you all are very similar to any generation. There are many of you that persevere when faced with obstacles previous generations couldn’t imagine. Unfortunately, those stories haven’t been featured on the cover of TIME as Gen Y stories. It would be good if the previous generations worked harder on communicating with this new generation to find what drives them and how to make it work instead of pointing fingers at what is wrong with the generation. Enjoyed your article.

    1. Jess Lively

      Thank you so much! There does seem to be a disconnect, you are right.

      Maybe it is time that we, as Gen Y, start to stand up for ourselves and start telling our side of the story. I am hoping to share at least my point of view – so that there can be a more well-rounded perception of Gen Y, rather than a quick reference to soccer trophies.

  13. Anna @ refeathered

    Well written, Jess! Your letter inspired me to write my own little essay on the subject for my blog. In my post I quoted you, and linked back to your letter and sight. I hope that is okay with you. If not, I will gladly edit or remove. (

    I get the entitlement “blerg” from both sides- I hear it about myself as a young adult, but I also hear it as a teacher about the upcoming generation. I think the pursuit of happiness is often confused with a sense of entitlement. It seems to be a newer concept to actively pursue meaningful or enjoyable work. As a teacher I am constantly trying to make the learning experience meaningful to the students, as well as teach the value of a struggle or failure. When I do, it is amazing the effort, care, and perseverance kids will put into their work!

    1. Jess Lively

      Thank you for sharing your thoughts on the subject as well! : ) Your post is great, too. I love hearing about how you feel about it as a teacher, too.

      Great point about entitlement and the pursuit of happiness, too.

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