Gen Y’s Resignation Letter to Bosses

What we like about Ryan’s guest post is the cheeky, yet relevant undertone to his message. Ryan’s post, Gen Y’s Resignation Letter to Bosses, has a different tone than what other’s have shared. We like that too.


Dear Boss,

The time has come, dear Boss. I have decided to pack up my bags and call it a day here at the company. It was a good run, but we both know that it’s time for me to move on.

As I depart I want to share with you the reasons why I am leaving because they probably aren’t what you think. I also want to share with you a little bit more about my new endeavors as a solopreneur.

Before that, I want to thank you for the opportunity of working in your traditional, corporate office.

You see, my coworkers here at the company are great.  Every morning after clocking in, John, Suzie, and I drank coffee together at John’s desk, checked the latest Facebook gossip, and caught up about last night’s episode of the Bachelorette before we actually did any ‘real’ work. It was a great way to waste two hours before you finally arrived in the office around 10.

I’m also thankful that you never asked for personal feedback or input into department operations.  God knows that a lowly employee on the front lines like me never had valuable insights into how the company could help me work better.

My favorite thing about your traditional office was when I was done with my work at 2pm, but you made me sit there until 5pm. Or if you were having a good day and I wasn’t afraid to ask, you generously let me leave at 4:45pm. Your flexibility in wasting my time fit the old-school office template to a T.

And lastly, there were blue-jean Fridays. Whoever thought of that should get an award. Wearing jeans on Fridays was a great way to show your appreciation to us for our hard work, and it showed us what a cool company we were!

But as great as it was here in the office, I’ve decided to transition out and fly solo into entrepreneurship.

My transition from corporate life to solopreneur hasn’t been overnight.  In fact, I’ve been working on my transition for the past three to six months, working diligently on my business before and after work, and weekends. I have already duplicated my income on the side, ensuring me that I can pay rent next month. Officially quitting my corporate gig is the final piece to the transition.

As an entrepreneur, I’m able to be the boss: I work when I want and under my conditions. Unlike in your office, I am able to focus 90% of my energy on what I’m good at doing, and hire out the other  10% to somebody else. While this may sound like I work less, the reality is that I actually work way more than the “factory 40”, often from 6am until I go to bed. It doesn’t bother me though because I’m building my dream doing work that I love.

Working for myself has also proven to be more profitable than working for you. Because of my expertise, I can swiftly and professionally do work for my clients and not have to share the profits with you. This is more fun and it gives me more confidence in my retirement than banking on not-so-secure corporate retirement packages or crappy buyouts.

I can also work from anywhere so long as I have an Internet connection. Unfortunately, boss, you did not allow me this freedom, even though working from home would have eliminated overhead costs for you and would have provided me a quiet, distraction-free space from coworkers to focus on my work. Oh well!

All in all, I’m thankful for having worked for you. You made me realize that as a young person, I had to get out fast or else I would settle for mediocrity like a majority of the working American public.

Working for myself is fun, fulfilling, and profitable. Quitting is winning, and at this point it’s a no-brainer. Thank you for showing me why.


Generation Y

Connect with Ryan

Ryan Eggenberger teaches others how to make their career, business, or entrepreneurial dreams into realities. He is also a marketing professional, entrepreneur, blogger, and social media consultant for political, religious, and business organizations. He blogs regularly at

Ryan Eggenberger teaches others how to make their career, business, or entrepreneurial dreams into realities. He is also a marketing professional, entrepreneur, blogger, and social media consultant for political, religious, and business organizations.

  • maybe these kids will shake the system up completely – they are in demand, here is another trending article on the changes companies are making to get the most out of employing millenials –

    we cant expect to change the way kids are taught in school and then ask them to fit into a work culture that doesn’t make any sense to them in return for cash – i think it is all a step in the right direction, will encourage good delegation skills, critical thinking and will have positive outcomes where it is embraced.

  • People like to take pot shots at Gen Y. These are the leaders of tomorrow. What we see as “non-traditional” today is the norm for the future. I like this guy’s style and regret that the corporate arena can’t provide anything meaningful and worthwhile for Ryan…and millions of others. Go get ’em, and live your dream on your own terms!

  • ” In fact, I’ve been working on my transition for the past three to six months, working diligently on my business before and after work, and weekends”

    You left out during…

  • I’m with you, Ryan. We’re not after clocking in just to put in the hours. We’re about making a difference in the world.

  • I love every aspect of this post! As a Gen Y professional, I can relate to the inefficiencies of the current corporate culture. My hope is that more and more Gen Y professionals find their voice and spark the change that is desperately needed for the future. Great post Ryan!

  • Funny, true, and well-written. I love it. My resignation letter wasn’t nearly as clever(or honest).

  • Joe Schmitter

    Many of us Gen-Xers feel the same way. Well stated!

  • This is great stuff Ryan. I keep proudly nodding my head all the way through the entire letter. Anyone who is willing to openly question the madness of most corporate cultures is definitely a friend of mine. Please know that I’m fighting the good fight alongside you on my blog too. Keep it up man, the world needs more thinkers like you.

  • Funny how every other generation in the history of employment had to fit into the workplace, yet now all of a sudden the workplace must conform to fit a generation. Is it just me, or is this out of kilter? Perhaps the newest generation of workers could put down the iPhones, give the OMG’s and LOL’s a rest for a few hours each day, and be a bit more concerned about actually doing work for their respective employers than posting status updates on Facebook.

  • Good perspective, Ted!

  • Wow Ryan! That was dead-on! Especially the Jean Friday, who gives a hoot! The problem is we know that “Jean Friday” screams “We are a cheap company and don’t want to invest any money in the enjoyment of our employees”.

    I just opened my website a couple weeks ago while still working a day job, but the idea of starting a side project all stemmed from EVERYTHING written up there.

    If i finish work at 2, why oh why do I need to sit there until 5. Us Gen Y kids don’t have that attention span, but we also think differently than other Generations but they don’t understand that and just go along with “We have been doing this for decades, we know how it works.”

    It’s crazy. I wouldn’t mind doing 12 hour days as they do at Facebook if I’m doing something stimulating and I know that the Company cares about me as well!

    Thanks Ryan, loved it!

  • Haha, this was great for a laugh, but at the same time, I can definitely see where a lot of friends fit into this. Writing emails/checking facebook to “kill time” until 5, or the opposite – spending hours and hours of overtime doing work on evenings and weekends without any compensation.

    I think the biggest disconnect between a lot of companies and their employees these days is showing mutual respect and appreciation. Unpaid overtime shouldn’t be expected to show your “commitment” to the company, that’s only going to result in resentment when at the end of the day, the company makes higher profits, and the employee has been the one doing the sacrificing. When employees have too much time to kill, it kills their motivation when actual work does come in. Times have changed, people don’t feel they need to stay with a company for 30 years anymore, they want a workplace where they feel appreciated and respected, or they will move on!

    As an entrepreneur, I love the life I’ve created for myself; if I work hard, I see the successes from that, if I slack off and it’s no one’s fault but my own. Although, I worry my productivity for the next little while may plummet as I read through the rest of your site. :)

  • Kunal Joshi

    Good work mate ! I have always thought about thesethings and tried to write but this is perfect. Cheers to Soloprenureship !!

  • Dan

    Great article Ryan

  • george

    The first paragraph exposes both the truth and success of the writer. He is lazy and wastes a great majority of his time and the company’s by BS’ing around the coffee pot. I can’t wait for this guy to really go out on his own and sell everyday to keep the pipeline full. And the person he hires to help him out is also wasting his billable hours working on his/her own stuff. I would so love to receive a letter like this, he trashes his colleagues and now I would know who I need to replace — just like a whining gen-y. Oh, I will more than likely be your prospect however, if I am now forced to outsource I might as well save some money and hire a staff from India, Russia or the Senior Center. So go ahead and wear your jeans, you’ll need them digging fence posts in your parents back yard.

  • Anita R

    This is a Super cool mail. As HR person myself i do see most of the employees facing the same problem. Unhappy with the productive time they actually get at office. And to reduce this we have small color code days at office, which does not in any case act as a stress buster or engage employee to work or office. In the same regards i like the views of Mr. Jason Fried as well.

  • Today’s thinking won’t solve tomorrow’s problems because today’s thinking is what got us into today’s problems.

  • Ryan!

    I’ve encountered the robot manager argument, “MUST BE IN OFFICE 9-5” in numerous corporate jobs. It’s always frustrated me. Who cares when I get the work done–or how I get it done–as long as it *gets* done?

    Kudos for sharing Gen Y’s letter. That kid’s got balls.

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