Are Gen Y Millennials Screwing Themselves On Purpose?

Generation Y

A 25 year old acquaintance just told me he quit his startup of two years because “it felt too much like work.” What? Run that by me again, because these old ears don’t understand the logic. He told me the company is doing fine and the rest of the five person team are as dedicated as ever. He just wants to take a break and do his own thing. I thought he was doing his own thing!

I’ve never heard of someone quitting their own company because it felt too much like work. A bad business model, profitability issues, a fall out with fellow partners, 10+ years of the same thing…. fine. But too much work? Ridiculous. Good things don’t magically appear. There’s no such thing as a quarter life crisis. We’ve got to put in our dues and work like no other just for the chance of making it!

Although I do my best to empathize with folks 10+ years my junior, sometimes I just can’t understand their thought process. I’m not sure if I’m stupid, or simply ancient in beliefs. Perhaps it’s a little of both as each generation always seems to look at the next generation with peculiarity. If you are a Gen Yer I sure could use your perspective!


If you’re constantly being told you’re special growing up it’s going to be hard admitting blowups to your friends and family. It’s hard to admit getting laid off in my generation as well, but I find we are more open with our setbacks. We open up because we need help!

2008-2010 were brutal times. People were getting fired left and right as firms cut costs. It was customary to pray to Paulson, Bernanke, Congress, and Obama our saviors. There is no shame in getting laid off or fired during this time period. Yet, for some reason, very few will ever admit getting retrenched.

When you read someone’s bio that says they “quit their job to pursue their passions” in the fall of 2009, understand this is whale poop. Nobody quits their job when the world is coming to an end unless they are already wealthy. Certainly not a 24 year old with barely any experience who starts a site to tell you how to follow your dreams!

Because everybody knows that nobody quits their job voluntarily during Armageddon, I wonder if Gen Y is screwing themselves by keeping quiet. Gen Y’s don’t hire Gen Y’s.  Gen X+’s hire Gen Y’s. When managers come across someone who claims they quit their job to pursue a dream during the worst economic crisis of our lifetimes, the resume gets tossed into the bin due to a lack of authenticity.

It’s the same way with business school students who graduate two or three years after a downturn and say they quit their jobs to go to business school. Those in hiring positions know the reason why business school applications soar 30-40% during a recession is because people are getting blown up! The bottom 10% during a recession go to business school, not the top 10%. They are surviving and maybe even thriving.

For all of you who made it through the downturn, don’t be surprised if our younger, better looking friends just call us “lucky.”


Whenever someone senses a lie, not only will they not like you, some will go to no end to discredit you. It’s much better off to say, “I was let go due to the economic downturn and decided to go pursue my dreams as a travel photographer because I had nothing to lose,” than respond with some sensational answer like, “Life is too short and I quit my job to follow my true calling.” People have a natural tendency to help those in need.

I’ve interviewed hundreds of candidates before and I will unequivocally tell you that all bullshitters don’t pass the first round.  Bullshit detectors are tuned to the highest of sensitivity. It’s also why the act of saying and writing what we don’t know is a big time head scratcher. How on earth can you talk about having a great career if you’ve only worked for three years? How can you talk about the benefits of homeownership if you’ve never owned before? How can you talk about being such a great investor when you’ve only got $5,000 to invest? Don’t bullshit us.

As soon as you tell the truth, you will gain advocates. Not only do you engender trust, you gain empathy.


Be patient. It’s ludicrous to think a 25 year old  deserves the same amount of wealth and recognition as someone who’s spent 20 years longer working. I’m worried people don’t get this disconnect. Compare yourself with someone your own age or with the same experience for goodness sake. Here are some examples where long term thinking triumphs.

* 401K portfolio. It often takes a full year before your match and vesting kicks in. After another time frame hurdle, you not only get a match but also company profit sharing. For the past 8 years, my friend Tod has receive a match + profit sharing of $23,000 a year. Add that to his $17,000 contribution and that’s $40,000 a year! Multiply $40,000 a year X 8 years and that’s $320,000 sitting in his 401K. If someone keeps hopping firms every few years, they lose out on such benefits. See: How Much Should I Have Saved In My 401k By Age?

* Real estate. Transaction costs are high in real estate thanks to a powerful lobby group which insists on charging at least a 5% commission to sell a property. Even Zillow and Trulia cannot lower such egregious pricing because they are part of the machine. By holding real estate for decades, it’s easier to digest such costs thanks to the magic of inflation and consistent debt repayment. Just look at how wealthy our grandparents got with their real estate holdings. Now compare them to the typical homeowner who owns for 5.9 years and complains why they can’t make any money. See: Buy Real Estate As Young As You Possible Can

* Education. If you decide on going to college, you better finish college unless you are filthy rich. You should also narrow down your desired areas of study to no more than three things and make a decision by sophomore year. Can you imagine taking out $50,000 in student loans and quitting junior year because you decide anthropology is not for you? My close friend is just finishing up 10 years of medical school and fellowship after college to become a cardiologist in New York City. 10 years is a long time, but now at the age of 33, he’ll be starting at around $350,000 a year and is set for life.


Time is more on the side of the Young than for the rest of us bozos. However, unless there can be an admission of failure, it doesn’t matter how much time a young person has, s/he is doomed.

Admit failure. Admit mediocrity. Admit being too entitled to work hard and move on! Accept failure as a blessing as it makes each successive try that much more promising. Nobody will blame you about losing your job or living at home since the 2008-2009 financial crisis. The downturn was so bad, EVERYBODY gets a free pass. Hurry up. The whole world is waiting.

Related: No Wonder Why Millennials Don’t Give A Damn About Money!


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Photo: A wanderlust in Wandermunde, Germany. SD. Updated for 2021 and beyond.

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