Dear self-styled Millennial

 In Productivity, Work relationship

Dear self-styled Millennial

(An answer to a letter written to me and other Boomers)  


On a flight from Copenhagen last night, I read an article that piqued my interest until it blew my mind.  It was written by a self-styled Millennial, Tim Denning, whose description in Medium is: Viral Blogger – Inspiring the world through Personal Development and Entrepreneurship. Nice. 

This blog had three things going for it: 1) it was published by a respected company, Medium; 2) personal development and entrepreneurship are both passions of mine;, and 3) the subject matter was of keen interest for me. As an executive coach grappling with how to best take in and support Millennials, I’m constantly on the lookout for insights both for my clients and for my organization.

Alas, I found his article less than inspiring – and more antagonizing cynical.  As for personal development and entrepreneurship, I’ll let you be the judge.  That is not to say that I didn’t find value in it.  Mainly, it helped me draw some conclusions about my own frustrations that are more nuanced and go beyond pinning labels of entitlement and laziness on Millennials.  Indeed, prejudice and bias are of help to no one, and so I am committed to giving each person I meet in my life a clean slate.  In this case, the slate was sullied before I could get passed his introduction.   

Instead of tossing the article, however, I kept reading to see if perhaps he was (brilliantly) using satire.  Perhaps he is posing as a Millennial to ingeniously make his point!, I marveled.  Even as I write this play-by-play rebuttal to his letter to me  to us BoomersI worry that I am not catching on to his irony.  If in fact that is the caseand I am boneheadedly making a fool of myself, please disregard all that I have written, and accept my apologies for the folly. 

I will proceed now, with a point by point examination of his letter. Before commencing, however, I want to point out that I do not know Mr. Denning, nor is it important that he, in particular, wrote this letter. I see his comments as a reflection of a portion of those in his generation — but, I want to stress, by no means by all or even the majority. The aim of this response is not to castigate but to defend Millennials who don’t subscribe to Mr. Denning’s viewpoint like Lauren Birchlove, who recently wrote this excellent Millennial themed article. Also, when I refer to “you”, it is to Mr. Denning, not everyone from his generation.

After a short preamble (which you can read in the linked article) he begins: 

Dear incompetent leaders, 

I guess he means me, us. Ouch.  Not a soft leadin meant to take me by the hand and help me understand his plight.  But one should note here that he assumes that Millennials aren’t leaders – unless they too have no hope of understanding themselves.  I’m already aghast and confused. 

  • You hired us hoping that you could convince us to take a mortgage and follow your reign of terror. You wanted us to give up our time, holidays, dreams and career goals so we can serve you, almighty master. 

Ok, so immediately my hope for inspiration and understanding is dashed by generalization and hyperbole.  It should be pointed out that many employers of Millennials like me ARE trying to understand the new generations and it was for this reason that I actually started to read the article. 

  • Unfortunately, you forgot that we have the freedom to do whatever we want and that includes ignoring you. 

Two paragraphs in and I can see that things are getting dark.  Even menacing. Perhaps he recently saw the movie, Joker.  I’ll get back to the previous sentence in a bit. 

  • Yes, we’re obsessed with social media, we post weird and wonderful things online, we’re not afraid to share our thoughts even if it get’s us fired and we’re ‘a rebellious lot of young folk’ as you like to say. 

Actually, each generation has their rebel causes, but what I think sets the Millennial generation apart (and I want to re-state that I am not insinuating that ALL Millennials have this characteristic) is the focus on internal rather than external factors.  The generation previous to mine dealt with the Vietnam War.  I, during my university studies, protested Apartheid and fought for divestment in South Africa.   

While I do see many Millennials involved in protests throughout the world (i.e. Hong Kong, Catalunya) most of the “protests” that I read about from Millennial writers focus on the unfair cards they have personally been dealt. A lot of “me, me me”.  This article is no exception even if the collective “we” is used rather than me.  To my point, the author rants “we” 70 times.  Unfortunately, that plays right into the Millennial stereotype that “we”, non-Millennials are trying so hard to avoid. 

  • We may dress weird, value the latest iPhone, wear a backpack that we think makes us look cool, take a career break to travel, say what we think and wear a pair of Converse Chuck Taylors to work instead of black dress shoes. I get it, we’re different. 
  • Regardless of whether you agree with how we look, you’re stuck with us. Every year we make up more and more of the workforce so it’s in your best interests to understand us. When you do, you’ll realize we’re not that bad and we can be led (for the right reason, of course). 

Whoa. Before you get to the explaining part below about your freedom, I think we should clarify a few things: First, I agree that we’re stuck with you (You being those in your generation who vacillate between victim and persecutor instead of taking responsibility) And I agree that it’s in our best interest to understand you as a generation. But what I’m not good with is your fuckyou attitude.  That’s where I draw the line.  Bridging, collaborating, understanding, compromising — all good. Fuck you, there’s nothing you can do about it? Tell me. Where is the inspiration in that?  

  • Unfortunately, you forgot that we have the freedom to do whatever we want and that includes ignoring you.

I absolutely haven’t forgotten that.  I read it several times over the first time.  That’s the first part that piqued my attention. But if you have the freedom to do whatever you want, why are you bothering with this rant?  Just go and DO what you want.  Ignore us!  

Let me explain in simple terms why millennials (like me) quit incompetent leaders: 

There’s no meaning in it 

  • Millennials have been brought up on picture quotes, memes and Harry Potter where for some strange reason, we’re looking for meaning. 
  • We’ve seen our parents chase the so-called ‘American Dream’ of home ownership, 2 cars, 2 kids and a perfectly groomed dog ready for the Saturday dinner party with the Jones’s. For some reason, this doesn’t seem to give our parents any meaning and as a generation, we’ve learned to question everything. 
  • Millennials are discovering minimalism, freelancing, entrepreneurship, side hustles, life without a mortgage — and even life without children. Anything goes because we all derive meaning from different things. 

I think you make some good points here.  I’m all for defining what has meaning for you personally. “Anything goes” sounds fun. I’m also for fun, so good on you. 

  • Unless you can help show us how the work we do will give our life meaning, we’ll quickly become disengaged, take the paycheque and then find a way to quit so we can do work that has meaning. 

And there it is.  BOOM. The challenge we “pre-Millennials” consciously or unconsciously rub up against all too often, causing us to stare back at you with dead fisheyes.  This idea that somehow it is our responsibility to show you how the work you do will give your life real meaning. Oy. 

It seems to me that you have already figured out that of the two types of lifemeaning, (intrinsic and extrinsic), you’re searching mainly for intrinsic.  I get that, and to your generation’s credit, a true understanding of what brings us happiness is going through a transformation. So bravo, and I mean that sincerely.   

But here’s the thing.  Intrinsic meaning comes from a deep understanding of what is valuable to you personally.  This is where the conversation becomes difficult because the majority of your generation missed out on something significant that many of us Boomers take for granteda slower, harder adolescence that taught us core values in a way that your upbringing didn’t.  

This brings me to my hypotheses for why you don’t like or understand us: we have a totally different concept of one of the most basic core values anyone can have: work.  Like you and your generationwe developed our core values through life experiences.  In contrast to yours, however, we did it in slow motion and it included plenty of labor.  We spent thousands of hours with our families and best friends (one, two or maximum three – not 4,342) without minute-to-minute interruptions (read: social media and chat).   

When we bought a record, we listened to it until we were intimate not only with the music but the stories on the album cover.  Sometimes so intimate, we bought a second copy because we wore the grooves out  seriously.   

When some of us were lucky enough to get our first car, it was usually old and had a bit of rust, but we washed it regularly and even changed the oil ourselves.  Our experience was the experience of the physical world, not the virtual one – and I’m not at all saying it is better or worse than the world you grew up in, but the point is that we are a generation of improvisers and self-starters through necessity.  We couldn’t Google it.  We couldn’t message our friends.  We had to walk, bike or hitchhike. 

Another important experience we had growing up were the chores that our parents forced on us, and when we didn’t complete them, there were consequences.  Some of us got paid an allowance for chores and others didn’t.  We saved the money from our paper route, babysitting, and mowing our neighbor’s lawn. It was hard.  We felt misunderstood. But we learned three hugely important concepts: how to workhow difficult working is, and the value of money.

And btw, all of that wisdom was handed down from our parentsMy generation, the one with the crap for leaders, according to you, can’t take one iota of credit for any of that. We are just the beneficiaries.

When we started making real money for our hard work, we felt empowered, enthusiastic, enriched.  Not because the work we were doing in our early careers was that interesting or that it allowed us to finally let our imaginations go wild, but because our expectations were not only met, they were surpassed.  But think about it, we had already been working for five to ten years before we landed our first “real” job.  That warm-up, it turns out, was EVERYTHING.

Personally, I have had at least a weekend job since I was 12 years old, and I am not by any means unusual.  And while that may sound trivial to the new generations, I can say without a doubt that the reason why some Millennials complain about their lot is because they have had no transition from “do whatever I want” to “do what my boss tells me.”  That must be an incomprehensible nightmare.   

Here I want to reiterate that we had nothing to do with deciding our upbringing – just as you didn’t.  But let’s not dwell on the past – which is part of my grand solution. 

We like solving interesting problems 

  • When you understand that we chase interesting problems that have a meaning in our lives, you’ll understand how we choose jobs and why we quit. 

Exactly my point. You view work as a kind of option, and if you’re going to choose that option, well, it better be interesting or fuck you, I’m out-a-here.  If that is true because you are independently wealthy or decide to become an entrepreneur (someone who works 18 hours a day to avoid a 9 to 5 job)fine, but the majority need to work for someone else, so I’m not sure where you are headed with that. 

But let’s cut to the quick.  I do understand where you are coming from because if nothing else, we Boomers have an overarching perspective that you too will have when you become the target of generation AA or whatever comes after Z, and to earn this gift, all you have to do is stay alive until you reach 50.  Totally doable, unless you quit — so watch that bad habit.  

Back to my hypothesis. No one made you shine your father’s shoes every weekend.  You didn’t have to clip the grass – or you couldn’t go to the party on Saturday.  You got to play video games before you finished all your homework.  Instead of fighting over whose turn it was to do the dishes, your parents did it.  They also took out the garbage, did the food shopping and vacuumed.  You missed out on all of that.   

Perhaps at this point you have a big question mark on your face. How could missing out on a bunch of menial bullshit chores that had no future intellectual or other value cast a dark shadow on someones life?  This is harder to explain.   

If you’ve seen the 80’s film, The Karate Kid, you’d remember the wax on, wax off scene. That scene, for my generation, was epiphanic. It clarified for us that our parents weren’t, after all, self-serving sadistic slave drivers. No. We were being taught Karate!  

No. Actually, we were being taught work.  And not just work per se, but the understanding that work is hard, boring, invigorating, precise, illogical, exhausting, fun, confusing, fucked-up, collaborative, along with endless other expletives and adjectives.  The one thing it usually wasn’t was an opportunity to show just how creative and full of fresh ideas we were – unless you count my inventive ways of efficiently mowing the lawn and shoveling the driveway or my shockingly brilliant idea to turn off the power at the fuse box the next time I changed a light fixture.   

Time for a joke: How did the Millennial change the lightbulb? Mom! The light in my room is out! Yes, I know that some of you have changed a lightbulb, but I’d bet my right arm that most of you haven’t – and even fewer know why that matters. 

Think about the difference between your generation and ours.  When we got our first job, we thought freedom!  When you got your first job you thought freedom!  The difference is that for us freedom meant the opportunity to find a job – any job, in order to be independent and to start earning real money so that we could (pay off our student loans) start building a life – often from scratch.  You, on the other hand, thought that freedom meant that (one day) you would find the job of your dreams (without any real effort) so that you could begin imparting your wisdom and making a difference in the world while you guiltlessly lived at home where you contributed nothing but the favor of your presence.  It must have come as a shock that we were not interested in your sapience.   

One day, you graduated from college (or even grad school, for many) and all of that freedom from work and responsibility came to a crashing halt when you got a boss. A boss who lived in a world where it’s all about the customer – not you, not him but someone you don’t even know.  (Oh, and please don’t argue that you had responsibilities as a college student because, of course, we had that too. I’m talking about work that is repetitive and mundane and responsibilities that you can’t weasel out of no matter how adroit you were at that special skill at home and in college.) 

You were catapulted into a world poles apart from anything you’ve ever experienced. A world where not you, nor I, but the customer rules. Far from being able to extol your enlightened understanding of social media, you were given unsavory tasks to complete by a specific deadline. 

Suddenly all those dreams you had of adventurous travel and tapping into your imagination to invent new products or design new services dissipated into a 9 to 5 job that doesn’t explicitly illuminate how it adds meaning to your life.  So you quit because, wellit doesn’t meet your expectations 

Why wouldn’t you?  You weren’t taught at thirteen that quitting wasn’t an option unless you wanted to starve that night — which we sometimes did. You weren’t taught that quitting meant not getting the equivalent of an iPhone, something we worked and saved for months to buy, thus helping us understand the value of money. 

  • A frustration, for a millennial, can become our entire career or the reason we get out of bed every day.

Same for us bub.  We also have passion.  We just don’t wear it the same way you do.  Does that mean it’s not as valid? 

  • Something as simple as ordering a taxi using our phone can be game-changing for us and a problem we’re willing to dedicate some part of our career towards — notice how I didn’t say ‘whole career’ because we tend to chop and change between the problem we enjoy solving. 

Yes.  That makes sense because you never learned the value of grit – sticking with something even when you didn’t enjoy solving the problem.  That is what builds character; not in some theoretical bullshit way, but in the way that helps us penetrate tough barriers and solve problems that at first, we see no meaning in, but which brings us to deeply important insights. 

You obsess over titles and hierarchy 

  • We’re focused on one thing: who can get shit done? 
  • Millennials worship the doers more than we will ever worship someone who has a title, but can’t do anything resembling work or see the most obvious problems and decide to help solve them. 
  • Ten years at one company, while chasing promotion after promotion, doesn’t make sense to us. We want to work for multiple companies and acquire new skills in the process. Having the corner office, the black suit and the executive car that comes with hierarchy seems weird to us. 

I’m pretty sure that almost every generation says that.  I never imagined that I would sit in the corner office and indeed mocked those who wanted that.  But how much of the world can you possibly know about at 15, 20 or even 25 years old?  At that age, you’re still mainly a product of your environment and conditioning.  Of course, you are probably 30 or older at this point.  Maybe it’s time to realize that it’s ok to be an executive so that you don’t have to personally manufacture ibuprofen or design and assemble your own Macbook Pro. 

  • We choose what title we give ourselves. 
  • We choose titles like change maker, block chain enthusiast, wannabe entrepreneur, Chief Love Officer and half-time developer. Our title says something about who we are and what we stand for — not authority or hierarchy or importance or ego.
  • While I agree that a title has limited value, titles enable us to understand our function in a company. 
  • We can be a CEO tomorrow of our own company that makes €18.14  a year if we want to and we completely don’t give a crap what anybody else thinks. 

I think it’s fine that money is not important to you.  I don’t think I valued it too much up to my late 30’s, but then I hit the wall.  I suddenly realized that I was going to be in eternal struggle living hand-to-mouth.  It limited my choices as to where I could live, what I could eat, the life partner I could have The idea of a vacation or even not working weekends to make ends meet were no-goes.  So, while I applaud the idea of not getting sucked into the materialistic maelstrom, I hope you don’t confuse that with eschewing making a decent living.

Numbers in a spreadsheet are boring 

  • Cogs, EBITDA, or ARPU are all nap worthy financial terms that appear in spreadsheets and are thought of by the older generations as a reason to come to work or a way to track performance. 
  • Of course financial metrics matter but they should never be worshipped like a statue of Michael Angelo’s David. 

Those are terms for financial calculations that aid us in determining whether we can hire more millennials. There is no serious business in the world, whether run by older women or young boys that can avoid them – once their business has matured.  You might just as well have mentioned Lean Six-sigma and SOP’s.  They may not be the most exciting elements of work for many but try imagining a world where planes fall out of the sky.  WTF? 


  • Us millennials care about what’s behind the numbers and how the numbers change people’s lives. 
  • We use the numbers as a way to measure impact and we don’t obsess over them in the same way. We see the numbers as a measurement of happiness, culture and meaningful work. 

And where exactly does the customer fit into all this?  This vacuum you call work seems to be devoid of all the things that are in place in order to ensure that a business survives and can continue to support its customers.  We all want happiness, a great environment and meaningful work.  Make it better.  Work the system. Continuously improve yourself.  Just do it – instead of complaining that the system is rigged and how you have different values. 

Culture is better than money or perks 

  • You’d think the highest salary wins when millennials go on the job hunt. Turns out it’s not the deciding factor and you can’t buy us with poor leadership. 
  • You can offer the office fruit, snacks, ping pong tables, alcohol, and beautifully furnished offices with waterfront views but we’ll still choose culture and people we like above all of that. 
  • We’d rather work in an abandoned warehouse on a pile of milk crates, with people we’d die for, than work in a corporate office that has the atmosphere of a cemetery full of dead people waiting to retire and collect their cheque/gold watch. 

Awesome!  Go do it.  No one is stopping you.  There is one caveat: if you work for us, you’ll need to collaborate on making the system better, not expecting it to be better and if not, march away after we have spent thousands of dollars training you.  We absolutely want your help, but don’t forget that it’s a process, not some big idea.  Btw, while you’re working on your milk crates, who is going to care for your infant?  Who is going to pay the rent?  Where does earning money – that universal necessity that even you can’t avoid needinghowever repulsive it is to you, fit in?   

Flexibility needs to be okay 

  • Cause, like I said, us millennials want to be able to explore the possibilities. 
  • What would it look like working four days a week? What does compressed working hours mean?
  • What if we want to spend a few hours a month sitting with another department? 
  • If you’re not open to flexibility, you’re going to get a rude shock because plenty of companies (including your competitors) are open to it and that could be enough for us to quit. 

Yes, you are right.  Nothing really new here. But your incessant reliance on quitting as your weapon of choice is as childlike as it is faulty.  ALL companies want to innovate.  Not some. ALL.  Most don’t know how to do it well.  We need Millennials to show us how.  If we’re not open to your new ideas, then COACH US ON HOW to be open.  If you can’t coach us on how then figure it out because it’s YOUR future.  We’ve got our nice cars, vacations and houses.  Let’s work together so you can have time for the things YOU value.  We’re not the enemy and, paradoxically, we want collaboration more than you  obviously. 

Travel is in our DNA 

  • So let us buy extra annual leave with our salaries, take time off, travel as part of our work to visit customers and other offices, and don’t hold this false idea that you can shackle us down for years on end. It won’t work. 

That sounds great.  All you have to do is show how that adds value for the customer – think Omotenashi. You have the power to change the system.  You can do it.  Just stop asking us how.  We don’t know.  If we did, we would have done it already. 

We hate being micro-managed 

  • This management style tells us that you don’t trust us and we hate it. 
  • We don’t want to be held accountable to a stopwatch and would rather focus on results than minutes worked. This style of management is something that we think belongs back in the days of factory workers who ride a horse and cart to work. 

Agreed.  What would you like to be accountable for or is being accountable off the table?  I’m serious.  I don’t hear anything in your arguments that represent any kind of solution.  It’s all we, we, we and life is not fair.  The latter part is true, so focus on the customer, and find a way to make your experience as painless as possible. 

  • Millennials can’t be creative when we have someone breathing over our shoulders and asking their permission for everything we do. With inspiring leaders being the rage, we no longer have to choose micromanagement. 

Be that leader.  But until then, when your boss is breathing over your shoulder, find a creative way to turn that into a win.  Maybe that’s why toothpaste was invented in the first place. 


The Millennial Generation 


  • Treat us well and we’ll treat you even better. Understand how we think and we can work together to do work that will be remembered long after we’ve left this planet. 
  • Treat us badly, and you already know what will happen. 
  • The time is now to change the way we lead. 

I absolutely love your postscript because that is exactly what I have to say to you. Verbatim. 


Michael Hoffman

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