
Simon Sinek.
The one guy who might convince you to keep your day job and tuck away those grand notions of early retirement. You may have heard of Mr. Sinek, especially if you’ve seen his YouTube talk about the problems with millennials in the workplace.
His TED talks are ubiquitous. His books are best sellers. For those of us armchair psychology nerds, interested in the anthropological arena of our wacky offices, Simon is “The Man”.
Simon’s background is telling. He’s a good egg. He went to good schools and got sweet gigs after achieving his diplomas. He looks young, but he was born in 1973, making him just a year younger than me.
Must be the hair?
At any rate, he’s spent enough time in the trenches and has done enough research to speak with authority.
And let’s be clear: It sure doesn’t hurt that he has mastered the art of speaking with authority. Give anyone that skill set, and he or she could sell you snow on January 21 in Minnesota.
The Simon Sinek Fan Club
I recently went through some intense training with a new Team (capital T) at work that focused on E.Q. There were admissions. There were high fives. There were tears. Of course, there were laughs. And in the end, we all bonded. All that was squeezed into three days, before we returned with gusto to our inboxes and back-to-back WebEx meetings…
Part of the training involved watching YouTube videos of Simon Sinek. You start watching, and immediately this guy’s presence, voice, and inflection hook you. The anecdotes resonate. You feel you’re in the presence of an old-time preacher. Honestly, he could probably get the entire congregation to drink that fatal Kool-Aid.
Sinek makes his point that millennials are instantly dissatisfied with their jobs right out of the gates. Sure, he’s generalizing. We don’t know if this mainly applies to college grads in white-collar gigs, or if there’s a broader brush being painted across all 20-somethings. Sinek says that this generation is on a “scavenger hunt” to find the job they feel passionate about.
Pausing for a moment… The first person who comes to mind when I watched this clip is our old friend Jiro the sushi maestro. There was no scavenger hunt for that guy. He just dove right in. And it was not pretty for him, for several years. And yet, Jiro stuck with it.
He fell in love with his job, and in his 90s, nothing satisfies him more than his work. See, it’s fun to be a student of this crap – you get to tie together these disparate themes to help you make sense of it all.
And the bottom line is this: Quit searching for work you’ll love as if it’s some kind of scavenger hunt. This $h*t is hard. It’s WORK. And it’s exceedingly rare that you’ll have your brain fully wired for success in your 20s. Maturity requires a lot of experience and time.
Simon Sinek on Millennials in the Workplace
Sinek throws out his “mountain” metaphor at the 5:40 mark of the clip linked earlier. Yep, you’ve got to strap on the crampons, and inch your way up to your career ladder “peak”. But he graciously allows for shortcuts (maybe because he took advantage of them??) For instance, you could take a helicopter to the summit.
But the point is, there is a summit. There is a mountain.
Life is not a flat walk in the park. It’s an up-and-down slog, with peaks and valleys.
But all too often, Sinek says, our bright and optimistic millennials see only the summit and ignore the treacherous mountain that lies before them. As if a scavenger hunt for the perfect “Valhalla job” could yield a summit-like existence from age 20 to 100. Or, if you’re an early retirement type, 20 to 40, say.
You have to do your time. Recognize the mountain and the journey that’s required to reach the shimmering summit. The good news? YOU are SMART. You’re a student of E.Q. and a devotee to becoming a stellar leader and employee at your workplace. (And you read this particular blog.)
At base camp, you hitch a ride halfway up the mountain with a few promotions. Someone likes the work you do and asks you to come to join him or her further up the mountain. And on it goes. Honing leadership skills requires time and effort.
Sinek Is Simply the Messenger
Some would even say he’s full of hot air. I prefer a more balanced approach. Again, the guy knows how to give a great speech. That is not an easy skill to master. And he is among the best. He’s also apparently a decent writer. Again, no small fete. There is nothing revolutionary in his theories or models though.
Simon’s is fairly straightforward stuff. You quite simply need to engage. You need to CARE. Not just about your work, but about the human beings around you. If you’ve never heard of the term “servant leadership”, then tune into Simon Sinek.
You’ll get an earful, and if nothing else, you should come away motivated and inspired to give a bit more of yourself. (And that applies not only to the workplace but at home too.)
So, is there “institutionalized impatience” among Millennials? Are they quitting (or just Quiet Quitting) en masse because they’re just plain not “feeling fulfilled”? I don’t doubt it. Plenty of Gen-Xers feels that way. Plenty of baby boomers probably did too, especially among the hippies.
Take Simon’s lessons on life and leadership with a grain of salt. In all likelihood, his generalizations still apply to YOU. And his anecdotes hold powerful lessons.

Finding a Path to Tolerable Careers
Simon Sinek would probably support early retirement if it meant simply a five-year break to raise a child, start a blog, and fire up a business or two. (You know, like grandma and grandpa’s retirement? Haha…)
I believe we’re all capable of making the most of our careers if we choose to engage, and if we choose to constantly learn, fail, grow, and take informed risks.
At the same time, millennials can do much to eliminate all the crap that complicates their working lives in Modern America:
- Live closer to the office. Kill the commute – don’t let the commute kill YOU
- Pedal to work at least when the weather is nice
- Watch and read your Marie Kondo (i.e., minimalize)
- Spend a lot less than you make (by avoiding big fat houses and big fat pickup trucks and boats and cabins and fancy vacations etc. etc.)
- Meditate (something I need to learn more about and practice myself)
If nothing else, follow the above and listen to what Simon Sinek has to say. Early Retirement is for many a far-out-there goal that may be several years in the making. The least you can do is attempt to grow, build some resilience, learn the game, and stay motivated in your job.
And when an early retirement option becomes available, you might be surprised that you’re not jumping at the chance to escape that daunting little hamster wheel, after all…
Postscript
I’ve written about the company Basecamp on this blog thanks to a book by its founders, It Doesn’t Have to Be Crazy at Work. It’s a fine complementary piece to this post as it offers a flip side to the “grind it out” path Sinek suggests you may need to take.
At Basecamp, they are experimenting with a sustainable work environment. No crazy hours and no fits about employees working from home, or taking all of their vacation time.
In my evolving opinion, the best blend is an environment that empowers teams to create and be themselves, while also providing flexibility to enjoy life. Imagine that!
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It reminds me of a girl I hired at my old job who was a millennial and hired to be a coordinator but wanted to be a producer in less than a month. She was dissatisfied, then became a huge pain to work with. And I once asked my friend if he liked his job, because so many people I ask hate their jobs, and he said he was pretty content. I said, “stay there!!! you found the holy grail of jobs!” lol!
Hi Tonya! Less than a month? Wow – that is pretty extreme impatience! Good advice to your friend — pretty content is a fine place to be, so long as you’re not getting too comfortable.
That’s interesting. I used to think early retirement is a good thing, but now I realize that work is better for most people. You need a certain attitude to retire early and live a happy life. Most people lack that elusive mindset.
Most people are happier working a regular job. With that in mind, I think Simon’s message is right for most people. You’ve got to put in some hard work and become good at something. Then you’ll be happier with work.
Hi Joe! I still think early retirement is a good thing, but the question might just be “how early”? You’re spot on about the attitude (and preparedness) needed for leaving the workforces in one’s 30’s or 40’s. But I’m not sure if it’s an elusive mindset about ER or one that needs adjusting with respect to career…?
Most may not be happier working a regular job, but the alternatives aren’t necessarily going to make you happier. At the very least, work hard, adjust/adapt, and serve. There’s bound to be at least an ounce of fulfillment in the mix if you do.
Makes me think of a Millennial egomaniac I worked with. 6 years ago, he told me he was going to be the CEO of our $10bn+ global corporation within 3 years.
He’s still a grunt. And he’s still impatient. He left for a promotion, and has been stuck in a job he hates for the past 3 years.
Gotta serve your time. But never stop working the shortcuts up the mountain.
Wow Fritz. That is quite a bold prediction on his part. Sometimes you need to make sure your superiors know you’re hungry, but you better bring some humility along for the conversation, and let your work speak for you!
Most kids (including me) are really good at overestimating themselves too 😉
Here here! 🙂
Some of this is about the “new normal.”
In the “old days” doing your time was climbing up the company ladder – with one company. The “new days” are climbing the ladder at different companies.
I think there is an over generalization about Millennials. Much the same way Boomers, Hippies and Gen Exers tend to over generalize the generation that follows them. The old “back in my day” comments.
Hi Mr. r2e! Truth to that my friend. You can’t really expect to have too much company loyalty in era of spreadsheet accounting where saving shareholders requires layoffs. I’d definitely argue that jumping 3 or 4 times is probably a good thing in one’s 20s and 30s. Maybe once or twice at most after 40?
I too wonder about the generalizations of generations (say that 10 times fast!). I agree some have taken it a bit too far with Millennials, but the numbers do reveal some observable trends among this cohort.
One of the many tidbits I’m passing along to my daughters reinforces the work they’re doing before exiting college.
You’ll hear “put in the time”. It means “build up the skills you need to perform at the next level” — and that takes time.
That is an excellent tidbit, Joe! One of the talks Simon gave speaks to the idea of cultivating average kids so they have that much more room to grow and take risks into adulthood. The very young and very high achieved (the theory goes) are less willing to take risks and change and come down from their safe pedestals. Interesting theory – though I’m not sure how much water it holds.
I left school at 16 with no qualifications and no great script or master plan, got a job – an apprenticeship really – with a steelwork company in 1974. Took each day (year) as it came while still remembering to enjoy life as best my modest income would allow. Returned to full-time college later and picked up an engineering degree, after which I started to fly with a series of good jobs. Promotion didn’t figure, I didn’t need it, I could engineer good and I’d have been wasted in management none of whom could function fully without me (always a strong position to be in, my skills were usually in demand). When it suited me I changed jobs mainly for a different challenge. I think in life it’s more important to be able to change a situation you don’t like than chase promotion (of course for some the two might be related) – this I could always do, the boss’s chair was never for me and working life continued to my satisfaction at a reasonable level. I retired very happy and quite well off, totally on my terms, at age 46 – no regrets !! These professional talkers can certainly talk, do they really know that much, do they really have that much experience? – not sure, life is such that not one pattern fits all !!
Hi Ben,
Good of you to share your experience. Certainly yours stands out as exceptional among the masses. Not to say others can’t follow, but I think it points to the fact you paid your dues and reached the summit without a lot of baggage (a lot of debt, no savings).
I agree that one should always take professional speakers with a grain of salt. Skepticism can serve you but just like a bad popcorn matinee movie – sometimes you can enjoy the ride and come away with your own inspiration and a smile on your face. 🙂
Cheers!
you’re right, cubert. you gotta pay some dues if you’re just a regular working person from a regular working family. i bounced around and screwed off a little more than you (though i know you enjoyed your youth) but most of the past 15 years were doing the hard work. find a good partner in crime and a good market and that hard work earns you the freedom to make more selfish decisions later. that later is now for us but folks should remember it came AFTER we busted our humps for a period. now we can say no to crap we don’t want to do.
oh, and once i didn’t need it i don’t hate my job any more. i really hated it when i felt shackled to it.
Thanks, Freddy. Really an excellent kernel of truth in your comment. Pay your dues now, or pay them later. But at some point, society will require you put in the effort. Even Mr. Money Mustache spent 10 years of paying his own dues. If you figure out this working gig, you could put in 20 or 30 without too much pain.
I had never heard of this guy, I’ll have to check out his videos – thanks!
He’s a card! Smart, engaging, and by now, pretty dam wealthy. Enjoy!
Nothing has changed over the generations when it comes to human nature. We are still all generally lazy, we still have a superior brain to most other animals on this planet. Some of us decide to use it, other less so. The concept of retiring early because you frontload work and savings has been around. The real difference is we have a lot more options today to choose from thanks to Automation and technology (think of blogging to reach out to the World). Constant notifications, distractions, choices to be made leads to frustration and dissatisfaction. You feel like you always miss out on something. This is why I love FIRE. To become FIRE once need to learn what to focus on, what brings the most value and happiness to one‘s life and learn to be ok with missing out on many other things.
Hopefully our brains remain superior to ALL other animals. 🙂
The main point of this post was to point out that PERHAPS because of all those modern distractions, we now have a generation that is less inclined to settle for a job they don’t like right away.
I think perhaps a big difference is that now the internet and all things online are so prevalent that it’s easy to see alternatives that weren’t there with previous generations. Outside of a very few, working hard at a traditional 9-5 job was the way to set yourself up for a good future.
That said, even the best jobs are freaking HARD. The first year of my job I was just focused on not drowning and I barely kept up with that. The upside to sticking with one job for a long time though is that you get to a point where you can be really confident in what you’re doing.
That’s so true re “sticking with it”. I read the book “Talent is Overrated” a few years back. Even Tiger Woods had to learn how to play golf. And when you force a kid to swing a club starting at age 2, they’ll have no choice but to be very good years and many reps later.
I have noticed that a lot of the engineers that I work with fall into this category. For me, I was lucky. I was told to take the jobs that no one wants, and here’s the key, do them well. You will be rewarded for that. My career has shown that to be true, and I was able to find fun and engagement in most of those jobs. It’s not easy, and it’s not always fun to do it. But, as my father always said, that’s why they pay you for it. There is nothing wrong with looking for better or more engaging work, but there is a mistake to expect that hard work is always required. There is just no other way.
Right on, GenX! I’ve held some pretty crap jobs in my life. And I never shy away from bragging about. I’ve painted dorm rooms, packed pickles in jars, taken password reset calls all day and in one summer job, made over 70 cold calls a day for 8 hours every day. If nothing else, you get paid and earn a little humility.