What homeschooling and job-hopping trends have in common

That picture is from eight years ago. Me with my cofounders for Brazen Careerist. Here’s what that site looks like now. Hopefully the company will exit soon because I would really like to cash in my founder’s stock.

Until that day, I can cash in on how cute this picture is. People always used to come up to me and say about the cofounders, “Wow, those two are so cute.”

Now, as I look at the picture from eight years ago, I think, “Wow, I used to be cute, too.”

I should make that picture my headshot or something. I need more mileage from that picture.

When I first started writing this blog, Gen Y was just entering the workforce. Their parents had raised them to believe everything they did should have meaning and be fulfilling. So when Gen Y entered the workforce they thought work was a joke. Because, as we all know, entry-level jobs suck.

But unlike other generations, ones that paid their dues, Gen Y just quit. And it was elevated to some sort of national crisis that their generation was spoiled, entitled, lazy, immature.

I never set out to be the spokesperson for Gen Y. But their reaction made total sense to me. You do not have to be older to have a good idea. And of course you should not have to spend years getting people coffee before learning something interesting. So I wrote that in my syndicated column. And then I got fired from a few newspapers.

Then I wrote about how job-hoppers are the most engaged employees, and job-hoppers have the strongest careers, and job-hoppers have the best resumes. Yahoo fired me. Then I launched a startup with two Gen Yers who gave me street-cred as I became more and more vocal about how much we benefit from Generation Y.

The credibility worked: Companies paid me $15K a speech to talk about the Gen Y workforce and I used that money to fund the startup. My blog took off, the company took off, and, things came full circle when the Gen Yers got sick of working with me because I was old and had kids and couldn’t work as many hours as they did.

Or maybe they got sick of working with me because I kept arguing with the press instead of just giving a good soundbite and shutting up. “It’s bad for the company brand,” my partners would tell me over and over again.

Which may have been true, but that’s not my point.

Robert Wolcott, from Kellogg Business School, finds that successful people do not need to be able to predict what the future will look like. Rather, success depends on being able to see the direction of change and adjusting to move in that direction yourself. Of course, cognitive dissonance holds us back; most people feel comfortable working within a set of rules, and maintaining the status quo. The people who are most comfortable breaking rules generally make the most money. And in many offices the people who are most concerned with following rules get fired fastest – for inflexibility.

In the book Daring Greatly, Brene Brown says that “being ourselves, risking judgment, risking being seen, actually leads to happiness.” Brown writes about vulnerability, and that’s an important tenant to taking action on a trend. If you do what everyone else does, it’s unlikely they will judge you harshly. So it feels safe. But Brown explains how staying safe is akin to being unable to be vulnerable.

Today switching jobs is totally acceptable. In fact, the average 29 year old has had seven jobs, and the job hopping does not decrease as people get older.  I could see that was coming. I knew.

So often we read about trends and we hear predictions, and we do nothing. Because it feels prudent. But that’s actually the most high-risk move – to avoid moving in the direction of a trend. Not because you’ll miss the trend, but because you’ll miss opportunities to live your life according to your own values.

People used to ask me how I knew how Gen Y would change the workforce. And it was so obvious to me when I looked at what was happening around me. Now I think the same thing about homeschooling: It’s the next obvious thing that is happening, so we might as well get on board before getting left behind. The same type of person who was desperately trying to hold on to an outdated workplace yesterday is desperately trying to hold on to an outdated education system today.


34 replies
  1. Alyson
    Alyson says:

    I love this so much! You’re totally right of course. I’ve been saying for years that our movement is growing and is the shape of things to come. Off to share the heck out of this.

  2. Harriet May
    Harriet May says:

    On Friday I quit my job. My boss was out of the office in the morning and I emailed her my letter of notice. I’m fed up with the company, but I really respect my boss. I had a stress headache all day; waiting for her reaction in the morning and then dealing with my emotions and plans in the afternoon. I went home, fell asleep at 8pm after having a beer for dinner. In the morning I stepped on the scale and weighed the least I have in nearly three years.

    I got offered a job managing all the marketing for a fintech startup, which is terrifying and exciting, and might fall through because my notice period at my current position is so long– two months. But even if they rescind the offer, I know I’m making the right decision to leave where I am. Everyone who works at my current company has been there for years– decades in some cases– and it shows in the way they think about the world and the way they approach their jobs. I want to be on my toes. I want to talk trends, and link ideas together, and invent new ways of doing things. The other day I had to explain Uber to my colleague.

    I haven’t had seven jobs yet, but three months before my 30th birthday I want to live bigger, riskier, harder than I have been. I’m distracted all the time thinking about it; it’s making my small talk around the coffee machine terrible. But perhaps it will make my life great.

  3. Joy
    Joy says:

    Penelope, your picture on the top right of the blog is much more flattering than the one in this post. You look great. Stop worrying. :)

  4. Laura
    Laura says:

    Yeah, everything you said and more from a Gen X’er who has lived like a Gen Y’er despite the struggles and criticism along the way! There is so much value gained in listening to that still small voice inside.

  5. harris497
    harris497 says:

    The only objection that I have to what you wrote is that people home-school for many reasons: Religion, Fear, Best education and social atmosphere for the kids, etc. We are in the last category but does what you suggest hold true for those in other categories?
    Food for thought…

  6. YesMyKidsAreSocialized
    YesMyKidsAreSocialized says:

    It’s hard to imagine Gen Y not homeschooling their own children. I see lots of learning centers for homeschoolers to take classes together becoming more accessible, online learning platforms with access to professionals through skype, and whatever new trend they make a “thing” in the homeschool community over them just sending kids to an outdated learning factory. It will have nothing to do with special snowflake syndrome and everything to do with innovation and trends.

    • jessica
      jessica says:

      I find avoiding special snowflake syndrome has more to do with feeling/knowing they actually earned their place in life, versus feeling entitled because the world told them take steps xyz and you too can have a mcmansion. The snowflakes took the steps, and realized they climbed the wrong ladder with the wrong end goal and don’t know how to adjust.

      I think the snowflakes are more conflicted than people give them credit for. :)

    • Penelope Trunk
      Penelope Trunk says:

      I really like the last line — about how it’s not special snowflake syndrome but rather innovation. That’s so true! I think private school is the special snowflake thing. Where parents are not innovating but rather reassuring themselves that they are special because their kids are special.


  7. Chang
    Chang says:

    The last funding round for Brazen Careerist appears to be for $4.7M in June of last year. Based on current software trends for exits – albeit from data on startups on the West Coast – there’s another 1-2 years before a statistically probable exit for the founders will be available.
    Fun read, but I don’t see the connection between how the job-hopping was foreseen with the possible/probable rise of home schooling. Unless its implied that this is also being foreseen?
    Home schooling sounds like a good idea – I have 4 daughters, 3 of which are in high school now – but it would require giving it the time and effort of a part time job. Maybe even a full time job for some? I can’t do it. And my wife refuses to even consider it. Considering she is a homemaker, I have some minor issues with that attitude. But what can I do? Keep the girls in regular school. Besides, they seem to be doing so well.

    • jessica
      jessica says:

      Great comment. I love this.
      What are the cons? The extra time required? Have you asked your girls? And lastly, how are they succeeding, in your view? How would HS help them now?

      I’ve personally found that we have more time versus being in school and the conflicting schedules.

    • Mark W.
      Mark W. says:

      Maybe a better question is – Who approved it? I don’t care for it either. We’re probably missing something as it doesn’t come across very well by itself without more supporting information. It’s too concise.

  8. Summer
    Summer says:

    “Rather, success depends on being able to see the direction of change and adjusting to move in that direction yourself” YES!! Thank you. I’m a Gen Y but I have never fully identified with my fellow millennials- but I don’t identify with Gen X either. Maybe that’s why I’ve had a hard time adjusting and finding work that is truly satisfying? I was homeschooled from the 4th grade on and resented my mom during this time because she home-schooled out of fear. Homeschooling was not so widely accepted when we were doing it either (1995). I feel like it’s time for me to move on from how I thought things would be and accept how things are- and identify what I want and work towards this…

  9. ESI Money
    ESI Money says:

    We were early adopters of homeschooling. We have one graduate and one finishing her senior year.

    There’s so much more offered now than when we started — having those resources would have made life much easier.

    Anyway, the kids turned out great, are fine socially (which is the question we addressed a million times while schooling them), and we would most certainly do it all over again.

    • Unschooling Mom of 63
      Unschooling Mom of 63 says:

      Wow!We were an “early adopter” of homeschooling (unschooling) I would say. Our children are 40 & 36 now. They have wonderful lives. They both ended up getting advanced degrees from “prestigious” universities summa cum laude on full-ride scholarships.

      I didn’t even know there was a “summa cum laude.” Neither my husband nor I ever received that distinction, for sure. So I don’t take any “credit” for their accomplishments other than allowing them to learn & explore at their own pace & follow the direction of their interests.I sure learned a lot from them. I got a lot of education by allowing the experience for them with my husband’s support & involvement when he was off work.

      One of the funniest comments we got from “regular” parents was how were they going to learn to read without Sesame Street! They thought our children would be stunted by growing up with no T.V. in the home. If there truly was something exceptional to watch we had numerous neighbors to visit!

      Have you ever read John Holt’s “Unschooling” periodicalls? They are very informative & from the era of us “early adopters.” In the S.F. Bay Area at that time there were many homeschooling groups that pooled resources for camping trips, “field trips” & learning from the particular expertise of the different parents from science to ballet to foreign language & more.

  10. Beans
    Beans says:

    Long time reader, first-time commenter. I’m 36, and I though I don’t feel like I identify with either Gen X or Gen Y, the part about successful job-hopping resonates with me. I’m on my 7th job since getting my MBA in 2009.

    My Baby Boomer dad warns me all the time that not staying with a company long enough will damage my resume and scare away potential employers. Perhaps this was true in the past, where employees were expected to devote years to their employers, but I have fortunately yet to encounter this problem. I think a couple things have changed:

    1. I re-entered the workforce during the last recession with an incredibly measly salary, but happy that I was in the small percentage of my classmates who even received a job offer before graduation
    2. I work in the tech industry where business moves quickly – startups are born and die in the blink of an eye

    I’ve since doubled my salary in the past 7 years, never quitting the old job before finding another better-paying position. Haven’t gotten laid off, haven’t gotten fired (luckily). Don’t regret job hopping at all – in fact, I think my experience at many different companies has helped me gain a ton of valuable perspective I wouldn’t have otherwise had.

      • Penelope Trunk
        Penelope Trunk says:

        That’s interesting – I’ve never seen anything about this generation. But my younger brother, who fits squarely into the date range, has a t-shirt he wears all the time that says, “You have died of dysentery.”


          • J.E.
            J.E. says:

            I’m 36 as well and I too never felt that I truly identified with Gen X or Gen Y. I was too young for a lot of the things that define Gen X and already past the things that defined Gen Y

        • Karen L
          Karen L says:

          That is the perfect name for that little in between period between Generation X and Generation Y. I was born in ’79 and we did not have a computers in school until I was in 5th grade. It was 1 apple computer in the classroom with the green screens and we would all clamor for time to play Oregon Trail.

  11. Lumi M.
    Lumi M. says:

    I belong to the Gen Y. I was privileged to be raised by a hard-working family, so I understood early the importance of hard-work and self-training.
    I’m not a parent at the moment, but I plan to be someday. I keep wondering: how fine would a child be in terms of social skills with homeschooling in those times with tons of gadgets?

    • YesMyKidsAreSocialized
      YesMyKidsAreSocialized says:

      In my experience, gadgets make it even easier to develop social skills. My 9yo can skype/facetime with friends while playing video games together. Same with any other kid. I don’t see how tech and homeschooling interferes with developing social skills.

        • Penelope Trunk
          Penelope Trunk says:

          Yes. Such a good standard. Someone just asked my eleven year old, “Why do you have so many social media accounts?” And my son answered back, “Why do you have so many friends.”

          Clearly he sees technology as a way to make a friend and maintain that friend.


  12. Erin
    Erin says:

    Cool moment: I grocery shop once a week at the same local market. The people who work there all know us. A few weeks ago, one of the cashiers smiled and asked, “Are you homeschoolers?”

    “Yes.” I said.

    She smiled, “I thought so.” Then she turned to Phoebe. “I have something for you.”

    She went into the back and came out with a huge, perfect dragonfly. “It just flew into the widow and dropped dead into a bag. I have one just like it at home. I thought I’d give this one away.”

    Phoebe was mesmerized. We put it in one of the empty jars we’d brought for bulk food and now it’s on her shelf in her room.

    Community supported homeschooling FTW.

  13. Christopher Chantrill
    Christopher Chantrill says:

    I’m all in favor of homeschooling and all in favor of job-hopping.


    There is going to be blood on the floor over school choice and homeschooling. Mainly because the folks working in the school system demand lifetime tenure as of ancient and immemorial right.

    And most people want “security” not opportunity. That’s what the Trumpkins are all about.

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