The joys of Generation Y: Having a midlife crisis at 27

I often sit and question my nomadic lifestyle, I wonder if I’m doing the right thing. I was left disillusioned after one year in the corporate world and knew I had to find a different road, one that would lead to location independency and allow me to travel and see the world. Whether it was work for 6 months and travel for 6 months (like many of my traveling friends), find a job abroad, or as I’ve been lucky enough to do, build a small business that I can take with me as I travel. But if you don’t always enjoy your work (which I’m guessing is nearly everyone because not everyday is perfect) it’s natural to consider other options, perhaps I should return to university and study Marine Science and Conservation, or maybe I should go to London like most of my peers and get a high-paying job with good rewards, will that give me more satisfaction? But hang on, I want to help the world, not make money for money’s sake. Maybe I should just shhh, and carry on with what I’m doing, after all life aint that bad!




I decided to write this post after speaking with my childhood friend the other day. She started a new job as an assistant manager of a brand new restaurant in the centre of one of England’s biggest and trendy cities. The restaurant is owned by a very famous celebrity chef and is set for big things, so I was excited to find out how it was going. To my surprise, she hates it! 70 hour weeks, lots of pressure and all for less money than her previous job as a waitress where the tips were generous. To add to this surprise, her husband, a self-employed tennis coach with a long list of clients and a place at one of the most prestigious tennis clubs recently had a breakdown, and it was all because he doesn’t know what to do with his life! Thank god it’s not just me then!

So I started thinking, why are we like this? Is Generation Y destined to be unhappy, unfulfilled, and wield a disposition that the grass is always greener elsewhere?

(For those of you who haven’t come across the term Generation Y, my friend and fellow blogger Ryan explains it nicely on his blog dedicated to all things Generation Y. So here it is… Generation Y refers to the specific generation born between the 1980’s to the early 1990’s and was the term given to this Generation after proceeding Generation X. Generation Y have been raised within a time period where they have constant access to technology. Computers, mobile phones, the internet were all accessible and part of their youth. Read more HERE)

Technology changed everything! Not only has it helped us to discover what the world has to offer through text, high quality photos & videos, and soon virtual realities will take over and we’ll be exploring the depths of the Amazon jungle from the comfort of our living rooms. Technology and more specifically, the internet, has provided a means to make money, from freelancers to small business owners, and not forgetting the tech-giants that have generated some of the world’s richest people (Gates, Page & Brin, Jobs and Zuckerberg are/were all billionaires). And it won’t stop now, as more and more people rise up through the ranks of the tech industry, invent new products, or develop new software. We’re all waiting for the next average joe to change the world with a microchip (or similar), and have a hefty bank balance to show for it. This is the idea of the ‘New Rich’ that Tim Ferriss discusses in his best seller ‘The 4 Hour Work Week‘. Achieving success isn’t completely dependent on a great education from a top university, a successful father to help bump you up the ladder, or inherited wealth to kickstart a business, it’s about being innovative, driven, and a bit of luck! So with this in mind, the gates to success are open to everyone, or at least a much larger proportion of society than in previous generations.

Having been brought up in England, like a lot kids in Western civilisations, there were plenty of toys, a nice house, family holidays, good schooling and mum’s home cooked meals everyday. But maybe this is the problem… We never had it hard. We didn’t get beaten at school or at home, we’ve never experienced food rations, most of us have never really had to go without. We might have experienced suffering in the way of losing loved ones or dealing with illnesses, but for most members of Generation Y we’ve had it pretty damn cushdy!

So this is my theory… Generation Y are confused. The world is at our finger tips, the internet has provided a means of working anywhere, finding a job anywhere, learning new skills independently and cost-free. There’s no excuses anymore! There’s no ‘we can’t afford it’ or ‘we’re not educated enough’ or ‘I don’t know how’, Google has the answer for everything! Secondly, we had it so easy, we lack fire, ambition and the tenacity to do better, be better and change our lives. Is traveling the world and doing as little work as possible a real aim? Tim Ferriss thinks so. I’m not so sure, because I already know what it lacks. It’s devoid of competitiveness and achievement. To be truly fulfilled we need these things, or at least, at 27 years old, I’ve realised that I do. I challenge myself everyday when I get on a surfboard and throw myself into 5 foot waves, when I try to speak Indonesian to a stranger, or travel to a remote island and live without western comforts. Travel tests me and pushes me out of my comfort zone which is fantastic and one of the reasons it’s so addictive, but it doesn’t make me feel successful. To feel success there needs to be more. Is it accolades? money? status? fame? adoration? admiration? What am I trying to succeed at? I guess I’m just as confused as the rest of them…




Are you part of Generation Y? How do you feel about career vs free time? What makes you feel successful?


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39 Responses to The joys of Generation Y: Having a midlife crisis at 27

  1. written by Heather's health blog 17 June, 2019 at 2:06 am #

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  2. Carly 7 August, 2014 at 10:43 pm #

    I’m going through much the same. I quit my 9-5 in the States and moved to Australia. After 4 months I’m going crazy with not feeling successful, that I’m contributing, and most importantly that I’m progressing.

    • Beth 1 February, 2015 at 2:04 pm #

      Hey Carly, sounds like we’re in the same boat. Are you still travelling? Or have you returned back to the States?
      Beth recently posted…Wanderlust is killing me…My Profile

  3. Megan 15 May, 2014 at 6:30 am #

    Hey Beth!
    This is a really great read! I feel like I’ve been in my gen y midlife crisis for a few years! After 2.5 years of living in Thailand we are about to move on elsewhere…another adventure awaits. :-)
    Megan recently posted…Thai Iced Coffee, I Love YouMy Profile

    • Beth 1 February, 2015 at 2:05 pm #

      Good luck Megan! If you’re looking for somewhere really special, check out the Philippines, it’s truely magical :)
      Beth recently posted…Wanderlust is killing me…My Profile

  4. inpursuitofadventureblog 9 April, 2014 at 2:26 am #

    I actually just shared your article on our fb page the other day. We definitely resonate with this article especially since we are planning to quit our career oriented jobs that we love to travel for five years. In the end though traveling, for us, will be more fulfilling and make us happier. We don’t plan to just idle our days away but to work for our living and hopefully create some good and beauty in the world.

  5. The Caffeinated Day Tripper 8 April, 2014 at 2:49 pm #

    I, too, am in my 40’s and have to smile at this. I tell my kids (23, 21 & 16) that I’m just as lost as them. Felt this way in my 20’s, 30’s and 40’s. Just quit my job in retail to start my blog. Maybe it’s just the nature of a mind that swims in the deep end of the pool rather than the shallow? To question and strive for more? Life may be easier for those who swim in the shallow end but WE get to see what’s deep down under the surface.

    • Nelia 27 February, 2017 at 9:38 am #

      That really caueprts the spirit of it. Thanks for posting.

  6. aluxurytravelblog 6 April, 2014 at 10:13 pm #

    Midlife…? 27…??!!! No, you are still young!!! :-) I’m in my forties and don’t like to think of myself as being in mid-life yet… you’re only as old or young as you let yourself feel! ;-)

  7. Jempi 5 April, 2014 at 2:03 pm #

    I can totaly understand your situation of having doubts here. Been there, done that :) I’m in my 40’s now and at this point our biggest tought is “are we going to stop working in 3 or 5 years” :)

  8. mytanfeet 5 April, 2014 at 1:41 am #

    Nice read! I completely agree with you on our generation being confused. It’s hard for our generation I think mostly because we were given this idea that you go to school, graduate, find a job, get married, have kids and that’s it. Then all of a sudden we find new paths in lives that we weren’t exposed to before and we’re torn between what society expects of us and what we’re trying to figure out what makes us happy and there’s more than just one way to get there.

  9. Angela Anderson (AngelaTravels) 4 April, 2014 at 10:23 pm #

    I completely feel the drag of full time work because it is a job and our twenties is about finding out what works and doesn’t. I recently read a book 101 Secrets For Your Twenties by Paul Angone that was similar. It definitely a great read for those who are struggling at finding their dream job or enjoying their life. I hope you have time to read it. It is on sale through today for $1.99 on Amazon. (Not even trying to plug it too much).

    • Mitchell 27 February, 2017 at 9:46 am #

      Furrealz? That’s mausvlorely good to know.

  10. Manouk - Bunch of Backpackers 4 April, 2014 at 5:55 pm #

    Interesting article and can partly relate to this as a 28-year old. One of the things that also happened to our generation is just the immense amount of information that we have to keep up (all social media, the news, whatsapp). I think these thing are also part of the problem. We all want too much ;)! I don’t think traveling will always help. It has to be the state of mind that is calm and happy :)!

  11. Bemused Backpacker 4 April, 2014 at 5:05 pm #

    I can completely relate to this! I’ve been through the same thing myself and it has been cured by constant travel over the last decade and more. I think more and more people in my generation (I’m early thirties) and below now are starting to feel the same, rebelling against the status quo that society tries to force you down (school, work, marraige, bills/mortgage, death), completely burned out by work, lack of opportunity despite education, the credit crunch, no chance of getting on the property ladder because we are priced out, etc etc. I agree that disillusionment is a hard hit. It’s no wonder people are saying *** this and finding an alternative path that makes them happy, and travel certainly does that for me! Great post, I’m really glad I found your blog! I’ll have to spend a bit of time looking through your back posts! ;D

    • Beth 10 April, 2014 at 2:35 am #

      I totally agree, the whole property ladder is something I didn’t mention in the post but it’s definitely a big decision we’re facing at the moment. Is that just the first step to getting sucked back in though? It’s nice to hear from other bloggers who are still on the road, it gives me confidence if we decide to do the same thing for the next ten years! Thanks for commenting :)

  12. iputmylifeonashelf 4 April, 2014 at 2:21 pm #

    I am in my 40’s and I have never cared about success in any way. Life is not supposed to be about your career, it is supposed to be about your life. Trust me on this.

    • Beth 10 April, 2014 at 2:15 am #

      Thanks for the wise words! It’s great to hear from bloggers who’ve been through this stage and have made it out the other side just fine :)

  13. She Dreams of Travel 3 April, 2014 at 9:18 pm #

    I have definitely found myself feeling confused at times about my life path and I think it’s because as you said the possibilities are essentially limitless for our generation! Is it possible to have a midlife crisis at 23? haha While working at an English academy in Miami I had a coworker who used to have this awesome high paying job on Wall Street and just decided to quit one day to move to Ghana and teach English. Now he spends his years going between working corporate jobs to traveling to working at academies in the states. I think at the end of the day it’s more about following our dreams and what makes us happy and not being afraid to change that path as we go along. As my coworker told me… it’s ok to switch careers!

    • Beth 4 April, 2014 at 6:11 am #

      Haha I think it’s possible to feel like this at any point, especially in your twenties! That’s a good bit of insight about changing your careers at any point. It always feels like it’s such a huge deal, and you worry it might not work out. But most of the time people come out of a career change much better off, whether it’s more money, more time, more enjoyment at work, new skills, etc. I guess, it’s about not being afraid to take a leap. And I suppose time is on our side at this age!

      • Jaylen 27 February, 2017 at 10:15 am #

        Als Wilders aan de macht komt… dan mogen mijn Marokkaanse vriendje en mijn Turkse slager onderduiken in mijn berging en dan ga ik bij het veI.tezAta:‘rk kan het niet vaak genoeg benadrukken, maar de Israëlische component mag absoluut niet ontbreken in dit verhaal.’Ach, in welke van jouw verhalen mag de Israelische component [b]wel[/b] ontbreken?

  14. Hannah Elliott 3 April, 2014 at 6:38 pm #

    After spending 7 years abroad, snowboarding in The French Alps and basking on Greek Islands the novelty of joining the ‘real world’ has sorely worn off and my job is no longer that exciting.
    Where as a few years ago everything that I did seemed new and worthwhile.
    I am not that flattered anymore that I have a job with big responsibility.
    One minute I am embracing the desire to feel to grown up, settle down, get a mortgage and career, when I should actually be shouting ‘I’m 26 years old! I don’t have to make these decisions for YEARS! I don’t need to settle down – in fact, I might go and live abroad for a while!’ #GenerationY

    • Beth 4 April, 2014 at 6:07 am #

      Hi Han, I think you summed that up pretty well. One minute you’re fine with settling down and the next minute you think hold on, what am I doing?! Everytime I think about returning to UK and jumping on the career ladder I have this massive fear that the novelty will wear off and I’ll be left bored and wondering why I ever traded in my nomadic lifestyle. As you say, the flatery of big responsibilities soon wears off!

  15. Jon @ 3 April, 2014 at 3:57 pm #

    Nice post! Unlike a lot of people I never really had that corporate/office job, and after travelling/working abroad for nearly 4 years, I can’t imagine any other way to live.

    • Beth 4 April, 2014 at 6:04 am #

      Thanks Jon! You probably don’t need to have worked in the corporate world to know it’s not for you! I’m really glad to hear you’re loving life abroad. What do you to earn an income?

    • Bette 27 February, 2017 at 10:09 am #

      Your answer shows real ineitlegencl.

  16. After 2,5 years of backpacking and sailing around the world I came back to Europe and I´m still asking myself these questions! I think I´m more confused than before…came back thinking that it is time to get a real job again (I´m a Civil engineer) but can´t really see myself stuck in the office again and end up surrounded by things and goods that I don´t really need. As much as I was convinced that it was time to take a break of travelling and have normal life…don´t think I can do it anymore.

    • Beth 4 April, 2014 at 6:02 am #

      Hi Elena, I know exactly what you mean. When we returned home after our first year away, all I could think about what traveling again. I think once you do it, you’ll never be the same again! And this is why so many of us end up feeling like we’re in no man’s land.

  17. Raphael Alexander Zoren 3 April, 2014 at 2:00 pm #

    The problem is that many people are keen on following THE dream instead of focusing on THEIR dream. Just because the average citizen has a 9 to 5 job doesn’t mean that everyone should follow that example!

    • Beth 4 April, 2014 at 6:00 am #

      Very true Raphael! It just feels weird when you grew up expecting to be a 9-5er and then realising you don’t have to!

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  18. Britany Robinson 3 April, 2014 at 1:22 pm #

    This is something I’ve been through myself and it is a constant battle. Finding a fulfilling career is so important to me, and a lot of people (ie my parents and friends with real jobs) don’t get that. But we also have a lot more freedom than any other generation before us. We have more options for working remotely, and it’s culturally acceptable to not be tied down by a family or a mortgage when you’re in your late twenties. I love the opportunities available to us as GenerationY and will continue to try and build a career that I won’t dread each day. And it’s OK to be confused — it keeps us striving for more and working hard for the best life possible!

    • Beth 4 April, 2014 at 5:58 am #

      Hey Britany, thanks for the advice! It’s a blessing and a curse all at the same time. Working remotely and choosing to settle down a bit later in life is great, it just means there’s a million more options. But as you say, it’s perfectly OK to be confused. I think the high reaction from this post confirms there’s quite a lot of people out there suffering the same problem!

  19. karendwarren 3 April, 2014 at 9:15 am #

    I’m not quite Generation Y – more baby boomer! – but the feelings you describe can occur at any time of life. I had the chance a couple of years ago to leave my job and do more travelling and writing, and I’ve never looked back.

    • Beth 4 April, 2014 at 5:55 am #

      Hi Karen, It good to hear that it happens across all generations. As I’ve grown up I’ve realised I don’t think anybody ever really has a clue, everyone’s just trying their best to have a good life. I’m glad you’re getting to travel and write! Live the dream :)

  20. Amandine 2 April, 2014 at 1:40 pm #

    Re-assuring article for me, thanks for sharing this feeling! I also got my midlife crisis. After working hard on a 9-9 job for almost 4 years, I decided it was time to live my dream.
    The day before I turned 27, I resigned to my boss. Since then I have declined a couple of “really good offers for [my] careers”. Who cares? In a couple of months I am on my way to new adventures!

    When people ask me what I am gonna do, I just like to answer “I am gonna be happy” :-)

    • Beth 4 April, 2014 at 5:52 am #

      Thanks Amandine! I’m really happy you decided to live out your dreams, I hope you have an amazing time! And that’s the best answer to ‘What are you gonna do?’ Think I might steal that one ;)


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