Should Your Twenties Be for Work or Play?

I recently turned 21. In a discussion with a friend, we decided there are two major perspectives people take when approaching their twenties: work or play.

In the first, people view their twenties as the time to make ambitious career moves. Working 60 or 80 hour workweeks in university or at a job is easier when you don’t have a family. Also, if you work hard early you can enjoy a more comfortable lifestyle at a higher rate of pay for the rest of your life.

With the second view, people see their twenties as a time for adventure. If you don’t have a family or career, you have more personal freedom than any other point in your life. World travel, exploring different jobs and relationships and pursuing alternative educational paths aren’t going to make you rich, but they might mature you into a more productive, happier adult.

Work or Play: Which is the Right Choice?

I really don’t have an answer to this question. I’ve seen people pursue both approaches to varying degrees and make it work for them. Also, these two approaches assume you’re planning to settle into a career, marriage or family in your later twenties and thirties. If you don’t operate under that assumption, then the question itself is flawed. The single, childless factotum may see their twenties no differently than their thirties or forties.

Avoiding the Dilemma

My approach to the problem is an attempt to have both. Microentrepreneurship, whether running a blog-based business like this one, or some other online venture, is hard work and difficult. But it is also location-independent and offers greater flexibility than most entry-level positions. Having a digital lifestyle means I might be able to pursue the adventures of my twenties without having to start from the bottom after they end.

But obviously this solution won’t work for everyone. Most careers don’t neatly avoid the dilemma. Also, even if you were pursuing a path that offered both, there is no guarantee you or I can make it work easily.

Other Solutions

I’m less interested in spouting advice than I am in hearing your thoughts. How do you plan to live your twenties, or if you’ve already passed them, how did you live your twenties?

Which path do you think is better? Or do you reject the dichotomy altogether? Maybe you feel that pursuing one of the paths is impossible in your current situation?

I’m interested to see how other people are approaching this problem, since it really boils down to your approach in getting more from life.

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  • Justin Fenwick

    It’s about what satisfies your full well being. I’m trying to do both. Blast through school and masters degree while milking my networking opportunities to get positions that are fun and have flexibility. We are in an age of personal branding, so make yourself stand out. Stuck in a job? Use your free time to volunteer, pro Bono, or consult and gain experience. A few years of crammed schedules will leave you with all the right people around you if you have filed as much of your time as you can with things you are passionate about. What pays your bills will soon come to mimic that. Who are you going to the bar or traveling with? Make fun purposeful, let fun become your purpose.

  • Jeff Standing

    I think I’m going to go for play. It’s much easier (and more respectful) to take on responsibilities as you age than slough off the ones you’ve already got. That’s why no one cares about backpacking nomads, but everyone feels contempt for fathers who abandon their wives and children.

    I definitely don’t assume I’ll be married and have kids in my 30s and 40s, but I can’t be sure.

    The question is really one of gripping life by the balls right now, or waiting for it to give you delayed gratification. And really, although I’m pretty sure I’ll continue to be fit in the coming decades, the twenties are pretty much your time of peak natural physical prowess for anything except endurance racing. Life should not be experienced as an awesome, wealthy retirement when you’re too feeble to take advantage of it.

  • Colin Wright

    I don’t think you have to choose. No way.

    When I graduated from college, it was after the wildest and craziest school year of my life. I went out almost every night, dated several different girls and had a fantastic social life. I also started up two businesses, work a couple of jobs, completed two majors and got several solid job offers, one of which I ended up taking.

    Once you get the momentum going, it’s easy to get into the ‘work hard, play hard’ mentality.

    The real question is what do you do when you’re exhausted after a few years of that and want to take things to the next level?

    That’s where I’m at now, so I’ll let you know what I find out. Pass on anything you pick up, too, because we’re all in this together!

  • Matthew

    I left home at 22 travelled to the other side of the world and spent the next few years travelling through Europe and working in the UK. However I did end up working full-time in a fairly steady job through the latter half of my twenties (and getting married and buying a home too!)

    Looking back I think that it doesn’t matter which path you take, however your twenties should be about risk.

    You can afford to take greater risks, financially and career wise when you are young and single, knowing that time is on your side.

    This could manifest itself in extensive travel, starting a business, or joining a startup.

    What it shouldn’t be is safe and steady.

    I agree with you that these decisions aren’t exclusive choices, nor are they limited to those in their twenties. For instance my wife and I left our jobs and spent 3 months this year travelling in South America and Australia. However I think my acceptable comfort level has risen with age!

    You should start building assets up as soon as possible – either business, property or shares. It’s never too early to start building capital – it gives you more choice as you get older. Personally I should have bought a property as soon as I possibly could in an area I could live in. When I was single I could have flatmates in to help pay the mortgage, and when I travelled I could have rented it out.

  • Ashish Gourav

    I’m also 21 yrs old. I plan to work efficiently in my twenties and early thirties so that when I get settled with my own family I have enough financial freedom, career contentment, “inner-call heard” , I’d have met many successful people and they would help me guide… albeit to support just work may be a completely wrong paradigm…

  • Anthony

    Hi Scott,

    I made the decision to get a graduate degree and build a company in my 20s (which was exhilarating in parts, and also very, very hard in parts).

    Now in my 30s, I work as much or as little as I want to. I have significant passive revenue. My stress levels are very low. In the past 2 years, I have traveled more than in all my 20s. I’ve started doing things that I didn’t have time for in my 20s, such as learning another language, becoming good at certain arts I’m passionate about, and that sort of stuff.

    At this point, I’m glad I chose the path I did. If I were to do it again, I would do a bunch of things differently, though (in particular related to how I built the business). Having said that, the idea of creating an income generation base which will give you flexibility of time and location seems pretty sound to me.

    Best of wishes in planning out your 20s!

  • Hey

    Stuff I want to do:

    Several businesses
    Survival compound
    Top-notch physique
    Become master of pick-up arts
    Music career
    Writing career
    Build an awesome network of high-level contacts
    Work towards personal development in all areas (spiritual, mental, etc)

    I simply don’t have time for the traditional college & job :p

  • Mark

    Hey Scott!

    I’m in my early twenties and for me a third alternative seems the most natural. My plan is to work hard at removing my hang-ups and perhaps later start a career or spend my time enjoying myself.
    I reason that it is the most important to get rid of my inhibitations as they lower the quality of my other ventures. I also base this reasoning on past experiences where I’ve usually worked hard for something and then been forced to quit because my anxeity has increased with my level of success.

  • looeess

    Hi Scott, what a great question.

    My opinion is…a little of both. Have as much fun* as you can but don’t lose sight of your goals.

    You want to strike the balance of having good memories to look back on when you are much older, whilst at the same time not feeling like you have wasted all those years.

    Also, you will probably have the most energy and the most time-on-your-hands in your 20s than you will when you are older (no, really!). When you get to your 30s, 40s, 50s, 60s you’ll often wonder how you had so much energy when you were younger, and/or how you managed to fit everything into just a measly 24 hours.

    I see your 20s as the time to build your life. You are fresh out of young adulthood, now is the time to learn, grow and experience as much of life as you are able to, or want to. In your 30s/40s you will know yourself better because of it and will be able to decide where you want to go next.

    *”Fun” isn’t always about being wild and going partying every night, it can be making new friends, learning new things, climbing Everest, having enjoyable, meaningful experiences. Truthfully, you can do this at any age, but see above comment re time/energy depletion…

  • Armen Shirvanian

    Hi Scott.

    I recently was talking to someone who said he was working hard in his early years so that he wouldn’t have to work hard later, so he would choose the “Work” option in the article question. Choosing the “Play” option is a tough one unless play has long-term benefits associated with it. Other people only tend to tolerate one’s play for so long.

    I think some get more work and play done as a whole than others.

  • Jeffrey

    Well, Scott. I’m wrapping up my twenties (just made 29), and I spent the first few years in school, and the last few bouncing around from one unsuccessful job to another. I’ve only recently decided to take the proverbial bull by the horns and make a difference. My goal is to create an online lifestyle that is location independent, just as you mentioned in the post. And with the help of guys like you, Leo, and Chris Guillebeau, I’ll be there sooner rather than later.

    I say ditch the dichotomy and set up passive income so you can have the time of your life.

  • Ian

    Learn ’til you’re 30… Earn ’til you’re 40.

    PS – Learning doesn’t necessarily mean academically.

  • Maxine

    Hi Scott

    Interesting question, now that I’m in my thirties, it makes me ask myself 2 questions: 1) what DID I do in my twenties? 2) What would I have done differently given a choice?

    I would probably have liked to be in the 1st camp i.e. working hard, setting myself up for life but realistically, I was probably in the second mainly because I spent a large part of my twenties relatively clueless about who I was or what I wanted to do with my life.

    I think the twenties are the time to make mistakes – regardless of which camp you’re in. While the 1st camp sounds better in theory – aiming to have yourself set up for life by the time you’re 30 sounds like a quarter-life crisis in the making.

    In any case, it’s rarely ever an either or. Truth is, some of the best, most fun experiences I’ve ever had have been when I was doing activities squarely in the 1st camp – going out on a limb in terms of my career. As much fun as it may sound to live a totally hedonistic lifestyle, there’s actually a limit to how much fulfilment you can gain from it – eventually, you have to be working towards achieving something to really squeeze all the juice out of life.

  • Karthik Kumar

    I’d like to point out a couple things here… I know you wanted to hear stories more than you wanted to hear an intellectual discussion, but I couldn’t resist it. 😉

    1. Working hard does not always translate to wealth:

    – You might earn a huge income, but if you spend 60 hours a week at work, you are more likely to get loose with your spending.
    – Burning out is not a great wealth creation strategy in the long run.
    – It really depends on how you define wealth… I define it as fullness of spirit and joy.

    2. Freedom is only ever internal:

    – You can never be externally free, as every situation will limit you in some way… if you are traveling the world, for ex, you might not have the opportunity to maintain old friendships to the same level.
    – True freedom is the ability to accept the external limits of your situation, and see what it is enabling in your life

    3. You don’t need external freedom to find yourself:

    – You can be stuck in a dead end job and find yourself… the monotony and boredom might open you up to a new, deeper dimension within yourself…

  • Scott Young

    I think I like Ian’s response the best, however, I would argue that the learning should be non-stop.


  • Waski_the_Squirrel

    When I finished college, I decided to try my big adventure. I moved to North Dakota (from Pennsylvania). I figured that if I didn’t like it, I could always return home. I also figured that if I didn’t try it then, I never would.

    Anyway, 11 years later I’m still in North Dakota and glad I took the adventure. I’ve switched jobs a few times to find a better placement within North Dakota, but my life is good right now.

    It is best to try the adventures before they start to affect other people (spouses, children, etc.)

  • eric Autenreith

    I think I almost 52…53! I have been a whitewater rafting guide for 24 years and recently transitioned to being a reluctant carpenter. I finally completed a BS Environmental science/biology degree at the age of 36 and really have never used it to make money. I am involved in a local environmental/economic development organization and am contemplating returning to school to become more effective in these activities- law, social science, marine science…

    The circle of friends leading similar lifestyles- boaters/raft guides, climbers, ski patrollers- are more in the category of play first and work later. There is some joking that we have enjoyed our “retirement” in our youth and now have to work for a living. Nursing, environmental fields, computer/web businesses and construction trades are common fields we transition into. Things that have some mobility to them.

    Many are college graduates. Some people were fortunate to have means to “afford” their retirement early in life and some actually manage to make ends meet by being frugal, creative and smart in moving towards a more prosperous and sustainable lifestyle.

    Being in these tourism/service industries puts these guides and patrollers into contact with thousands of people from all walks of life, and after varying numbers of years(3 to 25) most raft guides and ski bums diverge onto some other course of interest. Sometimes guest contacts are inroads to other careers.

    We also see many “normal”, successful people who have “made it” and who are looking at retirement and a comfortable, secure life at the age when we are just getting our act together. It is a little unnerving but here we are and, it seems that some of us professional, migratory people are more or less well suited to the uncertainties of their not-normal approach to life.

    I guess people generally end up on the path that best suits them. No one way necessarily better or worse than another. I think it is helpful for young people to see these diffrent approaches to life AND see how these things play out through old age and death. Some people keep working- have to keep working- until death is near and some people can afford decades of slow decline and lengthy convalesences before the end.

    Again, no one way is better than another, just choices.

  • Steffany

    I’m 24. I graduated in 2007. During my four years in college, I thought I would lead the cookie cutter life because it was the easiest thing to do. I didn’t really think I needed to do anymore than to settle down and reproduce. I had the boyfriend in tow and knew that by the time I was to graduate, a marriage, home, and possible baby would fall into place.

    However, literally, the day after I walked at graduation, I was on a flight to New York City and my life hasn’t been the same ever since. I stayed in New York City for two years (I was supposed to come back that same summer), had a full-time job, traveled to seven countries and experienced a cross-country train ride (from NYC to San Francisco). It was the best time of my life. But of course, I had a lot of “figuring out” to do. Now I’m back in my hometown (in California) and anticipate my next move. At the moment, I have a chance to live in Hawaii for 4 months OR take on a supervisory position at a major hotel chain. So do I take on the responsibility of wearing a suit in exchange for some stability, or go live in paradise in exchange for a place to sleep while I work on an Eco-Resort?

    I don’t want to be rich anyway, so working now to make my lifestyle “comfortable” in my later years doesn’t matter too much. However, I do want to be comfortable. I don’t think I’d want to live in a tent all my life…

  • Andy

    Well, as someone who’s 28 and spent most of my 20s taking the second path, living the life of adventure, I’d have to say that its absolutely worth having adventures in your 20s but that you should try to pair that with some sort of constructive goal. I moved to Japan to teach English when I was 24, expecting to be there for a year before I went on to graduate school. I had so much fun though, that I ended up staying there until I was halfway through being 27.

    I wouldn’t trade that time for anything. I made a lot of great friends, had all sorts of unbelievable experiences, made a enough money to live fairly comfortably and made some progress in learning japanese. But… when I came back to the states last July in the middle of the recession, I found myself unable to find any sort of decent job and am now working as a school bus driver and living with my parents as I prepare for grad school at the end of this year.

    I’ll finish my grad degree by the time I’m 30, almost 31 at which point I’ll hopefully be able to get a proper job and start living like a mature adult. I didn’t feel behind until I came back to the states, but I definitely feel behind now. A lot of my friends are married, or will be married soon, are already a couple of years into their careers and have a very clear idea of what there life is. I’m more or less starting over and even though I still have plenty of energy, it’s fairly humbling and a little bit frustrating to not have those things figured out by now.

    I’m applying to a grad school in Japan right, partially because I love it over there, but mainly because the one skill I did develop was my Japanese ability and I don’t want to have the one concrete skill I did develop in my 20s go to waste. So, my advice would be, go have your adventures but find a way to make them work for you. I probably spent a little too much time going out to the club, riding my motorcycle around in the mountains and just enjoying life and not quite enough time developing a concrete skill.

    On the other hand, I can say all of this now because of everything I learned about myself and life by having those adventures, and I think that knowledge of life and self will serve me well as I move on.

  • Scott Young


    Thanks for sharing your story. I agree, the conflict between pursuing adventures in your twenties and the pressure to pursue achievement oriented goals can sometimes be difficult to resolve.

    Best of luck to you!

  • Abby

    Well let me just say that I really enjoy this topic of conversation guys – great stuff.

    I’m 24 and I have done some travel, some study and full-time work. I’ve had some relationships, some flings, some highs and lows and wouldn’t trade it for anything.

    What I’ve come out knowing, is that my path is different to generations before me, and mostly, the alignment that binds all contributors on this page is that we have ‘choice’.

    I won’t be buying a house until I feel comfortable in my career. And I probably won’t be comfortable in it until it assumes a stance which requires extensive, paid International travel. This goal is how I align my play/work ambitions

  • Charlotte

    I’m 23. And spent my late teens experimenting, getting it wrong, sometimes very wrong, studying, working job after job just to survive and quitting job after job craving to live.
    After qualifying to be a make-up artist i spent my time proactively seeking out jobs, and eventually landed an agent. I spent about 4 years working for publications i never thought i could, travelling with the job, meeting new people every day, some great, some not so great, making some more mistakes and trying my absolute best, while my friends were having their wild university days. I have always been ambitious and after leaving my agency and being completly on my own i realised that although i love my job i still have some fire in the pit of my stomach that needs to be fuelled. After meeting a man whose path is so similar to mine it’s scary, i feel i not only have not only the freedom that comes with meeting someone so like-minded, but also someone i want to share those experiences with. So, i guess my opinion on this whole disscussion is: I think it’s really important to find what makes your hairs stand on end, career wise so you can make the old saying of: ” work at something you love and never work a day in your life” a realtiy. Therefore you have the means to fund things you crave which varies for everyone. Some people want their dream house, others to travel, a family, whatever it is, and it changes throughout your life. The fact is, most of us need to pay the bills, but i don’t think that means you have to just work for the money, you can actually enjoy it! I’ve learnt that through doing jobs i have hated, just for the money, and it really can effect your life in a big way. I say, find what you love doing, persue your passions, be 100% honest with yourself and never settle for anything less than the best for yourself, go out there and live the life you’ve imagined.

  • Craig Allan

    Im 21 and asking my self the same question. I have just got out of a 7 year relationship, and at the time it felt like the end of the world. I pictured my self spending the rest of my life with this person. 🙁 Now im starting to realise that, its probably the best thing that could of happened, and has given me unlimited options with my life. I’m currently on a gap year from uni gaining experience in the field i study in. I think the way I would like my life to plan out is: finish my degree, work long enough to save money to travel, then get fly somewhere new. I will probably travel for a couple of years, then continue to fufil my personal goals until I’m 30ish. Then try and settle down and start a family. However who knows what life has in store, and i have now learned you cant plan your life. Do things today because you don’t know what tomorrow has in store. I just dont want to look back when im older and regret any option i didnt take. So now im going to try as much as i can. least that way i will know if i dont like something.

  • Spencer

    I just turned 20 a couple months ago, and I’m sort of clashing with myself as to how I want to spend my next few years as well. I recently landed a high paying job as a freight railroad conductor, however I am still not completely satisfied with my lifestyle. My social life is severely lacking due the odd hours of my job, and my thirst for adventure is stronger than ever. Ideally I would like to start a side business via the internet and break away from conventional employment, but do I really want to throw my career away to chase a pipe dream. Sigh.. time will tell I guess. Thanks for the read

  • Apples

    I’m 26 and I spent my twenties working my butt off, and finished college, with that ol creative adhd brain… wish i had started meds in my early twenties, I’d have a career by now! but since starting them (concerta) im finally starting to catch up to my graduate friends. Probably wouldnt have had to work as hard and so miserably if I had been diagnosed sooner. So do yourself a favour and get help for anything holding you back! I’m going to use my new animation job pay for traveling 🙂