10 Things I Wish I had Done in my 20s

Today All Groan Up is honored to welcome a guest article by the wise and witty Katie Milton. Enjoy!

 “We’re happy, free, confused, and lonely at the same time.  Its miserable and magical, oh yeah!

Taylor Swift croons in the back ground and reminds me of all the fun I had when I was 22.  Her lyrics and pop rhythms bring me back to a summertime.  A lake in northern Minnesota.  I can even hear the jet skis humming and can taste the bitter burn in my mouth from a jello shot.  I am reminded of the beach volley ball game I played and feel anew the embarrassment of losing a bikini top in a particularly difficult volleying maneuver.  I’m reminded of heart break, motorcycle rides, and discovering Europe.

Needless to say, my twenties were awesome. However, now having pressed on to that magical age of 30 and beyond, I want to share with you ten things I may have done differently to help you avoid the same mistakes I did.

10 Things I Would've Done Differently in my Twenties

(Also check out the popular article “4 Things I Wish I’d Tell Myself at 21-Years-Old”)

1. I wish I hadn’t paid so much for my education. 
Don’t get me wrong, I am a huge proponent of ‘gittin yerself edumacated’, but as many of you have noticed, a BA is the new High School Diploma and an MA is now the equivalent of yesteryear’s BA and so on and so forth.  All signs point to this trend continuing and with the high unemployment rate, educated and uneducated people all around the world are being forced to be more creative when it comes to getting yourself noticed and landing that high paying job that you deserve.

So, before going into debt just to attend your family’s alma mater, consider other creative ways that you might break in to that niche or industry that you feel so passionate about.  Lots of universities in Europe have internationally credentialed programs that cost a fraction of what stateside schools charge.  Or, it might not be such a bad idea to be that lowly office gopher for a summer just so you can network and brown nose your way into some creative solutions.

2. I wish I had run that marathon. 
In your twenties, your body is in peak physical condition to place some awesome physical challenges upon it.  Do your best to not take that for granted. Spending an alarming chunk of my time perfecting my keg stand techniques in my 20s has significantly impacted my ability to break that 8 minute mile I ran in high school.

3. I wish I had learned Korean. 
I lived in South Korea for a year and a half during my late 20s and during my time there I did not even once try and learn the language.  I argued that I was never going to need it for anything. Ever. In my entire life.  Combined with the mixed feelings I was having as a result of culture shock, that excuse seemed to be a fairly valid reason to not waste my time.  You want to know the 1st question that everyone asks when I say I lived in Korea?  You guessed it- Do you speak Korean?  The answer to that question always weighs heavy on my heart because I know that acquiring even a little bit of that language would have at the very least provided me with a challenging diversion while I was there as well as more hearty pats on the back in future networking sessions.

4. I wish I had worn more sunscreen.  Does this need an explanation?  Put it on like frosting, folks

5. I wish I had gotten more sleep.
While in high school my strict parents enforced a 12am curfew.  At the time, it felt too restrictive and ridiculous. I argued incessantly. They argued back, “Nothing good happens after midnight.”  I spent a lot of time in my 20s learning that lesson personally.  I proved to myself that they were right.  Think about it?!  After midnight is when someone gets naked, someone gets hurt, someone gets involved in senseless drama, something gets broken, someone gets cheated on, or someone cheats.  Inevitably, someone gets sick and on occasion permanent sharpie art begins.  Don’t forget, nothing good happens after midnight.

6. I wish I would have slowed down or said no. 
The decade of your 20s is a tumultuous time.  Everything is exciting, energizing, interesting, and fascinating. Combine that with some misguided peer pressure and you have a recipe for someone feeling, at the very least, uncomfortable.  It is easy to get swept away in the tide of exciting emotions but I wish I would have been self aware enough to press the pause button on some of the more hasty decisions I made.  Some bitter memories may have been different if I would have taken some extra time to decompress and reflect instead of rushing head first in to what ever excitement was presented.

7. I wish I would have journaled consistently and kept more detailed notes. 
As it was, I journaled a fair amount, took lots of photos, and kept “the memories” more of less organized, as far as I knew. But after a recent trip to my parent’s attic to review the journals and keepsakes in search of some solid adventure stories, I was disappointed to find stacks of pathetic scribblings with long stretches of months and even years between entries.  As an aspiring writer, you might be able to imagine how disheartening it was when I realized I might have to write fiction instead of memoirs.  Point is, you never know when that stuff is going to come in handy and keeping it detailed, organized, and safe is something you will appreciate.

8. I wish I had maintained more quality connections.  Life is busy and it speeds up a bit as you near the end of your twenties.  Well, it feels that way because you are no longer in the same geographical location as your best friend from high school or your college roommate or that one person that took off on an amazing adventure and is now earning six figures from selling the movie rights.  Maintaining quality relationships amidst a cross country move, a marriage, a family, a divorce, or death is a considerable undertaking and requires commitment and intention.  Keep your close ones close and you’ll experience less friendship angst in your 30s and 40s when the shiz really hits the fan!

9. I wish I would have been more disciplined.
Comparatively, I have a decent amount self discipline but overall I am a self proclaimed jack of all trades and a master of none.  Which is fun during a social networking session when you can bust out a Tom Cruise move from Cocktail using a Malibu bottle and follow that up with an acoustic operatic rendition of Se tu m’ami by Alessandro Parisotti, all the while bragging about your pirate adventure off the Caribbean coast of Mexico.  But when you aren’t good enough at any of those things to nab a job offer, you are just a fun party trick.  Having the self discipline, focus, and dedication to become an expert in some area (even if it is fire dancing) will not only strengthen your character but it will also fend off future anxiety attacks in which you wonder if you lack credibility in any one area.

10.  I wish I had worried less.
During your twenties there is a a lot of pressure to answer all of life’s profound questions.  What is especially confusing about these questions is that it is all the “adults” that are pestering us with the meaning of life even though they don’t have the damn answers themselves!  In your twenties the answers don’t matter.  Rest easy knowing that some people never find the answers even after an entire lifetime of searching.

So, go forth, be brave, challenge the status quo, and remember that hard work can cover a multitude of sins.

I’d love to hear from you in the comments below:

Based on your experience, what would you add to this list?

Conversely, what things did you do in your 20s that you are grateful for?

Katie Milton is an aspiring writer living in Mexico who is incredibly grateful that she had the courage to quit her corporate job and sell what little she had in her mid twenties to travel the world and never look back.  Find her at www.katiemilton.com and follow her on Twitter.


  1. Angela

    Excellent reflection. I completely agree that too many people get themselves in too much debt.

    I would have traveled more between jobs without such a focus on money. Live a little and let everything fall into place when it is needed.

    I agree with the discipline as well. I am well rounded, but most companies are looking for specialized candidates. Your well-rounded resume doesn’t even justify a phone call. . .

    • Katie Milton

      @Angela, I agree with your sentiments!

      Debt is a huge bummer and once in a lifetime opportunities are just that. It can be a challenge to weigh the pros and cons of a cool opportunity that might be more expensive than we can afford. In my experience, I have found that if one is creative and perseveres you can almost always find a better value!

  2. Katie Milton

    Paul, Thanks for this wonderful opportunity to guest post on All Groan Up!

    • admin

      Thanks Katie for the wonderful, thought-provoking article. Great to have you join the community here at All Groan Up!

  3. Katie (@AsktheYoPro)


    Thanks for sharing your honest reflections on your twenties. 5-8 are my favorites. It’s got me thinking… while I’m basically smack dab in the middle of my twenties why don’t I make a list of what I want to do and make sure I don’t not do… I’m happy to say you gave this Katie something to think about with an iPad in the part on this sunny afternoon. 🙂

    • Katie Milton

      @Katie, Glad to hear that this post cut through the noise for you! I am a big fan of lists and think that you’re idea of jotting down some notes about what you think you’d like to do vs things you think you’d not like to do is a great way to find clarity, purpose, and passion! I’d love to hear about what’s on your list once your done! Cheers!

  4. Rachel O'h-Uiginn

    As a 29’er now…all those “mistakes” matter because you personally needed to realize what matters most to you. Settling into 30 feels amazing because I don’t look at my 20s as “why did/didn’t I do that?” — it just is, you learn, and more forward.

    • Katie Milton

      @Rachel, you are SO right! I am thankful that the past opportunities that I had shaped me into who I am today and I don’t spend time regretting the decisions I made. However, hindsight is 20/20 and if I could apply some of the wisdom I have today to situations I experienced in my 20s I think I may have been able to save myself some angst- or some debt at the very least! Cheers!

  5. Anthony Moore

    Katie, awesome advice. I’m happy to admit that I’m already already of some of these! The best one for me was learning to speak Korean – me and the soon-to-be-mrs. want to live abroad somewhere, I’ll definitely make sure to try and learn the language!

    I’m just curious – can you tell me 2-3 things that you’re ‘glad’ you did in your 20’s??

    • Katie Milton

      @Anthony – Congrats on your decision to live abroad with your soon-to-be-Mrs! It will be a mind blowing experience for sure!

      Great question about 2-3 things that I am glad that I did in my 20s. Off the top of my head I would say:

      1. I am glad that I listened to my “gut” and had the courage to leave my corporate job for something unfamiliar. That experience taught me A LOT!
      2. I am glad that I left the US and pursued living and working abroad (Prague, South Korea, Mexico, and still going!) I also learned an immense amount here too!
      3. I am glad that I didn’t buy a house and get wrapped into a mortgage a few years ago when I thought that was what I wanted. I now split my time between the US and Mexico and have very little “baggage”. 🙂


  6. Peter DeHaan

    Katie, these are wise observations, but these experiences also shaped you into who you are today!

    • Katie Milton

      @Peter, thank you for the compliment! I am so very grateful for the opportunities that have led me to where I am today I cannot even begin to list them all! However, as I mentioned to Rachel above, I believe that if the wisdom that I have today could be applied to some of the situations of my 20s, I’d have experienced less angst and most definitely less debt!


  7. Ericka Vaughn Lashley

    well, at the ripe old age of 25 🙂 I’m halfway through and this is definitely a great mid-twenty reminder-thanks Katie!

    ok, I think I would add to the list. I wish I hadn’t been so stuck on doing everything right the first time. When I was younger, I often found myself making no decision for fear of making the wrong decision. We get so caught up in what will happen if we make a wrong move! when honestly. what’s the worse thing that could happen?! you fall down? pick yourself up. You hit a dead end? turn around. You come to a closed door? knock, kick it open, find the key, or move on to another door. Really, it’s not that traumatic and the quicker we get moving, the more time we’ll have to learn from our mistakes! A quote I really like is “God can’t steer a ship that’s docked in the harbor.” As long as we’re still moving, He can keep directing.

    • Katie Milton

      @Ericka, Ahh, I remember 25 so fondly! 🙂 And I like your addition to the list! Perfection doesn’t exist so wasting time waiting for it to roll up in a fancy sports car and announce its arrival isn’t going to happen! I’m not encouraging anyone to make hasty decisions but you’re right- many decisions that we fret over in our 20s are not life and death and we’d benefit from just having any experience at all! Love your saying – I use a similar rendition – “God can’t steer a parked car!” Just keep on keeping on!

  8. Margaret

    You do know that it’s not too late to learn Korean, right? Learning a new language is great exercise for the brain at any age. Languages that make you use the verbal and graphic parts of your brain are fantastic for keeping that organ in tip top shape in the up coming decades. I also know people who ran marathons in their 30s and later. Live well with no regrets 🙂

    • Katie

      @Margaret, You are so right! You are never too old to tackle anything! As a matter of fact, since leaving Korea, I have become quite advanced in my Spanish language ability (living in Mexico provides daily practice!) and I have recently started to tackle Italian for an upcoming trip! Personally, I’m not sure that I would enjoy the physical ramifications of running a full marathon but do intend to run a 1/2 marathon in the near future! Thanks for the reminders!

  9. Jeanna

    Katie! First off, hi! Second, great list and article. Fun read.
    I’ll add to this by saying I wish I were not so afraid of life. I held back many times from great opportunities all because I was afraid of … What? What would happen? What people would think? That I might be tired the next day? Nothing that I look back at and really know the answer too. It saddens me to say, it took me loosing my beautiful, fearless sister Suzy to understand what I missed out on. She lived life, she always was on board and would always stand by her word and be there for you- even if it was only the two if you. She lived a short, yet full life and truly loved life. We never know what day is our last. Have fun!!! Be safe of course, but enjoy this beautiful world, life and the amazing people you share it with.
    Oh, also, good advice – never judge. You will miss out on so much and also the most interesting and touching people out there. Take time to talk to people.
    Thanks for the good talking points going into the weekend!
    Jeanna (Baratto) Landon

    • Katie Milton

      @Jeanna, so good to connect with you here! I really enjoy seeing photos of your little ones on Facebook – please tell your family I said hello!

      You’re right, we should spend less time being afraid and more time being actively involved in living our life fearlessly, just like your sister did! Her tragic accident is a poignant reminder of that oft times taken for granted reality of the preciousness of life.

      Not judging is a good one too! I find that I am able to curb this symptom of the human condition by avoiding gossip like the plague! I feel that the two are inexplicably intertwined and I use gossip as the benchmark. I know that if I hear gossip – judgment is either included or right behind.

      Also, I am really glad that you joined the conversation. Your additions are very important.


  10. Mike

    I am in my 20s now and I feel what you missed out on was not that bad. A lot of those things from learning to speak Korean to number 7-9 can be done anytime in life. However, it’s great to hear you enjoyed your 20s.

    I hate everything right now because while my friends had dropped out of high school and are making a lot of money now where as I am 25 and still in university on my 2nd degree. I haven’t been laid nor have I been a party go-er. I have no friends whatsoever. Everyone I’ve met in university so far have been complete liars and backstabbers. University has taught me that theres no actual meaning for friendship in life. I promised myself that in life, I will never again make a friend. ever! I plan to be alone all my life with no relationship whatsoever.

    In terms of your “brown nosing” theory, I am graduating university right now and have gotten rejected from every single entry level career I’ve applied to even after getting help from University Career Centres and Government Career Help Centres. I’ve even gotten rejected from McDonalds and Wendys etc for being overqualified. I’ve tried Freelancing but nobody wants to give a project to someone who is starting up. Just like careers, everyone is looking for someone with experience.

    Instead of running marathons, I run outside whenever I feel like it for 5-8 miles. Thats good enough.

    Anyways, so far I hate my 20s and just wanted to let you know that the things you’ve missed in 20s are alright but you still had fun and made the best out of it!

    • Katie

      @Mike, WOW, it sounds like you are definitely going through a challenging time right now!

      Although this may not make you feel better – Fact: navigating the human condition isn’t easy and it certainly isn’t fair. Add that to the tumultuous decade of your 20s and you have a recipe for despair. The good news is that is does get better and all of your hard work will pay off and will be worth it!

      Keep in mind that TONS of successful people experienced unbelievable amounts of failure before “making it big” — Oprah Winfrey, Michael Jordan, Abe Lincoln, Thomas Edison and so on. I commend you on your diligence in continuing to persevere. The world can be a difficult place and developing some thick skin can go a long way in protecting yourself from bad shit that happens. Remember to keep a positive attitude so that you aren’t contributing to the hideous cycle that can keep you down if you let it.

      A few recommendations that I might suggest:
      1. Consider forming your own Meetup.com that is specifically tailored to your interests and hobbies. Remember that it takes time to find and develop high quality friendships– and once you do, they are worth it! Or you might consider attending a MeetUp in your town that is off campus and not necessarily for students. That will give you an opportunity to meet others outside the “university bubble”.

      2. In the career realm, I highly suggest seeking out a Life Coach, maybe one that specializes in working with recent grads. I hired a life coach during my transition in 2005 and found that it was an amazing resource! I cannot speak highly enough about that experience.

      3. Although getting laid is fun and sex is a wonderful thing to experience with someone you love, I think its kind of over rated. Try not to beat yourself up over it. Although the timing of the universe/God/Whoever is in charge, doesn’t always arrive when we want it, it never arrives late. Try and find some peace in letting things evolve in their own time/way.

      Be proud of who you are! You are exquisitely unique and there are lots of “someones” (friends, lovers, careers) that are out there searching for someone just like you. You just need to make sure that you persevere long enough to cross paths with these someones.

      Go get em!

      • Kim

        I could say I worry a lot. These tips are awesome. I could say that I haven’t had friends since high school. With education, I try in class, but if I hear others talking about their experiences of parties, gatherings of others, then I feel my esteem goes out. Recently, I’ve decided not to receive Facebook messages in my email & to check it only a few times a month because of how depressing it is (others don’t keep in touch anyway). Another tip, don’t be afraid to contact others to ask about something if you don’t know their gut feeling. One of my goals is to have some friends by the end of this year without social media.
        The others points are good to; learning new languages helps to understand other cultures, competing in sport events are good, as then you might be able to be more disciplined.

  11. Ree Klein

    Hi Katie, you offer some really great advice to people of all ages. I never got my degree and spent my entire adult life working my rear off to prove I was just as good as my counterparts with degrees. I did well BUT I spent so many years working long hours inside a building and not drinking in the sun.

    If I could offer advice, it would be to save as much of your earned income as possible as early as possible and avoid debt like the plague. Until you have it, you don’t know how much freedom comes with no debt, a fat savings account and a little guts!

    I wish I had applied those simple principles in my 20s so that I’d be where I am now a lot sooner.


    • Katie

      @Ree You are so right! There are unbelievable and endless possibilities for someone with no debt and some guts!

  12. michele

    I’m 25 and my parents still use the phrase – nothing good happens after midnight! I nearly fell out of my chair when I saw that!

    Realizing, in my 20s hump years, that everything you wrote is absolutely true and starting to see it for myself. It seems like the biggest one – becoming less self-aware and more life-aware.

    Great suggestions!

    • Katie

      @Michelle, Seriously – did our parents compare notes or something?! I thought my parents were the only ones we used that line! It kills me to admit it but they’re right. Haha! Thanks for joining the conversation and I’m glad you enjoyed the post! Cheers!

  13. Joanna

    Half way through my twenties and something I’m working to do more of is learning the basics of a lot of things outside my main areas of study/expertise. Lots of young adults seem to slip into learning just what they have to to get their degrees (and absolutely nothing more). Apart from the personal enrichment benefits of learning widely, out in the workforce and volunteering I’ve been surprised by how much knowing even a little bit of things like marketing theory, photoshop, HTML code or behavioural economics can go.

    • Katie

      @Joanna, I agree wholeheartedly! As a resource to finding things to enrich your specialty, I recommend checking out the site expertenough,com There are lots of articles that can help you find things you didn’t know you’d be interested in and give you enough information to be dangerous during cocktail conversations. Cheers!

  14. Rebecca

    Great reflections! I’m still a couple years from my 20s, but I already feel you on a lot of these. If I could add one-I wish I’d studied abroad.

    • Katie

      @Rebecca, I so agree with you! I desperately wanted to study abroad when I was in high school and it didn’t work out but I definitely made up for it in my 20s! Remember that you can still do (independent) study abroad even if you’re not in school and often times it’s much less expensive that way! Check out Gap year ideas online!

  15. Anonymouse

    Stress less. I’m just starting it. Among other things, stressing less can actually make you poop on a regular basis which is nice and in turn makes you stress less.

    • Katie

      Yes, a reduction of stress and regular pooping is definitely part of the recipe for health and happiness.

      • admin

        Ha! Too funny Katie!

  16. Grace

    Thank you, thank you Paul for these pearls of wisdom =) I’m turning 20 this year and am so happy to have this to guide me!

  17. Ma

    U wrote the best list about this topic ever.


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