Updated on 08.14.14

Ten Things I Wish I Had Done When I Was Twenty

Trent Hamm

I’m thirty years old. Over the last ten years, my life has changed radically. I went from being a college student to being an office professional, then to being a writer. I went from being single to being married with children. I went from owning just enough stuff to fit in the trunk of someone else’s car to owning two cars and a home. I went from being debt free to being perilously in debt and part of the way back again.

Looking back, there are a lot of things I wish I could tell myself then (for one, avoid someone named Alison who lived in your apartment building during your senior year). I’ve often jotted down these thoughts in my personal writings, but I’ve realized that there are several very useful general things that are worth mentioning.

Here are ten things I wish I had done when I was twenty.

I wish I had saved just a bit.

If I had just put away $5 every time I spent money on something frivolous, I would have barely missed it at all. I could have just stuck it into a savings account if nothing else and just let it ride until I needed it for something big like the down payment on our house. Even a few dollars saved here and there over my younger years would have made a big difference when we went to buy.

I wish I had connected better with many of my college classmates.

There was a steady group of people that I saw time and time again in many of my classes, yet I never bothered to try to get to know many of them. I knew their names and their faces and that was about it – I was more content to just hurry home and go do something fun with my normal crowd. What I didn’t realize is that many of these people in my classes were people that wound up following career paths similar to mine – and having long-time friends in the same career as you’re in is incredibly helpful and quite fun.

I wish I had taken at least a class or two on writing.

Writing was what I was passionate about, but I always found it difficult to squeeze in classes from the English department on the subject. Even during the semesters when my academic credit count was low, I never even seriously considered taking such a class. Looking back, I passed up a great opportunity to get some training and encouragement in an area I was personally passionate about. If you’re passionate about something, find time when you’re in college to dabble in it.

I wish I had learned the art of postponing purchases.

It’s easy enough: if you’re in a store and see something non-essential that you’d like to have and weren’t originally intending to buy, put it down and leave the store. Give it some thought. Ask yourself in a few weeks if you still want the item. You might surprise yourself and find that you don’t actually want the item any more – and that saves you money. Instead, I bought strongly into instant gratification – and it cost me for a decade.

I wish I had engaged in overseas educational opportunities.

I had an opportunity to spend most of a summer in Australia, an offer I turned down because of the limitations I put on my own perspectives. I even let that perspective spread to others, talking a person very close to me out of considering a semester in Scotland, because I didn’t want them to leave. I regret both choices – and many other opportunities that fell through. Be serious about your own fears – recognize them when they pop up and try hard to knock them down.

I wish I had been more entrepreneurial.

I was around at the birth of at least two dot-com startups and could have easily been involved in them, but I avoided the opportunity. It seemed too risky. Looking back, I realize now that I had very little to actually risk by being involved except for my free time (which I had plenty of). There are opportunities all around you – don’t close your eyes to them, particularly when the only thing you really have to lose is some of your spare time.

I wish I had used credit cards more sensibly.

I racked up hefty balances on my first credit card quite quickly. Looking back, most of this was because I really had no idea how to reasonably use a credit card. It’s easy. Just use it for things you would already buy and you can already afford and a credit card not only builds up a positive credit report for you, it also can help you get some free stuff via rewards. I didn’t follow that basic rule.

I wish I had listened to more of my mentors’ advice.

I had three great mentors during the third decade of my life, all of whom were present in my life when I was twenty. They all offered me great advice over the years, but I was only willing to listen to some of it. When you find a good mentor that you can trust, they’re usually there to really help you – take everything they say with value.

I wish I had been more politically involved.

I loved politics then and I love politics now. What I didn’t see then is that all politics is local. Sometimes it’s difficult to see at first glance, but even the most national of politics grows out of a foundation built in your own community. Today, I see a lot of issues in my community and state that I wish I had the political experience to affect, but I don’t – I was too focused on national issues where I had little impact. If you want change, start on your block.

I wish I had started saving for retirement during my first day on the job.

Actually, I did do that, but I didn’t save nearly as much as I should have. The first day of your real job, contribute as much as you possibly can to retirement. Make it a habit right out of the chute. For one, doing it now before you’ve adjusted to your higher salary makes it much easier to do. For another, the earlier you start saving, the easier it is to reach big retirement goals.

I started this post as an email to a few college students I know. Instead, I’m going to send them the link to this post – and hope that they pass it on to their friends, too.

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  1. Your life isn’t over! Get out there and do the things you wish you had done. Take some college writing courses, you can audit them fairly inexpensively.

    Don’t feel like you missed out opportunity, but then not do anything about it today!

  2. Anastasia says:

    If you are passionate about something, don’t just dabble in it, consider it as a major! I find that my students are far more motivated to learn the material and complete the assignments in classes that they want to be in, compared to classes that they have to be in.

  3. plonkee says:

    Some of these things strike me as using the benefit of hindsight. If you knew that your life was going to take the course it has, then writing classes would have been a great idea. But, you didn’t know that when you were 20.

    I bet there are other subjects you didn’t study in college that in an alternate universe would have turned out to be helpful.

    Don’t look back, look forward. When you get to 40 there will be avenues you wish you’d explored at 30. Just do the best to do the things that really make you happy and it’ll work out fine.

  4. I wish I had been more politically involved in college. Everything else I’m pretty happy with. Being that I’m still in my twenties, I have time to get into anything I haven’t yet.

  5. Seth says:

    Some of these, I’m saving for my kid. Wonder if he’ll listen….

  6. Johanna says:

    On writing classes: The most important thing I learned from the two writing classes I took in college is that writing classes don’t really teach you very much about how to be a good writer. Good writing is mostly intuitive. There are some aspects of it that can be learned, but they are best learned by having your writing scritinized by other good writers – and you can do that without taking a class.

    On overseas opportunities: Your wife is a teacher, right? Does she have the opportunity to take a sabbatical? If she does, you can use that time to get the experience of living overseas. You have a job now that you can do from anywhere. You’re fortunate.

  7. Baker @ ManVsDebt says:

    Wow, this is a great reflective post.

    I am proud to say that I am 25 and in part do to blogs just like this one am already making headway on many of these suggestions. I consider myself lucky to have stumbled into enough of this type of information early on in my life.

    As my wife and I prepare to move to Australia in 6 weeks, I can really appreciate our ability to get our financial life in order and take a leap like this. Thank you for the part you played in helping us get there!

  8. Greg Retzloff says:

    Ah, to be 30 again. I have the same regrets as you multiplied by 10.

    But at age 54 I started a new career using many of the skills and talents that I’d never used before, in addition to some that have been dormant for years. I still don’t know two years later whether this will pay off.

    As to the past–meaningless. Now and the future are what matter.

    To paraphrase Dante: The road is beter than the inn. So enjoy the road!

  9. Debbie M says:

    I did a pretty awesome job when I was around 20, but here are some things I could have done better:

    1) Take out that extra student loan, buy a CD with it, and pay it (or a higher-interest rate loan) back immediately after graduation.

    2) Go to the cheaper in-state school. I would have probably been even happier and getting just as good of an education at a large university instead of in the largest major at a small university, more activities would have been available to me, and I would have had a lot fewer loans to pay back, so I could have gotten a car, house, and retirement savings going quite a bit earlier. I wouldn’t have gotten to live in Boston for three years though, which was also cool.

    3) Studied abroad.

    4) Talked to career counselors more. That might not have helped, but it might have. It never really occurred to me to do so, even though I was trying to figure out a career path. (One by one, I eliminated every job I could think of. Twice.)

    What I really want is some advice on what I should be doing now, though. It’s all very fine that I now know how to be a good college student and a good 20-year-old, but it would be more valuable to know how to be a good 46-year-old.

    As when I was 20, I’m doing some things right: making time for fun every day, paying off my house by age 50 (and having no other debt), retiring by age 52, diversifying my investments, losing those last 10 pounds, making an effort to stay close to my sister even though she’s had a baby. But should I be looking for a job that doesn’t drive me crazy, even if it means I can’t retire so wonderfully, fabulously early? If so, what? Certainly I need a back-up plan if they break my pension before I can retire that’s better than “quit immediately.”

  10. Tom says:

    LOL – Who’s Alison?

  11. George says:

    Alison… at least you started at the beginning of the alphabet. I was stuck on the M’s with Margo, Marla, Martha, Mary, Missy, Muriel…

  12. Studenomist says:

    You forgot one thing on that list: you wish you read Studenomics. All joking aside I’m not much older than 20 but a few of those things I know will be on my list in 10 years. I’m good with money, retirement, networking, and all that stuff but for some reason I do not have the guts to leave home and try something new. I have a million reasons but all excuses aside I just do not know why I can’t leave. I love to travel and all that but I wish I had it in me to study in a different country or even work abroad.

  13. SaveBuyLive says:

    Your list is a lot like one that I would write. Only I wished I would have liked to spend more money and done less studying and working. Not spending on random stuff, but spending on experiences (socializing, travel, studying abroad, taking internships in unusual places, etc.). I would love to have more to say about that period of my life than just how hard XYZ test was, how much I studied for ABC class or how many hours I worked at my part time job under a boss who hated me.

    I also wish I would have taken a wider range of courses. Not just ones related to my major/field of study.

    But all that’s behind me and now I’m moving forward. I didn’t get to travel when I was younger so I’m grabbing every opportunity I can now. I didn’t take courses outside my field when I was younger so now I’m addicted to TTC and AcademicEarth.

  14. DebtGoal says:


    This is an honest confession, which I’m sure many can relate to, including myself. But such lucid hindsight is a powerful tool for standing up right now and making serious changes to one’s finances. In the least, it has inspired me.

  15. Jackie says:

    I think I did well with my choice of classes/majors, and I did a fair amount of traveling– I studied aboard for a semester and did a cross-country road trip when I was 21. I do wish I had been more involved in campus groups and politics though, but I was too focused on work/classes/friends.

    I echo a lot of your advice about money, though. I worked all the way through college, but I spent every dollar– I didn’t even have a savings account, just a checking one. I never thought ahead and did way too much impulse-purchasing.

  16. Coupon Artist says:

    That is a great list! I would add to it that I wish I would have taken advantage of more of the free educational extra’s the school offered. We had a lot of amazing speakers and other presentations offered to the school that were free, or very lost cost, for students but I didn’t always take advantage of those opportunities because I had other social commitments (like frat parties) that for some reason at the time I felt were more important.

  17. Man… isn’t this the truth… all the things we wish we had done differently but we’re “too smart” so we had to figure it out on our own…

    I sometimes wonder… with each passing generation so much personal knowledge must be relearned. How far advanced would our society be if we could “train” a generation to actually trust the wisdom of those who have gone before… don’t relearn past life lessions, grow and conquer new challenges… wow, that would be so cool.


  18. Hogan says:

    Don’t dwell on these too much. A top blog at 30 are you kidding me, you are doing fine.

  19. blank says:

    really who is allison?

  20. craig says:

    Well, count me as one who started investing when he was still in college. I plowed as much as I possibly could into a basic loaded mutual fund as soon as I started making some money in college (the loaded fund was dumped for a no-load as soon as I had enough of a balance). almost 20 years later and we have 2x the value of our home in the investment fund, and it’s still growing (in spite of the economy). Even so, my wife and I are pretty frugal. Barring total societal collapse or major catastrophic illness, we will see seven figures long before all of our friends retire with little hope of ever drawing social security.

    Time is your very, very best friend. Start TODAY>


  21. I would have to say I like this list because I’m still in the low twenties so I can learn from this list and I now can better myself by taking action on this list, Great Post!

  22. I wish I had taken more classes I enjoyed, rather than ones I ‘had’ to take.

    I also wish I had stayed in touch with some old friends.


  23. Dana says:

    Thanks for passing this along. Very reflexive, and very informative for someone still in her twenties.

  24. Mike Sty says:

    Being 20, I can safely say I’m in agreement :D The only exception is education abroad – too expensive and not really what I’m interested in. As for the rest, I’m tearing it up :)

  25. getagrip says:

    Reflection is fine, but don’t dwell on it. Use it to shape what you want to do now and in the future. If you wished you’d spent a semester abroad maybe there’s something you could do now with your company to get a position overseas with them or an affiliated company. Maybe just plan and save for a long vacation overseas. If you wished you’d taken a writing class, or art class, or computer class, there are typically plenty of offerings at a local community college both for credit and non-credit you can take. People forget that looking back and learning from your mistakes and those of others and then applying those lessons to how you are living now is what wisdom is all about.

  26. Becky says:

    I’m going to be 30 here soon. This time 10 years ago, I was probably drunk. Good article for self-reflecting.

    I don’t really get the whole traveling abroad desire. I was sort of the freak for not doing it, but I had no desire and have no regrets.

  27. I can wish I did a lot of things back when I was 20, but that was then and this is now…all about forward thinking and implementing any mistakes I might have made in the past into lessons learned and wiser decisions.

  28. tammy says:

    I am 50 and I have found myself in a pit of regret over not saving for “retirement” (what ever that is these days…) Divorce at 35 forced me to start all over again financially. The last item on your list really resonanted with me.
    Trent, your posts are always wonderful and I really enjoy receiving The Simple Dollar in my mailbox!

  29. This is a really honest confession, which I’m sure many can relate to. I wish I had been more interested in the online in college. Everything else I’m pretty happy with. Being that I’m still in my twenties, I have time to get into anything I haven’t yet.

  30. K says:

    Completely agree on the overseas study. My college had a spectacular Junior Year Abroad program that I really should have taken advantage of.

    I’m in my 30’s now and I’m just beginning to understand the statement “youth is wasted on the young”

    I think the best part of thinking about what you could have done back then is what you could do right now. Also think about what mattered to you back then, what matters to you now, and then try and think ten years from now, to think what will matter considerably less to you then.

  31. Bette says:


    Alison? Do tell!

    My question for you, young man, is what will be on your list when you’re 40? Few of us escape our 20ies without some regret. That is life and hopefully, we learn from it. Even when we live as fully and engaged as we can at any particular age, if we don’t have at least a few regrets, or wishes that we’d maybe done a little something different, what have we learned on the journey? I think your list represents a very young life that’s been lived well, you’ve learned from it and you’re sharing it for the benefit of others. What more could one ask for, except to keep on this path.


  32. Brian says:

    This post was great!

    Being 21 (almost 22) It’s great to see what things can still be done before I’m “too old” to say “I should have done this or this.” All of these tips are so great. I think most important to me is **I wish I had listened to more of my mentors’ advice** There are so many people that have “been around the track” (20’s) and can offer absolutely amazing advice (family, teachers, co workers)

    Thanks for this post!

  33. Bill in Houston says:

    Back in my day the idea of studying abroad was for rich kids. Programs really didn’t exist. I’ve never wished I had studied abroad, especially seeing how long I spent as a college student.

    I was very active in politics when I was 20 (probably on the opposite side of the spectrum as I was a volunteer for Reagan-Bush ’80). I got that out of my system in the 90s when I was in my late 30s.

    Realistically, the MAIN thing I wish I had done when I was 20 was stay in school full time. I went to seven different colleges and universities and had NINE majors before graduating at age 43 with a Bachelors in Business Management. When I graduated I had 225 credits under my belt, all over the place. After graduation, though, I charged straight into grad school and got an MBA when I was 45.

    I wish I had stopped screwing around so much. While I really wanted to be a grown up (my first fiancee once said I was 22 going on 40), I didn’t put my full effort into life. I mostly had decent jobs that paid the bills but without the right education I had no real career. I fell into technical writing as a job filler and wound up doing it for 20 years.

    I never had my priorities straight when I was 20. People today would say, “But you’re only 20.” When my father was 20 he worked full time and went to college full time. He got married at 20. My mother helped support my father as he went to college, and after he graduated my mother attended college. When my mother’s father was 20 he was a college student who worked nights as a barman in Dublin, Ireland. My father’s father was fomenting rebellion against the British and organizing tax protests at age 20.

    At age 20 I was already a two time college dropout who worked as a clerk in a Houston manufacturing firm. I went back to school in the fall of 1980 and took one night school class at a local community college (Sociology, because my fiancee was taking the same class). I stuffed envelopes for the Reagan campaign and made phone calls on Saturday mornings. The rest of the time I was driving up and visiting my buddies at their colleges in Austin and College Station, drinking and partying. While I was doing a lot of different “things” I was going nowhere. I was arrogant, spoiled, and oblivious to the real world.

    I remember inwardly mocking my step-Dad when he said, “You should be saving 10% of your income for retirement.” I thought that I had plenty of time. Thing is, he was 100% correct. I’m playing catchup now.

    I could have had some focus to my life, but I didn’t. I wasted a good half of my life being a hedonistic fool with an exaggerated sense of self-importance. What brought me down to Earth? A heart attack at age 38.

    The only good thing that came out of all my wasted time? I met my wife when I was 44. I never would have met her beforehand. She is my bright spot and my other main reason for getting my life into shape. It took a long time but I’m finally on the right track.

  34. Sandy says:

    If part of your wish list is livig overseas, and your wife is a teacher already…there are innumerable teaching posts abroad. When we lived in Europe, I learned that every community that has even just a couple thousand expats from around te world, there is an InternationalSchool or American School. My kids went to both local schools when they were toddlers, and then another assignmet, I had thm in the American School of Paris. While talking to my daughter’s (incredible) Kidergartn teacher, I found that she had served t schools in Mexico City, Bulgaria, and then finally Paris. I often wonder if she stayed there, or decidd on another assignment somewhere else. Anyway, she mentioned a big international teachers fair in Chcago every year, that teachers who are interested in teaching abroad can go to and interview for assignments for posts anywhere on the planet. Be aware though…living broad sounds romantic, but there are many issues tha come up that smack you right in the face…..I’ve lived overseas for more than a year 4 times…igets easier every time, but the first go can be pretty rough….you must be open minded and LOVE adventure, as every day is a new one!

  35. Bill in Houston says:

    Oops, sorry about that. I tend to get into a groove and the words just fly off my fingertips. Sorry about the ramble!!

  36. Razlan says:

    Trent, I can’t believe you and I are actually of the same age! Your wisdom is astounding… and put me to shame, really.

  37. chris cruz says:

    At every point in our lives we reflect and wish we knew what we know now back then. In high school we wish we would’ve hung out with the cooler kids in grade school to fit in better. In college we wish we would’ve taken more AP classes to make life a little easier. Post college we wish we would’ve majored in something else or minored in something we’re passionate about. As an adult in your 50’s you wish you would’ve raised your kids slightly differently. It’s good to share this for other people to learn but dwelling too much just brings you down

  38. Gabriel says:

    …now tell us more about this Alison! ;-)

  39. Carrie says:

    I wish I had studied less and partied more. Academics are an important part of life, but so are friendships.

    I wish I had gone to the university I wanted to attend instead of the commuter technical college my parents forced me to attend. It’s okay to rebel. Really. Especially when you already know what you want to do with your life.

    I wish I had taken a writing class too. Scratch that: I wish I had gone to a school that even OFFERED a real writing class instead of English-for-engineers classes.

  40. Nancy says:

    Trent, I hate to admit this but I am in my 50’s. One can always look back and wish they had done things differently in certain areas of their lives and that may certainly benefit some of your younger readers who want to learn from things that others wish they had done at a younger age. Remember that you can’t go back you can only go forward. Have you looked forward at your life goals? Do you have a written list of things that you want to accomplish in your life and not just from a financial standpoint but from an experience standpoint? For example, maybe you want to have $ 2 million by the time you’re 65 and that is a good goal. But have you also written down that maybe you want to learn to speak French or Spanish or that you want to go to China. Or maybe you want to climb Mt. Everest. Or perhaps you want to be known for growing the best roses in the area where you live. Those are the kinds of goals I’m talking about. In addition to the lists, I would suggest making up a dream board using an inexpensive poster board to put pictures of things you want on. If it’s the roses find a picture of roses or take one and post it on that poster board and look at it at and the list at least once per day. If you start thinking about well beyond the financial goals I think you will find that when you reach your 50’s and beyond that life will be much richer and you will have fewer regrets. Nancy

  41. Alita says:

    I was 17 years old when i got married, had a baby at 19. Spent most of my days alone without my husband because he was either working or sitting at the bar with his friends from work drinking, or there would be the occasional visits to the jail when i had to bail him out. Attended most of his and my family gatherings & holidays alone with my daughter. During that time i worked, started college and took care of my family the best i could have. I found my many passions in college and through my counseler Lewis. After 5 years of marriage and that going nowhere, i decided to get a divorce and find somebody who did care and spent time with me. The divorce took 2 1/2 years and in that time i was working full time, raising my daughter, and through it all, with nobody there to support me emotionally. It was really hard…
    I met this guy who was really wonderful and we had a construction company that i worked realy hard in. I bought a house remodeled it from the inside out, took the equity out of it to start a trucking company so my boyfriend could work in that field since that’s what he wanted to do for the time being before we got others to work for us. When times got rough, he disowned everything and stopped with the financial help for the house and bills. The bank took my home and my ex boyfriend ditched free and clear from all the debt and still has my truck that he drives.

    I tell you what-i’ve had a really hard life from the age of 17 to 25. But… from all of this, i have learned so much and now the person that i
    am today. Do i regret anything? Would i have changed anything? YES-but life is full of regrets that we will have.

    Learn from your mistakes, grow stronger, get wiser with the years and move on. There is still so much life to enjoy out there-maybe we shouldn’t dwell on what we should have done yesterday, but see what we could do today that will change our tommorrow.

  42. Zach says:

    Hi! I have just been accepted to Study Abroad but am leaning towards not going because of the recession and the amount of debt I would be burdened with (I don’t have any debt at the moment).

    What were your reasons for not going? Why do you regret not going? Is there something you could have gained by going that you can not gain anymore?

    I wish you could help me make my decision!

  43. I’m with you on #10. While I did start saving for retirement almost immediately, we raided our 401K plans for the down payment on our house. The opportunity cost set our retirement nest egg back many years.

  44. SP says:

    I liked the note on study abroad. There is still a misconception it is for rich kids, but most schools offer exchanges which makes it nearly cost equivalent (unless you add in all the travels you’ll do while abroad). Go somewhere less common than Europe (ie, asia/africa) and there are a lot more scholarships available. I got $5k to go to Hong Kong and had the time of my life!

  45. SP says:

    Though I should add most of those I interacted with WERE quite wealthy, people of levels of wealth I never met at my state school. So you have to know when to say “no” if the group is going out to blow a ridiculous sum on dinner, and find like minded students for budget travels

  46. Bill says:

    You were age-appropriately incompetent :) Don’t regret the past. BTW, I enjoy your blog.

  47. Romyr says:

    I am 20 turning 21 this summer and thanks to this blog, I am on my way to financial success. I have opened a ROTH IRA with Vanguard, and converted my Schwab one account into a ROTH IRA as well for tax purposes. I read this blog religiously and I hope there’s more stuff that I can read while I’m still a young 20 year old. Thanks Trent!

  48. Rob says:

    I was a chronic study abroader, and while it can get a little pricey, I have experienced one major benefit: I haven’t paid for lodging anywhere in Europe in the past 10 years. The people that you meet from so many different countries, and the fact that you’re nearly forced to bond in such close proximity and in such a short period of time, allow you to gain a friendship that allows you you call them up years down the line to visit and stay in their homes, and be able to return the favor.

    Plus, I find the experience of going on vacation and living like a local far more culturally enriching than touring Holiday Inn’s all across the globe. Not only do you save money by being able to eat in with friends and catch up over a bottle of wine, you can also tag along with their social calendar, and do things like go to picnics, learn to play cricket, hit the museums on the free days, etc. It is also enriching to give someone the opportunity to show you their city, which allows you to create more memories and build your friendship.

  49. Hi

    I could re-write this post as “Things I wish I Had Done When I was 30!” – as I am now 40 :) I have been through the debt thing and am now out the other side but it is still depressing to realize the long-term consequences of my actions. Nothing for it but to try and move on.


  50. Sarah says:

    “Studying” abroad is the biggest waste of money. More likely than not, the classes you’ll take abroad will do nothing for your major, personal or professional goals, so just graduate early instead.

  51. MB says:

    Oh my word…I SO disagree with Sarah’s comment about studying abroad being a waste of money.

    You are not going for the classes, for heaven’s sake, you are going for the experience. I didn’t study abroad, but I have lived abroad and it was one of the best decisions I ever made. I had early financial goals that I threw to the side in order to do so as well…and I have not one single regret.

    I know many people who did study abroad though and they would all agree that the experience was worth every penny. My sister did a semester in Finland and made wonderful friends from her host family and would still tell you it’s one of the most rewarding experiences of her life.

    That being said, there are work abroad programs out there, which is what I did in Scotland, that might be more to your liking.

  52. Courtney says:

    Don’t graduate early. Money is an issue, but you will be able to pay back those student loans. Take the 4 years but make sure to actually study, take some classes that interest you outside of your major, get involved and have fun. You have the next 40 – 50 years to work and earn money, make sure you enjoy yourself.

  53. Woulda, coulda, shoulda . . . We all have those moments.

    The thing is we can’t change the past, but we can change today and tomorrow . . .

    Start doing today what you will wish you had done 10 years from now.

  54. I did almost exactly what you wish you had done (except the part about politics which I’m reserving for when I’m 50) and yet I also have a few regrets (I wish I had partied more and done more crazy things, but then again at that time, I was a different person).

    The summary result: I live in another country, I am financially independent, semi-retired, and also a writer (among other things, like the co-founder of a startup). My stuff still fits in a trunk. I have a wife but no children. I am 33.

    However, you shouldn’t forget that the sum total of your actions is what brought you to the point where you are today. Possibly some of your success as a pf-blogger has to do with experiencing things like being in debt and getting out of it. If you hadn’t done that, you would not be able to write as well about that aspect and not be able to connect with as many people.

    So what I’m trying to say is that the most important philosophical thing to realize is that many of the things you do merely act as means of getting you to the next step. They are part of a process called life. You should never regret single decisions, I think. Any regrets should be in the present and more directed towards your character e.g. I wish I was less arrogant, more gregarious, etc. It is essentially these traits that decide where you’ll be 10 years from now.

  55. Sandy says:

    Hey Trent, lovely post. I did almost all of those things at 20ish and I still have regrets (I’m in my late 20’s). I think even if you do all those things, you still lack the awareness at 20 to understand their importance in your life. And you still may wonder about ‘the other side’ of it. Your list suggests you wish you were more conservative back then? In contrast, I wish I was more wasteful and stubborn. :) (Maybe I’m not old enough yet to understand what you mean.) either way, awesome post :) gave me lots to think about.

  56. paula d. says:

    Reflection can be a great tool to see where you’ve been and where you want to go. As someone in their late 50’s believe me, I have some regrets that go back to my 20’s. i, like Bill in Houston, spent way more time partying than finding direction and to create what I really wanted.

    I can’t say that I have it all figured out now, but I’m pretty happy with where I am now. More than anything, I’ve let go of the regrets so I can move forward.

    I’ve been reading you for awhile now, and I know you still have some big goals you’re working toward. It’s great that you have figured out many of them by the time you’re 30!

  57. anonymous says:

    Actually, I do not regret not studying abroad at all, that would have probably just hindered my progress in school, and therefore I would have graduated at a later date and therefore started earning money at a later age. But now, i’m more open to visiting more places while working.

  58. Amy says:

    There’s actually a great discussion about this article at Blogged.com. http://www.blogged.com/login.php

  59. toxic brit says:

    I totally agree with all of these. I did all of them apart from the mentoring which is currently very annoying as right now people are quite self centered in this economy…


  60. John Salamon says:

    What an original blog, no wonder it has become so popular, a great read, it forced be to do a bit of reflecting myself. Thank You!

  61. Mel says:

    Alita…you are so strong! Keep reaching for the stars and respecting yourself.

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