What Would Your Younger Self Say to Your Present Self?

credit: Unsplash

credit: Unsplash

“Waking up to who you are requires letting go of who you imagine yourself to be.” – Alan Watts

I’ve read many posts asking what advice you would give your younger self if you could go back in time. When it comes to personal finance, many people might tell their younger self to not live above their means, to not try and keep up with the Joneses, or to start investing earlier. And of course, there will be people who say they would tell their younger self to invest in Google! Your present self is older and wiser, learning much from experiences that your younger self has yet to go through. It makes sense that we would love to go back in time to impart advice to our younger selves to save him or her from making the same mistakes that we did.

In one of the comments from an article asking what you advice you would give your younger self, one person said that it wouldn’t matter what advice he would have given because his younger self wouldn’t have followed it anyway. He said that sometimes you have to experience those failures or mistakes to truly learn from them. In an interview, Tony Robbins said that he would not change anything about his past, even after sharing his experiences growing up where his mother physically abused him. He said those experiences shaped how he is today and he wouldn’t be where he is if he changed the past.

I think those, “What advice would you give your younger self” articles are fun to read. While there is obviously no time machine so you can’t go back and give advice to your younger self, a younger person reading your experience would hopefully learn from your own mistakes and hopefully avoid making them. Thinking about this question, I started to ponder the reverse of this question. What would your younger self say to your present self? I thought it would be an interesting question to ask. And a question that only you could really answer as only you truly know your past self and your present self.

Your younger self was probably not as wise and experienced so it would be tough to ask him or her for advice. But your younger self was probably more ambitious, naïve, more of a dreamer, idealistic and less cynical than your present self. Would your younger self be excited about what you’ve done with your life or would your younger self be disappointed that you didn’t fulfill the dreams you had when you were younger?

Thinking back to when I was in high school and college and trying to put myself into the shoes of the younger Mr. Living Rich Cheaply, I think overall my younger self would be proud of where I am now. My younger self always thought that at this age I’d be married with two kids and working as an attorney. So I have crossed those expectations off the checklist. I was a frugal person even when I was younger so I wouldn’t have been too surprised that I am still living below my means.

However, I’d be lying if I said that my younger self wouldn’t also be a little disappointed as well. My younger self may have been the type to live below his means, but he always thought my older self would have BIGGER means to live within! I’m pretty sure my younger self would have expected that my older self would own a house, especially with a family of 4, rather than in an apartment that is about 800 square feet. Sorry, younger self…housing is expensive in NYC! Also, while my younger self thought that I would become an attorney in the future, I probably pictured one in a prestigious position or one who was helping to change the world. Hey, I was young and idealistic, okay! I’m pretty sure I didn’t imagine that I’d be working in a back office, mostly writing and doing research. Not to say I dislike my job. It’s okay and I enjoy parts of it, but I’m sure my younger self wouldn’t be daydreaming about it.

What would your younger self think about how your present self is doing in life?

22 thoughts on “What Would Your Younger Self Say to Your Present Self?

  1. Brad - MaximizeYourMoney.com

    What would I say?

    Beware lifestyle inflation!

    If I had continued to live as I did when first married – even when I was making 3x as much money years later – I could have easily retired in my 30s. But no, I bought cars, houses, vacations, etc. Thankfully I reeled it in during my 40s but that lifestyle creep slowed down my FIRE progress for sure.
    Brad – MaximizeYourMoney.com recently posted…Don’t Neglect These 4 “Walls” of Budgeting Your MoneyMy Profile

    1. livingrichcheaply@gmail.com Post author

      I think you misread the question. But you’re right that lifestyle inflation is something that our younger selves should beware about.

    1. livingrichcheaply@gmail.com Post author

      So would your younger self say that your present self is following that advice?

  2. Tonya@Budget and the Beach

    I love this question because unlike the first question about what would you tell your younger self, you can actually change what you don’t like about your present self that the younger you might be disappointed in, like not taking enough chances or settling. I think my younger self, on a positive note, would be proud that I turned into an athlete. Also that I’m tougher than I look and very resilient. On a bad note, I think my younger self would be a little sad I’m not married or in a serious relationship. They might be a little sad that I’m not as brave as I was when I was younger either, mainly because I am smarter about money, so scared to take some risks to lose some of that money. Great exercise!
    Tonya@Budget and the Beach recently posted…How Much I Saved Biking to WorkMy Profile

    1. livingrichcheaply@gmail.com Post author

      Thanks! Being resilient is definitely a very important quality. What do you think you’re not brave about when it comes to money? Not taking risks in investing it or taking risks in pursuing certain careers where the pay is not as stable?

  3. Brian

    A great reframing of the question. I think my younger self would be happy with the progress I’ve made, but I’d think my younger self would remind my older self to not be afraid to take chances or be afraid of your own abilities.
    Brian recently posted…Debt Discipline Turns FourMy Profile

    1. livingrichcheaply@gmail.com Post author

      I think the same of my younger self and actually the reason I think wrote this post. I need to have more confidence in my abilities and have to stop being afraid of taking chances.

  4. Matt @ Optimize Your Life

    Definitely an interesting thought experiment. I think my answer depends on how much younger haha.

    10 years ago would probably be asking why I’m not making more of a difference in the world. Why didn’t I go into politics or policy to do more to help people that need it?

    15 years ago would probably tell me to get back into writing and performing music.

    I think there would be a lot of positive comments, as well…I don’t want to come across as super disappointed with my life choices. But as far as the negative, I think that’s where those would go.
    Matt @ Optimize Your Life recently posted…Does the Meaning of Life Matter?My Profile

    1. livingrichcheaply@gmail.com Post author

      Great point. My 10 years younger self versus the 15 year younger self would have thought differently. I wouldn’t think that you’re coming across as disappointed with life choices. I’m sure one of my younger selves would be disappointed that I’m driving a minivan…but I’m okay with that! That younger self was…young and naïve =) I think Brian’s point and one of yours is what is on my mind. I’m a little disappointed that I’m not doing more to help people and that I’m sometimes too afraid to take chances.

  5. Laurie @thefrugalfarmer

    Great question! I think my younger self would be mostly satisfied with my present self, except for the money mess we’re digging out of. :-) But I was just thinking the other day; I’ve got it pretty good. I’ve fulfilled my dream of being home with the kids (and homeschooling as a bonus) as well as working a pretty cushy gig as a freelance writer. Fun stuff. :-)

    1. livingrichcheaply@gmail.com Post author

      I’m sure your younger self would be proud of how you guys are digging out of it though! Awesome that you have fulfilled your dream of being home with the kids. Those moments are truly precious!

  6. Adriana @MoneyJourney

    My younger self would be very proud of my present self.

    If I ‘d go back in time, I wouldn’t change the big picture on bit. I would still move abroad, I would still take mediocre jobs when there’s nothing else available, and I’d still keep a little YOLO attitude around.
    The only exception.. I’d probably slap myself silly for being influenced by others when it comes to spending habits. I was never interested in keeping up with the Joneses, but I did regret some purchases that weren’t necessarily important..
    Adriana @MoneyJourney recently posted…Can you distinguish frugal from cheap?My Profile

  7. DC @ Young Adult Money

    Hmm really interesting thing to think about. I’m not sure exactly what my younger self would think. I think they’d be excited that I had a decent job, was married, and was (fairly) healthy. But I also think my younger self being ambitious (which hasn’t gone away today) would be disappointed I didn’t launch a company and was still working a corporate job at 29.
    DC @ Young Adult Money recently posted…5 Finance Apps That Will Actually Improve Your FinancesMy Profile

  8. Oliver @ Appreneurinvestor.com

    “Sometimes you have to experience those failures or mistakes to truly learn from them”

    I like this line because there’s so much truth here – experience is still and definitely the best teacher. Although when it comes to finances, failures/mistakes can lead to bigger risks and more painful regrets. One should still proceed with caution and get expert advice to minimize chances of failing big time.

  9. Tim Kim @ Tub of Cash

    Lol, makes sense. My younger self, like my current self, was very stubborn. So I think you make a good point that he probably wouldn’t have listened to my advice anyways. That said, something as crazy as seeing yourself from the future probably would trigger some sort of obedience =P I’m not sure how he’d feel, seeing what I’ve been able to accomplish by age 31. Depends I guess on how far I go back.

  10. Erin

    Oh, I like the idea of flipping the question around, because like others, I probably wouldn’t change much. I don’t have many regrets, and I’m grateful for the lessons I’ve learned in the past.

    Hmm. I don’t think my younger self would have expected me to end up as self-employed, or working from home. I never thought that was an option growing up. Before college, I also thought I’d end up in a law enforcement career, even though I had aspirations to write. And lastly, I probably wouldn’t have guessed I’d be making this much money, as after college, I had sort of sentenced myself to office jobs for the rest of my life. I can also safely say I never saw myself living in NJ – even two years ago!

    However, I think I’m on point with most other things in life. No kids, not married, no house – none of that mattered to me even when I was younger, so I figured it would continue into adulthood. Overall, I’d say my younger self would be proud of where I ended up.
    Erin recently posted…Attempting to Escape the Need for PerfectionMy Profile


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