Men over 40, what do you think was the most important milestone you achieved in your early 20s, mid 20s, late 20s, then your 30s?
March 1, 2026
and it don't got to be things you talk about a lot but looking back what were some milestones you had in your 20s and 30s that you felt like is important to your life
29 comments
Here’s an original copy of /u/Affectionate-Drop689’s post (if available):
and it don’t got to be things you talk about a lot but looking back what were some milestones you had in your 20s and 30s that you felt like is important to your life
*I am a bot, and this action was performed automatically. Please [contact the moderators of this subreddit](/message/compose/?to=/r/AskMenOver30) if you have any questions or concerns.*
Getting married
Having kids
Going to therapy
Making enough money not to have to worry about money, or even working
Related to the last point, switching jobs/career to something you actually enjoy
My band did a few cool things like play on warped tour, but I didn’t achieve anything significant individually until my 40s when I bought a house, ran a marathon, started saving for retirement, traveled internationally.. shit I should’ve been doing in my 30s but didn’t.
Not giving AF about any of that.
Early 20s graduating undergrad
Mid 20s being accepted to and graduating masters
Late 20s starting doctorate
30s finishing doctorate , putting the brakes on binge drinking mostly. starting to run and mountain bike again. Then finally finding a well paying job so I didn’t have to sling it like the sucker I thought I was
Having kids at 34. Wish I did everything (job and kids) about 7 ish years earlier
Early 20s was just partying
Mid to late 20s had 2 kids
30s was just a weird decade for me
Married and bought our first place at 24. Upgraded from a townhouse to a house and got my career well established at 30. Kids at 38 and almost 40. Senior executive level at 40
I left a mediocre engineering job at 30 to start a career in wealth management and 13 years later I can confidently say it was the best, scariest decision of my life.
It happened to be around the same time I became a dad so it’s all lumped in with an extraordinary year for me back then.
Travel as much as possible while you’re young. I was fortunate enough to visit all US states before 30 and every inhabited continent before 35. Incredible life experiences and perspective gained
Buying a house in my 20s and getting married in my early 30s
Sober at 19 started a business at 21 got married at 23 had a kid at 28 and at 31 got divorced @33 got married at 37 and had another kid. Life is fucking beautiful
paid off student loan followed by paid off car.
Nothing is more important than not renting money.
Earning my Master’s degree
Early 20’s – engineering degree. Mid 20’s – first real job in my field. 30’s – marriage, kids. 40’s – finally moving out of our starter home lol.
-Early 20’s – graduated college, got over a big breakup, met lifelong friends
-Mid 20’s – began career, worked hard, kept a big friend circle, had a lot of fun
-Late 20’s – earned Master’s degree, focused on fitness, continued to have a lot of fun with friends, started to save/invest for retirement
-Early 30’s – met my wife at 31, married at 33, had a lot of fun with her and began to travel
-40’s – continued to work hard, bought a great house, continued to enjoy the relationship I had with my wife, continued travel and save/invest.
-50’s – couldn’t be happier to be married to my wonderful wife, lots of travel, fun, carefree lifestyle
-57 – Retiring next year (so glad I started saving in my late 20’s); lot’s of travel plans with my new wife (just kidding – married almost 25 years and it’s never been better.)
Looking forward to my 60s.
Early to mid 20’s was mostly grad school
Late 20’s: starting my career
30’s: buying a home (1-bedroom condo), then later beginning to travel more frequently
Having my two kids in my 30’s and finally achieving a stabilized “adult” “consciousness” in the latter half of my 30’s after some intense training, thought, pracrice and other spiritual work.
Probably moving 2,500 miles away from home. It only lasted 2 years but I don’t have many other miles stones. 4 years in the Marine Corps and a deployment to Afghanistan wasn’t an achievement because anyone can do that. I’ve never had a girlfriend so no achievements there. Yeah i’m cooked.
– Early 20’s Graduated uni. No big deal – expected.
– Mid 20’s Moved to another country and Started a business when my bank account went down to $300.
– Late 20’s Got a job in the Los Angeles School District after being rejected 7 years earlier due to my draft record.
– 30’s Moved cross country for a stake in a motel business. Finally made more than $20K a year.
Early 20’s – Honorably discharged from the military.
Late 20’s – Graduated with my BS degree and started my career. Also purchased may first home.
30’s – got married, had a kid, career progression and landed what I’d consider my dream job.
I’ve had to see some sacrifices and hard choices the last 20 years (I’m In my ,40’s now) but it’s all coming together and paying off.
Kids, most successful relationship, a lot of nothing then in my 30’s finally picked up a job that allowed for buying a house and saving money. Then, it sounds weird, but my dad wasn’t really conducive to pet ownership, so getting cats was a big deal.
You can see an obvious theme here, it’s almost all work and study.
23 – graduated college debt free (I wored 32 hours/week in college) moved to Korea to teach for a year
25-30 – decided to sit down and question everything I had been raised to believe. Changed a lot of my worldview
31 – realized my dead end job back home was leading nowhere, and that I was too tied to everyone and my social group was holding me back. So I cut ties with basically everyone except my family … move to Korea to teach for another 2 or 3 years.
35 – Set up an expat / Korean meet-up group so that Koreans could learn English and other expats could learn about Korea. I’ve hosted over 400 meetings so far
39 – Still in Korea, did an MA in Teaching so I’d finally be a skilled teacher. Now work at a university with 8 – 14 weeks of paid vacation a year. Now at 44 I think about going home every year, but there is basically no chance of me getting a good paying job immediately, so I just stay in Korea.
Ongoing – was smart with my money so I’m on track to retire with no financial problems whatever
Ongoing – learned to be less judgemental towards people different than me
Ongoing – learned to stop being so intellectually insecure, and that it was healthy to admit I didn’t know things.
Failed – I never figured out the whole romance thing
I feel contrarian today so I’m going to answer on what to avoid as I think avoiding bad things will take a young man as far as doing the right things.
* Stay away from drugs
* Don’t commit crimes and get arrested
* Don’t get deep into debt
* Don’t get grossly fat or hooked on booze
* Don’t get tangled up with evil, selfish or childish women
* Don’t get complacent with dead end jobs
Missing these rules can destroy any education, financial or career goals a man may have achieved. And really, just following these rules gets one close to being above average.
Despite the wild times, frivolous spending, promiscuity etc. I somehow had the maturity then to know to buy a house. Turned out that the early 2000s was the last time a dude earning average income could afford a house. I do not take that for granted.
I’ll be 40 in a couple months but here are my favorite milestones
– Raising my family
– Being married for 14 years
– Paying off my house 10 years after buying it (this was a lot of work but it was 100% worth the sacrifices)
– Running for and getting elected to a public office
Starting a business in my mid 20’s, it gave me enough money to start a family with financial freedom.
My whole life has basically been the American dream on fast forward. Married at 18, first kid at 19, enlisted, earned my BA, became an officer, bought multiple homes as the military moved us around, two more kids and a grandkid in my 30s, retired and bought my own business, became paper millionaire in mid forties, now prepping to help my daughter buy her first house and sell my business in my late 40s.
I was a highschool dropout.
In my early 20s, I went back to school and got my GED.
Finished a nursing degree by my mid 20s and started working in healthcare.
Began traveling the country doing locums work in my late 20s. Got to see a lot of America that way. Also started traveling internationally around that time.
Went back to school to become an anesthesia provider in my 30s.
Now I’m in my 40s making great money in a field where I’m highly sought after, and I have real freedom.
All of that said, my most important milestone came before I went back for my GED when I realized the decisions I’d made up until that point didn’t have to define me or what I was capable of. All I had to do was choose a different path. Once I made the decision to do so, it felt like everything sort of fell into place for me going forward.
I put in a lot of hard work, but I gave control over to the universe.
Happy I did.
I don’t…
I don’t really think I’ve achieved any important milestones…
29 comments
Here’s an original copy of /u/Affectionate-Drop689’s post (if available):
and it don’t got to be things you talk about a lot but looking back what were some milestones you had in your 20s and 30s that you felt like is important to your life
*I am a bot, and this action was performed automatically. Please [contact the moderators of this subreddit](/message/compose/?to=/r/AskMenOver30) if you have any questions or concerns.*
Getting married
Having kids
Going to therapy
Making enough money not to have to worry about money, or even working
Related to the last point, switching jobs/career to something you actually enjoy
My band did a few cool things like play on warped tour, but I didn’t achieve anything significant individually until my 40s when I bought a house, ran a marathon, started saving for retirement, traveled internationally.. shit I should’ve been doing in my 30s but didn’t.
Not giving AF about any of that.
Early 20s graduating undergrad
Mid 20s being accepted to and graduating masters
Late 20s starting doctorate
30s finishing doctorate , putting the brakes on binge drinking mostly. starting to run and mountain bike again. Then finally finding a well paying job so I didn’t have to sling it like the sucker I thought I was
Having kids at 34. Wish I did everything (job and kids) about 7 ish years earlier
Early 20s was just partying
Mid to late 20s had 2 kids
30s was just a weird decade for me
Married and bought our first place at 24. Upgraded from a townhouse to a house and got my career well established at 30. Kids at 38 and almost 40. Senior executive level at 40
I left a mediocre engineering job at 30 to start a career in wealth management and 13 years later I can confidently say it was the best, scariest decision of my life.
It happened to be around the same time I became a dad so it’s all lumped in with an extraordinary year for me back then.
Travel as much as possible while you’re young. I was fortunate enough to visit all US states before 30 and every inhabited continent before 35. Incredible life experiences and perspective gained
Buying a house in my 20s and getting married in my early 30s
Sober at 19 started a business at 21 got married at 23 had a kid at 28 and at 31 got divorced @33 got married at 37 and had another kid. Life is fucking beautiful
paid off student loan followed by paid off car.
Nothing is more important than not renting money.
Earning my Master’s degree
Early 20’s – engineering degree. Mid 20’s – first real job in my field. 30’s – marriage, kids. 40’s – finally moving out of our starter home lol.
-Early 20’s – graduated college, got over a big breakup, met lifelong friends
-Mid 20’s – began career, worked hard, kept a big friend circle, had a lot of fun
-Late 20’s – earned Master’s degree, focused on fitness, continued to have a lot of fun with friends, started to save/invest for retirement
-Early 30’s – met my wife at 31, married at 33, had a lot of fun with her and began to travel
-40’s – continued to work hard, bought a great house, continued to enjoy the relationship I had with my wife, continued travel and save/invest.
-50’s – couldn’t be happier to be married to my wonderful wife, lots of travel, fun, carefree lifestyle
-57 – Retiring next year (so glad I started saving in my late 20’s); lot’s of travel plans with my new wife (just kidding – married almost 25 years and it’s never been better.)
Looking forward to my 60s.
Early to mid 20’s was mostly grad school
Late 20’s: starting my career
30’s: buying a home (1-bedroom condo), then later beginning to travel more frequently
Having my two kids in my 30’s and finally achieving a stabilized “adult” “consciousness” in the latter half of my 30’s after some intense training, thought, pracrice and other spiritual work.
Probably moving 2,500 miles away from home. It only lasted 2 years but I don’t have many other miles stones. 4 years in the Marine Corps and a deployment to Afghanistan wasn’t an achievement because anyone can do that. I’ve never had a girlfriend so no achievements there. Yeah i’m cooked.
– Early 20’s Graduated uni. No big deal – expected.
– Mid 20’s Moved to another country and Started a business when my bank account went down to $300.
– Late 20’s Got a job in the Los Angeles School District after being rejected 7 years earlier due to my draft record.
– 30’s Moved cross country for a stake in a motel business. Finally made more than $20K a year.
Early 20’s – Honorably discharged from the military.
Late 20’s – Graduated with my BS degree and started my career. Also purchased may first home.
30’s – got married, had a kid, career progression and landed what I’d consider my dream job.
I’ve had to see some sacrifices and hard choices the last 20 years (I’m In my ,40’s now) but it’s all coming together and paying off.
Kids, most successful relationship, a lot of nothing then in my 30’s finally picked up a job that allowed for buying a house and saving money. Then, it sounds weird, but my dad wasn’t really conducive to pet ownership, so getting cats was a big deal.
You can see an obvious theme here, it’s almost all work and study.
23 – graduated college debt free (I wored 32 hours/week in college) moved to Korea to teach for a year
25-30 – decided to sit down and question everything I had been raised to believe. Changed a lot of my worldview
31 – realized my dead end job back home was leading nowhere, and that I was too tied to everyone and my social group was holding me back. So I cut ties with basically everyone except my family … move to Korea to teach for another 2 or 3 years.
35 – Set up an expat / Korean meet-up group so that Koreans could learn English and other expats could learn about Korea. I’ve hosted over 400 meetings so far
39 – Still in Korea, did an MA in Teaching so I’d finally be a skilled teacher. Now work at a university with 8 – 14 weeks of paid vacation a year. Now at 44 I think about going home every year, but there is basically no chance of me getting a good paying job immediately, so I just stay in Korea.
Ongoing – was smart with my money so I’m on track to retire with no financial problems whatever
Ongoing – learned to be less judgemental towards people different than me
Ongoing – learned to stop being so intellectually insecure, and that it was healthy to admit I didn’t know things.
Failed – I never figured out the whole romance thing
I feel contrarian today so I’m going to answer on what to avoid as I think avoiding bad things will take a young man as far as doing the right things.
* Stay away from drugs
* Don’t commit crimes and get arrested
* Don’t get deep into debt
* Don’t get grossly fat or hooked on booze
* Don’t get tangled up with evil, selfish or childish women
* Don’t get complacent with dead end jobs
Missing these rules can destroy any education, financial or career goals a man may have achieved. And really, just following these rules gets one close to being above average.
Despite the wild times, frivolous spending, promiscuity etc. I somehow had the maturity then to know to buy a house. Turned out that the early 2000s was the last time a dude earning average income could afford a house. I do not take that for granted.
I’ll be 40 in a couple months but here are my favorite milestones
– Raising my family
– Being married for 14 years
– Paying off my house 10 years after buying it (this was a lot of work but it was 100% worth the sacrifices)
– Running for and getting elected to a public office
Starting a business in my mid 20’s, it gave me enough money to start a family with financial freedom.
My whole life has basically been the American dream on fast forward. Married at 18, first kid at 19, enlisted, earned my BA, became an officer, bought multiple homes as the military moved us around, two more kids and a grandkid in my 30s, retired and bought my own business, became paper millionaire in mid forties, now prepping to help my daughter buy her first house and sell my business in my late 40s.
I was a highschool dropout.
In my early 20s, I went back to school and got my GED.
Finished a nursing degree by my mid 20s and started working in healthcare.
Began traveling the country doing locums work in my late 20s. Got to see a lot of America that way. Also started traveling internationally around that time.
Went back to school to become an anesthesia provider in my 30s.
Now I’m in my 40s making great money in a field where I’m highly sought after, and I have real freedom.
All of that said, my most important milestone came before I went back for my GED when I realized the decisions I’d made up until that point didn’t have to define me or what I was capable of. All I had to do was choose a different path. Once I made the decision to do so, it felt like everything sort of fell into place for me going forward.
I put in a lot of hard work, but I gave control over to the universe.
Happy I did.
I don’t…
I don’t really think I’ve achieved any important milestones…