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Don’t Know What To Do With Your Life: Why Not Retire Early?

One of my more financially interesting friends is my friend Jay (not his real name).  While the rest of us are beginning or in the middle of our “real” careers, Jay still works as a bartender at the same restaurant he worked at while we were in college.  He recently turned 30 years old, and if my calculations are correct, that means he’s been working as a bartender at the same place now for 8 years (longer if you count the summers that he worked there while in college).

Bartending always seemed like it was supposed to be a temporary stop.  My friends and I all graduated college in 2009 – right in the midst of the financial crisis – and found ourselves unable to get any “real” jobs.  I worked two minimum wage jobs and lived at home with my parents.  My other friends did similar things. One friend worked at a sporting goods store.  Another worked at a golf course.  Some people worked at restaurants – typical post-college jobs that you’d expect a 22-year old to have to take after the worst financial meltdown in a generation.

After a year or two in these jobs, we all moved on to try to start our “real” careers.  A bunch of people grabbed internships in hopes of getting their foot in the door somewhere.  Others went off to grad school.  As you can probably figure out, I went off to law school in an attempt to escape the financial crisis.  Jay just stuck with bartending.

Whenever we talk about Jay from a career perspective, the thought is that he’s still in this pre-career phase, just waiting to start his “real” career.  He’s 30 years old now and he can’t be a bartender forever, right?  Most people imagine that he’ll open up his own restaurant one day and that’s sort of the direction he’s been leaning as well.  I’ve always thought, instead of trying to “start” his career now, maybe he should just consider retiring.

Could A Bartender Really Retire At 30?

So is it really possible that a guy who’s been bartending for his entire working career could really be in a position to retire at age 30?  Theoretically, I think yes.

As a caveat, I have to admit that all of the numbers I use here are a complete estimate.  Like most people, Jay doesn’t talk about money with his friends very often.  And even though I love to talk about money on this blog, I can’t just go around asking people how much money they make or what they’ve got saved up. The primary purpose of this post is as a thought exercise and to help us think outside the box.

With that said, I do know two things that are definitely true about Jay:

  1. He doesn’t spend a lot of money.
  2. He saves a ton of money.

How Much Does He Spend?

Let’s address point one.  How much money does Jay spend?  Honestly, I don’t know.  I’ve never asked him, but I can estimate based on his lifestyle that he probably spends no more than $1,000 per month.  A friend of mine that is currently living with Jay thinks he might spend even less than that – maybe $8,000 or so per year.  For now, I’ll just assume that he spends about $12,000 per year, which I think is a fair assumption.

$12,000 isn’t very much money to spend per year.  Then again, I know there are people out there who spend even less than that per year.  (Jacob Lund Fisker from Early Retirement Extreme comes to mind, clocking in a yearly spend of just $7,000).  I’m sure there are other people out there who are able to spend $12,000 or less per person.

Obviously, with such a low estimated expenditure, we have to ask how is he able to spend so little money.  I see three things that allow him to do this:

  • Rent.  The main thing that accounts for his low spend is that he has never had to pay any rent.  Like most of us that graduated from college during the financial crisis, Jay moved back home after college.  A few years later, his parents moved to California and Jay was asked to stay at home and take care of the house.  That means that, since 2009, Jay has never paid any rent ever!  Admittedly, not all of us are so fortunate to be in a position where we can live in a house for free.  Remember, this is just a thought exercise to help us think outside the box.  Plus, even without rent, a lot of us probably couldn’t make it through a year spending $12,000 or less.  You have to have a certain mindset to get through a year spending so little, even without housing costs.
  • Clothes.  Unlike many of us, Jay also doesn’t buy a lot of stuff.  He never buys new gadgets.  He drives the same car that he had in high school.  And most importantly, he never buys clothes.  Seriously, he still wears the same clothes that he wore back in high school and college.  The last time I saw him buy anything expensive was a Groomsman suit he bought for a friends wedding. And that’s still the same suit he wears to other people’s weddings today.
  • Food.  Jay works in a restaurant, so he gets to eat basically for free on days that he works.  When we visit him at work, he’s nice enough to hook us up with food too.  Obviously, not all of us get this benefit, but I bet you have more opportunities to use your work benefits than you think.  When I was working in big law, I basically would eat for free during the summer by going out to eat with every summer associate I could find (the firm reimbursed us if we had lunch with a summer associate).  During times without summer associates, I would look around for CLEs and snag free food there.

How Much Does He Save?

With Jay’s low annual expenses, in theory, he wouldn’t need all that much in order to technically be financially independent.  Using the 4% rule, a $12,000 per year annual spend means Jay only needs to save $300,000 in order to be able to live forever off the returns.  And the great thing is that with his investments only generating $12,000 per year, he’d basically pay no income tax on his investments ever.

So could Jay have $300,000 already saved up?  I think he could or isn’t too far from it.  I know that back in 2009, he had $50,000 saved from a combination of working during college and money his parents gave him.  Given that he spends so little and assuming he makes about $50,000 a year at work (which sounds about right – I know back when we graduated college, he was making about $40,000 a year with his tips and presumably, he’s earning more now), I think I could see him saving well over 50% of his income.  Saving $30,000 per year for him wouldn’t be a crazy assumption.  If we add that up from 2010 to 2016, plus the $50,000 he already had, he could be sitting on $230,000 right now.  And that’s assuming he never received income from any other sources or invested a dime of his money.

It gets pretty crazy if we assume that he actually invested that money.  Saving $30,000 per year comes out to $2,500 saved per month.  If he invested that money into an S&P 500 index fund since 2010, he’d be sitting on about $432,000 today (I calculated that using this calculator from  Using the 4% rule, he’d be able to pull out $17,280 per year.  At a more conservative 3%, he’s only taking out $12,960 per year, still more than enough for him to sustain his current lifestyle forever.

What We Can Learn From Jay

I know, the usefulness of this post really depends on whether the assumptions I made are true, and honestly, I have no way to know unless Jay was willing to share that information with me.  The actual numbers don’t really matter all that much though.  The main benefit of this post is as a thought exercise to help us think outside the box.

And yes, I know that realistically, he’s probably not in a position to retire early.  He’s not going to be able to live rent-free forever.  One day, his parents might sell his house or he’ll have to go find a place to rent.  His expenses might rise one day.  Who knows?  It’s just another option that he could consider and probably has never even thought was possible.

As for lessons, I think there are three things that we can learn from Jay:

  1. Buy stuff you care about.  Don’t buy stuff you don’t care about.  This is such a basic thing when it comes to money, but it’s pretty hard to do in practice.  We’re trained to think that we care about a lot of stuff.  But when you really think about it, we probably don’t care about as much stuff as we think.  Jay doesn’t buy clothes because it’s not something he cares about.  He’ll spend money on sporting events or going out with friends because that’s something he does care about.  Look in your closet and see how many clothes you never wear.  I know my closet is packed with clothes I never wear now. What does that tell me about what I actually care about?
  2. Ignore what other people think.  Easier said than done obviously, but Jay has done this.  He’s not embarrassed that he wears the same clothes from high school or that he doesn’t buy fancy stuff.  Before you think he’s depriving himself, he’s definitely not.  He still goes out with friends and has fun.  And he does travel too.
  3. Be Patient.  I think this is really key.  A lot of people are in such a hurry to start their lives off that they don’t think about what they really want to do.  I know I probably hurried off to law school a bit too fast.  People kept telling me that I needed to get started right away.  Jay has spent almost the last decade building up his savings.  He’s been hearing people from all different sides telling him he needs to start doing something with that money.  Someone with a different mindset might have thrown that money down on a house or something else that would tie them down.  Instead, Jay’s taking the time to figure out what he’s going to do.

I know that Jay probably would never retire now, and he probably shouldn’t yet.  It’s just interesting to think that it could potentially be an option for him.  The important thing is at least he put himself in that position.  Most people don’t even give themselves that opportunity.

Do you guys have a friend like this who spends almost nothing and seems to be in a position that they could retire early, basically by accident?


  1. What a great story… its too bad most of us don’t live as frugal as that and save such a large percentage of our income!

    Now to kick my parents out of their house.. hmm…

    • Obviously, the only reason he’s able to do this is because his housing expenses are zero. But then again, he also doesn’t spend money really on anything else either. I know when I lived at home with my parents that first year out of college, I ended up with no money by the time I moved out. I spent everything I made!

  2. Jay is an excellent study in accidental retirement readiness. I don’t know anyone who has gotten to this point by accident, but I have a friend who is intentionally blazing a similar trail. He drives an older car, works multiple jobs, owns his own business, and lives in a modest town home which will be paid off in 6 years. He is going to be rich and live a dream retirement while still in his 30s. It can be done!

  3. It sounds like you had a very similar college/post college experience as me and my friends. Graduating around the financial crisis was tough. I had so many friends that ended up working retail after college or just going back to grad school. It definitely gave me an appreciation for a full-time grown up job!

    • Yep, it was tough post college. I remember getting rejected for an administrative assistant position that paid like $15 an hour.

  4. I have a friend like that, except he made over six figures. He quit his job, at 40, to plan his wedding. He told me how much in assets he had, nearing one million, and I asked why he didn’t retire. He didn’t answer.

    I think he’s afraid too. Now he’s married and has a new, much easier, six figure job. He also has bought a house. With no kids yet, I am certain he could retire if he wanted to.

    • That’s pretty amazing! The great thing is that it’s not like he has to retire. Just better that he gave himself that cushion at least.

  5. I enjoyed this thought exercise, as you called it. Really makes you look at things from different angles and truly consider whether Jay can/should retire.

    I also thought about what you said about the house tying him down. I’m with you there. We bought “too much house” back in 2011 and, after getting into some consumer debt, had to make the difficult decision to move to cheaper area with a cheaper house. And, as I go to a job I don’t really enjoy daily, sometimes I wonder if being a Jay would be easier. Or at the very least, by not being tied down, you would have more options. Again, another potential thought exercise there.

    At this point, it’s about righting the ship and moving forward. Getting successful side hustles together, paying down the mortgage, investing in rental properties, etc. Thanks for this post! Great stuff.



    • Thanks, Dave! Buying too much house is a definite problem that a lot of people fall into. I think a lot of us are in a rush to enter “adulthood” so fast that we don’t take the time to just assess our options. It sounds like you’re on the right track!

  6. Really enjoyed this post and thought exercise. While my first job out of school was no where near family and friends, friends that did move home for even a few years while they started their careers were able to save so much money. Most of them put it towards houses or other expenses eventually, but it is incredible to think about what they could have achieved if they thought about working differently than the traditional “work until 65”.

    Setting a FIRE goal really changed my perspective on what we need to spend. Calculating the exact number of what we had to save per month made me build my budget around that number, instead of saving what was left. Hoping to retire by 30!

    • Thanks, Chelsea! It’s really amazing how much you can save when your housing expenses are zero.

  7. It just goes to show you, if you put your mind to it financial independence is in reach almost no matter what your salary. It’s all the choices and sacrifices we make.

    • Right. What’s crazy about Jay is that he basically did it by accident just because of circumstances and his natural inclination towards frugality. He doesn’t try to be frugal, he just does it because he doesn’t care about clothes and other things that a lot of us put emphasis on.

  8. Interesting post! I actually happen to know someone exactly like this. They have been working as a server at a high end restaurant and never did start a “real job.” He was a better saver than I and is pretty close to being financially independent. His house is paid off, and roommates cover his expenses. You don’t need to make much, especially if you don’t spend much 🙂

    • That’s awesome! It’s funny, we think that we all need to go get that “real job” but really, doesn’t matter too much if you’re already doing well. Your friend sounds exactly like Jay.

  9. So who is paying property taxes on this guy’s house? If it’s his parents, then (unless that buffer covers the property tax) he is still financially dependent.

    But still light years ahead of many higher earning folks I know 🙂

    • True, his parents I assume still pay the property taxes on his home. But imagine if that’s all he had to pay for. He’d only have to earn a few thousand per year. It seems like if he wanted to, he could, in theory, work some part time job and still cover all his living expenses forever. Of course, just a thought exercise. Lots of things that probably make it not possible for him to really be FI, but just thought it was interesting to see where a bartender can be – considering the fact that we think of him as needing to start his “real job” sometime.

  10. This is a pretty cool analysis. Just goes to show that anyone can take control of their financial future. Sure Jay has an uncommon situation that gives him free rent, but even if he were paying rent, he would still be able to save a ton of money. Probably not enough to be financially independent after just 8 years, but he could be well on his way.

    Does Jay happen to read your blog? Would be funny if he stumbled upon this post.

    • Right, like is he actually financially independent – probably not. But he’s pretty darn close without even realizing it.

      And Jay definitely doesn’t read this blog. For the most part, none of my friends know about it!

  11. This is such an excellent post!
    Although I’m no where near being able to spend only $12,000 or less a year like Jay is, I can relate in how he doesn’t listen to others. A lot of people I know are car enthusiasts. They are constantly telling me to buy a new car and cannot comprehend why I wouldn’t want one. However, I just don’t care. I actually prefer public transit.

    That said, Jay should definitely aspire to retire early. In fact, he sounds like he would make the perfect PF Blogger/dividend investor based on how patient he is.

    He is in a pretty fortunate situation, though, since he doesn’t have to pay for any rent.

    Thanks for sharing the fascinating post!

    • Thanks Graham! The crazy thing is he definitely didn’t do it on purpose and I’m positive he’s never even thought about the concept of financial independence. I imagine he just figures you keep working until you retire in your 60s like everyone else He’s definitely in a fortunate situation – most people don’t get to live rent-free for basically all of their 20s. But I know that a lot of people who get that opportunity don’t take advantage of it either. When I lived at home in my year after college, I spent every cent I had. Jay avoided that trap.

  12. Interesting post! Although most people probably won’t be in Jay’s situation (they can’t live at home for free, don’t get free food from work, and don’t get money from their parents), it’s interesting to see that he was able to save at least $50K from a bartending job because he didn’t go crazy and spend all his money. Though I have heard of other bartenders who do quite well (even better than some office workers) because of their tips (which doesn’t often get reported as income). So a very viable solution for him would be to save enough money to later start his own restaurant or become FI and move to a low cost location (like southeast asia or south america) where he could easily live off of $12,000/year. Because, like you said, he won’t be able to rely on free rent and money from his parents forever.

    • Right, he won’t be able to live rent free forever, but what’s important is that he took advantage of an opportunity that was there. And his naturally frugal ways will help him a ton even when he does have to pay rent. There aren’t a lot of 30-year-old bartenders with $300k or more saved up!

  13. Very insightful post FP! I guess this really goes to show that, it’s not the job that you’re in, which will determine if you are able to retire, but your saving and spending habits that plays the most important part.

    Wonderful and thought provoking post, I hope more people get to read this!

    • Thanks T! I’m glad you enjoyed it. Really, I just thought it was interesting to think about.

  14. Mai Mai

    When I was fresh out of college and moved to a city where I’d never lived before, I house sat for like 6 months. That was 2 different gigs- one had me pay utilities, the other didnt. During that time I was able to pay off all the credit card bills I accrued during college and save for an apartment deposit. Want to talk about side hustles? House sitting is awesome!! Plus you get to live in rad houses that you could never afford at the moment, if ever, and you build connections and references of being trustworthy, a couple things I think could take you far in lots of different directions. Since this is an exercise in thinking outside of the box!

    • The housesitting is an awesome idea! A partner at my old firm once sent out an email asking if anyone could house sit for him, but I was too scared to do it. I didn’t want to seem like I was “the help” if that makes sense. I’ve heard of people house sitting as a form of long term traveling and that’s something that I’d love to try out one day. I guess my question is, where do you find the house sitting gigs? Is it just looking through Craigslist basically?

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