Our Experience Revealing Early Retirement Plans to Family, Accidentally

Revealing Early Retirement Plans to Family

Hello everyone! Thanks for stopping by The Green Swan. Today’s post is from Matt at Distilled Dollar. Matt is a 27 year old CPA living in Chicago with his girlfriend and cat, Pebbles. He started his blog earlier this year and is also on the path toward early retirement. I haven’t built up the courage yet to share my early retirement plans with the in-laws, but Matt and Mrs. Distilled Dollar did so with his future in-laws earlier this year. Enjoy!

Our Experience Revealing Early Retirement Plans to Family, Accidentally

When it comes to discussing retirement plans, I typically shy away. After all, money is one those taboo topics that rarely is brought up. As a CPA, I probably find myself in an above average number of conversations relating to money, but I was still completely shocked when our early retirement plans ended up being openly discussed with my girlfriend’s parents.

For the record, the conversation went smoothly and each party spoke respectively of the other. Often times, we associate a disagreement with an argument, and that was not what we had during our dinner conversation. While everyone had a different opinion to bring to the table, the final resolution was a healthy discussion on the topic.

To provide some background, My girlfriend and I plan on reaching Financial Independence, or FI, in our mid 30s. FI for us, means our income from accumulated assets can cover all of our expenses. In this sense, we can effectively declare, ‘early retirement’ and never have to work again.

If you’re familiar with the early retirement or financial independence community, then you’re already aware of dozens of examples of people in less than thriving circumstances who are faced with more obligation, yet they are still able able to reach FI or, aka ‘early retirement,’ in their 30s.

I use quotes for, ‘early retirement’ because the term denotes a lot of different things to different people. When I think of ‘early retirement,’ I think of the example left by Ben Franklin, where he worked hard every day until the age of 42. At that point, his business was built up so large that he stopped focusing on work so that he could pursue his interests in politics and science.

Ben understood that, “lost time is never found again,” and so I too feel like living a good life will only be enhanced by financial independence.

Even though pursuing financial independence is a deep belief my girlfriend and I share, we’ve held it close to our hearts until recently.

Before having that late night conversation with her parents, we recently had our plan “approved,” by a financial advisor. This was someone who cold called me out of the blue, so I took him up on his offer to walk through a few things.

For the first time for either of us, we were telling our plan to a “professional.” While I was confident in my own forecast, I was seeking some reassurance from an independent third party. Plus, it is always helpful to have a fresh set of eyes to spot any potential blind spots.

After hearing we were well on track, we had no intention to bring it up with anyone else again for some time, but it basically slipped out during a recent dinner conversation.

My girlfriend’s father had mentioned the trouble he faced with saving for retirement over his career. My girlfriend then mentioned how we are doing a great job today by saving a lot. One thing led to another and she mentioned we are on track to reach, “early retirement” in our 30s.

The initial reaction was that this was a foolish plan because it was impossible.

Being an engineer by trade, my future father-in-law asked for some numbers. I provided the often cited 4% rule and mentioned we would need to save in the ballpark of 25 years worth of our expenses. I also mentioned our annual expenses might actually drop after we leave the workforce because we can avoid many of the expenses related to working a full time job.

Again, despite our plan of being on track to reach our goals, the response was that it was impossible because of two reasons.

First, no one else had done it. I tried to explain there are various examples online of others who have accomplished what we are seeking to do, but without any real reference points of experience, we simply weren’t on the same page…

We quickly agreed to disagree on this point.

Second, was lifestyle inflation.

To some degree, I’ve already accounted for some lifestyle inflation in our plan because I do want to live in a nicer place, travel more frequently, and dine out more. I have no plans to eliminate many of my other frugal hobbies such as cooking, but I would like to vary it up more often.

A point on which we all disagreed was where we would see our lifestyles inflate. My girlfriend and I believed we would spend extra money on travel, or more wine and cheese nights. My girlfriend’s father believed we would spend much, much more on a larger house and cars.

We were not opposed to buying a home, but we definitely did differ on how much space we need to be happy.

Given the focal point of the counter argument against our plan was an unknown factor in the future, we basically resolved to see what happens in five years time. This will be the ultimate test to see if we were right all along.

Overall, I’m glad we briefly discussed the topic of pursuing financial independence at dinner because we all learned a few new things. If I had to do it over again, I would still maintain my shy approach. Even though we are excited about our plans, we are in no place to bring them up unsolicited with other people because others will often think of their own financial problems or stresses. Even when asked directly, I still prefer to say as little as possible because discussing early retirement involves peeling away many private layers to have a honest conversation.

Have you ever discussed early retirement plans or your pursuit of financial independence with others? How did the conversation go? If you stay away from topics about money, are there any situations where you do bring things up?

Master Distiller










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Martin - Get FIRE'd asap

Why is it so hard for those who don’t follow the FIRE philosophy to understand that it can be done and is achieved by many even when the numbers are in black and white? I guess we all know why really. Because they are too use to living the wasteful, consumeristic lifestyle we choose to leave behind. And that is why you can retire in your 30s and dad-in-law will struggle to retire at 65. And you can’t tell ’em can ya.


I hear ya, Martin. You can lead a horse to water…

It can be tough for folks to realize there are alternative ways to live life and to change habits.

Matt @ Distilled Dollar

Haha oh man! That reminds me of Warren Buffett’s quote, “the chains of habits are too light to be felt until they’re too heavy to be broken.”

I think the other situation for “more experienced” folks is they would need to “admit” their current lifestyle wasn’t ideal. If they make a radical change later in life it might be hard to justify it to their friends and to themselves.

Vicki@Make Smarter Decisions

We only talk about it with my brother (who finally woke me up to the fact that we were FI) and parents and finally our best friends (who are just retired, FI and share a similar philosophy). I’d love to offer up what we did to others and share more openly – but I haven’t. I’m not totally anonymous on the blog – but have yet to tell any friends. So glad you shared it and talked about money – hopefully they will take a look at some sites. As someone who could be your parent (OK- I’d have been a young parent!) – your plan and savings rate would have totally impressed me!

Matt @ Distilled Dollar

Since the initial conversation, the topic has not been brought up again. Either there is no curiosity on their end or they think I’m full of it. 🙂

Either way, we’ll keep chugging along with our savings rate and living our happy frugal lifestyle!

I have a feeling more questions will be asked as our foundations become more solid.


It is a complicated topic. You don’t want others to feel bad about themselves if they are older than you and NOT on a path to retire anytime soon. You also don’t want people to think you are foolish for even considering it. I’ve only ever discussed it in the context of saving aggressively because you never know when you’ll be laid-off. Or saving heavily so we can buy a business. People usually respond favorably to both of those.

To your father-in-law’s point, the lifestyle inflation will be interesting to see over time. I noticed you didn’t mention children. If they come into the picture at some point it may delay you a little bit. Travel soccer anyone? 😉

Nice post, thanks for sharing!

Matt @ Distilled Dollar

Kids is an up in the air topic. We figure if we have them or don’t have them, we’re still doing what we want to do in terms of securing as much of our financial future as possible. I’ll definitely need to write a more elaborate post on the topic soon.

I like your two approaches and I’ve started to copy the later one when the conversation comes up. Many of my high earning finance friends even respect hearing my, “from employee to investor.”


I have never shared my FI plans with family or friends. The only people who know are my wife and my fellow bloggers 🙂
You however raised a great point : most people think it is impossible because they do not know of anyone who’s done it before. And I was in the same situation 3 years ago until I found Mr Money Mustache. I couldn’t believe it. Then I found others and others and I realized that this was a real thing.
Maybe send them a link to MMM and a few others to convince them 🙂


Ha that’s basically the exact same circumstances I’m in right now. And similar timeframe that I stumbled on MMM. Funny! Thanks for sharing.

Matt @ Distilled Dollar

Yep – MMM would easily be the first place I send someone who is new to the idea. I’ve done it many years ago but I found the few people involved in the conversation never bothered to click on the link. I suppose some people just don’t want to know about these types of ideas.

As I mentioned above, the conversation basically happened even though I didn’t plan on it. It ended up going much better than previous conversation, but then again, I’ve become more accustomed to thinking and reading about the topics. The initial level of pure excitement has given way to a deeper level of appreciation for the work that is involved.

Frugal Familia

We don’t plan to share our plan until it is much much closer, maybe a year or two out. I think a lot of the push back that people receive and perhaps even the case with your father-in-law stems from jealousy. If you’re able to retire in your 30’s and they’re still working in their 50 or 60’s then they might infer that THEY are doing something wrong or aren’t as “smart” with their money. Especially if they make more than you do. Nobody wants to admit those kinds of things to themselves.

Holly Johnson

Most people know we plan to retire early. That’s because I write about money for a living and am not shy about it! I do have to laugh a little when people are critical of how we save/spend now. They don’t get our long-term plans or why we are so careful, but they will one day.

Matt @ Distilled Dollar

That’s awesome! I think we’ll start to tell more people in the years to come, but phrase it as we’re saving so we can transition away from employees and into becoming investors. I’m curious how those people will react once your plans start to look real for them.

Stefan - The Millennial Budget

This can be a very sensitive topic considering most of our parents have worked for 30-40 years so this concept may seem foreign. I think the idea of leaving the workforce so early in life with a lot of uncertainty, house, cars, children (yikes), can be uncomfortable for a parent to take in. I am sure your plan will provide you with some sort of income aside from the amount you saved and your interest may lead to money being earned.

I think many of us in the pf community are the “odd ones out” as this is a dream for many as it is not the standard path in life for many.


We are definitely the minority so it is understandable to need to explain ourselves when broaching this topic with family or friends.


Agree with Stefan above. Such a different world we live in compared to our parents. And needs to be handled sensitively.

My plan to share with my parents is to send them the J L Collins book which my dad will love. In that book, will be a little note on how this relates to my situation and we should talk once he has finished reading it. My devious way of getting them further educated and then spilling the beans. I will probably write a post on how it all plays out, for better or for worse!! Wish me luck!!

Matt @ Distilled Dollar

I should have mentioned this in my response to Stefan, but I think a large part of the pf movement is driven by the fact our economy has changed. Gone are the days when individuals relied on pensions. My parents generation basically got screwed over in that regard.

Now, a group of us are seeing our parents retire without enough money and it is motivating us to do better.

I haven’t seen any of the book but I’ve read a few of the many reviews. I’ve added it to my “must-read” list.


My dad retired ‘early’ (before 62) due to being booted out the door (gracefully & with a severance package, but still!) due to a change in upper management. My mom was a teacher, got fed up with the bureaucracy and also chose to leave the workforce before age 62. I use them as examples when I talk about “retiring early”, and making sure I have enough saved up in case I find myself in a similar situation. However I’d ideally like to be financially independent well before then, and choose what work to do and when.
I’ve been envious of my mom’s summers off, while I sit inside an overly air conditioned office watching the trees sway in the sunshine. How great would it be to (a) make my own schedule or (b) work remotely over looking a lake/beach/forest ? I’ve also found I can be a lot more efficient without office chatter and the ‘walk up’ distractions. *fingers crossed* Here’s to hoping. 🙂

Matt @ Distilled Dollar

This is great Jacq. Have you ever considered finding employment with less pay but more free time?

I basically made this move earlier this year when I left public accounting. My pay increase during the move, but the future rate of salary increases will slow dramatically. I made this decision because I wanted more of my time back. It has been a tremendous experience for me and I’m glad I did it. If the situation was right, I might decide to rejoin my old employer or go back into public accounting, but for now, it is perfect.


I started my current job less than a year ago and have stock options which vest in a few years. I am content at the moment to work in the corporate world to save up enough, build references and network to allow for a future shift. 🙂

Apathy Ends

I have made a few comments to friends about our goals and thy look at me like I am insane. We still haven’t talked to any family members yet, no one even knows My site exists and that is the way I want it for awhile.

Matts point about all the layers you need to pull back how this is possible is incredibly personal – without actually showing it, not one believes you though

Matt @ Distilled Dollar

The layers thing was learned the hard way. I had a roommate about three years ago who I tried to introduce Mr. Money Mustache to and discuss the idea of early retirement. I was new to learning about FIRE so not as knowledgeable within all the various saving, investing, and frugality aspects that went along with ER.

My friend would naturally say, “okay, I agree with that point, but what about XYZ factor?” So, I would be like okay, go research and come back and show him how you can afford healthcare even with ER.

He would be like, “okay, I agree with that point, but what this?”

I kept at it through at least a half dozen iterations until I realized he was never going to catch on. There was always going to be something else that made the entire plan fall apart.

Kalie @ Pretend to Be Poor

Glad to hear the conversation stayed amicable for you. We don’t have a firm early retirement plan yet but we are keeping the possibility to ourselves IRL. We don’t want friends and family to judge us or feel judged by for having more, spending less, or even judging our degree of generosity. Maybe this is assuming the worst in people; I’m sure most people we know might be mystified but not emotional about the topic. But I’d rather keep relationships smooth in this area, at least until we get closer to an end date.

Matt @ Distilled Dollar

That’s the ideal approach! It is also the approach I hope to maintain with my parents, especially since I plan on helping them throughout retirement since I know they have not saved enough.

And yes, I am lucky it stayed friendly between us. If I was a little younger and less knowledgeable about ER, then I could have seen it go very differently.

Paige @ Live, Laugh, Budget

My parents have always had the plan to retire early, so I’m not worried about the day we tell them. My MIL retired at 55 and my FIL will most likely retire before he hits 60. We don’t have a specific time frame set, too many variables to account for at this point in time. We definitely plan on retiring early, at least in our 50s (hopefully sooner, we’ll see) but I have no intention of avoiding the topic should it come up in conversation. I have always been a pretty open book about most things, even money. Mr. LLB is more reserved so I am constantly checking with him before posting things on my blog even though at this time only one IRL friend knows about it.

Matt @ Distilled Dollar

It sounds like you have some great friends! I have a few close friends where I discuss financial topics, but it is usually from the perspective that I’m saving money so I can invest. They can relate to that.

If I start to steer the conversation towards early retirement, I can begin to see their eyes glaze over.

Josh @MoneyBuffalo

Congrats on the progress made so far. Our primary goal right now is paying off our house that we are currently building and rebuilding our nest egg. Once we get that done we will be able to sock away more money for investing than we currently do.


When we mentioned it to Mrs. SSC’s parents, they had the same skepticism and almost exact same reasons why it wouldn’t work. He’s also an engineer, and after bringing it up more and more, and then finally showing him our numbers for spending and the fact we aren’t planning to go extreme with our “retirement lifestyle”, along with the amounts we will have saved, he has finally come around.

For him being an engineer, I think it was seeing the hard numbers, and what our current costs vs estimated costs let him realize we’ve accounted for inflation, even inflated costs with the kids as they get older, and the thoruoughness of our plan is what convinced him it may be doable. Especially, when he realized our retirement fund will be about where his is, and our current and projected spending is less. Plus, this is all assuming NO more income, which is pretty unlikely. We’ll both probably get income in some form or another.

It may take time, and may take revealing some numbers or spreadsheets, but hopefully your family comes around like ours did. Ultimately, Mrs. SSC’s dad is not only on board but a bit envious that we can spend so much more time with the kids, because he was working so much and stressed out about work while they were younger. He went from opposed to full support, but it did take a couple of years.

Matt @ Distilled Dollar

Yep – lucky for us, they were both more interested in the numbers over anything else. It isn’t as hard to explain early retirement when you talk about savings rates.

I’m looking forward to the full swing, but I won’t be proactive in making it happen. I’m sure more questions will be brought up as time goes by.

Jim @ Route To Retire

We do discuss our early retirement plan with my mom, brother, and a few select friends. Like you said though, I don’t think people believe that it’s possible. In fact, I’ll be retiring probably before my parents do.

The only thing that I have in my corner is that my grandfather retired at 47. However, he lived like he was still in the Depression, so they assume that’s how we will be living… um, which we won’t.

Although I enjoy talking about the path to FI, I usually just wait and answer any questions from friends and family as they bring them up.

— Jim

Chris @ Sleepy Capital

Hey Matt, great post as always.

My goal is to start my own company which I have spoken with others often about. I like to think this somewhat falls within financial independence because I’m working toward working for myself. Those I have discussed with have been very supportive and believe I should eventually do so.

Money is a taboo topic but since I work in the world of investing it comes up often with others. Particularly what’s going on in the market, how do I invest, and what companies I am interested in.


I have tried to explain our plans to a couple of family members. They don’t really say much and I get the feeling that they don’t believe we’ll accomplish our goal to semi-retire at the age of 40. My dad knows I change my mind a lot, but doesn’t quite grasp how financial semi-independence will give me more options to shift the “kaleidoscope.” The other day, when I was complaining about work, he suggested I go back to school for a career change. Um, we’re already paying back a decent amount of school loans. That wouldn’t help us get to where we need to be financially. So yes, I’ve told family members, but I don’t think they believe what we’re doing is possible.


Yeah I wouldn’t be surprised if my family was the same way, kind of like they’ll believe it when they see it. Well all in due time I guess!

amber tree

Good to read that alls others have a hard time explaining the plan and numbers to others. I briefly discussed it with my mother. AS I often have a lot of high level ideas that I throw at her, she had the usual whatever reaction. I tried to tell her otherwise… I hope she will be around the day I am FI!

Kelsey @ Tealmama

Great read Matt. The concept of financial independence is actually a very new concept from me. I always envisioned working until retirement (owning my own business – which is in-work in addition to my blog).

I am glad you all learned a lot by discussing your plans and I completely understand how things slip out in the midst of conversation. 🙂 In this case, I think actions will speak louder than words as they usually do.

Elsie @ Gundomoney

I think it’s really important to get people talking about early retirement. Our parents and grand parents have a hard time accepting it because they’ve bought into the idea that you’re just supposed to work and spend most of your money, and that it’s impossible to do anything different.

My own parents roll their eyes at the mention of FI. All the more reason to keep bringing it up.


Wow that’s a shame they aren’t willing to accept that as an option for you and your family! Well, hopefully they end up coming around to the idea. Thanks for sharing!

Matt @ Distilled Dollar

Great point. I remember many years ago, my dad and I were talking about money and I made a point about investing. He asked, “what’s the point of earning all that money if you’re not going to spend it.” I replied with, “What’s the point of spending all that money just so you have to work more to earn more.”

The conversation basically faded. I don’t think he shared the same ideas as I did then and I would guess he thinks the same way now.

Steve @ Think Save Retire

I discuss finances and early retirement all the time. In fact, on a business trip last week this topic came up and I had mentioned our plans to retire early to a guy whom I’ve only known for less than a week, though I mentioned “in a year or two” rather than in December. Almost universally, people I talk to about this are incredibly supportive, and most say they are jealous. It’s not my intent to make anyone jealous, but it is interesting how many people want this very same thing.

I suspect your future father-in-law was trying to defend *himself* as much as he was playing the devil’s advocate in your conversation. The “it can’t be done” defense is almost always untrue. If people want things bad enough, there is *usually* a way to get them. It might take sacrifice. It might require lifestyle changes. But it’s usually possible.


Good for you for so freely talking about FI with co-workers. Thanks for sharing Steve. Do you get a sense that when you bring it up that the co-worker is starting to think how he could restructure his lifestyle and finances to accelerate his FI?

Amanda @centsiblyrich

It’s really interesting reading about your conversation with your girlfriend’s parents. Thanks you for sharing and I’m glad to hear it went well, overall!

We finally came clean with my parents a year ago, though we haven’t shared a retirement “date” with them, mostly because we aren’t sure when it will happen yet. I feel guilty talking to my parents about it since they are in their mid 60s and have less saved than we do, but they aren’t resentful at all.

My in-laws, on the other hand, are just starting to piece it together on their own. This is not information I would like to discuss with them because I think they may be resentful. They ask too many questions and my father-in-law is obsessed with money, so it’s a conversation I dread having, but I think it’s coming.


Oh boy! The discussions with either side of your family sound like they’d be interesting, especially the in-laws. I wish you the best with the potential upcoming convo with them. It may be good to have over a bottle of wine :).

Matt @ Distilled Dollar

Yikes! Part of me says that is a great thing – since they are asking these questions to you AND NOT a financial advisor that will take a large portion of their funds.

I second JW’s suggestion of adding a glass of wine to the discussion! 🙂

Best of luck and keep us posted!


I agree with Steve’s comment above. It certainly appears you future father-in-law felt a bit jealous and perhaps even embarrassed that he had not thought of the idea himself.

I have broached the FIRE subject with my in-laws and parents, and generally, it has gone well. My in-laws don’t seem to understand why we would want to retire early but respect the goal.

I cannot imagine having this conversation on the fly! It sounds like you did well to be respectful, Matt.


Good for you Finance Superhero, and glad to hear the conversations went well. As I’ve mentioned before, I haven’t had the conversions myself yet but anticipate them soon enough. I’d expect them to go well with maybe a bit of surprise by the in-laws, but we’ll see. Thanks for the comment!

Matt @ Distilled Dollar

Oh man – I was totally unprepared when it got brought up. I knew right away that it was going to be a fifteen minute discussion.

I’m happy it happened though because at least they know. They might not truly care, but in time, as our foundations solidify and our finances become more apparent, they will likely bring it up again.

I can see why people disagree with working for a living. Even if we decide to retire, I imagine we’ll still be producing something for those around us.


Many may take offense to it because they view it as “gaming the system” in a way. Everyone should work until retirement because that’s the fair share of work in our society. Someone who retires in their mid thirties is “cheating”.

It’s difficult to ever bring it up in conversation because it directly leads to comparisons. It doesn’t help if you label anyone not retiring early as wasteful, driven by consumerism, etc. People value different things differently…our community values time to the extreme but that may not be the right answer for everyone!


Interesting view John, I appreciate you stopping by and sharing. Just to clarify though, do you feel retiring early is cheating because they wouldn’t be working and contributing to society as long as they had the capacity or more from the sense that over an early retirees lifetime they are contributing in taxes to society less than the benefit recieved?


Hi JW,

I apologize for being unclear. That is not my view, but I was saying it might be the view of others who don’t agree or believe in early retirement.

But I believe it’s more about the former than the latter. It may feel unjust to them that they are working their life away while they see someone else who is also capable but instead sitting around idle in retirement. However, we know those who can manage to retire early tend to be some of the most productive people in the world!

Matt @ Distilled Dollar

Yes! My icon here is Ben Franklin who retired early at 42. I would say the 2nd half of his life was VERY productive! 🙂

As for other’s opinions, I can see why that would be a driving factor to not having a discussion. That is part of the dilemma with discussing personal finance. To one degree, you want to share the benefits and mistakes you made so others can benefit in the same way. To another degree, people will resent your success and try to nit pick the details.

The later approach I feel is extremely destructive over time as no one learns and things fall into a negative spiral. The first example leads to an upward spiral of growth and constant learning.

On a personal level, I spent way too many years caring what others thought, then I realized most people are too concerned with their own situations. They might see your situation for a moment, judge it, then shift back to focusing on their own situation.

Thanks for the comments!

Dividends Down Under

Hey Matt and JW, nice topic.

We haven’t discussed early retirement plans with anyone, our family isn’t even in the ‘spend less than you earn’ phase, it would go over their heads.

I love talking with everyone in the PF community because we’re all on the same page – it’s inspiring and invigorating. If only we knew some people in the non-digital world to talk with.


Matt @ Distilled Dollar

If they’re still stuck in that phase, then maybe try to get them to read or learn the ideas from The Millionaire Next Door. That book gave me a lot of great ways to view that type of situation, where people spend more than they make.

Julie @ Millennial Boss

Oh man this could have went badly! I talk to my friends about it somewhat but usually it’s just me cracking jokes about what a crazy person I am. People don’t get it and they don’t like it. I’ve found people are more likely to support you going into debt than the other way!

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