Why You Have To Forgive Yourself

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Much has already been said by FIRECracker about this past week at Chautauqua UK, but the experience was just so big and complex and overwhelming that it’s really not possible to sum it all up in one post, so I’m going to take my Wednesday post to add my take on it.

I think the thing that struck me the most was this deep, intimate emotional connection we formed with each other.

But first, let’s back up a little bit.

Each Chautauqua is, at its core, a bunch of us FI weirdos gathering in a super-villain lair. Over the course of the week, each speaker gives his or her talk to the group, there are activities and events that happen, and any attendee can sign up for a one-on-one session with any speaker they choose to talk about pretty much anything they want.

And it’s in these sessions where the magic happens.

Jim “The Godfather” Collins in no uncertain terms instructed all the Speakers early on to treat these one-on-one’s like a confessional. Anything discussed at these sessions gets sealed in an iron vault a million miles underground the moment the session is over, never to be discussed again (unless the attendee wants to). The idea is to give each attendee their own personal bubble of protection where they can’t be judged or embarrassed or attacked for any reason. It’s a system that’s genius in its simplicity, and after doing this for a whole week I understand why.

People get judged All. The. Fucking. Time when it comes to money. Money is one of the most emotional things out there, because every dollar a person has or doesn’t have is a result of a whole series of decisions that led them to that point, and those decisions are twisted in with other emotion-drenched things like identity, politics, sex, love, religion. It just goes on and on. Hell, this site was created as an angry F-U to all the Boomers that kept judging US for having the gall to defy their wise old advice to go into debt to buy a house we didn’t want.

So once that bubble of non-judgment got created, the flood that came from inside it was overwhelming. We addressed the fears people had that made them bolt up at night with their pulse pounding. We dug up money ghosts from decades ago that were still haunting people, and together we figured out a way to slay them. We hugged each other and literally cried when they showed us their scars and realized we had them too.

It was cathartic. And humbling.

And it made me realize that everyone, no matter where they are on their journey towards FI, has a messed up history with their money that they’re embarrassed about. Everyone has mistakes in their past that they’re trying to dig themselves out of. Some mistakes have bigger effects than others, but everyone has them.

But the big difference between the people who manage to recover and get their money working for them and those that seem to spin around in circles is that the people who make it find a way to forgive themselves for their past mistakes. Those that don’t are the ones that can’t let those mistakes go, and keep throwing up their hands and saying “Welp, I’m screwed.”

This is how a typical conversation about money with our friends goes pre-Chautauqua.


Person A: Thanks for taking a look at our numbers, FIRECracker. I really appreciate it.

FIRECracker: Oh, no problem. OK so can you tell me little bit more about this recurring monthly expense marked “Misc”?

Person B: Oh, that’s how much money she spends on shoes. It’s so stupid, right?

Person A: Hey, I like my shoes!

Person B: Well, we wouldn’t be in this mess if it wasn’t for those shoes. That’s all I’m saying.

Person A: Hey, that’s not fair! You spend just as much going out with your friends!

Person B: I make all the fucking money! I’m not allowed to go out with my friends?

FIRECracker: *slowly backs away towards the exit*


And what we learned at Chautauqua was that not only does literally everyone have the same baggage when it comes to money, it’s pretty much impossible to fix anything unless all that judgment goes away first.

Now, after Chautauqua, all our conversations go like this:


Person A: How do my numbers look? Is it bad? It’s bad isn’t it?

FIRECracker: Look, whatever happened in the past doesn’t matter. It literally doesn’t matter. Let’s pretend that whoever screwed up in the past was a different person, and that person’s gone now. The only thing that matters is what we do going forward. Can we do that? Does that make sense?

Person A: …I guess…

FIRECracker: OK, so tell me about this number.

Person A: Well, that’s my credit card debt. See, what happened was…

FIRECracker: Don’t care. Doesn’t matter. Would you be OK if we shifted some money out of this checking account to pay that off?

Person A: Oh. OK. Well, I guess I can do that.


Because when someone doesn’t feel judged anymore, they stop trying to defend their past mistakes and instead start thinking about the future. That’s the big difference I’ve noticed between people who have money and people who don’t. The first group figured out a way to forgive themselves for past mistakes while the second group never figures this out.

So if you’re struggling with your own money issues, the first thing you have to do is Forgive Yourself.

Whatever happened in the past, it doesn’t matter who did it, what happened, or whose fault it was. It literally doesn’t matter.

The only thing that matters is what you do starting now.

And only when you can do that, only when you can Forgive Yourself for whatever happened in the past, only then can you start to fix it.



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39 thoughts on “Why You Have To Forgive Yourself”

  1. I am very glad I found the personal finance and FIRE community early in my career/life. By being part of this community, I am not only becoming more passionate and knowledgeable about personal finance, but I am also very comfortable discussing money. It saddens me that this is not the case for many people I meet. Oftentimes, there is shame, regret and/or jealousy tied to money that prevents meaningful and productive conversation. Chautauqua sounds like an incredible opportunity to break those barriers and help to get to the heart of the matter!

  2. There was an episode of Oprah, back when she had her talk show (pre giving things away days), at least a decade ago. She dragged a number of folks on stage who’d run up huge debts and discussed with ’em what they did to get the debts paid off.

    One was a couple who lived a lavish lifestyle, and when the money ran out, sold everything and became truckers who lived out of the truck. They paid off their debt and were saving money. I never forgot those truckers because they didn’t regret their lavish lifestyle (having paid off the bills for that lavish lifestyle).

  3. Mr. Wow always brings up this quote when discussing money/investing/etc: “The best time to plant a tree was 20 years ago. The second best time is now.” Of course, we all wish that we could have been better with our money 5, 10 even 20 years ago, but its not worth beating yourself up over it. Embrace where you are at now with your money and make the necessary changes that you need to. Remember this moment 20 years from now. Go ahead and plant those (money) seeds and make sure that all that judgment crap gets tossed in the rubbish bin.

  4. At the end of the day, every psychologist needs a psychologist. Your experience proves my observation that most of the time money consultants end up being counselors when discussing money issues with people. Good job you guys!

    1. The longer we do this the more I realize that money is like 10% numbers and 90% emotions. We know the 10% part down pat and we’re slowly learning how do deal with the 90% part.

  5. This can be applied to so much. I blew up my career and started over in 2016, I found myself in the beginning saying “in my last career, we did it this way…bla bla bla”. Had to eventually let go. Sometimes I wonder why I did it, but then I consider how happy I am, how i’ve been able to “plant that tree” as someone said, get my family back in order, and kind of reboot my life. Great advice, and great read, as always.

    1. Thanks! And how did you blow up your career and reboot your life? You don’t have to share if you don’t want to, just curious. It sounds like an interesting story…

      1. Simply put way too much time and effort into a corporate lifestyle 70-80 hr work weeks as a sales rep and eventually manager. Followed something that I had more of an interest in, instead of something that just paid the bills, and found a rewarding career. I had a lot of experience that I left behind to self educate into a brand new field for me. Scary, had to sacrifice, but it all worked out. That’s the TLDR version, can read my story in more detail on my blog.


  6. Made a series of stupid decisions early on. I remember my “bottom” moment at the ripe age of twenty. Eating shoplifted hot dogs from the package, Outside. In Minnesota. In January. It was -20 that day & I was homeless. Not my proudest moment. I buried that me many years ago.

    Earlier this year, I realized my sh1t filter was full. Being able to walk away from Mega-Corp before age 60 was “good enough.” Ya gotta let your old self go.

      1. I joined the US Army. I hated it at first. Structure, order, discipline, grueling fitness standards. But it was exactly what I needed. I eventually stepped up and made it into the Part 1 of my career (part 2 being mega-corp). I retired as a highly decorated master sergeant and a staff member for a 4 star general. Earned under and grad degrees at night with zero debt (yay!)

        Fast forward 25 years and I was a volunteer mentor for troubled youths about to graduate boot camp. Not the military kind, the kind a judge sentences kids to as a last ditch effort to avoid serious jail time. The biggest lesson I tried to impart on them was to get away from the place that got them into trouble. And guess what? The military is a great way to get FAR away from the street. By graduating boot camp, they were eligible to join the military (a criminal record normally closes that door), and I wholeheartedly urged these kids to do what saved me. Sadly, most of those kids eventually did time. But, I saved a few of them (and earned the undying gratitude of a few moms). One of my proudest moments (much more so than eating stolen cold hot dogs while freezing my ass off).

        So, while being late to drinking the fire kool-aid, we did okay. I was in my 30’s when I started LBYM. My “war bride”of almost 30 years is from Korea (another perk from my army career) and was a child in the harsh post-war economy (and ruthless dictators) that was South Korea from 53 to about the early 80’s. She whipped my financial ass into shape with the tenacity that FIREcracker sometimes invokes 🙂 And then, as you say Wanderer, life got pretty f#cking easy. Y’all still made a difference even or an old dummy like me. I was buying into that “you need 80/90/100 percent of your gross income in retirement. What horsesh1t. FIRE bloggers (including you and FC) saved me from another 10 years of work.

        What you two (and the other FIRE leaders) are doings is God’s work. Seriously. This sh1t should start in middle school (LBYM, budgeting, the simple stuff), and continue in high school (index investing, compounding, impact of fees, and the other math sh1t). Algebra? What a waste -the last time I used that crap was the undergrad final exam. Teach kids something useful and save them from the debt dungeon.

        One of my retirement “duties” is volunteering at the local soup kitchen 3-4 times a month. I think we’re all part of a team. You guys (and gals) keep evangelizing and shouting from on high. I’ll plug away helping those down on their luck. And who knows, someday, just maybe, we’ll be interacting with the same person. That would be pretty special.

        Apologies for the dissertation, but I felt called put it out there. Thanks!

        1. Wow that’s quite a story. Thank you for sharing.
          And glad we were able to help you out even in our own tiny little way. And totally agree with you, being able to have an impact on one person face-to-face blows away all the corporate drudgery in terms of moments to be proud of. Awesome work!

  7. It’s so true – we can’t do anything about the past, other than learn from it and use the knowledge/wisdom we’ve gleaned from it to move forward! Staying stuck in the shame and blame of the past isn’t productive for anyone! Just start where you are right now in the present and begin to create something new.

    At the end of the day we’ve got to remember – when it comes to what happened in the past, we did the best we could at the time. And as the saying goes, “when you know better, you do better”.

    1. Staying stuck in the past is the WORST thing you can do. I know lots of people my parent’s generation who are still stuck and can’t move forward because of something that happened during the Cultural Revolution in China, and still blame Mao for everything that’s happened to them even though he’s been dead longer than I’ve been alive.

      It’s so incredibly sad.

  8. Another very insightful post. I really think that judgment in general is something we should all try to avoid for the sake of our own peace.

    1. Ha. You can’t avoid judgement, I tried. Judgement comes and finds you. The best you can do is throw up a shield and say “I don’t care what you think anymore.”

  9. This is probably the toughest for me to forgive myself in all aspects of my life. Part of it I use as fuel to not make the same mistakes. So by keeping that pain/mistake close it allows me to focus and not go back to that place. At the same time, I get into constant self-comparisons with others regarding what they have and I don’t (e.g. career, money, etc). For example, I keep saying I am a decade behind my compatriots when it comes to saving, particularly the FI community. The truth is, however, I have more money saved than probably 90% of the population. That is a good reminder, but I still do the self-comparisons. I do need to forgive myself more.

    1. You sound like FIRECracker. She could be doing 99% of the things right, but the only thing she notices is the 1% of the stuff she screwed up. I guess that’s the mark of high-performing people. Not a bad club to belong to.

      Knowing when to use your scars to drive you and knowing when to let those scars go is a delicate art. It’s a delicate process and everybody’s balance point is different. All I know is the answer is never “All scars must never heal!” and “Scars are pointless. Ignore them.” The real answer is somewhere in the middle, and it’s different for each person. I hope you find yours.

  10. Sometimes I feel like my whole life has just been a journey of trying to avoid what other people think of me. Secretly, I’m a deeply shy person who can’t get away from the judgement of others. I’ve found that it helps to just develop a personality that celebrates my differentness and let my Nerd flag fly. It’s an invitation to judge me, so that I can inoculate myself against it. That’s why it’s so gratifying to talk on my blog about my love of heavy metal, beer, tattoos, swear words, science, and money. I’m a walking conundrum. Ha!

  11. This was a great article. You’ve got to forgive yourself for money (or career, in my case) mistakes, but others make it so hard. Sometimes you’ve got forgive yourself almost defiantly, even as others tell you to shape up and do things.the way they want you to do things.

    Right now, I’m failing in my career (so says my boss and his boss), but rather than–okay, “in addition to”–complaining about it, I’ve forgiven my money-limiting career choices by going for certifications to transition into a new career that pays more and is more exciting.

    I’ll fully forgive myself if I can make this transition before I either lose my sanity or get myself fired. Unfortunately, all of these are distinct possibilities.

    I’ve noticed than, in general, being judged and criticized and controlled constantly makes you more defensive, constantly evaluating the past to validate your work, your choices, and/or yourself as a human being. Wanderer and FIRECracker, you were smart to escape from your jobs when you did. Don’t look back.

    ARB–Angry Retail Banker

    1. Hi ARB,

      There is no need to follow what others think that one should do. If one cannot do it, so be it. The worst case circumstance is to be let go of the job. The most important thing is to have the investment portfolio as the buffer should one is axed from the job.

      In addition, I do not see the point in staying on the job which one no longer has the interest. We only live once. It will be more worthwhile to do things in accordance to one’s preference.

      My two cents worth of views.


  12. I am so glad I found you blog. I am naturalized Canadian living in the middle east but I have been going thru a rough patch, I was depressed, I was demoted from my job, I am daily stressed from threat of being laid-off , also the bureaucracy of this country is getting into my nerves. We have made a lot of stupid “investments” due to ignorance, greediness, etc. Nobody knows about index funds here, everyone invests in expensive financial packages were you only lose money due to high fees, I learn about https://andrewhallam.com/ and have recently opened an expat investment account to invest in index funds in USA, and doing research I ended up in your blog. Your story is very inspiring, it made me realize that I can lose my job and it is fine, I checked our numbers and we already have 1 million in different investments, some good some bad, but it gave me hope, and now we are going to consolidate and made a plan to get FI in a few years. Now, I am all positive, and looking forward to our future. I am forgiving myself for the bad investment choices and looking ahead.

  13. I needed to read this today! I have so $55K (it was more!) in schools loans and only BS in Psychology. I get pissed off and feel guilty every time I think of all of the actions that lead me to that number, but it doesn’t matter. It’s in the past. The person who made the decisions that lead to that number feel like another person. The person I am today is kicking ass to pay it off and wouldn’t make that same decision!!!

    1. “The person I am today is kicking ass to pay it off and wouldn’t make that same decision!!!” Oorah! Murder that debt monster! The past doesn’t matter, only the new kickass you matters!

  14. Dude! This is so powerful and it really spoke to me. I just wrote about this exact thing between me and my gf but you’ve said it so much better.


    This is at the core of every FI conversation gone wrong. Thank you for this post!

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