Ep. 596 — Mistakes Were Made

I truly think FI is for everyone. Can Brad please stop making his liberal political or anti Twitter/X/Elon Musk comments? I think he has made comments about Trump before also. This is not the first time he has done this. I think X now supporting free speech is now better than it ever was, it WAS a cesspool when people were banned for having different opinions. Regardless, ChooseFI shouldn’t get political or it may turn people off. Thank you.

I truly think FI is for everyone. Can Brad please stop making his liberal political or anti Twitter/X/Elon Musk comments? I think he has made comments about Trump before also. This is not the first time he has done this. I think X now supporting free speech is now better than it ever was, it WAS a cesspool when people were banned for having different opinions. Regardless, ChooseFI shouldn’t get political or it may turn people off. Thank you.

Great episode. Hope it makes people more comfortable with there own mistakes. Ive made more than i care to remember, and happy to talk about them as im nearly certain it would make everyone feel much, much, much better about theirs!

Great episode. Hope it makes people more comfortable with there own mistakes. Ive made more than i care to remember, and happy to talk about them as im nearly certain it would make everyone feel much, much, much better about theirs!

Absolutely loved this episode! One thing I really appreciate is that because of your courage to be vulnerable and share mistakes you made, it opened the door for my partner to share with me a mistake they made in the past. I think there's immense value to sharing and speaking aloud these mistakes from the past – it provides a freedom instead of allowing them to privately haunt you indefinitely. Thank you again!

Absolutely loved this episode! One thing I really appreciate is that because of your courage to be vulnerable and share mistakes you made, it opened the door for my partner to share with me a mistake they made in the past. I think there's immense value to sharing and speaking aloud these mistakes from the past – it provides a freedom instead of allowing them to privately haunt you indefinitely. Thank you again!

What a wonderful episode! It was so generous to share your mistakes in this way, not only giving us the opportunity to learn from your experiences, but also normalizing screwing up and course correcting.

And what a nice surprise to hear the "50 Ways to Say NO" book mentioned! Thank you! 💗 You know everyone who goes to my Boundaries Boot Camp learns about "Brad's Cascade"! 😂🍾

What a wonderful episode! It was so generous to share your mistakes in this way, not only giving us the opportunity to learn from your experiences, but also normalizing screwing up and course correcting.

And what a nice surprise to hear the "50 Ways to Say NO" book mentioned! Thank you! 💗 You know everyone who goes to my Boundaries Boot Camp learns about "Brad's Cascade"! 😂🍾

Great episode by 3 fun people.

I wasn't aware of the FI/FIRE community or any it's best practices until learning I/ we were already FI. I had brute forced my/our way just by what I thought made sense.

Had I been aware of FI/FIRE, I would have learned about DIY index fund investing. My biggest Accumulation Phase mistake was always investing with the family's trusted active management broker, who picked individual stocks, etc. Had I learned about this stuff earlier, I could have easily retired with the same FI Number 5+ years sooner (than my FIRE at 45), or retired at the same age with easily 20+% more in the portfolio.

My biggest mistake in FIRE, still ongoing and sorting out, is some misalignment in the competing priorities of "being a great husband and father" vs "making sure I get what -I- need and want out of life, for myself". I haven't yet decoded how to be appropriately selfish for the greater good. I do have some concern that I am in, some ways, "wasting" my best years of early retirement, waiting for the other stakeholders.

Great episode by 3 fun people.

I wasn't aware of the FI/FIRE community or any it's best practices until learning I/ we were already FI. I had brute forced my/our way just by what I thought made sense.

Had I been aware of FI/FIRE, I would have learned about DIY index fund investing. My biggest Accumulation Phase mistake was always investing with the family's trusted active management broker, who picked individual stocks, etc. Had I learned about this stuff earlier, I could have easily retired with the same FI Number 5+ years sooner (than my FIRE at 45), or retired at the same age with easily 20+% more in the portfolio.

My biggest mistake in FIRE, still ongoing and sorting out, is some misalignment in the competing priorities of "being a great husband and father" vs "making sure I get what -I- need and want out of life, for myself". I haven't yet decoded how to be appropriately selfish for the greater good. I do have some concern that I am in, some ways, "wasting" my best years of early retirement, waiting for the other stakeholders.

WOW! This podcast has helped me significantly financially…but this episode I truly feel is helping me grow into a better person. I actually teared up hearing Alan apologize to his friend Paul. Such a powerful moment. Thank you so much for sharing that vulnerable mistake. I also really identified with Katie talking about how much she doesn't enjoy making mistakes or reflecting on them (at least until she did and said it was cathartic - counting on that 😄)

And so, I'll share two of mine. One financial, one personal.

1. Financially, I feel super lucky and privileged to have worked for a company that was a smallish, successful, private start-up. It was a software company in the hey day of software and it was FANTASTIC. I was a customer and loved it (changed my life, not hyperbole especially considering how much impact our work has on our life). Anyway, I got shares of stock when I joined and about 5 years later we went public. My strike price was less than a dollar…the company IPOd at $16, I sold at $48 (didn't exercise my stocks and hold for 1 year so paid short-term cap gains/income tax rates in my highest earning years). I made a significant amount of money and I'm so grateful and again feel so super lucky. AND…the company sat at $120-150 for a long while. All that said, I know that holding a single company's stock isn't recommended but it was pretty much free money. And even if I had sold and immediately reinvested the profit into index funds (I was too scared to invest all of it, but did invest 50% of it into a balanced robo-advised fund which has performed very well the last 10 years thankfully!) that would have been better. And also…I knew the company, the strategy, the product (it was great AND WE WERE FUN!) and I could have double or tripled my profit or at least been smarter on taxes (even just holding for a year to get long term gains……..!). Sigh. I guess the lesson I hope others learn is that if they come into a windfall, try to get some help/education making the wisest decision (and of course also be careful of people taking advantage of you). If I'd have been listening (and acting) to ChooseFI I might be FI or 90% FI today where I'm actually 5-7 years away).
2. Personally, while I want to be super clear that I lucked out (blessed, however you think of these huge things working out better than you deserve), I got married too young (23). I'm still married and we just celebrated our 15th anniversary. And while we have and are still working to build a wonderful life and have had so much fun (and our share of not fun), I share it as a mistake given how poorly my life could have developed had my 23 year old self with 1.5 years of knowledge of this person, and very few years of knowledge of life on our own (I have never lived alone - another mistake tied up in this one I'm sure!) not lucked out. I really lose sleep over it thinking about how it could have been. SO thankful I'm not sharing this with lots of trauma though I've learned from many wise people who learned by more pain and suffering and I just feel so strongly now to share (and I've read some young people on here recently looking to learn!). You may actually have the best person ever at 23 (or 20 or 25, whatever age)….and if they are that great, they (and marriage, finances especially!) can wait some time for you to shore up your own confidence, experience, and growth. And coming from a super religious, conservative upbringing I reaaaaally understand you if you decide to ignore this advice and I hope and pray you get as lucky as I did! But this community is awesome and I see many out here supporting folks as we learn from and work out of our mistakes. I'm not a marriage hater I promise. Just…wish more of us had the encouragement and support to not rush into it. So maybe that is the lesson regardless of age? Anyway….

GREAT episode, thank you again for being so open and generous with your learnings!

WOW! This podcast has helped me significantly financially…but this episode I truly feel is helping me grow into a better person. I actually teared up hearing Alan apologize to his friend Paul. Such a powerful moment. Thank you so much for sharing that vulnerable mistake. I also really identified with Katie talking about how much she doesn't enjoy making mistakes or reflecting on them (at least until she did and said it was cathartic - counting on that 😄)

And so, I'll share two of mine. One financial, one personal.

1. Financially, I feel super lucky and privileged to have worked for a company that was a smallish, successful, private start-up. It was a software company in the hey day of software and it was FANTASTIC. I was a customer and loved it (changed my life, not hyperbole especially considering how much impact our work has on our life). Anyway, I got shares of stock when I joined and about 5 years later we went public. My strike price was less than a dollar…the company IPOd at $16, I sold at $48 (didn't exercise my stocks and hold for 1 year so paid short-term cap gains/income tax rates in my highest earning years). I made a significant amount of money and I'm so grateful and again feel so super lucky. AND…the company sat at $120-150 for a long while. All that said, I know that holding a single company's stock isn't recommended but it was pretty much free money. And even if I had sold and immediately reinvested the profit into index funds (I was too scared to invest all of it, but did invest 50% of it into a balanced robo-advised fund which has performed very well the last 10 years thankfully!) that would have been better. And also…I knew the company, the strategy, the product (it was great AND WE WERE FUN!) and I could have double or tripled my profit or at least been smarter on taxes (even just holding for a year to get long term gains……..!). Sigh. I guess the lesson I hope others learn is that if they come into a windfall, try to get some help/education making the wisest decision (and of course also be careful of people taking advantage of you). If I'd have been listening (and acting) to ChooseFI I might be FI or 90% FI today where I'm actually 5-7 years away).
2. Personally, while I want to be super clear that I lucked out (blessed, however you think of these huge things working out better than you deserve), I got married too young (23). I'm still married and we just celebrated our 15th anniversary. And while we have and are still working to build a wonderful life and have had so much fun (and our share of not fun), I share it as a mistake given how poorly my life could have developed had my 23 year old self with 1.5 years of knowledge of this person, and very few years of knowledge of life on our own (I have never lived alone - another mistake tied up in this one I'm sure!) not lucked out. I really lose sleep over it thinking about how it could have been. SO thankful I'm not sharing this with lots of trauma though I've learned from many wise people who learned by more pain and suffering and I just feel so strongly now to share (and I've read some young people on here recently looking to learn!). You may actually have the best person ever at 23 (or 20 or 25, whatever age)….and if they are that great, they (and marriage, finances especially!) can wait some time for you to shore up your own confidence, experience, and growth. And coming from a super religious, conservative upbringing I reaaaaally understand you if you decide to ignore this advice and I hope and pray you get as lucky as I did! But this community is awesome and I see many out here supporting folks as we learn from and work out of our mistakes. I'm not a marriage hater I promise. Just…wish more of us had the encouragement and support to not rush into it. So maybe that is the lesson regardless of age? Anyway….

GREAT episode, thank you again for being so open and generous with your learnings!

I appreciate the compassion in this episode. We're all human, we make mistakes and grow from them. Here are some of my mistakes:

1. I left too much cash in a bank savings account when I should have invested it. Instead of a 0.01% interest rate, just imagine getting 10% annual returns in the market.
2. I rarely looked at my pay statements and company benefits, so oblivious to how much money I was leaving on the table.
3. I didn't realize I can choose where my 401K was invested in. I was automatically enrolled in a Target Date Fund, which wasn't necessarily bad, but I changed it a more aggressive fund with a low expense ratio.
4. I regret not attending my friend’s wedding overseas. I made the decision not to go because I simply didn’t know how much it would cost, or how to manage the logistics. I just assumed it would be too expensive and too much of a hassle. It was a chance in a lifetime and I missed out on the memory dividends (to quote Bill Perkins in his book Die with Zero).
5. I didn't prioritize my health and stayed at a toxic job for too long. I ignored my health issues until I could no longer. I ended up in the ER and had to pay the full $7,500 deductible.

Question for you all: Was it a mistake to pick a health insurance plan with the lowest premium and highest deductible? I was relatively healthy and wasn’t planning on needing medical care aside from the typical checkups…until I ended up in the ER 😞… I'm open to your opinions!

I appreciate the compassion in this episode. We're all human, we make mistakes and grow from them. Here are some of my mistakes:

1. I left too much cash in a bank savings account when I should have invested it. Instead of a 0.01% interest rate, just imagine getting 10% annual returns in the market.
2. I rarely looked at my pay statements and company benefits, so oblivious to how much money I was leaving on the table.
3. I didn't realize I can choose where my 401K was invested in. I was automatically enrolled in a Target Date Fund, which wasn't necessarily bad, but I changed it a more aggressive fund with a low expense ratio.
4. I regret not attending my friend’s wedding overseas. I made the decision not to go because I simply didn’t know how much it would cost, or how to manage the logistics. I just assumed it would be too expensive and too much of a hassle. It was a chance in a lifetime and I missed out on the memory dividends (to quote Bill Perkins in his book Die with Zero).
5. I didn't prioritize my health and stayed at a toxic job for too long. I ignored my health issues until I could no longer. I ended up in the ER and had to pay the full $7,500 deductible.

Question for you all: Was it a mistake to pick a health insurance plan with the lowest premium and highest deductible? I was relatively healthy and wasn’t planning on needing medical care aside from the typical checkups…until I ended up in the ER 😞… I'm open to your opinions!

What an incredible episode - let’s start the petition now for more of these!!! I am listening to it a second time as I type this 😄

I work in healthcare and our organization’s journey is to be highly reliable, among many other things that are intertwined. One of the pillars of being a highly reliable organization (imagine air traffic control, nuclear energy, etc. where like healthcare, outcomes can be catastrohic) is transparency and the sharing of lessons learned - it’s by far one of my favorite parts of the quality work I do! So needless to say, I was overjoyed to hear this episode. So ofter, failures and even successes (the “how to” picture) are gatekept, and that’s disappointing.

So this was a welcomed episode that I hope will be repeated with many other guests; lived experiences are our best form of learning.

Key takeaway here for me:

Even amidst all these expensive, time consuming errors (that you each so freely shared), you each came out alive, on top, and living the FI life you desired 💜 These hiccups are part of the pathway, we live and we learn, and we do it again differently and better! I saw a quote recently and I feel it belongs here: “success is not final, failure is not fatal.”