12 Major Decisions and How We Feel About Them Now


Got a notification that it was my anniversary on a couple things this week (picking up my Lexus from Carmax (3 years), switching to Republic Wireless (5 years!)), and thought it might be helpful to see how we feel about it years later now :)

Do I wish I could go back on any of them?! Did any of them completely change my life??!

Here are updates on those, as well as other events that popped in my head when I sat down to write these out…

Fun exercise to do!


1 month anniversary of… buying a house! And so far so good, although we have still yet to move in! Haha… (probably why it’s going so good – the realities haven’t set in yet ;)).

1 year anniversary of… turning into a stay-at-home daddy blogger! One of my first goals when we found out my wife was pregnant again and I’m happy to report that everyone is still alive! Most especially my boys! There are days that are a real struggle and those I’m not proud of, but by and large I feel exceptionally fortunate to be able to watch them grow up each and every day and I’m slowly remembering what it’s like to live in “the real” world again vs online all the time… And I’m hopeful that my kids are enjoying it just the same! (Although I swear, as soon as Mommy comes into the picture she becomes the Queen and all of a sudden no one wants anything to do with me! Haha…)

1 1/2 years anniversary of… selling Rockstar Finance. Something that allowed me to have this better life/work balance and enjoy such things as above! So definitely wouldn’t ever go back and undo this one, though it is sad to see it slowly trickle out/stop?, now that it’s on its 3rd owner… I def. miss connecting with all the newer bloggers out there and spreading the love around. There were a lot of great things about that project.

2 year anniversary of… not working on the weekends! One of the top 5 decisions I’ve ever made in my life! I can’t tell you how beneficial this has been for me/my brain/stress levels over the months… It’s just so nice to have that *cut off* from things when so much of our lives seem to be mushed together by the internet and Go-Go-Go mentality of modern times… And when you put limits like that into your life it better helps balance things out and you STILL manage to get everything done you need to! Because there’s no pushing it off until the weekend when it’s no longer an option!

3 year anniversary of… quitting my podcast. Which is still rockin’ with Paula at the helm as she heads into episode #200 already! Work it!! But similarly to my feelings with leaving Rockstar, it’s hard to regret opting out of projects when it frees up so much extra time and opportunity for other things in life. Even if it seems crazy leaving a project that’s well on its way to success! I did recently hop onto the show just for fun though, and you can check out our reunion again here if you like ;) A helluva lot more fun on this side of the mic than the other, I’ll tell you that much! #199: The Three-Year Reunion with J. Money

3 year anniversary of… swapping my hooptie for a Lexus. Now this change out of all of them so far I get sad about every now and then… Not that my newer ride is horrible or anything (it’s one of the most comfortable, and reliable, cars I’ve ever had!) but I 100% miss my Caddy and wish there was a way I could have saved her :( There was just something about rollin’ around in that beat up ride, windows down and blaring hip-hop music without a care in the world…. She was great!! And even made me money at times! Haha… But such is life… Perhaps one day I can get a replacement when I’m no longer playing chauffeur 24/7 to my kids….(“BUT NOT BEFORE I GET MY MINIVAN!!!!” <— Wife)

4 year anniversary of… waking up at 5 a.m.! Another move I’ve made over the years that continues to pay dividends! Still very much waking up early and enjoying it (weekdays only), and definitely helps with the “getting everything done” during the week mission too. Though I also like to use part of the mornings to just reflect a little and soak in all the peace while everyone’s down and sleeping as well – including the sun :) It’s one of the only times I get 100% ME time!

4 year anniversary… of cutting cable!! And can’t even tell you what I’m missing! Haha… One of the easiest transitions over the years, and like others wish we had only done it sooner :) We still pay for internet and thus connected to cable companies for life (ugh), but it’s a helluva lot nicer not having to battle them every 6 months when they jack up those rates! I don’t think we’ve had to call in yet over the past 4 years – it’s been magical… (And we still get lots of shows too using a cheap $16 antenna from Target, including all Redskins games – woo!!)

5 year anniversary of… giving up my iPhone and switching to Republic Wireless! And now over $6,000 total saved which is enough to max out a Roth IRA!!! :) So def. still happy with this one, haha… And not surprisingly, Android phones do pretty much the same thing as iPhones or really any other smart phones for that matter these days… You can call/text/snap photos/download apps/get internet and pretty much anything else! So why not keep going and pocketing that free $100 every month?!

7 year anniversary of… having my first kid! And going so well I had to buy two more! Haha… Although my wallet doesn’t appreciate it nearly as much ;) Anyone remember that time I tried tracking every last penny they cost back in the day?!

8 1/2 year anniversary of… getting fired from my day job and becoming a full-time blogger! It’s hard to remember what life was like back then, but I do succinctly recall that initial excitement and anxiety all rolled into one and not knowing what the outcome would be… Promised my wife I’d go back to a 9-5 if I couldn’t figure out a way to make it work in 3 months, and now here we are almost a decade later! Hasn’t always been rainbows and sunshine, and I’m definitely tired of calling the shots on everything that a business requires, but it’s been an incredible experience so far and will keep going until something more exciting comes along. Even if that’s a 9-5 again! I’ve long since realized happiness comes in many forms, and will consider anything that makes life better for me or my family :)

And finally, it’s our 10th year anniversary of… hitting our first $100k. Which was not only the turning point of feeling more stable and secure, but also of the compounding growth since it really starts snowballing from there!

Here’s how long it’s taken to reach each additional $100k:

  • $100,000 net worth: 7 years, 11 months
  • $200,000 net worth: 1 year, 5 months
  • $300,000 net worth: 1 year, 2 months
  • $400,000 net worth: 1 year, 8 months
  • $500,000 net worth: 2 years, 7 months
  • $600,000 net worth: 7 months
  • $700,000 net worth: 10 months
  • $800,000 net worth: 1 month (when I sold Rockstar Finance)
  • $900,000 net worth: 1 year’ish (been going in and out of $900k lately)

So basically it took 8 years to get to that first $100k (from when I had my first “real”job), and then every year since we’ve averaged an additional $100k to the pile, due to both hustle and a variety of fortunate events. But it really was that first one that was the hardest to hit!


So that’s been my life condensed in a few paragraphs! Haha…

How about you guys? Any major events in your life change you for the better or worse lately? When was the last time you really stopped to think about it?

Give it a shot now if it’s been a while… so much changes over the years!

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  1. Kate June 26, 2019 at 6:54 AM

    1 year since getting our dog/love of our lives (she makes us happy a million times a day)
    2 years since getting married and buying a home together. In the same fortnight. I DO NOT RECOMMEND THIS! (I recommend doing both, just not at the same time!)
    3 years since a super crappy break up then meeting my husband to be a few months later (thank you universe!)
    4 years since quitting smoking (about time!)
    5 years since quitting drinking (best life decision I have ever made)
    6 years since joining YBAB and developing a love of personal finance (YEAH!!!!)
    10 years since starting my current job (which I still love)
    13 years since moving countries (so glad I did!)
    15 years since buying my first apartment (best investment decision I ever made)

    1. J. Money June 26, 2019 at 7:22 AM

      So fun to read!!

      You’ve had a wild last few years! :)

  2. Martinus June 26, 2019 at 8:44 AM

    I was at my god son’s grade 8 grad yesterday. That put my in mind:

    45 years (!!!) since my grade 8 grad!

    And let me congratulate you on your 8.5 anniversary of getting fired and going it alone for your employment. This month I am celebrating 33 years of self employment (I’ve never really worked for anyone). Good and bad to be sure (I served a 15 year apprenticeship at the school of hard knocks), but the good outweighs the bad (net worth around $7.5 million, and getting to $10 million seems inevitable).

    1. J. Money June 26, 2019 at 11:23 AM

      ***I BOW DOWN TO YOU, SIR***

      **And kindly await a guest post from you so we can share your tips/inspiration with the world***

  3. Christine June 26, 2019 at 9:38 AM

    I sincerely loved reading this list! So many milestones!

    Last month was my 1st wedding anniversary. Next month will be the 4 year anniversary of our first date. No regrets here…yet! Ha! My Facebook posts from 4 years ago at that time are hilarious to read in hindsight. One minute I’m bemoaning how hard dating is. Then I mention this guy I’m going to meet. Little did I know that that was going to be IT! Also, while I was sort of cursing myself for spending money on a wedding, looking back, I don’t regret it. It wasn’t exorbitant and was the source of so many great memories!

    Last month was also my 12th anniversary of my start date with my company. I have more mixed feelings about that. Thinking a lot about switching it up lately. I swore I wouldn’t stay past 10. I’ve had my ups and downs in this job but overall have ended up higher I’d say than when I started, and overall the ride has been good.

    And yikes, I just realized it’s been 25 years Since I graduated high school! Yikes!!! I remember my parents’ contemplating going to their reunion and thinking how LONG that was! Ha! Though I don’t mind getting further away from that period of my life. I was NOT one of those people who peaked in HS!

    1. J. Money June 26, 2019 at 11:24 AM

      You’re too funny, haha…

      Very much enjoyed reading your thoughts as well :)

  4. Stevo June 26, 2019 at 9:38 AM

    My wife was supposed to quit her job at the end of July as a CPA Tax Accountant because it was too much work and was stressing her out (for the past 6 years..). I was excited for her to be at home full-time with our 1 year old and to not be so stressed (and to experiment living bare bones on one salary!). Unfortunately (fortunately?), her employer offered to take her off the client that was causing all the stress and let her go down to 3 days/week from 4, so now she’s staying on. So we ALMOST had a life changing event soon haha

    1. J. Money June 26, 2019 at 11:28 AM

      Yeah you did, haha… But something tells me it’s not fully out of the cards just yet ;) In my experience the more freedom you get, the more you want even more of it!

  5. mobilehomegurl June 26, 2019 at 9:49 AM

    Great list of anniversary celebrations J! Kudos to you on waking up at 5 a.m. for the last 4 years. I do it for awhile off and on. Need to get on that train!

    Best of luck on moving into your new home. It’s a bit much when you’re in the process of moving. Though I’m sure you’ll all settle in. :)

    And nice to hear about your Lexus anniversary. Have been thinking about this one for awhile. Still have a Honda for now. :)

    1. J. Money June 26, 2019 at 11:29 AM

      Thanks friend!!

      And Hondas are great – those are hard to part with until they finally die :)

  6. Torrie @ To Love and To Learn June 26, 2019 at 10:46 AM

    What a great idea for a post! I might have to steal it, ha ha :) (I guess I’d give you credit, though…)

    We’re expecting our third baby now at the end of the year, so the minivan life is certainly calling us, since I don’t think we can fit a third carsesat into our compact Mazda! Although we might end up going for the 3-row SUV, just because I’m not sure I can ever bring myself to drive the traditional minivan, though I’ve heard everyone loves them. Time shall tell.

    Please do us all a favor and post a pic of you driving that boy boy around when you guys finally buy one :)

    1. J. Money June 26, 2019 at 11:30 AM

      You got it ;)

      (And please do steal this blog idea!! Will give all your new readers a quick update on your moves as well!)

  7. JPP June 26, 2019 at 10:52 AM

    Yeah its a shame about what happened to Rockstarfinance. What a great concept – best of articles from the Finance community lumped into one place. Now just a bunch of random filler articles dedicated to advertising. I’m not sure how these sites make what they are paying for them. Seems like all the traffic would die off quickly if the site changed from what you came there for.

    1. J. Money June 26, 2019 at 11:33 AM

      Agreed :(

      It was such a simple concept when it first came out, and over the years has gotten overly complicated… Even myself adding to it towards the end (though I will say the Directory was a genius idea too if I may! Hah!)

  8. Moneybee June 26, 2019 at 10:54 AM

    7 years since I graduated high school (which sometimes is a “wow, it was that long ago?” and sometimes is a “wow, it really wasn’t that long ago!”)
    6 years since I met the then-pre med *grin*
    3 years since I graduated college
    2 years since I bought my car (and hit net worth nadir… in terms of numbers that is, not to say I’m not happy with my car!)
    2 years since the erstwhile pre med graduated from med school
    1 year (in a few days) since we both moved states for his residency, and went from living 300 miles apart to living in the same house

    1. J. Money June 26, 2019 at 11:34 AM

      Yayyyyyy on that last one!!!

  9. Joe June 26, 2019 at 11:09 AM

    Congrats! Life sure moves fast.
    I have a few anniversaries in July.
    20 years married – it’s been great. Mrs. RB40 is the best.
    7 years retired from my engineering career – I’m much happier now.
    23 years in Portland – I’m ready to move.
    6 months our old condo is on the market – #$%!

    1. J. Money June 26, 2019 at 11:35 AM

      Maybe you can raffle it off to our community here and get a nice viral hit on your blog at the same time?! :)

  10. Steveark June 26, 2019 at 2:20 PM

    41 years since we married, 40 yes since we bought our current and only house. 41 years since I started work at the only company I ever worked for. 34 years since first child, 31 since second and 28 since third. 21 years since I started running the company, 14 years since reaching FI millionaire status. 13 years since personal best marathon and 5K races. 3 years since retiring slightly early at 60. 2 years since starting to blog. That was fun to think through!

    1. J. Money June 26, 2019 at 2:33 PM

      Holy crap – that is a helluva run so far! Haha… Literally and figuratively! ;)

      Your turn to blog about it to your audience!

  11. JR June 26, 2019 at 2:33 PM

    2 months since I stopped reading Rockstar Finance. It is unreadable now.

  12. Leila June 26, 2019 at 2:44 PM

    I guess my biggest anniversary is starting my debt free journey in June of 2018! Started with $82,200 in debt now down to $60,150, my student loans and my car.

    It was nice to see that it took you almost 8 years to reach your first $100K net worth. I’ll be 26 in a couple weeks and I’ve been doing the math constantly on how I can pay off more debt and increase my income. I get obsessive about it honestly. I started my current “career” in April of 2018 but am working to become self-employed as well!

    Great post as usual! :)

    1. ERIC D MEYERS June 26, 2019 at 4:24 PM

      Hey Leila,

      I had a similar situation to you about 4 years ago. I was obsessive about it and paid it off in about 3 years and 3 months. At first it took a lot for me to see progress, but once you get toward the end of your journey it will speed up. Keep up the good work – Looks like you are already on a roll!


      1. Leila June 27, 2019 at 8:09 AM

        That’s amazing Dan!! And thank you so much, I’m definitely looking forward to it!


        1. J. Money June 28, 2019 at 4:06 PM

          So glad you got something out of this post, Leila :) you’ve been working at your $$ long before I started at 28 so you will beat me to it by the time you’re old and almost 40 like I am now!! **But be sure to enjoy your youth along the way — we’d all rather have that back!**

  13. Nita June 26, 2019 at 4:10 PM

    Most of my anniversaries are July through September…

    13 years since moving out of family house at 18
    11 years since first date with my boyfriend (good time, but the future is still conditional), and since moving to Favorite City (stayed 8 years, had a great time there)
    7 years since graduation (I think I did my best, even though sometimes I wonder what else could have been)
    5 years since cat’s birth. This little thing is my pride and joy.
    3 years since moving in this city (still unsure, see above) and Quitting Teaching (BEST decision EVER, especially considering PF, I really busted my *** for peanuts)
    21 months (to the day) since signing the first of the long list of paperwork on homeowner path (happy too).
    6 months since starting following this blog (to the day or very close… it was somewhere between Xmas and new year) (good decision I think? ;) )

    1. J. Money June 28, 2019 at 4:09 PM

      I would say your last one is one of the best ;)

  14. Liberty @ Love Liberty Shelter June 26, 2019 at 6:08 PM

    12 yrs since marrying the love of my life.
    11 yrs since traveling Western America, going to massage school, & beginning to educate ourselves on health and finance.
    10 yrs since moving to beautiful Colorado.
    9 yrs since backpacking Europe.
    8 yrs since starting first business.
    7 yrs since baby #1 was born.
    6 yrs since Big C entered pre-med.
    5 yrs since baby #2.
    4 yrs since Big C left college, we left our house, & having no rent or mortgage payments.
    3 yrs of tiny house life and baby #3.
    2 yrs of realizing what FI could mean to us.
    1.5 yrs since Big C got his first well-paying job and saving/paying down debt with 50-70% of our income.
    8 months since sweet baby #4:)

    1. J. Money June 28, 2019 at 4:10 PM


      This one is probably my favorite — ” 3 yrs of tiny house life and baby #3.”

  15. Angela @ Tread Lightly Retire Early June 26, 2019 at 9:38 PM

    This is one of the coolest things about writing a blog for so long. You have a lot of your life – at least if you write about the personal stuff beyond just the numbers :)

    Loved listening to you back with Paula for a few minutes! The Money Show was pretty great (though so is Afford Anything).

    1. J. Money June 28, 2019 at 4:11 PM

      Thanks Angela!

      Very true about blogging – great way to document life :)

  16. Linda June 27, 2019 at 10:02 AM

    These anniversaries are wonderful celebrations, J.
    I am sure at least some of these were hard decisions to make at the time.
    I’d like to use this idea for my blog though I have just a few years on you and yours.

    Although I have been reading your blog for longer, I will celebrate my first year as subscriber along with my first year as a blogger!
    3 years anniversary as tenured professor teaching finance, law, marketing.
    3 years as professor, third career.
    12 years since graduating law school and practicing law.
    15 years having my two kids who are eating up personal finance topics. (They love your blog!)
    16 years since I left Wall Street as equity analyst/MD…very difficult move!
    That’s the gist though I forgot to mention my 37th wedding anniversary to Craig. Whew!

    1. J. Money June 28, 2019 at 4:16 PM

      heyyyy – I didn’t know your kids read the blog! Very cool!

      And yes – please DO steal this post idea for your readers. So fun getting to know y’all more and celebrating together :)

      Congrats on all the fun changes!

  17. L8 June 27, 2019 at 4:25 PM

    I used to check out Rockstarfinance every single day for the last 5 years, the previous owner increased the articles from 3 to 5 and was still pretty good. They still have the same articles from about a month ago right now. Campfirefinance.com is another alternative but not as good as what rockstarfinance was

  18. Tony June 28, 2019 at 2:15 PM

    Gotta be honest, Rockstar Finance hasn’t been the same since you decided to move on to bigger and better things. Thankfully, we still get our dose of J$ here!

    1. J. Money June 28, 2019 at 4:21 PM

      Well it doesn’t suck to hear those words, thank you :)

      Adding right to my “love” folder to help battle “the hate“! Haha…