8 Fails Over 8 Years of Blogging

8 years ago almost exactly, I wrote my very first article on this site and thought I was hilarious: Interview: Me on Me. In this landmark article I tackled important questions like “Are budgets actually sexy?” and the poignant “Who is J. Money?” To which was answered:

“That is I. You can guess what the J. stands for, but I usually answer to all of them; Jay, James, Jack, Jemima … everything except Joe Mama. Actually, I take that back. I probably would answer to that.”

As you can see, nothing much has changed :)

But while my cleverness is still in tact (uh, thank you), the knowledge accumulated over the years has been extraordinary. I’ve learned life-changing ideas about business, about marketing, dreaming, living a life on your own terms, and of course gobs about the almighty dollar. And more specifically, I learned what money really means in the end.

I’ve also failed a lot in the process too.

And rather try to impress you with all my stats and accomplishments over the years, I thought I’d do the opposite and share the things I’ve sucked at, as well as those I still struggle to fix today. It doesn’t help my image out much, but hey – it’s raw and real and the way life actually is, right?

Everyone has their problems, and here are some of mine:

#1. I still treat my businesses as hobbies

This is the best and worst part about me being an entrepreneur. Half of me wants to just blog and do my thing and not care about the income whatsoever (you know, what true blogs were back in the day), but the other hustler/entrepreneur half hates that I barely spend any time strategizing whatsoever. I always seem to make enough to continue forward, but not nearly enough to really be a business-business. Like some other blogs you may read who rake in hundreds of thousands of dollars or have sold for millions. They still love what they do, but they’ve focused more on the business-side of things than the hobby.

And I suck at that.

So over the years it’s been this constant struggle between doing everything for fun and not worrying about the money, vs trying to support my now family of 4 at the same time since we all live on my single income. Which is really like 10 mini-incomes scattered across a myriad of projects and consulting I do (and thus why you always see me launching stuff all over ;)). My lifestyle business is definitely more lifestyle than it is business.

#2. We’ve lost $80,000 in cash savings over 3 years

In October of 2012 our net worth reported showed $94,642.15 in our house savings account. A little over 3 years later it holds $17,351.84. There’s a slew of reasons why this has happened, of which most of them we consciously chose ourselves (having kids, working less, selling our house), but the fact still remains that we’re down almost $80,000 from our peak. Why haven’t I been pressed enough to fill it back up or change the ways I’ve been going? I can’t tell you. I know a lot of it relates back to trying to keep myself from being a workaholic again, as well as that whole hobby vs business dilemma, but we definitely need to make a change soon to start correcting the trend.

#3. I don’t plan well for the future

I’ve touched on this a little before in that article on the 6 areas of finance I hate (another great read if you want to feel better about yourselves ;)), but ultimately I just can’t wrap my head around what’ll happen next week, no less next year or the next decade. And magically I’ve been able to survive like this without getting into too much trouble (issue #2 above not withstanding). I thank my lucky stars every day that money and savings and financial freedom all interests me enough to actually invest and do all those things we’re supposed to do NOW, even though I can’t comprehend how it’ll affect me later. And I’m even MORE glad I’m not one of those YOLO people or we’d really be screwed!

#4. I asked to fail and the world provided. Twice.

The first couple years of blogging and running online projects were INCREDIBLE. So much so that at some point I started wondering/asking to fail big simply so I could get a reality check and gain those “invaluable lessons” you often read about in motivational books. It was one of the most moronic things I’ve ever done, and of course I soon got what I asked for but except without the lessons. (Unless you count being an idiot one of them)

First, I was asked to invest in a project that I kinda sorta liked, so I did hardly any research, thought it had decent potential, and $10,000 later was fully invested in it. Only it didn’t work out and I lost over half of it within a handful of months later. Around this same time another opportunity came, and again I subconsciously sabotaged myself and jumped in to lose around $6,000 this time around. So just like that I was out $12,000+.

Maybe all this would have happened regardless (after all, most businesses do fail than succeed) but I took it as a sign to never again REQUEST these lessons, and instead gain them due to my own wrong doings… Which leads us to the next one ;)

#5. I asked to succeed and the world did not provide. 10+ times.

While with the above I got loosey goosey with my money and failed, there are almost a dozen other times when I launched projects and went all-in only for them to be shut down later as well. And THESE are the experiences where you actually learn something after you tried and it didn’t work out :)

Some of you might remember projects like GiveawaysAreSexy.com, or BlogSexier.com, or even TakeOurStuff.com. All had the ingredients to succeed in my opinion, but the execution or passion or both were off and caused them to go under in the end. And of course not being able to plan so well into the future also plays a roll ;)

But with each and every one of these I’ve taken away the lessons both good and bad, and then did my best to apply them to the next projects. Like with RockstarFinance.com which is still humming, our since retired philanthropy project Love Drop, and now with M.O.N.E.Y. – our new podcast. All the lessons learned here will continue forward into the next projects as well.

As one of my new role models online Derek Sivers lsays, ideas are just a multiplier of execution. “The most brilliant idea, with no execution, is worth $20.Β  The most brilliant idea takes great execution to be worth $20,000,000.” And the more you build and fail, the better you get at it.

#6. I’ve created “jobs” for myself

Along these same lines of building businesses/blogs/projects, you have to know when it’s taken a wrong turn. And with many things in life, sometimes it takes you wayyyy too long to realize you need to stop and make a change or kill it.

This happened in the early stages of Rockstar Finance. I loved the idea and people seemed to be enjoying it from the start (the whole concept btw is like the Drudge Report, only for $$$ articles (so basically a curation site)), but at some point it had consumed me and I thought about selling it. Even though it wasn’t (and still isn’t, to be honest) making that much money.

I floated it around a few people I trusted to gauge interest, and I’ll never forget what one of my friends told me within seconds of hearing this,

“You know what you did right? You created a job for yourself.”

“Oh damn, I had!” I thought to myself. “I’ve built this thing that needs X hours of my time every day and without it it fails. It wasn’t a business – it was a job!” Which then forced me to either get rid of it all together, or start putting in systems – which I ended up going with. And now – over a year later – it continues to live on and grow with no small thanks to Cait Flanders, a fellow blogger who jumped in to help me :) Only time will tell if it ever generates any significant amount of income, but it’s a lot better structured than it was before.

(Btw, other “jobs” that we all create for ourselves? Living in email, obsessed with social media, any maintenance vs growth projects, etc. Not all of them are unavoidable and to some degree are needed, but it’s just good to be aware of where we’re spending our time, and *how*.)

#7. I struggle with Impostor Syndrome

You know when you accomplish something cool and people reward you for it, but deep down you feel like a faker? Because you’re just this regular person who happened to pull something off and people are now giving you labels like “expert” or “guru” and you don’t feel worthy of it whatsoever?

That’s the impostor syndrome talking, and unless you’re Kanye West or D. Trump it probably affects you too. Here’s how psychologists Pauline Clance and Suzanne Imes who coined the term describe it:

A feeling of: “phoniness in people who believe that they are not intelligent, capable or creative despite evidence of high achievement.” While these people “are highly motivated to achieve,” they also “live in fear of being β€˜found out’ or exposed as frauds.”

I’ve gotten better at squashing these doubts and trying to be more confident, but it still affects the risks I take and projects I launch (or don’t launch) because of it. Hell – I feel like a fraud even on our podcast sometimes! What gives ME the right to talk about money over someone else? I’m just a blogger?

#8. I’m still selfish with my time and money

I’ve come a loooong way in the past 8 years and realize more than ever how important *people* are over money and killing it with business, but I still have a ways to go. And it pains me to even share this and I kinda wanna go back and delete this whole section now! Haha…

But I won’t, because it’s true. And I do very much want to improve upon this :)

I’ve started by picking a new (small) charity or person to help each month (my favorite being the Sundara Fund btw, if anyone is looking for new places to support) but I have my spurts and eventually succumb to thinking inward again. Love Drop was by far the best thing I ever helped create since coming online all those years ago (we raised $90,000+ for people in need within 12 months) but that’s been retired for 5 years now and I haven’t done much since.

How will I improve on all this stuff in the future?

I have some ideas, but I’m not entirely sure. It feels good admitting it to the world though and just putting it out there. Similar to starting this blog all those Februarys ago. I had no idea where it would lead – or that I didn’t even know anything about money when I thought I did (hah!) – but we went after what we wanted and now here we are. With an incredible community and all!

Anyways, hopefully you gained some insight from this and at the very least feel better about yourself ;) I’ve done a lot of things right throughout this process too which I’m beyond thankful for, but no matter what stage we’re in we can always do better.

And that’s what I hope for each and every one of you. That we all become better humans over time, not only with our money and lives, but also to *each other*. I owe the 8 years of this blog to you for continually coming back and encouraging me, and for that I will always be grateful.


PS: For the things learned over the first 7 years, click here: 7 Things I Learned (About Money) in 7 Years of Blogging

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  1. Emma | Money Can Buy Me Happiness February 15, 2016 at 5:37 AM

    Wow! Congratulations on 8 years, you’re an inspiration :-)
    I completely relate to point 3 – I’ve always had this overbearing sense that everything will always be OK as long as I do the best I can, whenever I can.
    As for creating a job for yourself, that’s a tough one because there’s always that stage in any business where you really need to pay for help in order to scale but you’re not making enough money to justify the cost of someone else’s labour. So you burn out and start to hate it because your big vision is fading whilst your time is being sucked up working IN your business with admin or writing html, rather than working ON growing your business and implementing your brilliant ideas. That’s when you have to decide whether it’s something you want to grow and you have to spend the cash to get help or you just bail. It’s a rough time.
    Any yeah, charity. I’ve played the “charity starts at home card” for way too long now so I’m donating 1% of our monthly budget to charity. I’ll check out the Sundara Fund for my March donation. Carry the World is getting my February donation, they are donating baby carriers to help refugees carrying children in their arms for miles at a time as they make their journey into Europe. Can you even imagine that? I can’t carry my 3 year old for 5 minutes – let alone across a land mass.

    1. J. Money February 15, 2016 at 2:28 PM

      Love the 1% idea! Adding Carry the World on my list too – I can’t even imagine that :( The only part I hate about picking new places all the time is that you get spammed up the wazoo…. Sundara Fund is better than the rest and I actually *like* getting updates (imagine that?) but the big boys make me want to punch myself in the face… Another reason to give directly to *people* too – no constant barraging of requesting more!

  2. Slackerjo February 15, 2016 at 6:02 AM

    I am sort of um, happy, that you suffer from #1 (treat businesses as hobbies) because I do it too (and you seem to have your shit together). My side gig is writing books and selling them on Amazon but when I first explained/marketed this I rambled and made it sound like I was a distracted 13 year old schoolgirl doodling hearts in her notebook and writing lovesick stories about the captain of the football team. Since I didn’t take my writing seriously, nobody (including my own family) took my writing seriously. So now, more business, less hobby, more success.

    1. J. Money February 15, 2016 at 2:32 PM

      Hah – I can see that with writing. I’ve def. changed the way I write myself (which now takes 4 hours an article instead of 40 mins!) and it’s helped immensely over time… I miss the simplicity of just writing free flow, but it def. stunts the growth :(

  3. Mr. Tako @ Mr. Tako Escapes February 15, 2016 at 7:17 AM

    Admitting failures is a great way to grow from them J. Money. Congrats on your mighty success AND failures.

  4. Josh February 15, 2016 at 7:23 AM

    You’ve probably heard/read this quote before, but it seems relevant here:

    “The reason we struggle with insecurity is because we compare our behind-the-scenes with everyone else’s highlight reel”.

    -Steven Furtick

    Everyone does some things well, and other things…not so much. But that’s the beauty of being human. It makes for a colorful world.

    I’ve been reading this blog for close to three years now, and it’s literally because of this blog that I started tracking my net worth. And I’m pretty certain that from that, followed a greater effort to improve and pay attention to my financial life. Thanks J! :D

    1. J. Money February 15, 2016 at 2:32 PM

      Rock on!! That makes me so happy – way to go!!

  5. Kalie @ Pretend to Be Poor February 15, 2016 at 7:34 AM

    Thanks for sharing your fails, J! I’ve been thinking about mine lately, too, and what I’ve learned and what’s caused them. It’s worth reflecting on even if it isn’t the most fun topic.

    I think some of yours might stem from the same traits that have helped build your successes. You’re fun, creative, willing to try new things, want to help others out, and not willing to sell out for a bunch of sponsored posts you don’t believe in. Thanks!

    1. J. Money February 15, 2016 at 2:37 PM

      Thanks friend, I think you’re right… Great for community even if not so much for the wallet. If only I’d create a damn product or something of my own to sell! :)

  6. Chris @ Flipping A Dollar February 15, 2016 at 7:35 AM

    Imposter syndrome. It’s a real thing. I think everyone has always had it but the internet has helped us realize that others have it too. Instead of internalizing it like previous generations and just boozing it up or holding our feelings in deep, we can anonymously express ourselves without fear of being judged face to face.

    I can’t decide if my blog is a job that isn’t worth it. I’ve had (very) small growth, and it’s paid for itself so far, but that’s not a good thing from a time perspective. I enjoy writing and all that, but if I don’t have a lot of free time as is and the added stress might not be worth it. I get good feedback, but that doesn’t mean that it’s worth my time. But then I hear time and again that bloggers always struggle the first few years so who knows!

    1. J. Money February 15, 2016 at 2:39 PM

      I think as long as you’re *enjoying* it it’s a win. If it starts becoming a thing you “have to do”, esp after a few years, then that’s the time to reconsider. While it’s true it all does take time, it’s more of a matter of doing a lot of marketing on top of the blogging than it is just blogging over and over again. Without getting it in front of more eyeballs the chance of it to explode is pretty low :(

      1. Chris @ Flipping A Dollar February 16, 2016 at 9:54 AM

        That’s a good point. It’s one of those chicken and egg things. “I can’t get popular before I have more content. But I can’t get popular if I’m not promoting my content!”

  7. Amy @ DebtGal February 15, 2016 at 7:55 AM

    Congratulations on eight years!!!

    I’m a relatively new reader, so it’s fun to get this retrospective, and comforting to see an expert acknowledge areas for improvement.

    I LOVE the podcast!! I’ve been binge-listening to all of the episodes, and I’m finding it very inspirational – thank you!

    1. J. Money February 15, 2016 at 2:42 PM

      THANK YOU SO MUCH!!! We’re having a blast doing it and glad it’s useful at the same time :) Even if I feel like a fraud half the time! Haha… (Esp around Paula – that girl is SO SMART!!)

  8. Karen February 15, 2016 at 8:18 AM

    Oh wow! Eight years, that’s quite an achievement. I’ll be approaching 4 this summer, which I think it quite a feat for me, considering I was on and off with the blog. The majority of the time, I really was more “off” than “on”. Late last year, I made the decision for probably the 5th time to get serious about the blog, but specifically get into that mindset and actually work on it almost everyday.

    Thank you so much for sharing your failures. A lot of the times we only hear about the successes. Don’t get me wrong, they are great and inspiring, but sometimes we need to hear the failures as well.

    I will never forget and am forever grateful when you mentioned my blog as a standalone on one of your posts a few years about it being up and coming or something like that. My traffic hit an all-time high from that and I was on an all-time high. lol.

    1. J. Money February 15, 2016 at 2:44 PM

      Wow, really??? That’s so cool! I know I’ve loved your blog name for quite a while but can’t remember that post exactly… It must have been good if I dedicated a whole post around it – I’m pretty picky! :) And 4 years blogging btw is HUGE. Most burn out within 6 months – if that – so you’re dong great. Hope you keep going with it if it’s bringing you joy!

  9. Elise@ Uphill To Easy Street February 15, 2016 at 8:27 AM

    I am just realizing Impostor Syndrome runs rampant in the blogosphere and I’m trying so hard to change my ways.

    Your list is awesome. It is really interesting to see what you consider failures. There are some on your list that I would have never even considered. It really makes me want to sit and think about what failures I’ve encountered and how they are affecting my productivity.

  10. Bobby February 15, 2016 at 8:39 AM

    Congrats on all your success J! (I know that’s not what the post is about, but everything you’ve done is really impressive).

    You’ve been a big help to me over the past year just by answering my questions and being cool! I can’t wait to see what you come up with in the future!!!!

    1. J. Money February 15, 2016 at 2:45 PM

      Thanks man :) I may be up to something pretty cool here if I can work out the details… If so, I’ll give you a shout as I’m gonna need all the help I can get!

      1. Bobby February 16, 2016 at 12:57 PM

        Sounds good just let me know and I’d be happy to help (I owe you anyways for the rockstar finance love) :)

  11. Tom February 15, 2016 at 8:41 AM

    I very much understand #7 – “I struggle with Impostor Syndrome”.

    Even though I tend to do most things well enough I never seem to feel like I know enough. I can always find others who know much more than I do. I can always find something I am doing for the first time. But from time to time I look the other way, and see what has changed in myself and my thinking. And looking at that can often make me realise that, while I may not feel like I belong (or know enough), there are still a lot of things that I have learnt over the years.

    Keep up the good posts!

  12. Ashley February 15, 2016 at 8:47 AM

    Congrats on 8 years! Are we going to see a follow up on 8 triumphs over the last 8 years? After loyally reading your blog for the past two years I know you have enough material to work with :D

    1. J. Money February 15, 2016 at 2:48 PM

      Awwww, well I wasn’t going to, but maybe I’ll do one down the line.. Perhaps for 9 years? I’ll have to do something pretty freakin’ cool though or else it means I didn’t grow this year!

  13. Mike @ TipYourself.com February 15, 2016 at 9:20 AM

    Amazing self reflection J. Thank you for sharing. I’ve always found lessons learned from experience to be the most valuable, and any opportunity to read and learn from others is a huge bonus on this wonderful journey we all call life. :)

  14. LIsa O February 15, 2016 at 9:28 AM

    Congrats on 8 years! I have been reading your stuff for about 2 years and enjoy your work. I must say that this article was pretty deep from you and it really was wonderful for you to share so much of yourself. Keep on Keeping on Cause You Have It!

    1. J. Money February 15, 2016 at 2:49 PM

      Haha, thanks Lisa… I try to be serious every now and then :) Don’t want people thinking it’s all smiles and rainbows up in here!

  15. Brian @DebtDiscipline February 15, 2016 at 9:33 AM

    Thanks for Sharing J$ and congrats on the 8 years. I’m sure you could not have gotten to this point without a few bumps in the road and learning a thing or two from them.

  16. Stefanie OConnell February 15, 2016 at 9:40 AM

    I love the “creating jobs for myself” point. How rockstar would it be if we all approached our work in this way? Instead of conforming to job titles and descriptions, we pair our greatest skills and offerings with our greatest interests and the greatest needs of the world to create our own function. Love it!

  17. Broke Millennial February 15, 2016 at 10:02 AM

    I really appreciate you addressing #7. It’s such a common feeling, but so rarely talked about because if we dare admit we might be an impostor than it’s possible we’d get called out! And I know you don’t listen to a ton of podcasts, but Gimlet’s StartUp (season 1), might be worth your listen (and it’s storytelling style so really engaging). The founder of StartUp really addresses the pain points of asking for help/finding the right match, which ties in a bit with #3 and #6.

    1. J. Money February 15, 2016 at 2:52 PM

      Okay friend, I’ll add it to my list to check out :) I’d say I wish I had a commute so I could listen to all these great shows, but of course I don’t! Haha… I have been getting into ted talks before bed lately though… I think it helps the smarts sink in more :)

  18. Tonya@Budget and the Beach February 15, 2016 at 10:06 AM

    Hey man, thanks for keeping it real, but even your mistakes or failures are really not that bad! I really admire the route you’ve taken with your business and I’ve told you offline why I think that is. To me, that vulnerability is what I relate to the most, and i think other people do too, which is why you’ve sustained more long-term success instead of just trying to hit it big quickly. Mad props buddy!

    1. J. Money February 15, 2016 at 2:53 PM

      Thanks Tonya – means a ton coming from you :)

  19. So February 15, 2016 at 10:35 AM

    I started my personal finance blog (in spanish) in 2008 too and I’ve bee following you since then. I confess that form all other personal finance blogs that exploded on that year you are the only one I still follow. And I’m pretty sure It has to do with your hobbie aproach to your teaching. BAS is your business but It is also your hobbie and you are passionated about it, you are having fun and it shows.
    Having fun and write with humor on a difficult subject as personal finance to me is key.
    More life to budgets are sexy

    1. J. Money February 15, 2016 at 2:54 PM

      Wowww you’ve been around from the beginning?? So cool!!! And that you’re still rocking it too after all these years! Cheers to both of our blogiversaries! :)

  20. Carol in Mpls February 15, 2016 at 11:18 AM

    Congrats J$ on eight years! I think I’ve been reading you for about six years, and I’ve learned a lot in that time as well. Additionally, I really like Rockstar Finance, as it’s opened me up to new writers in the field. My favorite series that you’ve done was the ‘Challenge Anything’ project. It made me go back and re-evaluate what, and how, I was spending chunks of my money. As a happy recipient & winner of a GiveawaysAreSexy.com, thanks!

    1. J. Money February 15, 2016 at 2:56 PM

      Hah! Glad someone got something out of that project :)

      So glad you’re enjoying the sites – it’s pretty wild thinking something in your head and then putting it into the real world and seeing how it takes it… Those you think will kill it just bomb, while others you kinda just throw out there take off. Just more reason why it’s good to start stuff and test the waters before jumping all in! Especially with business!

  21. Abigail @ipickuppennies February 15, 2016 at 11:32 AM

    Here’s to many more years!

    I know what you mean about not treating the blog like a real job. I put in plenty of hours like it’s a real job, but I don’t really appropriately look for enough profit opportunities. I can’t believe I’ve doing this for 7.5 years. So here’s to us old-timers, eh?

    1. J. Money February 15, 2016 at 2:58 PM

      Hell yeah! I think there’s literally only 5 or 6 blogs left from when we first started… and almost all of them have been sold! We’re some of the only ones left, for better or for worse haha… (or did you sell yours too and I just don’t know it? ;))

  22. JayP February 15, 2016 at 11:53 AM

    Congrats on the 8 years! There is definitely something to “writing it down” in addressing our mistakes and exploring them, so that we don’t continue down those paths! And yes, you are a guru when you think about all the people that are terrible with money and need help. Your ideas inspire and motivate.

  23. Tawcan February 15, 2016 at 1:23 PM

    Congrats on the 8 years, that’s quite an achievement! I think #1 is very important. If you’re having fun with your businesses and treating them as your hobbies, they won’t seem like “jobs.”

  24. Chris "Stasher" February 15, 2016 at 2:18 PM

    Yet another article posted dropping great info and insight into what it takes to make this whole website/blog world go round. Good or Bad doesn’t matter as long as it is the truth, that wins all the time.

    1. J. Money February 15, 2016 at 3:00 PM

      Ooooh I like that….. I’m horrible at lying anyways – I can’t even trick myself! :)

  25. Stockbeard February 15, 2016 at 3:54 PM

    Thanks for reminding us that even successful bloggers are still only humans :)

  26. Mr Zombie February 15, 2016 at 4:16 PM

    8 years! Amazing, way to go J$! Like you said above, it’s not been without it’s hardships (much like Tom Corley on your podcast!). Something to be said about learning from your failures and also persisting :)

    I feel like a fraud a lot of the time – “You’re going to pay me more because I passed some random exam…ok”. It’s weird, I’ve studied and got two professional qualifications after university and worked in finance for over a decade…yet I still feel like that.


    1. J. Money February 17, 2016 at 7:49 AM

      I guess it would be worse if we really DID suck? :)

  27. Our Next Life February 15, 2016 at 4:28 PM

    I’ve learned to have an inherent distrust of anyone who DOESN’T have at least a slight case of impostor syndrome, because not having it means you think you know everything and are clearly delusional (see the current slate of presidential candidates if you need examples of what I’m talking about). So I think that’s normal, and something that conscientious folks just have to learn to roll with. All the rest of what you call “fails” seem deeply normal and understandable, too, and while I admire your honesty in admitting them publicly, I hope you don’t beat yourself up over them. Because you’re doing great things, you’re influencing and helping a lot of people, and those things matter a ton!

    1. J. Money February 17, 2016 at 7:51 AM

      Thanks, friend :) By and large I feel good about everything, yeah. Just wanted to share that it’s not always so rainbowy up in here and that we all have our issues for those who think we don’t.

  28. Linda February 15, 2016 at 6:53 PM

    Wow! Congrats on 8 years blogging!
    Thanks for sharing all your mistakes, although I think it’s great that after all this time, you still think of this as a hobby. It shows in your posts how much you enjoy doing this. I think if you started thinking of blogging as just a way to make money, your posts would be different.

    Oh, and I love Rockstar Finance and check it almost every day. So thanks for keeping that around!

    1. J. Money February 17, 2016 at 7:52 AM

      I’m glad you’re liking it :) I’ve had a love hate relationship with it but we’re currently on “love” haha…

  29. Fervent Finance February 15, 2016 at 7:39 PM

    Congrats on 8 years. Can’t hate on the fails, because of how much wiser you are today because of them :)

  30. Jason Butler February 15, 2016 at 8:48 PM

    Congrats on 8 years of blogging. I too have felt the imposture syndrome. It disappears more and more as my blogging gets better.

    1. J. Money February 17, 2016 at 7:54 AM

      Well that’s good! It’s getting worse and worse for me haha… Fortunately I have a horrible memory though so I don’t dwell on it too much :) (and which is also why it’s probably not getting better – because I have trouble grasping successes over long periods of time)

  31. RichyC February 16, 2016 at 2:03 AM

    Quite possibly the best post I’ve ever read!
    Superb work Mr Money!

    1. J. Money February 17, 2016 at 7:55 AM

      Wow. Way to make my week! Thank you!!

  32. Erin February 16, 2016 at 5:36 AM

    If the results were guaranteed, everyone would be doing it, right? Tales of missed successes help us find better strategies to reach our goals or identify things that should be avoided altogether. Your blog and other financial bloggers help your communities of like-minded people when you share your wins, sure, but I bet we gain more from stories of “failures.”

    Please keep sharing! Laughter is the best medicine, even if we are laughing at ourselves.

  33. Mrs. Groovy February 16, 2016 at 8:07 AM

    Congrats on 8 years J$! Thank you for sharing this. It takes a lot of courage to show raw emotion in public. But in another way, it shows confidence in yourself and your readers. You know it won’t scare them/us away because your fan base is loyal. I’ve only been around this community for six months, but your writing (and now your podcast) has helped me tremendously. And thank you for showcasing so much talent on Rockstar!

    1. J. Money February 17, 2016 at 7:58 AM

      YAYY!!! Thanks for reading/listening!! And you’re right – I feel incredibly lucky to have such a great community here where the worst I fear is only embarrassing myself :)

  34. songbird February 16, 2016 at 8:08 AM

    Congrats on 8 years! I’ve been reading your blog around the time you were “fired”! I’ve learned a lot of things and been encouraged by your writing. Thanks so much!

    1. J. Money February 17, 2016 at 7:59 AM

      Holy wow! You’ve been around forever – thank you! We’re both so much older since that blog post! Haha…

  35. Financial Samurai February 16, 2016 at 10:09 AM

    Howdy J, thanks for sharing your reflections. You got one of the best sites out there because it is entertaining and very genuine. I think as soon as you start making the side and other sites more like a business, the interest will fade. You probably can make more money, but then the site might not last as long.

    I wouldn’t get hung up about how much other bloggers make either, because the fact of the matter is, a lot of the numbers are not true. They are published always go up no matter what because that is what their community expects . Just looking at the sites traffic and comparing it to the revenue is easy enough to calculate that the CPM rate is impossible. For example, you can’t make $40,000 a month if your traffic is only 100,000 to 200,000 pagesviees a month if you don’t have your own products. A $200 CPM rate is unheard of, even for the most luxurious of brands.

    Keep on having fun and writing entertaining stuff! and if you want to make more money, nobody is going to follow you for trying to promote more products. If they do, then they are the ones who are selfish!


    1. Financial Samurai February 16, 2016 at 10:12 AM

      Oops, sorry for all the typos. This voice diction function isn’t as good as I thought!

      Nobody is going to “fault” you, not follow.

      1. J. Money February 17, 2016 at 8:03 AM

        Hah! Thanks man… you’ve been good to me over the years and I appreciate that. Glad we got re-connected again and are now grandpas together in the space :)

  36. Ann February 16, 2016 at 4:17 PM

    If you still enjoy it and are still going strong, you’ve won a lot of the battle. I don’t think it’s easy to post on a consistent schedule with new material several times a week. (I’m the kind of person that, when I want to learn something new or have something new to play with, I go at it full force, but lose interest fairly quickly. I couldn’t do it.)

    Something I was listening to on youtube talked about success not being defined by all the good days and good things that happen. Success is defined by how you handle the bad thrown at you.

    Are you still toiling away on your Ben Franklin schedule?

    1. J. Money February 17, 2016 at 8:06 AM

      Indeed I am! At least the morning-only rituals – I believe today marks somewhere in the 140 work days-in-a-row I’ve waken up around 5? I’ve long since given up trying to take 2 hour lunch breaks or more inward thinking in the evening, but my days certainly seem more productive with the new schedule. Even if some are harder to wake up than others :)

  37. Revanche February 16, 2016 at 8:30 PM

    Cheers to one of my favorite bloggers and cheers to you staying one of the OG without selling BAS off :)

    As much as I’d love for you to get that payday, it just wouldn’t be the same without you at the helm here. You know what you need? We talked about this, what, 4-5 years ago?, you need to be the ideas guy and have someone taking care of your big picture and business steering. It would be such a good match. :)

    1. J. Money February 17, 2016 at 8:07 AM

      I could be like Kanye and get someone to invest in all my ideas!! :)

  38. Lady FruFru February 18, 2016 at 8:06 AM

    I love this post. This kind of brutal honesty and self-reflection is what propels growth–personal, financial–or any kind. And putting it out there can hold you even more accountable. Bravo! Inspirational.

    1. J. Money February 29, 2016 at 4:16 PM

      Thanks FruFru :)

  39. superbien February 19, 2016 at 6:01 PM

    Thanks J, I love this site and your honesty about the good and the bad is one of the reasons.

    1. J. Money February 29, 2016 at 4:17 PM

      So kind of you to say – thank you :)

  40. Brittney @ Life On A Discount February 21, 2016 at 11:47 AM

    Thanks for sharing! Admitting failure can be really hard to do, but recognizing it and learning from it helps us grow.

    The “impostor syndrome” section really resonated with me. It’s the weirdest feeling I can’t quite shake. I received a huge promotion recently to an executive position and while I had “proven” I earned it over the years, I still have moments where I feel like they are going to think I am not capable of doing it. It’s been 7 months since I took the new job and things are actually going quite well, but I feel like any day now, they will find out I am an impostor.

    1. J. Money February 29, 2016 at 4:23 PM

      Welcome to the club! But you’ve GOT THIS! And soon you’ll be thinking the same about the next promotion up too, and the following and the following :) But I guess if everyone feels the same then we’re all good? Haha… that’s what I always tell myself now.

  41. maria@moneyprinciple February 22, 2016 at 10:25 AM

    $J, reading this I do share most of your failings – it is an almost complete ‘snap’ kind of situation. So, I though you could help me out here and tell me which ones do you think are the key ones; the ones that can transform everything if you rememdy.

    1. J. Money February 29, 2016 at 4:25 PM

      Tricky! I think it’s one of those things that you slowly figure out over time :) Though, If I had more money saved up it would certainly nix a handful of those right off the bat, haha…

  42. nicoleandmaggie February 24, 2016 at 4:53 PM

    I think we’re down about 20K from this summer in terms of our savings. But that’s ok– I saved 84K extra for the year and we’re actually doing a bit better than where I thought we would be at this point.

    1. J. Money February 29, 2016 at 4:26 PM

      84k?? Holy crap – you’re killing it! Congrats!

  43. Dr. Beard March 9, 2016 at 10:49 AM

    I totally identify with creating jobs for yourself. When I was in graduate school getting my PhD in Badass, I had a little side business selling a particular type of item on eBay. I was good at it, too. I could sell the same thing for more than my competitors because I had branding and great ad copy for the same Chinese made stuff. But man, this was a job. I had real work to do every single day, and as volume increased, so did the amount of work.

    So … genius idea. Cut out the retail customer, and deal with fewer folks while increasing volume. I wrote a book on how to sell this item. I marketed that with this little one page website and sold it for some ridiculous amount of money. The book did go into detail on what I did, my ad copy, etc. but it was mainly one big ad for a dropshipping company I set-up. I was building an army to sell for me. Well … it worked. My volume went way up, but so did the amount of time I needed to spend each day. The work didn’t scale with client numbers. It scaled with volume. I created a job, and after running the numbers, I wasn’t really making that much per hour. And, I hated the work I had to do. Data entry, customer service, customer complaints, supplier problems. It sucked. I couldn’t outsource that stuff because then I wouldn’t make any money. Lesson learned. I had to shut it down so I would have time to graduate.

    Moral: it’s actually really easy to make money online, but if you’re not careful, you’re just creating another job for yourself.

    1. Dr. Beard March 9, 2016 at 11:00 AM

      Holy crap! This little story reminded me that the book was probably still listed on the self-publishing site I used. I just logged in and I have $600 they’ve been trying to send me for years, and I hadn’t updated contact info since two moves ago. People are still buying the book. Free money!

      1. J. Money March 15, 2016 at 7:36 AM

        Hahahhahahhaha… See – it was all worth it in the end! And I’ll only charge you 10% for reminding you of it ;)

        Very fascinating stuff to read this morning for sure though – thx for sharing it with us man. I love all this hustling/entrepreneurship stuff, even if it drives us mad at times!