pondering life

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.  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 ‘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