From the Brink of Failure

Last Monday, I unleashed the beast of a post on 36 bloggers and their investing styles. It took a lot of time, persistence, and energy to compile and polish up that piece for publication. Some of you reading this are probably laughing at how many times I badgered you with emails saying “Hey, just following up on that investing style paragraph – got it ready yet?” Half the battle was summoning up the courage to cold call so many bloggers and compiling the paragraphs. The other half was actually taking the raw material and crafting it into a finished product. Let me tell you a story of how it almost never happened.



I started blogging in July 2013. I had been interested in finance and investing since 2011 and after attending WDS in July 2013, I had this most original idea to start a blog.

From the Brink of Failure Portland 2

Man, did I start out with a bang! I had so much energy and excitement. Blogging was new and shiny. Whoa, I wrote things and people liked and commented on them. It was all pretty neat. I was hooked and I produced some great content those first few months (please do not go look through the archives for those posts).

I was steadily ramping up my activity moving into the fall of 2013. I was connecting with other personal finance bloggers on Twitter. I was starting to follow and comment regularly on other blogs. I was starting to think about expanding my presence through guest posting on more established blogs.

December 2013 was the best month of my early blogging career. I was featured on a guest post on a relatively prominent, but now defunct, blog in the personal finance niche and it drove a lot of traffic back to my blog. Just like Leonardo DiCaprio on the bow of the Titanic, I was feeling like the king of the world.

From the Brink of Failure Stats

Check out the WordPress stats month-by-month going back to the beginning. After December 2013, I started to lose confidence. See the gold arrows where it says “Confidence Shot to Hell”? That’s where I almost gave up. Well, the slide actually started in January 2014 and I reached a low point in June 2014. I was on the brink of failure. I was about to throw in the towel. I had visions and plans of where I was going but I lost all confidence. I was ready to quit. I was terrified of failing.


You know what’s funny? I went back to WDS in July 2014. I went knowing full well I was about to quit on blogging and quit on my idea. All I wanted was to go down to Portland and have a good time over a nice, warm summer weekend. Perhaps it was being immersed in an environment surrounded by so many people doing so many amazing things. I’m not really sure, to this day why, but I left Portland after that weekend with a renewed sense of conviction.

From the Brink of Failure Portland

And I came back with a vengeance. I came back with a confidence and swagger I thought I had completely lost. Since that weekend in Portland, I’ve really committed myself to mastering this craft and turning my visions into reality.

But a really ironic thing happened recently as I was putting together the mammoth post on investing styles: I was scared. But this time, I wasn’t afraid of failure – I was afraid of success. I knew this was going to be a great post. I mean, how could it not be? It was going to feature over 36 different bloggers and the material I had gathered up was so good. But I sat on that material for over a week and completely ignored actually bringing it all together and crafting a finished product.

The more I thought about it, the more I understood I was procrastinating from putting it together because I was afraid of it potentially being successful. It’s totally insane but it’s true! That fear of success really paralyzed me and I was finding it difficult to get moving on what I was doing. Even with my confidence back, I found it fascinating that I could still get paralyzed with inaction. Thank goodness I snapped out of it fairly quickly or that post might still be collecting dust in my draft folder never to be seen again.


In a little over a year on this blogging journey, I’ve experienced a roller coaster of ups and downs: from excitable beginnings to fear inducing paralysis to a voracious re-emergence. I almost quit. Then I got stymied by fear even after I found my confidence again. And it’s so easy to give in to our fears. It’s so much easier to avoid discomfort and roll with contention day in and day out.

To achieve any of our goals, we need to get out of our comfort zone. We need to continuously re-evaluate, re-assess, and adapt. Reinvention is the key to life. Reinvention is about identifying fears and acting to correct them. It is so much easier to let our fears dominate us. It is so much easier to keep doing what we are doing even if it isn’t working. Why do you think so many people show up to their dead-end jobs for 40+ years? Why do you think so many people watch endless hours of TV each and every night? Why do you think so many people talk about doing so much more with their lives but never do anything about it? What do I know about reinvention?


After spending 6 years and +$50,000 of higher education, I understood I did not want to be an academic. It was terrifying to think that I had spent so much money and so much time to no longer pursue something I thought I had wanted to pursue.

After 12 years of exercising exclusively with weights, I put myself through the uncomfortable process of becoming a runner. I had told myself for over a decade that I was not a cardio guy, and the thought of change was frightening.

And after a few months of blogging, I almost gave up because I did not want to face the uncomfortable reality that I needed to re-assess my goals and act to change my direction. Thinking back on it, my goals for this blog have been a continuous metamorphosis and each iteration has been uncomfortable and scary.

But in order to get harder-better-faster-stronger, we need to face our fears head-on everyday. Become comfortable with the discomfort. Enjoy the pain. It’s ok to fail.

Strangely enough, failure is the key to success. Reinvention is all about failing and adapting. This is one of my favourite quotes of all time:

I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.

If you have been wavering lately on big goals you have set for yourself, I hope this can give you a kick in the ass to go accomplish whatever it is you want to accomplish. I hope you can find your confidence and swagger and unleash all of your creativity and genius you have bubbling inside of you.

Like what you’re reading? Than maybe it’s time you get bursts of inspiration like this sent directly to your inbox automagically. No spam. No ham. No nonsense. It’s super easy to unsubscribe if it ain’t for you!


33 thoughts on “From the Brink of Failure

  1. My own blog’s journey has been similarly hit-or-miss. The good months and the bad months each have their different reasons of course. The only thing I’ve come to understand for certain is that it’s not a focus on content that makes the difference…

    1. Interesting – would you care to expand on the idea that it’s not a focus on content that makes the difference? In your experience, what has been the difference? I’m super curious!

      1. Oh hi, I’m back!

        To start, I’ll say that I always focus on content because I enjoy writing, and would enjoy it whether my audience was one reader or one-bazillion. This is reflected in my nearly 300 posts in only 17 months of blogging.

        That said, the months I’ve done better have come when I paired that writing with promotion. I’m pretty convinced that a focus on promotion would net me more views. Now, if you’re wondering how MANY more and exactly what KIND of promotion would be best, I don’t know.

        And, of course, there’s a bit of randomness thrown in there as well. My most popular post ever was this tongue-in-cheek snarkfest, which I wrote on a bus ride:

        It’s titled, “Ladies, are you making these five costly mistakes in the bedroom?”

        1. Interesting thoughts Mario. *If* one is interested in getting their content out there, unfortunately, I think hustling promotion is just something you have to do.

          I know I much prefer just writing much more than the promotion side of blogging. But it must be done to get your writing out there.

  2. You can’t appreciate the up’s without the down’s. If life is in cruise control then what do you ever have to work for in life. It’s not enjoyable going through challenges but the reward at the end is great. Totally know what you mean with workouts and weights vs. running. I hate running, couldn’t even comprehend how people don’t lose their minds with boredom doing anything over a 5k. Then I started running consistently and doing 7-10 miles was no big deal. Just like everything in life, you have to build yourself up to do hard things. Great post!

    1. I think a lot of people are scared of both ups and downs and keep themselves content with stability through mediocrity. They know deep down that this actually isn’t making them happy but fool themselves to think that it is good for them.

      Running was such a pain in the ass to get into! It took over a year of consistent training to become comfortable and excited about running. Haha, like you, I can do +5K no problem now. Of course, it took a lot of hard work and discomfort to move to that place.

      I really think all the “discomfort” I put myself through (be it exercising, saving money, eating healthy, learning, etc) is to remind myself never to stay put and never to get content. To always be hungry is the goal 🙂

  3. Very cool post. I’m just starting out with my own PF blog and it has been interesting so far. I’m trying to write articles that I think are important to me and just not articles that you see elsewhere. Hopefully that will make my site stands out. I’m also trying to reach out to more bloggers out there.

    It’s all about getting out of your comfort zone in order to grow. 🙂

    1. I think one of the most important things I’ve learned thus far is to constantly experiment and learn from mistakes. By making mistakes – which can be uncomfortable and uneasy – you learn what worked and what didn’t work and improve as you go forward. It’s not easy but you have to continuously push yourself to try new things and incorporate what works and discard what doesn’t work.

      Like Jordan says in that clip, you have to fail and fail and fail to succeed 🙂

  4. Great post Steve! One thing about bloggers is that they are friendly people and are always willing to help. Part of it is because they know how difficult the initial portion of the journey is. I’ve always been thankful for all the advice I’ve been given since I started, and will continue to turn to these wonderful people in times of need.

    1. The blogging community is most definitely amazing and on the whole full of really amazing and helpful people – you’ve stumbled into a great community to be a part of 😀

  5. Good stuff! I usually pretend I’m just blogging to myself. And if someone reads it then that’s fine. It’s always nice to receive a comment or two for your post. It’s nice to see that you found your spark for blogging again. It can be scary to put yourself out there for others to judge, Anyways, keep at it. Always enjoy what you have to write. Cheers!

    1. Thanks Henry – glad you enjoy the writing!

      I think you are often far too modest about your successes and the writing on your blog because I know you have excellent material over there! You keep at it too because I’m consistently excited to read your material 🙂

  6. Great comeback, Steve! You’ve really jazzed things up and have started back full force. I have to laugh because I remember dropping in on Silver Maple Leaf before but you weren’t very active and the impression I got then is totally different from now.

    I loved your investor approach post, and I’m just sorry I didn’t get my act in gear in time. Of course, I would have to admit that my investing approach is currently “What my broker says” and somehow in the PF community that sounds totally uncool.

    1. Maybe it’s so uncool that it IS cool?? Haha seriously though, I think it’s all about what one is comfortable with. I’ve had many people tell me they couldn’t imagine having so much money on the fixed income side. All I could do was shrug and say “whatever works for you I guess?” I’m sure you could tell from the investor series that even in that small sample of 36, people are at all different levels and abilities.

      HAHA and The Silver Maple Leaf….. I honestly think you might be one of the only ones who remembers that 😛 most people seem to think it has been Kapitalust the whole time. As you could see from those monthly stats, I started getting VERY inactive in the new year.

      Curious, when did you first come across TSML and does that correlate to your impressions with that monthly stat picture I have above???

    1. There would definitely be lots of traffic for your niche in UGifter during the holiday seasons for sure and that’s kind of funny the correlation with those stats above 😛

      But I definitely think I could have kept building and building the traffic after December 2013 up if I hadn’t gotten cold feet and started to ignore working hard on the blog!

  7. Steve,

    Great post. I’m glad you conquered your fear of failure! 🙂

    Fear of success isn’t something I’ve personally ever tangled with. However, I did take an extended hiatus from blogging in the summer of 2012. I pretty much gave up on it for a time there. My reasons were really just due to being burned out. I was working 50+ hours per week and my time management needed some tweaking. I also felt like I wasn’t producing the best content I possibly could, and vowed that if I ever came back it would be everything I could give. I kicked around some ideas for a couple of months and the reboot was far better than the original product because I decided to move past being burned out for the greater good of producing something I could be proud of. Plus, I just plain missed it. I missed the interaction with others where I felt like I was making a real difference, missed keeping myself on track, and missed writing.

    Glad you came back from the brink, bud.

    Best regards!

    1. I never would have thunk someone like you would ever have gone through a funk like that! Dividend Mantra is so big and it’s hard to imagine that you too could experience blogger burnout and take a hiatus.

      It’s cool to know that you pushed through that slump and really made DM work for you cause it is a wicked blog with great content! 🙂

      And I think fear of success is a bit harder to identify than fear of failure, but I’ve heard many people talk about freaking out and almost quitting amazing projects because they got scared of the success they might achieve.

  8. As a new blogger, I’m still learning the ways, but loving it so far. I’m an avid reader of fellow PF bloggers and love the interaction. I’ve been stricting posting my investment activity but will definitely branch out a little for more interaction. Overall, our little community is very interactive and supportive. I love it!

    1. Another awesome blog to check out – thanks for dropping by SAD (just realized the acronyms spell sad, I’ll stick with it though!).

      You will probably hit this rough patch of “burn out” that most (dare I say all?) bloggers eventually will run into. For me, having clarity on why I was blogging and where I wanted it to go helped me tremendously with gaining back confidence and motivation to solider on.

      Again, welcome to the PF community 🙂

  9. I love this post about being intimidated by both success and dealing with the possibility of failure. I’ve been thinking about that a lot myself as I’ve taken some risks with my career this year.

    I came over from Mr. 1500’s blog. I’ll definitely subscribe to see what else you have to say. 🙂

    1. Oooooh now you have me curious: what kind of risks have you taken?

      I’m actually in the midst of contemplating a switch over at my current day job which is FULL of risk!

      1. I’ve switch from a career of technical sales to building up a freelance career in writing and marketing. I also traveled for a month this year. The journey isn’t over yet, but at least I’m building a career in the right direction.

        I have two posts planned at the blog — one with a timeline of change (this Tuesday) and one with three lessons I’ve learned about failure along the way.

  10. Great motivational piece! In the 3 years that I’ve been at it, I’ve had some pretty major high points and droughts when it comes to writing. The important thing always is to focus on why you do what you do. If you love it you will always find meaning and make your blog worth reading.

    1. I’m hoping there aren’t any more extreme fluctuations in motivation after going through that serious one early on in my blogging career 😛

      Thanks for dropping by MMD!

  11. Very cool journey Steve! I’ve never been to WDS, despite it being close by to SF, b/c I can’t get over the ticket price hump! lol. How did you do it?

    I have felt EXACTLY how you have felt before in terms of “king of the world” feeling, and then a slump. But I soldiered on b/c I like to write, and I like to connect with folks and family.

    I’m happy to pitch in on investing questions too next time. I worked on Wall St. in Equities for 13 years from 1999-2012. It was quite a trip.



    1. Thanks for dropping by Sam, I feel honored that you grace us with your presence!

      We actually didn’t buy tickets to goto WDS this year as we balked at paying the ~$500 ticket price again. Instead, we conference-hacked and just went to all the cool meet-ups that were happening after the “official” conference. The first time we went, we spent so much time in the conference we felt too burned out to goto the after-parties and meet-ups in the evenings. So this year we did the reverse and didn’t attend the conference but attended all the after-parties and meetups happening outside of the conference. There were some cool PF meetups and one was a FinCon14 meetup. I would highly recommend conference hacking 🙂

      I’m glad I didn’t quit after that major slump, because I really felt like quitting. I read a bunch of your writings on FS and Yakezie on this exact topic and it gave me inspiration. I remember one of your posts (or was it several?) talking about how perseverance year in, year out was one of the major reasons for your online success.

      I would have LOVED to have gotten your insights on your investing style – I think you were on vacation in Hawaii, according to your email autoresponse. If I were in Hawaii, I would be fairly unplugged too!

      If only I lived in San Fran, I would probably really annoy you with questions on all things investing and your experience from Wall Street. I guess it’s a good thing I can only badger you online, from a physical distance 😛

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