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Blog Confessional: Seven personal career mistakes to avoid and the lessons I learned from them

Red Fail

flickr photo By griffithchris

They say confession is good for the soul and it is Sunday so here we go. Starting tomorrow I’m venturing into another new project with high expectations for success but it also includes a lot of work. Along with having a new baby on the way due in January, to say I’m nervous, stressed and excited at the same time is an understatement. Plus with working with a bootstrapped startup, TriOut that’s has huge potential. Now I’m about to help launch an incubator/coworking office downtown Raleigh. I love what I’m doing, the community in NC and I believe both will work over time. This year at SXSW when Leo Laporte was live video streaming from the Mashable party, Robert Scoble stopped and asked me on camera when I was moving to Silicon Valley to become a millionaire. I told him never, I love NC and I believe we have the people, companies, etc for entrepreneurs like myself to become successful and on the East Costs in general… or something like that. But money does talk…. #justsayin

Regardless, I just finished listening to Tony Hsieh of Zappos audio book “Delivering Happiness” and it has positively inspired me to become not just motivated about upcoming projects but making me want to be a better person in life and “deliver happiness” with everything that I’m involved in. The book did make my have a few flashbacks on past mistakes, missed opportunities and failures of past ideas. But taking a note from Tony, don’t look at failures as just being a …”fail” but look at failures as one step closer to success. So here are a few “failures”, I mean steps to success I’ve made over the years that I hope you can learn from.

1. SXSW 2009: Telling Dave Morin and Gary Vaynerchuk no thank you.
It was my first SXSW and I was with a group of friends, Kipp Bodnar, Jason Keath (I think), Jason Flint, and George G. Smith Jr. and we were walking to some party when Dave Morin and Gary Vaynerchuk passed by. Dave said hello and asked if I wanted to join him and Gary for dinner. I looked at my friends and said no thanks to Dave but I would catch up with them later. My friends looked at me like I was crazy and we kept walking. At that point Dave was still working at Facebook and Gary was still crushing it as usual. Note, I haven’t seen Dave any more since then and we didn’t catch up later during SXSW. Dave has left Facebook to launch his own company and as for Gary… you can now listen to him on XM radio.

Lesson: If you have an opportunity to network with individuals who you may never see again or are in a good position to further develop your career or relationships… Do it! Besides Dave and Gary are two of the smartest guys in the startup social web space. #WayneFail

2. – 2001-2002
I’ve been a web/tech/geek/entrepreneur for years. Back around 2001 two business partners and I launched It was an online sports marking company. We were planing sporting events for charities, highlighting local athletes online via videos and blog articles. This was before ESPN and blogging was huge but right around the first dot-com bust. My partners freaked out and we shut the site down. Think about it, if we would have continued with the site we could have been millionaires by now… maybe.

Lesson: If you’re passionate about your startup or idea. Don’t stop, never give up… Jimmy V!

3. Not writing for – 2008
Before the “social media” bubble really started to bust and Mashable was a growing tech blog. One of their writers asked me if I was interested in writing for the site. At that time I was working for a local TV station, was getting off the ground and my primarily responsibilities was blogging, video and email. I asked my boss if he was ok with the station and said sure go for it. I wrote one article, it was called “Is Plurk the MySpace of Microblogging?”. I had too much going on, started to focus on more and the guest blogging opportunity slipped through my hands. I saw Pete Cashmore at SXSW 2009 and he told me to continue to submit post but by then everybody wanted to write for Mashable. Since then I’ve submitted maybe two post but they didn’t make the cut and I’ve kept what could have made it for Even though I think it was smart of me to post more content on my blog, writing for Mashable would have paid huge benefits and possible other opportunities in my career.

Lesson: Write your behind off! Especially if someone asked if you’re interested in guest writing for their site.

4. Not blogging for Vincent Nguyen – 2007
When the iPhone first launched every smart blogger was buying iPhone domain names, Vincent purchased a few and I purchased and the both of us were blogging about … you guest it, the iPhone. After seeing my blog he contacted me about writing for his site for a small fee. I was interested especially since his site was generating more income and had a lot more visitors than my site was receiving. I can’t remember how many post I wrote if any, but I do remember sending him an email saying due to time constraints I can’t continue. I think I was switching jobs or something. Regardless Vincent Nguyen has continue to be a successful blogger and entrepreneur.

Lesson: Balance your projects and life. Make time for projects. Especially ones and that can generate some extra income.

5. SXSW 2010 – What was her name again?
This situation hurts me every time I think about it. It was one morning during SXSW and I was headed to the bloggers lounge. I was with Kipp Bodnar and was very tired from everything. The LA trip right before SXSW, the road trip to SXSW, the sessions, the people, I was just tired. No, I don’t drink or smoke so that had nothing to do with it. But right before going to the bloggers lounge a rep from, I think Sony walked up and introduce herself to me. I said hello, shook hands and said nice to meet you. I then said I’m going to the bloggers lounge and take care. Kipp was like dude! Do you know who that is? I said no, he said her name and the company she works for and was like dang! I believe she and I had been sending tweets back and forth about meeting at SXSW to discuss some projects. Ouch!

Lesson: Make a note of people you plan to meet at conferences. Write down their names and look at the list through-out the day. Also take the time to ask how may I help you or just stop everything and have a real conversation with individuals who you meet at events. They will value the time and you can build a strong a relationships that may lead to future opportunities for the both of you.

6. My Gadget blog /Blog Network joins the dead pool
I launched a blog and blog network called the “W4Network” It stood for the “wayne on the world-wide web”. I had a gadget blog that was started around 2004 the same time as Gizmodo, Engadget and others. It received a decent amount of traffic and making some money via online ads. Because of the blog it help the local TV station hire me for their community content creator position. Due to all of the blogging responsibilities for the TV station I let it go. I started spending more time on Twitter and other social networks and soon after realising that was a mistake I launched in 2007 and have been blogging constantly ever since. You can also add a few video blog shows and podcast to dead pool the list too (

Lesson: If you have something working, stick with it. Maybe ask for guest bloggers to keep the site going but don’t let your blog die.

7. Not having the Social Media Business Forum Conference in 2010.
In 2009 OurHashtag held a very successful social media conference in Durham, NC. It was the first real social media conference in the Raleigh, Durham, Chapel Hill area. We had sponsors, guest speakers, great wi-fi and more. We planned it in three months. For 2010 we had big dreams/goals for the conference. We wanted to bring in speakers such as Evan Williams, Dennis Crowley, Pete Cashmore, Matt Cutts to put together with the awesome local talent we have here in NC for another Social Media Business Forum. Well, what happen was… I gave the agency world a try, Kipp moved to Boston, Jeff took Kipp’s old Job, Ryan continued to code, and it seems as if there was a social media event every other week in the beginning of 2010. I was about “social media” tired out and once we started planning the conference we looked at two different venues. One took a while to say no and by that time it was too late. Take all that in consideration with me focusing on TriOut and traveling, the conference will not take place this year but we are planning one for 2011.

Lesson: Plan ahead as much as you can, prioritize and work with people who can get things done around you. Also learn to delegate, something I’m bad at doing.

Whew, it’s posted, said and done. Now I can move on. Someone once told me in life there are “opportunities and situations, the outcome of both is up to you”. I may not have made the best decision with each opportunity or situation I’ve had over the years but I’ve learned from each one of them. Tomorrow starts another journey in my life and I’m as motivated as ever to be successful and provide good customer service to partners, clients and friends. Emails will get answered faster, phone calls will take place and events/meetups in NC will continue. TriOut will become success and the new incubator/coworking space will open doors soon.

In closing from Tony Hsieh, via Delivering Happiness “No matter what your past has been, you have a spotless future!, author unknown.

successful business woman on a laptop
Flickr photo by: Search Engine People Blog

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