Although marketing and branding was definitely a part of my professional game before coming to WebDevStudios, my primary skill (and passion) is writing. The starving artist mentality is alive and well, and something I strive to reject; the concept of “selling out” is wholly ridiculous and exists as a class barrier that romanticizes the suffering of the poor and stigmatizes working class artists. What better way is there than to make a living and fund your personal passions than applying your greatest strengths, however functionally useless they may seem on the surface, practically to your life?

As I’m such a staunch advocate of the writers and artists in my community utilizing their artistic strengths to their financial gain, I often find myself having the conversation about how to be capital-P Professional while also wielding their unique voice and attributes as a tool. This conversation isn’t just exclusive to the creative types; it’s a conversation I have had many times with prior marketing clients, too. 

There’s a common misconception that professionalism requires being a whole different person than most of us actually are: flawed, funny, a little awkward, opinionated, shy. There’s an idea that professionalism is one part stuffy and one part hyper-obnoxious salesmanship; there’s an idea that selling your work, marketing yourself, and operating competently in a professional setting requires being more of an automaton than a human.

There are some corporate offices where this is true (trust me, as a former administrative assistant of a certain very popular hotel chain whose name may or may not rhyme with Spilton, I can promise you that), and of course there are folks who thrive in that environment. Arguably, though, that’s a minority, and most of us find greater satisfaction in spaces where we can can feel like we’re being authentic while also operating within the confines of professionalism. There is value in revealing our personal faces in the professional realm; telling your story is crucial to connection.

When I first started with WDS, Dre was headed to PressNomics for his presentation “An Interview with Dre,” which was hosted by Joshua Strebel (CEO of This interview delved into Dre’s history: how he got involved in tech and WordPress, how Sucuri came about, why he walked away from Sucuri and eventually joined us here at WebDevStudios.

More recently, Lisa delivered a similarly personal presentation at the most recent Prestige Conference, where she discussed how she switched careers entirely. Lisa went from being a Registered Nurse to a full-fledged WordPress entrepreneur–and WordPress was barely a year old at the time.

If you have met Dre or Lisa, you know that they are both extremely analytical, pragmatic people with a bevy of technical knowledge, and the presentations they give largely reflect that. They tend to focus on the practical and technical know-how because it’s clearly a major contributing factor to their continued success. These presentations, though, were different from what they had done before: Both explore the trajectory of their professional lives as told through the personal lens. Since this was so different for the both of them, I wanted to get their perspective on this balance between the personal and professional and share it with you.

Here’s what they had to say: 

What was different about these presentations versus other presentations you’ve done?

LISA: As an author of tech books, I am most often asked to give presentations that are more tech driven and in the area of giving users of the WordPress platform information on ‘how to’ accomplish things with the software. These topics are generally non-personal. The presentation I gave at Prestige was a very personal one because I shared my story of my journey as a business owner and entrepreneur and it has a much more personal focus, rather than a technological one.

How did you feel about sharing those personal details?

DRE: Chatting about my history and my career timeline was interesting. It wasn’t a conventional way to get to where I am today and that made for some anxiety; since my history in general wasn’t typical, those differences can create a feeling of not doing it the “normal” or “right” way.

It was challenging for me to talk about these things because I didn’t go to college or business school; I didn’t go into the corporate world. In the tech world, we see all these people with math degrees and the like being really successful, so in comparison, talking about those things was challenging for me because I didn’t go through what I perceive as the “traditional” pathway. One of the things I’ve learned through talking about this is that there really is no traditional path to success, and that success is defined differently for everyone.

What was the reaction?

LISA: I think it was well received. My story is an unusual one, at least in this community, so I think there was a fair amount of curiosity about how and why I accomplished the career change that I did. It never hurts to throw in a couple of funny nursing stories from the ER! I did get many comments after the talk, both immediately after from audience members, and then later via Twitter and email about how sharing my story really helps people who may be in the same position today as I was then (single mother, single income) understand that it’s not impossible to make such a drastic career change and realize the planning and challenges that come along with it.

Do you feel like, going forward, this has encouraged you to use more of your personal story in the future?

DRE: It certainly has. I gave a keynote at WordCamp Salt Lake City recently where I tied in a lot of those stories and personal career points to show that if we’re focused and work hard, we can all be successful.

In what ways did you benefit from these personal things in a professional setting?

LISA: Technology is cold, unfeeling and hard; sometimes understanding the people behind the screens and keyboards has value to us as human beings. Success can look so easy from the outside looking in, and those who are just starting out their careers can sometimes get frustrated or discouraged because of how seemingly easy it looks sometimes. Sharing personal stories, like Dre and I have, helps people understand that it’s not always easy, that there is a person behind all of it who has struggled, faced challenges and did not always have an easy time of it, no matter how it looks! That can break down a lot of barriers for people who are in the same boat.

What kind of advice would you give to someone who is worried about oversharing? How do you strike a balance between sharing your personal story without going too far?

DRE: Transparency is powerful! I think it’s important to not overstep but it’s OK to share successes and failures. We learn from both! When you share, it’s important to consider your audience–ask yourself, “Is this useful to this person?” Maybe that particular instance in your story worked for you, but won’t work for other people–and may in fact get them in trouble. Basically, you should look at your personal experience and make sure that there’s value in what you’re sharing. If you’re noting things that really don’t have any thing to do with the topic at hand, it’s just noise. Asking “What value am I providing to the audience?” is crucial.

Transparency is important; it has helped me get to where I am today.

LISA: Personal insights and stories behind successful people in any industry are always interesting.  Sometimes funny, usually always inspirational on some level, so don’t think that people out there aren’t at least marginally interested in the “who” of your story.  If there is one thing I’ve learned in my journey through the technology space is that no matter how much the machines take over our lives in the name of being more productive and efficient as human beings–human nature and human relations will always remain extremely important. I think it’s vital that we all remain connected at that level and not let the machines take over our entire being; so please don’t stop sharing personal stories and don’t stop being transparent and vulnerable. It’s how we learn and grow together.


My overall philosophy on business is not dissimilar from my philosophy on personal socializing: If you share yourself, if you come at people with a realness, they will do so in return. Sure, you won’t win everyone’s affections, but who wants to? Watering yourself down to be palatable to every single person makes you nice but forgettable, and even worse, most reasonably intelligent adults can tell when someone is pandering to them.

Risking that vulnerability is key to finding your people, and figuring out who your people are means that it’s much easier–and quicker–to build lengthy, positive relationships. Brad has constantly emphasized the importance of working with people you like; the only way you can find out if someone is going to like you and if they share your values is if you are behaving like the bonafide you. 

As much as some folks want to pretend otherwise, our personal and professional trajectories are inextricably connected. The things that make us who we are and the events that shape our lives directly inform our professional paths. While common sense is a necessity in the how, what, why, and who when it comes to sharing, shying away from everything personal is not the answer. There are benefits to be reaped from being genuine and sharing where you came from, foibles and all.



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