Meet Willie Jackson. Willie is an entrepreneur using his talents in all things technology, currently serving as the Director of Web Optimization at W3 EDGE. I was introduced to him when I watched the documentary I’m Fine, Thanks and thankfully he agreed to sit down with me and share how he overcame his fear to leave a job that no longer fit and do work that allowed him to be more of himself.
V: How would you describe the goal or the dream that you had but were afraid to go for?
W: The goal for me was working on interesting projects that mattered, working with people who I enjoyed being involved with and living life on my own terms, meaning that I didn’t have to show up during any pre-set hours, execute any particular tasks for anyone else’s impression of me doing a good job.
V: So, what about doing that made you afraid?
W: I come from a background with some intense professional development and mentoring so the goal was always to be this high powered board room executive. So it was a little tough as I got closer to those goals and really got in the corporate world that the life just wasn’t interesting to me. And when I looked around and saw people who were successful in that world and I saw what it took, what sacrifices they made in terms of their time and their life and failed marriages and things like that because of the dedication to their career, I just wasn’t willing to give that. It was tough when I had to take a look at my ambition and realize that the path forward that I thought was for me actually wasn’t gonna work out. So I really didn’t have a blueprint because you know, when you’re out here working on projects that you care about and you really take a look at the way that the world works, this is a project based society. The currency of the new world is not degrees and distinctions, it’s your reputation, it’s how much you care, it’s who you know, not in a “I’m cool” club way, but like who are you taking care of? Who can vouch for you? Who knows what your character’s about? Who’s gonna speak good about you behind closed doors when it really matters? So it was just a little tough because I didn’t know what that world looked like. There’s no class to take in this, you just kind of have to do it and trust that it will work out.
V: So how did that fear manifest for you? Was it thoughts you were thinking?
W: It was actually anxiety attacks. I’ll never forget it. I wrote a little bit about it on my blog in a post series. It reached the point where I was trying to straddle my corporate life and my freelance life that after a particularly bad day after some bad scheduling decisions I made, I had an anxiety attack on a Friday and it really shook me up. And I had another one that Sunday when I was packing to fly out on Monday again and that’s when I called my manager and my mentor and my parents and I was like “I can’t do this anymore.” So that really was the beginning of the end for me.
V: Panic attacks suck, for lack of a better saying.
W: It was the first time I had ever experienced anything like that. It was terrifying.
V: So, what did you do to help you move forward?
W: I’m not wired in a way that benefits a lot from planning. I’m really a fly by the seat of your pants kind of person so I just had to correct course and for me that was quitting my job and trusting that it would work out. I had a little money saved up, but more than anything I had assurance at that point that regardless of what it took I was gonna figure out how to make it work. So I quit, I had to leave my job. The full story is that following the anxiety attack my manager had me agree to come in because the flight was already booked. I agreed. But that following weekend, I was scheduled to attend something called “LiftOff Retreat” with Pam Slim and Charlie Gilkey in Mesa, Arizona. And it couldn’t have come at a better time, because I was just shattered. My confidence was gone. Things had come to a head. And when I went to the retreat, I was around people like me, crazy people who didn’t fit in anywhere, people in search of different things. But ultimately the purpose of the retreat was to level up your creative business and it gave me, just by virtue of being there and being around that creative energy, that’s really the confidence that I needed and the assurance that I needed to say, “alright I’m gonna do this.” So I decided on the flight home that I was going to quit. What turned into a plan to take two weeks off tentatively, turned into never returning to that job again.
V: So how did you deal with the uncertainty? I mean, you knew you had to do it, but sometimes the uncertainty can keep people from even trying.
W: I think I thrive in uncertainty. What certain people view as uncertainty, I view as opportunity. And when you really view it and you free yourself from the mindset that you need structure in your life, from a job perspective, that you need that structure to provide your income, it’s pretty straightforward and at that point I had been freelancing on the side for a while so for me it was more so a realization that I had more time to do the kind of projects that were making me money on the side instead of doing the same old thing which was living a double life and it was pretty challenging. I mean, everybody has to do that when you transition from full time employment to self employment. It was a little tough because I didn’t exactly go on my timeline. My body kind of decided for me that it was time to go so I attacked it head on.
V: So, how did you feel after you quit and you started doing your own stuff?
W: Number one it was a huge burden lifted. There are a lot of things that go along with the 9-5 routine that are just a really poor fit for how I’m wired. And it was also a really big challenge because I’d developed a lot of really bad habits in working in corporate America. I think the most egregious was the fact that I would sit in front of my computer even when I wasn’t being productive and when you work for yourself that is a very bad thing because if you don’t work, you don’t get paid. So I have to be very mindful of the fact that when I’m working, I’m working.
V: What would you say you learned about yourself through taking that step?
W: Well, a lot of these things I had learned already because I had already started along the self employment path, freelancing, before I officially quit. But what it allowed me to do is actually leverage more of my skills and things I already knew about myself. Number one I enjoy taking care of people. I’m really a people person. I used to call myself an introvert, but I’m a very bad introvert ‘cause I really love people. I do enjoy my quiet time and my personal space, but when I meet somebody who I share a connection with I always look for a connection with people and freelancing and delivering services around my technology experience, allowed me to solve problems in a way that people really appreciated. One of the reasons that I was good at my job was not because I was so talented technically, but because I shielded my clients from a lot things that terrified them, like the acronyms that govern my life like PHP, FTP, HTML. People paid me not to have to worry about the things that terrified them. And because I understood my role in that ecosystem, I was able to really make a name for myself down in the Atlanta area without needing to advertise or really market or anything. I was very fortunate because when you take care of people, they’ll refer other people and I had a line of people waiting to work with me. Working in a more freelance capacity allowed me to just be more of who I am, if that makes sense.
V: Yeah, that makes perfect sense. So do you still experience fear now?
W: I do. I’m at a point in my career where I can see the next level in the distance and it’s on the other side of the mountain. And what’s required of me, as an executive in training, is not only to be able to do the work of two or three people but I need to make it look effortless and I need to do everything else. So it’s really challenging because it’s not that the work is so hard or complicated, I can do the work. It’s that you have to do it every day, you have to do it quickly and you have to think really critically about the problems that are coming down the pipeline. So the fear manifests itself really indirectly, like I’ll want to sleep in, and I’ll want to ignore urgent emails and just things like that. Steve Pressfield is one of my favorite writers and he talks about this concept of resistance which in plain English is the invisible force that keeps people from doing the work of their lives. And he talks about how there are two lives in all us, the life we live and the unlived life within us. And that mental framework was so powerful for me because when you’re cognizant of it, you can see how it manifests itself in your life through things like procrastination and avoidance of important things and really letting important parts of your life just really go poorly, to use polite language. Things like not following up with people or not taking care of things in your personal life, there are all these ways that the resistance is manifested in your life and it’s not so much that I live in fear, I’m not a fearful person actively, but the fear of getting to the other side of that very much manifests itself in ways that I have to be very mindful of. It’s like the Marianne Williamson quote, you know, we’re not afraid of the bad, we’re afraid of the greatness.
V: So what advice would you give to someone who was thinking of doing something but they were stopping themselves because they were afraid?
W: It’s a tough question to answer because fear is good. Fear is a compass when you leverage it right and you’re really in tune with it, it’s one of the things that I learned from Seth Godin. Seth used his fear as a compass, when he’s afraid of doing something, he moves in that direction. He’s at the point in his life and his career where he knows if it’s fearful then or if it causes him to feel fear then that’s probably the direction that he should be going. I’d have to ask some follow up questions, but I guess for the purposes of this interview I would say: understand why you’re fearful. Are you fearful for any practical and realistic reason like is this something that could cause you to suffer financial loss? Could it cause you to be ostracized by the people you love and care about? Are your feelings of fear rooted in feelings of self worth and confidence or are they real practical fears? ‘Cause I don’t think that there’s anything wrong with fear, but the type of fear matters and what’s triggering the fear matters and how legitimate it is, these all matter. So I’m not at the point where I would say “Do it anyway!” Because I think there’s some very important implications around the decisions we make with our career. I’m not really in the advice giving business, I can only speak to the challenges that I’ve overcome and how I’m wired and I’m not like everybody else so I’m very careful when dispensing advice.
V: Do you have any final thoughts?
W: In the context of fear and overcoming it? There’s a few things. Number one I started writing more. Writing has been really transformative in my life. There was a period for a while, months in fact, where I was writing every day and it’s such a brilliant record of what you’re thinking and how you’re thinking. And I feel like for me writing gives me access to the subconscious. Because there are things that you’re always churning through, the day to day tasks, but there are a number of things that you don’t actively think about because you’re busy and for me I find that writing, particularly in the context of journaling, that gives you access to what you’re really thinking. So when you combine journaling with writing in public, like showing up every day and actually putting yourself out there, risking shame and judgment by sharing your thoughts with the world combined with proper rest and giving your subconscious mind the time to churn through the things that you’re dealing with, I find it to be a really powerful combination. And I find that my writing has improved over the years which means that my thinking has improved over the years. David Heinemeier Hansson who is a partner at 37signals and the creator of the Ruby on Rails web application framework talks about if he’s considering two different applicants for a job and one of them is the better writer, he’s going to hire the better writer because a better writer is a better thinker. So one of the gifts that I’ve given myself and I’ve experienced along this journey is the gift of becoming a better writer and a better thinker through habits like journaling. Another really critical lesson that I’ve learned is that the path that you’re going on in reaching your goals is just as much about the journey inward as it is about the journey outward. Mastery of self, that’s not something you do after reading a couple of books and going to a Martha Beck retreat. It’s a lifelong, not only learning about yourself, but making adjustments and becoming the kind of person that you want to be. And a lot of my friends are in the health and wellness and coaching space and I learn so much from the philosophies that govern their life. It’s almost like that becomes your number one job, what you do for a living actually comprises only a small subset of your existence because it’s like the culmination of everything that you’re learning and putting together. Most people are on autopilot and when you live consciously and you’re going down this path, it just changes what you do so instead of it being work, your work is art. I do some of the things that I do, it’s almost like meditation because of the focus it requires. I’ve done a lot of reflection on how work can be meditation and how focus enhances all of the things that we do, specifically like it’s easier, particularly in my position because I deal with a lot of inbound email, it’s easy to just jump from message to message and try to keep people happy with responses and not actually get anything done. But when I find my real breakthroughs and the real progress I make on tough projects is when I block out the world and I really focus and I lock in on a task. That’s when I can apply the things that I know, the things that I’m thinking and my hunches and I come through with solutions that really move the needle on my work. So I think there’s a lot of overlap between things like art and meditation and focus and the craft of your vocation that you don’t really realize when you’re on autopilot.
So what did you think? Lots of great stuff, right? My favorite part was when Willie spoke about the other ways that resistance (and I think fear) can manifest itself. So often we consider things like procrastination as just a bad habit or worse, “just the way I am,” but if we look closer, it’s likely that it is a symptom of a fear that we’re not addressing. And if we ask the questions that Willie suggests, we can get to the bottom of why we’re actually afraid and then move forward.
I also second his recommendation of writing. I’m probably biased because I’ve been journaling almost daily since I was in my preteens, but writing (even if you never share it with anyone else) can help you really get to know who you are and it can be extremely cathartic if you allow yourself to be open and honest on the page.
If you want to learn more about Willie, visit his website here and also I recommend reading his posts on his site to learn even more.
If you liked this interview, you might also like:
Interview with Tom Ewer – “Fear is not there to be avoided”
Interview with Duane de Four – Conquering a fear gives you momentum