The F-Word: Jess Robson


I first met Jess Robson back in 2013 when I moved to Vancouver and started working for lululemon. We were only coworkers for a short few months however before she said sayonara and struck off on her own into the wild frontiers of entrepreneurialism. Ever since, Jess has been busy spinning her love of words, communication, and community into an enriching career all her own.

Her journey’s been anything but linear, but one thing’s constant—her willingness to candidly share raw, openly, and honestly about life’s “fuck yes” highs as well as those “oh shit” lows. Which of course makes her a perfect candidate to sit down with us to chat about the life of a freelancer, how her childhood dance career influenced her definitions of failure, and everything she’s learned along the way. Here’s my conversation with Jess.

The F Word: Conversations About Failure with Jess Robson



It was a whirlwind year for sure. It kind of shook up what I've been up to. Professionally, I took a full time contract with a client in The States and threw all of my best entrepreneurship-based practices out the window by focusing on one client as opposed to diversifying my income streams. I kind of learned the hard way to really keep that in perspective, because that contract kind of fell apart at the end of June. The company is one that I had been working with on a part-time, freelance contract basis since 2014. I was managing a lot of the content development for them. I started working with them full time in January of last year. And it was great up until about May, when I had a bit of a personal ‘Come to Jesus’ if you will and realized that I had really left behind a big part of my biggest self when I quit freelancing. A lot of what I was feeling with the work was actually just that I was working in a way that didn't work for me anymore. And then it took a couple months for that to shake itself out.



It definitely was! It happened on a beach in Tulum. I was traveling with my client and her business partner. We were about to host about six or seven of their clients in a high-level coaching mastermind. They were coming from all over the States and meeting up in Mexico and the day before all of her clients came, she had her photographer down from L.A. to do some branded photos for her website. And it was literally like in the middle of one of the photoshoots on the beach that it just hit me like a ton of bricks.

I was like ‘What am I doing?’

I'm pushing someone else's brand forward again. I'm selling myself as something that I never wanted to be again. I’d stepped into this concept of being a full-time team member for someone else's business and it just didn't sit right with me. Everything just kind of snapped into focus. It's interesting to feel such a visceral reaction to something that's so normal for so many people.



I often feel like in the moment, I get the full roller coaster belly. My stomach drops into my butt, basically. Like it just kind of like feels like I've taken a plunge down a roller coaster. And it's something that's lingers for a long time. It's a place of me feeling not confident, me knowing that I'm working in a way that actually doesn't work for me. Or maybe now I know that I'm overworking my physical body or my mental emotional body I'm not taking good care of myself.

If it's one of those slow burn failures, one that kind of mounts up over time. I get crazy heartburn. It's a stress response in my body that started when I was 15 when my parents split up and I was carrying around a lot of stress. So I get this crazy burning in my chest, from my ears to the tips of my shoulders and down to my right shoulder blade. All of my breath comes into the top quarter of my lungs. I'm not in my body; I'm not grounded at all.



Thankfully, I've grown very friendly with what failure feels like. And when those things are going on for me I don't necessarily catch them at the moment, but I can catch them quickly enough. Sometimes, it’s literally as simple as getting into an Epsom salt bath. From a physical perspective, it's really good for relaxing sore muscles so it's really nice to let my muscles, my physical body, move to relax a little bit. Also I kind of feel like it's like an onion—the outer layer is the physical body so that’s where I start because that's often the most simple thing in the moment I can do to take care of myself and get some kind of release. Then you can move inside to take care of the mental and then finally, the emotional body.

And so for the mental, I'll be quiet after taking the bath and start to ask myself ‘Okay, what's really going on; how am I really feeling right now?’ And so that's checking in with what the ‘self-talk’ sounds like and then often I can deduce like ‘Oh, maybe it's a money stress coming up, maybe it's a relationship stress with one of my clients, maybe my family is starting to bleed into how I'm just showing up.’

And then after that, that's when I get down to emotional level. And nine times out of ten if I really look at it, I probably haven't been meditating. I haven't been quiet in the morning. I’ve just been letting myself jumpstart the day immediately. I probably haven't been journaling and checking in with what I want and feel. It's really interesting that every time that it gets to a point where my physical body is freaking out, it's often because I haven't been doing this self care that actually keeps my entire self, spiritual/mental/emotional/physical health in check.



I grew up dancing competitively in a team environment, where we were required to pull off these really amazing group numbers. You needed to be so connected as individuals, but there was always a little bit of competition between each individual dancer within the studio for the solo parts. That was how we tried to assert our self-worth. I also played volleyball in high school and obviously wanted to win. The whole point would be to go to Provincials and get the trophies and get the medals.

But it was healthy. It definitely instilled that little idea of immediately thinking about what I could do next time. Like for the team stuff, how can we be better together or how can I be better as an individual contributor to change the result. So in that way, it was a pretty healthy way of learning how to grow through the failures.

But as I grew up, something shifted in my relationship with failure. All of a sudden, it wasn't necessarily about me and my underperforming because now it was about how I was letting people down around me. I turned into a bit of a people-pleaser. When I was about fifteen, I started working at Earls Restaurants in the service industry. Then eventually I transitioned to working at Lululemon. And I found that being in customer service, being customer-oriented, was an easy win for me. Unfortunately, that perspective of putting other people's needs first kind of bled out from work and into my whole life. Letting someone down and being considerate of someone else's needs became non-negotiable to the point of putting myself last, always. Failing someone else became my top concern. And only if everyone else was good could I allow myself to be okay.



From a personal perspective, there was always this insidious little worry of being left behind. And I had a experience in grade 7 where that was like a real issue. There was a group of girls that I was a part of. We’d rotate through who was kind of on the outside, who would be on the chopping block. Someone would be kind of excluded from group activities for any period of time and for whatever reason. And when the day landed on me, it was more intense than I think I’d expected. All of a sudden, I had this kind of sense that I had somehow let these people down and they had decided that I wasn't allowed to be a part of what was going on in their group anymore. It was really confusing, not knowing what I had done. I think that experience that kind of locked in this perspective of ‘If I keep the peace and if I'm really good, everything around me will be good.’

From a work perspective, customer satisfaction had become so tied to my tips. All of a sudden, there were things that were really tactile to judge myself by, which inspired me to perform and encouraged me to be great at my job. Being that way became a strong suit of mine and stuck around for a really long time...until it really stopped working for me in my late 20s.



In the three years I guess leading up to that decision to leave, it was an experiment of me trying my best to fit into different boxes and getting really excited about the prospect of what was possible. I’d draw up a new definition of myself over and over again, using the skills that people said I was really great at to help other people.

But two to three months into a new gig, there would be this tiny voice would tell me ‘You’re not going to be happy here; you're not really using all of you.’ And so at some point I realized that who I wanted to be in work and how I wanted to show up weren’t going to happen on someone else's time or within someone else's agenda.

In 2012, I had the opportunity to participate in leadership development programming through Lululemon. I got into a conversation around the difference between what I'm really good at and what makes me feel strong. I learned the difference between doing what people think I'm really great at vs. what I know to be true about me. I learned to really take ownership and responsibility around my goals and the things that I want to be up to. And I knew I had to move on.

If I looked at my life that week that I handed in my resignation letter, like oh man I was a solid 15 or 20 pounds heavier than I think ever been before.  Not that weight or body shape or size matters, but I’ve always been an athletic person and that was a warning sign I was ignoring. I wasn’t being conscious about what I was putting in my body and how much I was drinking. I was so checked out from the things that really like fueled me and was just totally numbing all the time. There was laundry all over my apartment and my kitchen was a hot mess. I had let so much of my life slip.

That picture was enough for me to recognize that something had to change. But when it comes to being prepared, I was zero prepared. I had no plan. I just was trusting what my gut was saying and going with what felt correct.



What got me through was the people around me. Your community can help support you when you choose a path that is completely unknown. Now, success for me is actually completely parallel with choice. So I feel successful on the days that I can look at what I've been up to and I feel like I've been in complete choice about my schedule. About the people that I've spent my time with. Whatever you want to consider balance; when it comes to how taking care of my physical body, mental body, how it stimulated my brain, what I'm putting into my environment, who I'm spending my time with - all those different things. And at the end of a day, if I can look back at it and I feel like I've completely owned my sense of balance all day long, then for me that's success. It’s completely regardless of my bank account balance, the nature of the clients on my roster, like any of that shit just doesn't really matter. How well I feel in my body—like, that's plenty for me.



I'm just kind of diving into the creative side of things to see what happens. I know now that that's somewhere that I want to hang out and spend time. I want to bring more dialogue to the concept of conscious communication. Because word choice matters.  It's not what you say but how you say it. What are we doing with our language and what are we creating with it? How are we actually creating impact for people?

I feel such a need to feel connected to the work I get to do every day. In any kind of job or even business ownership there's a bunch of shit that we don't love to do, but to find those moments where we’re completely blissed out and losing yourself in what you're up to? That's super special and something to appreciate and embrace in a big way.


Stay tuned next month when we’ll dig deep into some entrepreneurial realness with the lovely Elim Chu, freelance fashion stylist and consultant.