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First thing’s first: I pitched this article to Caylee. She did not ask me to, nor is she compensating me for it, and I took way too long mulling over and writing it! Like I said in my previous article for this site, “I often don’t know what I think until I write it.” I wanted to write this article because Caylee’s course Level Up, The Creative’s Guide for Getting it Done, has had a significant influence on how I go about achieving my own goals, and because I’m obsessed and fascinated with productivity, doing it and the idea of it. Think of this like a Level Up testimonial from an overly enthusiastic fan about the ongoing lessons they learned and the insights they gained.


I technically finished Level Up in 21 days, which is not suggested by the course! But, like I said above, obsessed with productivity here. A part of it is an unhealthy obsession with finding “the perfect system” to achieve my ever-growing list of goals, books to read, projects to start, projects to complete, etc. Somedays, I am more realistic about the unreality of this goal – most days, I am not because I am equal parts enthusiastic about and exhausted by the miracle of human consciousness. Combine these things together and you get a productivity geek who happens to also be a writer.

Also, Level Up is really pretty, and I like pretty things. In particular, I like things that are equal parts pretty and equal parts functional. Did I mention I am also a design geek?

So, basically I saw Level Up and salivated like any productivity-design geek creative type would. But, that’s not all there is to it, and I wouldn’t be “uncomfortably honest” (see bio) if I didn’t share that part of things. My therapist was on hiatus for the time. I felt stymied by my current work situation. I was in the process of losing a very important relationship and in complete denial about it. The act of writing paralyzed me. I was spending countless hours consuming information and tricking myself into doing things that appeared productive, but was really just stalling on my priorities. Oh, and I was, and still am frequently, plagued by self-doubt, a fear of failure, guilt, and all those big and little things that inhibit us from self-expression, creativity, and self-acceptance.

It’s not like Level Up solved all those issues, because nothing does. But, Level Up has helped in a multitude of little ways that have added up and continue adding up to bigger insights into myself and my own productivity habits. So, here a few big things I got out of working my way through Level Up.


We all have creative impulses. In Elizabeth Gilbert’s Big Magic (a suggested reading from Level Up), she points out that humans have been creating art since the beginning, even if it did not serve an evident purpose. Yet, creativity for the sake of creativity is often treated like an indulgence, not a necessity, so we feel guilty when we do it. (I blame Calvinism.)Aren’t there “more productive” things I should be doing like running this “important” errand, doing these chores, taking care of this person, and so on? Maybe I will feel less guilty if I can make some money off my creative habit? (Hint: Nope, you’ll just end up constantly overworking yourself because of it!) In some ways, I’ve had to trick myself by labeling creativity as necessary and always “productive,” even when it’s just for its own sake.


I love a new system to try! It’s like a new exciting challenge for me to master, and I love mastering things. I am competitive, I have a Master’s degree, I like gold stars! Personal coach, Toku, hits this desire on the nose:

The reason you want a perfect system is because, as a high performer, you are a master of systems. You’ve conquered educational institutions, corporate environments, and social circles. So, whenever you encounter a problem, you start looking for the perfect system to fix it.

See, “looking” is the key word there. Looking means I seek a perfect system rather than creating my own. One of my favorite things about Level Up is the space to experiment and try different things, which is also continued in the community afterwards. I have to tune into what I will actually do and use, not what my idealized self thinks I should be doing.


Your idealized self, admit it, she’s kind of a tool and probably passive-aggressive. (It can’t just be me!) Idealized self has to accept that my love of sitting on the couch on Friday nights watching Netflix and drinking wine is a huge motivator that I have to exploit to be productive during the week. My idealized self tries to convince me that I will earn free time that I can then use towards my other goals, that I will make productivity the reward for productivity. Yeah, no, lizard me wants Gilmore Girls and wine, and she has to be satiated, so that person somewhere between idealized self and lizard me can get shit done.

You deserve a break. End of story.


I am talking Mariana Trench deep. I don’t know if “overcoming” it is really a thing you do when it comes to the fear of failure. But, I do know continous practices that disrupt the fear are crucial – that usually means creating as a regular habit, that means writing or drawing anything, even when you feel the most unmotivated, so you can at least say you did it. That means carving out time for it, no matter what, so you can feel whole and human. For me in particular, that also means having spiritual habits that directly tie to my creativity because I need something outside of my head to kick around my own inner self-critic, or my passive-aggressive idealized self.

In sum, what you get out of Level Up will be your own. You will find lots of helpful hints, tips, shiny new things, and so on, as well as a healthy dose of a kick in the butt with a side of self-love. Experiment with these new things, adapt them to where you are right now. Talk to the community in Slack, say hi to me, message me directly if you want! But the sum of those parts is that you learn a thing or two about yourself and how you have to work with where you’re at to achieve your goals.


Jenna is a writer, editor, and creator. She is arguably over-educated and most certainly uncomfortably honest.

Say hello on Twitter (and tell her Caylee says hi!)