Anna Brozek Puts the Rest to the Test

It’s been almost a full six months since I became CEO here at Big Cartel.

That is a straight up bananas statement. Anytime I think about my time in this position (which is still hard to say when I meet someone new) it feels like it was just last week that Matt and Eric asked me to step into this role, so hitting a six-month milestone is really hard to wrap my brain around.

What’s even harder is that right at this six-month mark, I’m about to embark on a six-week sabbatical, totally unplugged and away from work. I did this once before, sort of, when I had my second daughter - I used Big Cartel’s generous family leave and unplugged from work for twelve full weeks, but any new parent can tell you that baby-leave is not truly “time off,” and I wasn’t a CEO back then.

My current sabbatical was in the calendar before I became CEO and, if I am being perfectly honest, in these months leading up to it, I planned on cheating. I planned on working some evenings or the occasional early morning. I planned on checking my email two or three times a week and chiming in where needed. I was basically planning a working vacation, which, if anyone else on my team was doing, I would have pushed back on, because that’s not the point of the benefit we’re providing. But it was me, and this role is still so new, and Big Cartel hasn’t ever been without a CEO for six weeks, and because of a dozen other tiny excuses I kept telling myself, I was convinced that this was an okay exception.

Thankfully Matt and Eric (our co-owners who are still very much actively advising me) called me out, told me to read Rest, and suggested I get a plan in place to take a real sabbatical. All of this is outlined in the sabbatical benefit in our employee handbook, I had just lost sight of why it applied to me, right now, no matter my role at Big Cartel.

So here I am, it’s still a few days before my sabbatical kicks off, and I’m only halfway through Rest (but it’s already been incredibly insightful) and I’ve got a plan put together so I can truly unplug from work during my time away from work.

Starting my sabbatical

To kickoff my plan, I took notes for about a week documenting what my daily tasks looked like: what emails I was answering, what conversations I was a part of, what calls I was on, what decisions I was making. Then I began delegating those tasks. A great side effect here is that I will come back to only the essential Anna-work as some of these tasks I can delegate permanently, I just shouldn’t even be doing them now because my team is already fully capable. It’s great!

Looking to the future

Phase two of my planning involved looking ahead. We’ve got some features launching around the time I’ll be gone (OMG!) and we’ll have some new folks joining our team (Ahh!). At this point I’m asking myself the same questions as phase one, but for the future and instead of the immediate past: what conversations would I expect to be a part of, what decisions would I be making, what tasks belong to me, etc. Then, surprise!, I mapped out where I could delegate those tasks. A lot of this step involved simply giving my leadership team account access to various apps to do tasks without me. Getting me out of the way of feature releases has been a goal over the last six months, so I think our team won’t have any trouble there.

Although I won’t lie, these will be the first major projects we complete since I became CEO (still hard to say) and I have mixed feelings about possibly being gone during their launch. BUT, the leadership team and I have worked hard to set clear goals and expectations, and our teams have been collaborating and producing incredible work thus far, I have no doubt it’s going to go just fine without me. Still, the butterflies are there.

Communicating clearly

Phase three of planning is about communicating all of this with my people. The work I’ve delegated out falls to our leadership team and our office admin (thanks, Stephanie!), but it’s important that they know who will be doing what, and that they have some written documentation to reference if need be. We do all of that in Basecamp, which is a great tool for collaborative work, and since we use it daily, my people know that is where they can find any breadcrumbs I’ve left behind.

Setting goals

I’m regretting working in phases now, but here we are at phase four, which is a much more fun phase: setting goals for my sabbatical. I intentionally planned my time away to fall on a pre-planned three-week family vacation to Sicily to visit my younger sister and her family. But the overall goal shouldn’t be to just vacation, I could do that anytime thanks to Big Cartel’s generous PTO, this time-off needs to be more meaningful and purposeful, and I’ve come up with two primary goals.

The first goal, thanks to the first half of Rest (I hope it doesn’t take a sharp left turn in the second half of the book), is to test out some new routines and find one or two that can be brought back into my working life. No spoilers, but the book digs into the benefits of routines and building them around when we know we are our most creative-selves while balancing periods of intense work and deliberate rest. Even prior to reading the book I’d been craving something like this, but I didn’t have the experience or science to get there on my own. Needless to say, I’m very excited to experiment with my work and rest routine.

My second goal is much more personal: I want to be a more playful mom. I have my own suspicions (and years of therapy) suggesting why I am not currently the playful mom I want to be, but I think I can get better at it, or at least be more present for my girls. It’s a theory of mine, that by building this intention into my new routines (thank you goal number one), that I’ll be able to build on this skill even when we’re all back to the normal life of work and home and school and chores.

Honestly, it’s super hard to even write about this here because, as a powerful-CEO-feminist-mom-woman, I think maybe the pressure is stronger to put my best Instagram-worthy-face forward and not show the hard shit, but any working mom can tell you this shit is hard. The struggle is real! Even with the best job at an amazing and generous company, sometimes (most of the time for me) it’s just hard to turn on playful-mom mode at the end of the work day. I want to get better at that, I think that six weeks totally unplugged from work will help.


This takes me to phase five. I’ve filtered emails from more well-known senders into specific folders I can easily check upon my return. And very soon I’ll be removing all of my work related apps from my phone completely. No email, no Slack, no Basecamp, no nothing. 😱

I’ll grab my passport and a couple of books (and a million bags because I’m traveling with two kids, duh!), and I’m outta here. Wish me luck! 🤞🏼

If you care to follow along or want to offer me hot tips for Rome or Sicily you can find me on Instagram where I’m @annaiscanceled. Ciao!

Anna Brozek

CEO of Big Cartel, previously Community, Customer Support, and Operations. Started from the bottom now I’m here. ✌️

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