Why I’m a shitty boss to myself, and what I’m going to do about it.

A photo by Matthew Wiebe. unsplash.com/photos/2Ts5HnA67k8I had a fairly startling realization last week, and no matter how hard I try, I can’t un-realize it. I’m a shitty boss to myself.

As the newly minted owner / founder / doer of all of the things of a small business, for the first time in my life, I don’t report to anyone other than me. No weekly check-in meetings, no annual reviews. No one to call when I’m going to be in late, no one who asks me about my progress on projects. Also, no health benefits, painfully long staff meetings, or regular paychecks. It’s a mixed bag.

At first, I was thrilled by all of this freedom. FINALLY, I could escape the 9-5, which was a schedule that never worked particularly well for me. Soon, I became overwhelmed by the immensity of this freedom, because, as we know, with great power comes great responsibility. What kind of schedule actually does work for me? How do I structure my days? What does community look like when you don’t have coworkers? These are questions I’m still wrestling with, and it’s not easy. But one of the hardest parts, which I completely did not see coming, is not having a boss.

My view of having a boss has done a 180 since I quit my full-time job. Okay, maybe a 170. I still think that sometimes, bosses can add unnecessary stress to their employees’ workloads. That’s the 10 degrees that I’m standing by. But the other 170: man, things have changed. I used to get frustrated by having to do things according to my boss’ timeline. But guess what? I ACTUALLY GOT A LOT DONE ON THAT TIMELINE. The external accountability, coupled with a power dynamic, was pretty damn effective at motivating me to get shit done. I won’t argue that it’s the best motivation, but there is no doubt in my mind that it made a significant difference in my productivity. Also, weekly check-ins? It’s kind of nice to know that someone else wants to make sure you’re doing okay. Sure, my friends and family ask me how I’m doing, but it’s not the same as an intentional, sit down discussion focused on my accomplishments, challenges, and the support I need to be successful in my role. I can’t believe I’m saying that I miss these things, but… I miss these things.

So let’s get down to brass tacks. Below is a list of the ways in which I’m a shitty boss, and the strategies I’m going to employ (no pun intended) to be less shitty:

  1. I haven’t given myself a set work schedule. I know I know I know. I need a set work schedule. I think most freelancers and solo business owners would agree. Do you know how easy it is to make excuses for sleeping in, showing up late, and otherwise not getting shit done on time? INCREDIBLY EASY. Because I know why I wasn’t able to do the thing I was supposed to do, I’m ridiculously lenient on myself. Excuses tend to be valid when they’re your own. Which is exactly why I need a set work schedule. Since I’m still working part-time, I’m setting aside specific days and times during which I’ll sit down to work (outside of my home, as I’ve learned that I get very little done there). Please ask me how this is going!

  2. I haven’t given myself any vacations. This may seem to conflict with #1, but hear me out. Since I haven’t taken any actual time off since starting my business six month ago, I haven’t had a break. Part of my realization last week was recognizing that I’m always thinking about my business. If I’m not working, I’m thinking about how I should be working. If I am working, I’m thinking about the work I should be doing that I’m not currently doing. I need a fucking break. Addressing this is tricky: I don’t have a lot of money and thus can’t afford an expensive (read: any) vacation. I think what I’m going to do is take a full three-day weekend off from all things work. It’ll be a staycation (free 99!), and intentionally work-free. I’ll also think about when I can do this again in the future, because one vacation does not a balanced human make.

  3. I talk really, really poorly to myself. It dawned on me that if I spoke to an employee the way I speak to myself, HR would show me the door in an instant. My internal monologue leaves very little space for acknowledging success, celebrating the little things, or anything that isn’t a damning (and convincing!) critique of all that I am. This is a drain on my energy, and it definitely doesn’t motivate me to work harder. New strategy: take note of when my inner critic is broadcasting KFUCKED radio and change the station. I’m going to bring back the practice of writing down what I’ve accomplished on a given workday so there’s a paper trail of success behind me, easy to reference when I feel like I haven’t made any progress.

  4. I make myself work alone. Again, if I put an employee in a corner and made them work by themselves day in and day out with little to no human contact, I would be fired faster than you can say “sadistic mofo”. This intensive extrovert wilts like a flower in the summer heat when she’s alone for too long. I need conversation and collaboration to keep me going and inspire new ideas for my work. Steps I’ve already taken: I’ve started co-working with a friend one day a week. Potential next steps: joining a freelancer meetup or incubator, and finding a small business coach to work with, for extra people time and external accountability.

The evidence is clear: I’ve been a shitty boss to myself. But, I still think there’s hope. Even if I don’t have anyone to hold an annual review on my behalf – or especially because of that – I’ll continue to keep tabs on my progress and adjust accordingly. My job is on the line.

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