30: 6 months in
A few observations on the first 6 months of Office Hours
(Page 1 of my "Dream Office Hours Interviews” list. If you have a connect to anyone on this list, hook me up?)
Let me start by thanking some people.
Office Hours would not exist without four women who I am very grateful to exist in the same orbit with: My wife Maggie, Judnick Mayard, Hannah Wittman and Samantha Irby.
The four of them were beyond supportive when I mentioned that I’d like to start writing regularly again. They also called me out and kept me motivated — I once got a text from Hannah that I think simply said “DO IT” — and now there are 300+ of you subscribed and there’s a newsletter and a podcast and none of this existed at the start of the year and all of it makes me so happy. Every single one of you made the choice to subscribe to this thing and I appreciate that choice and will work my hardest to provide value as a thank you for believing in me in this early period.
After 6 months of Office Hours, I have a few observations from my experience building this thing that I’d like to share for anyone feeling creatively stuck or wants to start something new:
1- Be ok with feeling stupid.
Let’s say you want to learn how to make Youtube videos. Your first one is probably going to be brutal, right? You hate how your voice sounds, your final result doesn’t look like the videos you were inspired by. Imagine the feeling of focusing all your energy towards something that that you honestly suck at — and then doing it again and again and again. I believe the real key to success is getting past the pain of feeling stupid. Of putting something out that you don’t feel measures up to your taste level and then doing it over and over and over until it gets better. Ira Glass did a really good speech about this, btw.
If you work out, you already know how this mindset works. When you work out or go for a run at first, you expect to feel discomfort — if we don’t, we know that we aren’t working hard enough. When it comes to learning new skills, the same rule applies. If you’re not willing to experience the feeling of failing or feeling awkward or being nervous you’ll get judged, then you won’t improve. You’ve heard “no pain, no gain”, right? This is the same idea.
2 - Celebrate small wins.
Amid the clumsiness of beginning something, figuring out the fundamentals and making small improvements on that skill can feel amazing. Celebrate your progress, be it big or small.
3 - Embrace the uncertainty.
I don’t think we have a realistic understanding of how people actually learn new things. I don’t think it’s this steady, linear thing like a RPG. I feel like learning happens slowly (and painfully) at first, and then things pick up really quickly. I think it’s also why imposter syndrome is a thing: When something you struggle to do starts working all of a sudden, you mentally can still feel like you’re getting away with faking everyone out vs embracing that success isn’t a straight line. Focus on getting better every day.
4 - If not you, then who?
Nobody else is going to make your thing. Nobody else is going to care about it as much as you will. Nobody.
If not you, then who?
5 - Forgive yourself.
This one is the most important piece of advice I can give anyone: Forgive yourself! My assumption is that the source of all self-hatred or negative self-talk is a overblown sense of our own importance in the world— when we fail at something, we think everyone is watching us fail and freak out accordingly, or we feel like everything we do must be the best in order to compensate for the voice in our heads telling us what we’re making isn’t measuring up.
Remember: People can be really hard on themselves. For not being perfect. For not having a ton of cash or time to put towards a passion project. For me, I was hard on myself for not being mentioned when friends talked about their favorite podcast or newsletters. For not promoting enough. Hell, I was hard on myself when I messed up editing podcasts. I PROMISE I was super hard on myself for never seeing my name on this damn list:
Self-love to me isn’t how you celebrate your successes, it's how you mentally process your failures. Forgiving myself for making mistakes or failing from time to time helped me get rid of the need to do everything right or be perfect or even correct when trying new things. If anything, I’m more excited to dive into projects that used to scare me because I don’t have a fear of looking stupid at first anymore. Forgiving yourself is where true growth comes from.
NEXT WEEK: IRL OFFICE HOURS HANG
Thursday, July 19, 2019 at The Freeze (2815 W Armitage Ave) co-hosted by Chicago-based music writer/world-class human Leor Galil. Come eat ice cream and hang! Fun starts at 6:30pm.
TUNES:
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Office Hours is written by Ernest Wilkins. Follow him everywhere @ErnestWilkins