Skip to Content

I should fail more.

Yesterday, I got rejected by the Recurse Center.

rejection

(feel free to open the image in a new tab, the text is a bit small)

I really wanted to get in because I believed if I were to do a sabbatical next year, being around other really motivated people would help push me get better.

Then I remembered that I explicitly predicated the desire to do a sabbatical on publishing twelve featured blog posts on our company blog. One blog post a month. The last one I published was back in May. I haven’t published one since then.

Then I realized that I haven’t published a lot of the side projects, or done a lot of the stuff that I told myself I would do in my New Year’s Resolutions. I’ve been in the workforce for two years, and what do I have to show for it? How can I convince people from my currently exposed work that I deserve further external investment?

And the answer is, I can’t. There’s a lot of software engineers for the number of slots being filled, and a lot of those angling for a position either have a solid track record of contributing to open source projects, making operating systems, filing RCE bugs, writing blog posts, or otherwise demonstrating their skills. I remember one friend in college saying:

“Undergrad is likely the hardest part of your career; slightly lower in stress would be grad school, and way down the totem pole is working at a company”.

I think I’m afraid of failure. And that’s why I’m coasting on my Duke pedigree, my knowledge of Python (picked up at my previous job and only marginally expanded here), and ended up getting burned on the first thing I pick up. I haven’t even gone on a date – ever – and that was the first priority I made for myself this year.


This isn’t a pity party. It’s not like anybody shows up.

Seriously though, I think I’ve had enough failures in my life where I’m not deathly afraid of doing things. I skydive. I ask people out. I can do these things. But I don’t make failing a regular occurrence. And I think that might be what’s missing.

I need to fail more often so that:

  • I can overcome my impostor syndrome: How do you identify your limits? When you start failing. I haven’t been pushing my limits, and that just makes me paranoid that I’m “falling behind everyone else because they’re all studying”. If I started failing more, I would have found out how limited my abilities been, and addressed them with discrete actionables.

  • I can shorten my grief cycle: It’s still painful when I fail and takes a week in order to go through (denial –> anger –> bargaining –> depression –> acceptance) of whatever I failed at. If I ever hope to push really hard in some direction (which is the only way to do great things), it has to not hurt while pushing.

  • Ensure that I can trust my mind: I remember when I suffered through depression, I could not trust my brain to make the right decision. That paralyzed my decision making and crippled my ability to generate results. If my brain tells me, “you’re doing great”, how can I believe it? The proof has to be in the pudding. I also have to make failure a regular part of my life so that if I start pushing myself in the future, I can differentiate between regular failure and “I am pushing myself too hard and I will start breaking down again” kind of failure.

I added to my productivity tracker the weekly habit “What have you tried to fail at this week?” in order to remind myself to fail more. Hopefully this will result in some accelerated personal growth in the final months of 2018.