Working for a Start-up: The Art of Switching Gears

Published  October 21st, 2010

When you build something that you pour a lot of sweat and tears into, it's very hard to let it go. You build something awesome, execute with high quality and you're asked to let the project go because it's not in the product's best interest at the time being. Even if the decision is right, it's a tough pill to swallow. Your natural inclination is to fight tooth and nail, but you need to let it go and switch gears as it's your job to do what's best for the product. So how is this done? Well, thanks to our CCO (Chief Creative Officer) Oliver Lubin, I'll be able to tell you exactly how it's done.

Oliver recently built an awesome prototype for thredUP. When you're logged into, there is a 'lid' in the top right that contains all the useful information a user would want to have access to when logged in (link to your account, sign-out link, etc.). He made a killer design to re-do the lid and added some sweet functionality for it. He passed around the design for feedback and I think we all thought two things: 1. it looked awesome. 2. it was information heavy/dense. At this point, no one expressed enough serious concern to squash the feature. So Oliver entered the implementation phase of the feature.

Quick tangent - for me, this is where I bond with the features I make - when I put all the nuts and bolts together behind the scenes. I think the reason for this is because after you mock-up the design for the look and feel of the prototype and you start putting the code in place, the feature has gained momentum and it's harder to pivot its direction. Every step you take forward with the project further cements the rigidity of the feature and your ability to detach your emotions of what you're building. Time spent working is energy used. Wasting energy is not something I enjoy, it's something I struggle with, but enough of me, back to the story.

Oliver finished his implementation and it worked exactly liked the mock-ups envisioned. When the feature's entry into the website was discussed, it was ultimately decided that his initial conception of the 'lid' needed to be scrapped. He took the news in stride and got right to work on the new 'lid'. I was in awe. 'That's it?', I thought. Not even an ounce of complaining? Nope. Smile on his face he went back to the drawing board. I had to know how he could do this, so I wrote the following email to him:

Oliver, I'm writing an entry to the dev team blog and would like to know if you have any advice on switching gears. Specifically, how did you accept the fate of the lid that you spent days (and nights) building?

His response was:

Sometimes your gut will tell you things you ignore. Luckily this time wasn't one of them. I'd say the key in these critical moments is listening to and trusting your gut. I had a feeling something wasn't right. Creative things often make sense better in the minds of their conceivers -- I know where every little nuance is and why it all just makes sense, to ME. But that kind of bias can get you in trouble. You have to watch people's reactions, see how many questions they ask, how much explaining you have to do of the things that you think are just obvious. Observe yourself and others no matter how much you like it. If you hear yourself saying "man, I really hope people get this." you're in trouble. At that moment where you have to switch gears you have to recognize what's really broken. Is it the idea or the execution? And don't be afraid to let it be the idea more often than not -- your ego will thank you later either way.

Oliver's humble approach to design is very refreshing. Integrating his philosophy into your everyday workflow helps keep peace of mind because in the ideal world, every feature would be agile enough to permit changing the direction at any moment, but we all know this is rarely the case. Even if it were possible, letting yourself let go of the time you sank in the project is hard - it's conceived as wasted time. If only someone would have said something earlier... Well we don't live in this ideal world and this situation presents itself to an engineer at one point in their career whether they like it or not. Don't look at the time or energy as wasted when the project is axed - it's a learning experience to value and build upon next time. I would be surprised if you didn't gain some new tools along the way as well. If you always put the company and product's best interest at the forefront of your decision making progress, I guarantee you will become a valuable asset to your team.