Tips: Five things I’d tell my 21 year old self

Yesterday, Daum and I hung out at HackHarvard and gave a presentation about how we started Setfive, the challenges we faced, and some of the lessons we would tell our younger selves. The feedback and resulting discussion was pretty interesting so it seemed like it makes sense to share. Some of these things are probably mistakes you have to make for yourself and 90% of advice is crap.

Don’t get bullied

Looking back, a lot of the early “negotiations” I did with clients was really them pushing me around and me accepting whatever terms they ultimately demanded. People were using veiled threats of yanking the deal, asserting that “I didn’t know how business was done”, and being overly demanding with changes and calls to manipulate the direction of the deal. In addition to professionally, I also remember several instances of real estate brokers and landlords trying to strongarm me personally. Anyway, so the takeaway has been in life or work there’s a difference between negotiating and bullying.

Don’t be afraid to say “I don’t know”

During highschool and college, I’d always been conditioned that when someone asks a question, especially an “adult”, I should obviously know the answer. Professor singles you out to answer a question? Better know the answer. Unfortunately, this feeling stuck with me into the “real world” and I had a tough time admitting that I didn’t know the answer to a question on the spot. This usually resulted in overpromising, having to backpedal later, or being stuck bullshitting through some half baked explanation. After being around the block, it became clear that saying “I don’t know, let me get back to you” was acceptable and the better move. Turns out, in the real world everyone isn’t a walking manpage.

“Big” $ numbers are just numbers

Coming out of college, the largest check I had written was for $5000 and the largest check I’d probably cashed was for around the same. Because of this, I had a hard time taking myself seriously while asking for “big” dollar numbers. After a while, I started to realize everyone has a different concept of what a “big” number is. $5,000 might be a mountain of cash to me but to someone else its just their monthly subscription. Once I understood this, it became much easier to walk into a meeting and confidently talk about money.

If they look clueless, they probably are

Throughout highschool and college, I hadn’t experienced many instances where someone was trying to seriously cover up the fact that they were clueless. Over in the real world though, this seemed to start happening frequently. Initially, I had a hard time wrapping my head around the fact that the “Senior Developer” explaining his “master/master” setup was just entirely wrong. The issue with having these blinders was that it made it difficult to effectively communicate with stakeholders when there was someone bollixed in between. Once I realized that cluelessness was really cluelessness, it became much easier to marginalize the people that were lost and get shit done.

Everyone is not like you

Something that took awhile to realize was that not everyone is like me. I had a hard time figuring out why everyone didn’t “get” how to use certain websites or why everyone didn’t immediately jump on new tech products. Turns out, everyone isn’t a heavy drinking software engineer that reads Hacker News. After realizing that, it became easier to emphasize with different types of users and also better connect with stakeholders.

Anyway, these are my notes to send back to 2009. Would love any thoughts or feedback in the comments.