Something has changed, permanently, in me. I’ve been trying to figure out how to express it, because the transformation has been so interesting, unexpected, and meaningful to me. If you are a first time founder, or planning to be, this might resonate. I’d love to know if you’ve had a similar experience and what that was like.

Jobs I Don’t Do Anymore

These aren’t job titles, but roles I’ve played in the past that I no longer care to play. During YC (Summer 2012) I made a clean break from a lot of these things in order to totally focus on building Referly, and after letting those activities go for a few months I discovered something cool: I don’t want them back in my life at the same level of importance as before.

Professional Extrovert

For 3 years I was paid to be many things at Twilio, and one of them was what Mark Suster calls a “Conference Ho”. I’m not cynical about it, it was necessary and I made sure I was damn good at it. I did that job so that the three Twilio founders could completely focus on building the company, but I don’t do that job anymore.

I don’t feel like being around people all the time, and never have. Friends who know me understand that there is a deep divide between my public face and my private life. People who don’t know me that well assume I am so transparent online that there couldn’t possibly be more below the surface. I was paid to be extroverted, and I loved it, but I don’t do that job anymore.

Professional Hobbyist

I love hackathons and always will, because they were the first place where I really felt the warm embrace of the hacker community. I came to developers I respected, hat in hand, and asked for help and advice and a safe place to ask stupid questions and I am so grateful. I didn’t have to worry about my code being elegant, and I only built little prototypes to demo the Twilio API for cool videos and live demos at conferences. Now I write code 50% or more of my time, and it has to work. So I don’t do that job (of being a professional hobbyist) anymore.

Startup Mentor

I sometimes thought I knew how to pick the startups that were winners, but as time passes and companies I referred to investors or invested in myself struggle, I realize I still have no idea. I could say that picking Twilio was my stroke of genius, but in truth it was a lot more of luck meeting preparation. I like mentoring founders, but more to help them with personal struggles than company struggles. Lately I’ve taken a big step back from mentoring and decided to double-down on people I already have relationships with. I don’t do that job anymore.

Marketing “Guru”

Twilio was the first place I ever had a marketing job. I’m not a marketing guru, and when Jeff hired me it was to do customer support and make blog posts and video. I told him we should put a reasonably senior job title on my business card so I could get meetings, so we did. I wasn’t really operating like a true Director-level person until probably the last year I was there. I was an avid student of marketing, and I wanted to earn that title and stop feeling like the business card was a lie. I achieved that, but I don’t do that job anymore.

I’m Taking Me with Me

When I say I don’t do these jobs anymore, it isn’t that I don’t take their lessons and skills with me. I carry them every day, to every conference, conversation, interview, coding session, morning walk, phone call, lunch with a founder, late night freak out. I loved those jobs, and when I did them I believe I did them well and gave them my all. But now I am learning to do new jobs, and I have new interests. I am passionate about making things – both with code and with prose. I’m either building Referly or using it to create content, and that’s all. I’m working on being a good CEO, good product person, and better developer.

So if you’ve pinged me about stuff related to any of the jobs I don’t do anymore, and haven’t heard back, I hope you understand why. I don’t do that anymore.

This blog post doesn’t really convey how strange it feels, to let go of things that were so important to me. Things I worked on and worried about and shaped my identity. But if I hold onto them and stay the same, and just get better at those things and lean on them then I know I won’t grow… so I’m putting them away for awhile. It kind of feels like breaking up, that’s the closest experience I can compare it to.

This video kind of sounds like what it feels like: