Often, people ask me for career advice or how I got to where I am, or more tactically if they should advise companies, invest in companies, start a company or become an executive or whatever. My first instinct is to say, “Why would you ask me? You certainly don’t want to follow any of the steps I took!” To try to make my advice more actionable than that, I thought I’d document some of the key decisions I went through to make a signal out of my career noise.

My career choices have been somewhat unconventional from the outside. I graduated summa cum laude in undergrad to just take an internship at Apartments.com. I joined a 15 person startup to start a marketing team at 25. To say I was unprepared is an understatement. After building up a team and growing Grubhub over five and a half years into a public company, I took an IC role at Pinterest, instead of many executive offers. After three years there, where we tripled the user base and unlocked international, I then decided to… hang out at a venture capital firm. Then started an advising business. Now, I’m a Chief Product Officer at Eventbrite, a public company.

No one would draw up a career path this way, but I focused on learning potential at pretty much the cost of anything else, and it’s served me well. What a lot of young people don’t understand is that if you bet on increasing your learning potential, your earning potential compounds over time. The money will be there if you gather differentiated skills the market values (my knowledge of obscure electronic music, for some reason, is not one of those skills the market values).

This advice is fairly easy applicable and, I think, well understood by a lot of people. If you are making a choice between learning and earning, the former will almost always make sense not only from a happiness perspective, but also from a financial perspective long-term. I want to talk about what happens after you self-actualize in this direction.

Let’s say you’ve spent a decade plus collecting valuable skills, applying them in interesting ways, and you are differentiated on the market. Problem solved, right? You’ll never have to worry about a job. You’ll have all these opportunities. Well, not really. They say in startups the problems never get easier; they just change to different problems. I think optimizing your career is the same way. What people don’t tell you is if you optimize for learning, there are fewer and fewer jobs where you can mix all that you’ve learned together. And that you actually have to pick amongst many competitive opportunities. Not picking or not leveraging all your skills can leave you unfulfilled, like you’re not at peak potential, or lead to some of your skills atrophying from lack of use.

As someone who went through this issue after Pinterest, I did some deep reflection on what makes me feel fulfilled on a path to a personal mission. I’ll share that mission as perhaps a useful example, but yours will almost certainly be very different, or even optimize on different attributes like industry, problem type, relationships, etc. After reflecting on what I liked and didn't like at all the different companies I worked for or with, I realized I really enjoy problem solving. Specifically, figuring out problems related to building businesses and ensuring those solutions can be shared with others. Now, those solutions aren’t growth hacks or tips and tricks, but generalizable frameworks that can be wielded in the appropriate situations. I eventually landed on a personal mission of discovering and scaling the best practices of building companies.

What I found from my advising work is that the best practices of building companies are very unevenly distributed. And it isn’t that one company has all of them and isn’t sharing. It’s that companies are good at different things, and there isn’t even cross-pollination of these best practices so that every company gets better at operating. In fact, I’d say most companies in Silicon Valley in aggregate operate poorly. It’s a weird paradox that the best performing companies are some of the most poorly run, because they can be. As Rick James might say, product/market fit is a hell of a drug.

Like finding product/market fit for a company implies a product people value and a way to make money at it and scalably distribute it, the next question comes in how to deploy this personal mission. I played around with almost every model: full-time employment, advising a handful of companies in-depth, investing and helping the companies I invest in, creating courses with Reforge that anyone can take, and blogging for anyone who wants to read. There is an implied breadth and depth of impact and learning from this model. Focusing all your time on one company has the most impact on how it operates, but that scales the least of any model. Blogging reaches the most amount of people in aggregate, but with no customized learning.

What I have found interesting about my personal mission is that while there are clear trade-offs, there are also win-wins. The blog creates advising opportunities. Operating full-time at one company makes me a better advisor, course creator, and blogger by the depth of problems I get to work on. Advising allows me to see fresh perspectives that broaden my problem solving at my current company. I have not found a perfect formula to optimize the ratio of time spent between these different avenues to deploy against my mission, but what I did learn is that it is likely best to vacillate between the different circles, which is part of the reason why I am not a full-time advisor like I was in the past. This is basically a form of optimizing for different steps in my learning loops to continue to unconstrain my personal growth, much in the same way I optimize for unconstraining growth in the companies I work with.

Finding a personal mission and thinking about how to deploy against it is something I would recommend more people spend time exploring for themselves. I think it helps optimize for personal happiness and growth in an environment where there are seemingly competing opportunities all the time that are hard to judge against each other.

Casey Accidental

Career Paths, Personal Missions, and…