San Francisco’s Financial District on a particularly Karl the Fog-gy day

Last month I had dinner and drinks with a friend and he said to me (paraphrased). “Wow, you’ve been through so much out here. I’m waiting for you to write a book or something.” While I don’t really consider myself that much of a writer, especially a long form writer, this comment made me consider sharing some of the things I’ve experienced and learned in my career so far.

In the past 7 years I’ve worked for 10 individual companies, seven of which were startups. Many of those startups don’t exist any more or are otherwise not doing so well, with Secret being the latest company to shutter its doors. I’ve been at small 3 people companies and everywhere in between, all the way up to huge public corporations with 20,000+ employees. I’ve been laid off 3 times and fired twice, and quit many other jobs before it ended up coming to that. I’ve been publicly yelled at in front of coworkers by founders, at one company I was told by the founder “Stick with me, I change people’s lives”, and I’ve also been fortunate enough to work with some genuinely great founders(I feel great to count my current employer, Bugcrowd, in the latter camp).

In hopes of helping others, here is a collection of thoughts and things I’ve learned through these experiences. Again, this is all based on my personal experiences, so your mileage may vary.

You will get another chance to do great things. Because of the nature of startups and my tendency to become completely immersed in the company (aka I drink the kool-aid), I’m very hard on myself when things don’t go well. When I realized that things weren’t going well at Secret (May 2014), I was extremely hard on myself because I thought that that company was finally my chance to have professional and financial success after a string of disappointing outcomes. When it ended for me, I felt like a huge failure and that I’d never get to do something like that again. Several months later I would go on to start a job at Bugcrowd, which has been going well and I feel has potential for a lot of success. This has happened many times in my career, where one “awesome” job comes to a crushing demise and another opportunity presents itself later. It’s a hard emotional journey to ride out but it can be worth it.

Advocate for yourself and believe in yourself. In the high pressure, high stakes world of startups it can be very easy to lose faith in your abilities. It can also be very easy to be overlooked and lost in the shuffle at a fast paced startup, so it is very important to trumpet your successes and push for help and guidance when you need it. While it’s important to be humble and a self-starter, you need to be on management’s radar and you need to be headed in a direction that matters for the business.

Being a startup generalist has diminishing returns. When I started working at startups as a 20 year old, I found it to be valuable to be a team player and fill in gaps when stuff needs to be done. While this can be valuable in various ways and I think it’s great to be a team player, if you spend too much time doing stuff that ultimately doesn’t impact your goals in the company or your personal career, then question whether it’s worth doing. This is something I still struggle with today, but I’ve ended up wasting a lot of time doing stuff that was helpful in the moment but didn’t result in any material benefit to my professional growth inside or outside of the company. Most of the time it just results in people liking me and thinking I’m helpful, but not much else.

Keep your eyes on your goals and don’t get distracted too much or otherwise pulled away. I’ve joined companies and done a poor job of negotiating pay and titles. I’ve had roles doing work that doesn’t align with where I am in my career and the responsibilities and projects I should be charged with. This is a very tricky thing to balance, since it’s very important to be flexible and do stuff that is valuable to the business, which sometimes means doing work that is “below” you or your pay grade. But hopefully you can find balance here and make sure you are doing stuff that results in upward and forward movement in your career.

Don’t be afraid to leave a bad situation. Whatever that means to you. Don’t waste time, mental of emotional energy on companies or people that don’t benefit you in some way. I’m not saying don’t be selfless, because I fully believe in being selfless and helping others, but it’s also important to look out for your happiness and personal growth. If a job sucks or people are treating you badly, and you have the opportunity to leave, you should probably leave.

Reach out to others and build a support group of friends, family, current and former coworkers, therapists, etc. I’m someone who needs external validation and it has been extremely helpful for me to talk to others about my experiences and issues. Last year I started going to a therapist, I’ve got a very supportive girlfriend & family, and I reach out to friends and peers when needed. Sometimes it can just be helpful to know that you’re not alone, your feelings and needs are valid.

Startups and technology companies are a very fickle beast. One minute you’re hot, one minute you’re not. People will take you seriously because of the company name on your Linkedin or business card, and if they haven’t heard of you, they’ll just pass you by. Fight hard to not take this whole thing too personally because more often than not, this too shall pass and there are more exciting things on the horizon.

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