Five Things I’ve Learned Since Leaving Wall St. For Startups

This article also appeared in Forbes.


I know, it’s almost a cliché.


In December 2011, I left investment banking for the world of startups. During almost a decade at the same firm, I wore many hats but never found the right “fit”. I deluded myself that if I just kept working that little bit harder I would wake up one day, truly fulfilled, basking in the glow of prestigious titles and seven-figure bonuses. It didn’t happen and, eventually, I burned out.


When I left I had no job lined up, no masterplan, and a pretty feeble network outside of financial services. Crazy? Perhaps. Liberating? Absolutely.


In January and February I chilled out and went on a long vacation. By March, with a clearer head, and a growing desire to explore, I was ready to embark on a voyage of discovery, which would necessitate some (strategic) spaghetti throwing. Since then, I’ve landed a few freelance gigs red-penning investor decks and business plans, as well as dabbling in business development, social media, and marketing. My network, which is growing like (friendly) bacteria on a Petri dish, has yielded multiple exciting collaborative conversations. That said, I’ll admit that there have also been several moments of panic!


So, here are five important things I’ve learned on my journey so far.


1. Burnout = Long Hours x Wrong Context


Many people attribute burnout exclusively to the hours you put in. I was burned out primarily because I wasn’t in the right industry for me. If you don’t love what you do your efforts disproportionately drain you of energy. Conversely, when you’re emotionally connected with your work, burning the midnight oil is relatively easy. If you want to work for a startup, make sure you love the mission as no matter what your official title is, everyone is expected to be an evangelist.


2. Forget the Resume, Try a Rendezvous


When you’ve made a career of eclectic roles, albeit at the same firm, it’s tough to articulate what you do in a punchy paragraph. Resumes are great for demonstrating linear progress through career paths in professions like law or medicine, but not so good for Professional Spaghetti Throwers. Moreover, I’m not blessed with the creative skill to warrant a portfolio – expressing myself in Powerpoint has been the high-point of my artistic career! I like LinkedIn and always attach my profile URL to my emails but even that is better suited to people with linear careers. At least it allows for visible recommendations and widgets to boost your caché.


In my efforts to gain experience and find mentors, I have largely set aside the traditional resume in favor of networking. Fortunately, startup folks are generally very friendly and accessible – the challenge is making networking relevant so you can foster substantive connections. Nevertheless, even if you do identify appropriate people, be prepared to put the effort in.


Kate Huyett, Director of User Acquisition and Business Intelligence at HowAboutWe, found developing mentoring relationships more challenging since leaving Wall Street. “At Goldman, it was really easy to find the right people to network with – they were in our centralized corporate database. Now, while both parties know it’s valuable, neither of you are getting directly rewarded for your efforts so you have to fight to make it a priority.”


So fight right and go to MeetUps, and other events, on topics that interest you. The more niche the event, the more likely you will get beyond small talk and forge stronger connections. Additionally, if you are looking to develop skills that startups value, try a Skillshare class where you’ll hopefully find other like-minded folk.


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