Leaving Corporate America For A Startup

Corporate America Startup

Three months ago, I took the biggest leap of my career.  I decided to leave my stable and comfortable corporate job at a Fortune 50 bank to work at a financial startup with fewer than 25 employees.  I’m definitely not alone, and if anything, I’m a cliche New York millennial chasing the startup craze and all of the hype that goes with it.  That said, I was still unsure of what to expect and how smoothly my transition would go. Simply put, leaving corporate America for a startup isn’t as easy as it sounds. 

I had a few friends who had made similar transitions, so I reached out to them first.  I then corroborated some of their feedback with blogs and news articles.  After doing this high-level due diligence, I felt like I had a good idea of what the major challenges and opportunities would be in moving to a startup.  First, I would need to find more creative ways to get things done, given more limited resources and fewer defined processes.  I would also have to step up (and down) in my job responsibilities given there would be a flatter hierarchy and fewer team members in general.  Finally, I would hopefully see the benefit of being able to make decisions and implement ideas more quickly given the reduction in bureaucracy often seen at large corporations.

During my first three months at my startup job, I experienced all of these things. However, one thing my due diligence could not have prepared me for would be my personal adjustment to a “startup culture.”  While I realize that every startup is culturally different depending on industries/founders/etc., I do think there are some common cultural elements that naturally occur when you’re at a smaller high growth company.

The Importance of Individual Impact

First, each individual employee has a huge impact on the company.  That impact can be positive, negative, or both; but the bottom line is, on a smaller boat, every rower counts. For example, one of our employees in operations recently resigned for another opportunity.  That one employee leaving was like an entire department at a large corporation leaving.  Everyone felt the impact immediately.  In addition, I realized how critical hiring is in a small company.  Each incremental hire has the potential to dramatically change the dynamics of your team.  In startups, you can’t afford hiring mistakes and you can’t afford losing good people.

Encouragement of Finding Better Solutions

Second, there is truly a bias to innovate and use leading technology at startups.  In my previous corporate roles, I often found the burden of proof to change something was a level of benefit significantly greater than the status quo.  At my current company, I’ve been encouraged to regularly seek better solutions even when the status quo is working.  People are not wedded to processes and egos are kept in check, making ideas and suggestions much more welcome.  I also find myself using the latest technology and software, both because we are a part of the tech ecosystem, but also because it’s often cheaper than traditional options.  

Authentic and Open Conversation

Finally, I’ve found the startup environment to be much less formal than the corporate environment, which has been both challenging and refreshing at the same time.  There are the obvious things on the surface, such as a casual dress code, funky office furniture, and weekly happy hours.  But digging a bit deeper, I’ve found that people are much more authentic and open when put in a smaller company environment.  I find myself being less guarded, less worried about whether I’m coming off polished, and more willing to talk about my personal life.  This doesn’t mean that I’m becoming less professional, it just means I’m less anxious about whether every move I make is increasing my political capital.  One challenge I’ve found about the more casual work environment is finding the right boundary between work and life.  That said, I keep hearing more about work life integration, which is perhaps something I should explore further!

Three months in, I’m glad I’ve made the leap in leaving corporate America for a startup.  I’m not at the point yet where I’m fully bought in, but I do know that I don’t regret my decision.  The things that I have learned and gained exposure to in these first few months has proven invaluable to me in my career development.  I’m looking forward to what additional challenges come next once I get past this “Honeymoon” phase!



  1. Sounds like its mostly for the better. I have been working for myself or as a partner in a relatively small family company since i am 28 (20 years). I enjoy the freedom and the focus on getting things done rather than on other metrics like punching a time card, etc. Good luck!!