When to leave your comfy corporate job to become an entrepreneur

Let me start by saying you will never be 100% sure that now is the right time to leave your comfy corporate job to become an entrepreneur. In fact, I would aim for 52% sure as the best case scenario.

We stay in that comfy corporate job because it’s what we already know. Ever heard the phrase ‘better the devil we know than the devil we don’t know?’ Work may not be the devil (well, most of the time) but the phrase can apply to work situations. There is comfort in familiarity, in the routine we currently have, the place we already know. Change is scary, even if it’s change for the better that awaits us.

Landing a corporate job right out of college seemed like ‘the thing to do’. I contemplated starting my own business ,however I kept hearing words like “401K” which seemed like ultimate adulting to have one. At the time, the only options for health insurance were through your parents or your employer so that was also a huge magnet to working for a big established company. The idea of running your own small business didn’t seem to fit the planner in me with a student loan to pay off.

Fast forward to 7 years in to Corporate America. I participated in all the sales trainings and ate all the office donuts. Though I fumbled in the beginning to find my place (hello, housing crash and economic turmoil of 2008-9!) eventually, I found my groove on the sales side. My favorite part was interacting with customers and developing the relationships. It was fun to learn about different businesses and be a part of finding the solution.

Here’s the part that wasn’t my favorite: the environment I worked in. As a southern hispanic woman, it was hard to connect with the boy’s club. Deals and promotions were discussed at the strip club and the few women in the mix had a ‘better me than you’ attitude. It’s sad that the competitive nature kept us separated rather than rallied us around each other and help move up together. Not to mention the toxic work relationships and dynamics from affairs in the office to hazing.

Yet I trudged on for 7 years in hopes of moving up in the ranks. There was a new hire, a 23ish year old that had played for the office favored local college football team. He was fresh off the pitch. (Reminder: I’m in Texas, football ranks up there with Jesus.) I helped train him on a few things and bring him up to speed. It took less than 6 months before he became my boss.

That’s when I knew: this environment wasn’t the right place for me.

It was time to stop reaching for a goal I didn’t even really want and start working towards the life I was created for.

So the next day, I quit.

Just kidding! It never happens that fast.

The dumpster fire had to keep rolling down the street a few more miles before I would finally make my move. I did however, start working on my business plan for my new company.

A few months passed and I got hitched and shortly after, found out I was pregnant. The lack of support while I was pregnant was obvious. I was even written up for going home early too many times. To state my case for the record, I was on my feet all day outside in the Houston heat visiting customers at yards and warehouses (did I mention I was pregnant?), then 1-2 times a week would head to my desk at home by 3/4 PM instead of going back to the office. Always reachable by cell phone and answering emails into the evening. Clearly they were building the case to fire me and I could feel the pushing out.

Then came the ultimate dagger when I was on maternity leave. Even though I had increased my sales numbers year over year with great customer service feedback, when I was on maternity leave they permanently reassigned half my customers to another, newer sales associate.

Considering I had been mostly commission based - meaning I had a small base salary yet earned 75% of my income the year prior through commission - this was a huge blow. Not only to loose the relationships I had built with clients but also to my wallet. It would have been like taking almost a 40% pay cut, just for taking time off to bring a human into the world.

Did I mention there was zero paid maternity leave? I was living off of savings for the unpaid FMLA to care for my newborn.

I had no choice but to leave. It was so humiliating the way I had been treated and the blatant pushing out the door - I couldn’t go back. If I could have had my personal desk items shipped, I would have to avoid the awkward conversations!

Don’t feel bad for me. I may have been treated like disposable garbage, however, it was truly the only way I was forced to redirect my life towards my small business and my new baby. The Corporate America chapter had to end, in a painful no-other-way-forward kind of way.

So to answer the ultimate question of when.

When you are ready to leave your comfy corporate job and become an entrepreneur?

Is it when you are financially set? When your new business is finally taking off? None of those.

When you’re finally so fed up of the bullshit and tap dancing that you’d rather jump off the metaphorically cliff into the unknown waters of entrepreneurship rather than one more day as you are currently living.

It feels like the world is giving you the ultimate ultimatum: jump or be miserable.

Life is way too damn short to live your life on someone else’s terms.

JUMP. The water feels cold at first but it’s the most alive you will ever feel.

Cheers amiga,