What was it like to leave a stable job in favor of corporate life?

Updated on : January 21, 2022 by Gage Ramsey



What was it like to leave a stable job in favor of corporate life?

In my case, it was a heartbreaking but incredibly exciting decision. It's routine now, but so is entrepreneurship.

The decision

Many others who make the entrepreneurial leap hate their jobs or find themselves in the middle of dead-end careers.

I was the opposite. In fact, I really liked my job and went places.

I was a Senior Director of Strategic Marketing at Washington Capitals / Monumental Sports and Entertainment.

I had just received a promotion and they were going to give me a lot more responsibility. I was in the fast past to top management.

I had a great boss who gave me tons of aut

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In my case, it was a heartbreaking but incredibly exciting decision. It's routine now, but so is entrepreneurship.

The decision

Many others who make the entrepreneurial leap hate their jobs or find themselves in the middle of dead-end careers.

I was the opposite. In fact, I really liked my job and went places.

I was a Senior Director of Strategic Marketing at Washington Capitals / Monumental Sports and Entertainment.

I had just received a promotion and they were going to give me a lot more responsibility. I was in the fast past to top management.

I had a great boss who gave me a lot of autonomy.

I went to high school specifically to get a job like this.

And I worked in sports!

Aside from being the general manager of the NY Yankees or Giants, it was essentially my dream job.

But I felt that the work did not provide me with enough progress.

Yes, we would improve our marketing season after season, but the improvements were like going from 1.0 to 1.1. I wanted to go from 0 to 1 and build something from scratch. And I had some ideas.

The decision was very difficult because I really liked the job and I was wondering if the entrepreneurship thing was not working (yet to be determined), could I find another job like this? Would I find another dream job like this that I worked so hard for and paid so much money to get?

In the end, I couldn't imagine sitting on my deathbed and regretting never having made the entrepreneurial leap.

Yes, the job I had was great, but there would be other jobs for me. They may not be as good as the Caps, but it would be nice.

After the decision

So exciting!

Before I quit my job, I got a couple of consulting clients so I could have some income while working on my startup idea.

The first year was very exciting. New projects, new networks, a lot of activity.

Then the shine wears off, if you're not seeing the success you hoped for.

In my case, I had a fight with my co-founders and left the startup I was working on. Consulting projects were going well, but it became routine.

5 years have passed and I am on my third start-up. The other two were dead ends, but I have learned a lot.

Learned lessons

Entrepreneurship, especially the life of a startup, is difficult.

In the corporate world, you can climb the ladder in a linear fashion. Strong performance reviews, raises, and promotions are clear indicators that you are doing well.

I'm not even sure what success looks like anymore.

I always had a high performance and I know that if I stayed long enough, I would be the top management in some company right now.

And although I am happy for them, it is difficult to see my friends with good titles and great salaries.

I hardly ever doubted myself in my previous jobs. But I have daily doubts about how good I am at what I do and where my career is going.

My starting story is still being written. I've had failures in the past and I'm sure more will come. But I hope that if I work hard enough, success will come too.

All I can do is work every day.

About a year ago I made the leap to join a small 10-person startup called MindSumo. What I left behind was an easy job in corporate finance on a Fortune 500 that paid me six figures and offered me a fast track up the corporate ladder.

Before taking the corporate finance job, I got my MBA and turned down an offer to return to a senior management consulting firm that offered to pay off my $ 80,000 in loans.

It was the best decision I ever made.

I traded stability and a significant amount of money because I would never forgive myself if I woke up one day at the age of 60 full of regret for not having done so.

Keep reading

About a year ago I made the leap to join a small 10-person startup called MindSumo. What I left behind was an easy job in corporate finance on a Fortune 500 that paid me six figures and offered me a fast track up the corporate ladder.

Before taking the corporate finance job, I got my MBA and turned down an offer to return to a senior management consulting firm that offered to pay off my $ 80,000 in loans.

It was the best decision I ever made.

I traded in stability and a significant amount of money because I would never forgive myself if I woke up one day at the age of 60 full of regret for not having seen what else was out there.

These are the main things that I would highlight from my experience:

  • Going from a structured corporate environment full of processes to a disorganized and undefined startup environment is stressful. When you encounter obstacles, it has no precedence to guide you on what to do, which often leaves you wondering if you made the right decision. On the positive side, you will have the opportunity to define new processes yourself.
  • Most of the sophisticated frameworks and strategies I learned in business school helped me in the business world, but they became useless in the startup world. Being successful in a startup requires experimentation, creativity, and hustle and bustle. I had no one to call and save me if I ran into a problem or question. I was stuck figuring it out and felt like the corporate environment didn't really prepare me for this.
  • In my steady job, I felt like a cog in the machine with a job to do. I was a white collar assembly line worker made to follow processes and report problems. I didn't feel connected to my job or the people I was serving. All that changed when I joined a startup, because it was my decisions that determined the performance of the company and the user experience. I became more involved in my work because I could clearly see the correlation of my actions with the objectives of the company.
  • You spend a lot of time having to worry about finances. I was lucky enough to join a profitable startup that could pay a decent salary and did not have to be in a constant state of worry due to high spending of cash. However, I met several founders and employees in the early stages of startup who did not have this luxury. Being under constant pressure to find the next big customer or investor to keep the lights on can really take its toll.
  • You have to reevaluate your priorities. By choosing the business route, you are essentially saying that my business is the most important thing in my life right now, and I am willing to sacrifice my time, sanity, and financial security for this to be successful. It is a completely different mindset from someone who prefers stable life where their priority is outside of work and a job simply provides the means to support a family or enjoy a certain lifestyle.

While User-10636879368092969429 highlights several great reasons why being an entrepreneur seems like a no-brainer, I don't think it's for everyone.

75% of startups will fail. Personally, I am unemployed after only 8 months at MindSumo because the startup decided to turn around and go in another direction.

However, if you are a person who needs passion and satisfaction in a job like me, you will never be happy in a steady 9 to 5 job. Some people are fine being unhappy at work for the salary and stability, and I hope that may they find happiness in another part of their lives.

If you want to hear my full story of why I chose business life over safe career, read my full article here:

To be truly happy in life, I left the largest company in the world to join a startup as employee No. 11

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