3 Biggest Surprises in Transition from the Corporate to the Startup World


Whenever I speak to entrepreneurs who have left the corporate rat race to pursue their own ventures, their experiences always echo my own. Sure, new small business owners expect additional flexibility, less bureaucracy and longer hours. However, as someone who left the corporate world in search of greener pastures as a startup founder, I discovered that the biggest surprises involve job satisfaction, the first month of work and organizational structures. These surprises inspired me to create #entrepreneurfail, a comic about the ironies of starting a business.

Job satisfaction


At the beginning of a corporate job, or a role within any large organization, there is a sense of pride that comes from the brand, the paycheck, and the responsibility. With time (and, of course, there are exceptions) the satisfaction decreases and plateaus out. The probability of this happening is consistently high because soon enough the reality of red tape sets in.

At the beginning of an entrepreneurial venture, however, the sentiment and satisfaction is uncertain and riddled with fear and budgetary constraints. The level of job satisfaction is variable. The stress can result in more confusion and change in direction. With time there is potential to reach a high level of success and job satisfaction, but the probability of that is extremely low. The most recent count of failed startups is too high to rationally think about. However, we’re a risky bunch, so we think it’s worth it!

First month of work

Entrepreneurs want to dive right into their new ventures. Unfortunately, the first month of launching a startup is punctuated with administrative overheads, such as paperwork, forms, IRS registrations, writing checks, and balancing projects and accounts, with a little bit of actual work sprinkled on top. To make things worse, these administrative tasks can create a perfect storm of procrastination. In contrast, in a new corporate job there are a few clerical details to take care of, like benefits and tax forms, but then you are off and running!

As a new entrepreneur, be mindful of how these administrative overheads may take over as you embark on your journey.  And remember that no company has failed just because you didn’t print business cards in time. Prioritizing the truly important aspects of a new business will ease the amount of set-up work you need to do to get your business going.

Organizational structure

Finally, climbing the good ol’ corporate ladder is a tried, true and relatively predictable, yet slow, way to reach the top. Heeding the speed limit and traversing the dotted lines can get frustrating, as there is no magical formula for upward progression. And cracking office politics and the favoritism code can be a mystery.

This is a reason you may have pursued your own venture: so you could declare yourself the boss. Good luck with that! Sure, the org chart will be leaner than in a corporation, but you are never actually your own boss. You are reporting to your customers, vendors, suppliers, and investors. They drive and dictate your promotions, pay raises, perks, annual leave, and responsibility. Welcome to your organization. It’s the flip version of the corporate org chart. You are barely hanging on as it grows larger above you. Be ready to adapt and draw the org chart as you go and the transition will be much smoother, as I realized.

Any surprises you’ve experienced transitioning from a big organization to a startup? Share in the comments below.

About the author: Kriti Vichare

Kriti Vichare is a marketer, entrepreneur, and cartoonist. She is the illustrator and co-founder of #entrepreneurfail, a web comic about the ironies of starting a company.  She is also the founder of IdeaKube, a company that facilitates brainstorming through ‘ideation parties’.  Kriti was a former marketer at PepsiCo and Kraft Foods. You can connect with her at http://about.me/kritivichare.

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