This is the third in a series of posts on startup risks. I’m not trying to dissuade anyone from starting a venture – I just want to help make sure you are aware of the risks. And don’t worry – I’ll blog about the rewards, too.

Career Risk. While some entrepreneurs start company after company (aka “serial entrepreneurs”), others turn back to the job market. Unfortunately, your resume can look odd after a few years at startups, making it tough to fit neatly into any well-defined corporate roles. And if employers sense that you’d rather be starting your own businesses than holding a job, they might perceive you as a “flight risk”. If you manage to land a job after being an entrepreneur, you might find it difficult to fit in. Once you are used to turning on a dime, the slow pace of change at a large company can be frustrating. And after being in control, it’s tough to follow orders. The first time your boss Doogie Howser tells you to get on a plane to Timbuktu on a Friday afternoon for a meeting you consider a waste of time, you’ll know just how spoiled you’ve become.

Finally, entrepreneurs are likely to have rollercoaster careers, often with extreme highs and lows. They may dip into savings and forgo income while planning a venture, pay themselves just enough to get by during building years, and earn big payouts upon selling a business. But they can also experience sudden, significant challenges. Like rollercoasters, entrepreneurial career paths require intestinal fortitude. 

…After I posted this, I got two amended charts from a lifelong friend of mine and fellow serial entrepreneur, Scott Kennedy. Just had to share: