Just had an interesting conversation with a former co-worker at a mid size corporation. She stuck to the standard corporate ladder while I jumped to start-up wi

Just had an interesting conversation with a former co-worker at a mid size corporation. She stuck to the standard corporate ladder while I jumped to start-up within the corporation - experienced lot of growth but then laid off in the midst of the great recession. Since that time I have added to my technical skills and become less of an industry analyst and market consultant and much more of a builder. I have lived the much higher risk professional life than her. Start-ups both venture backed and lifestyle, consulting and gig economy. She jealously commented on how I was constructing a current 'career' that took the best of the several different roles I have held over my professional career. And, in truth I have optimized for interesting and potentially high payoff. However, I found myself looking with some longing at her "boring" but corporate journey with its good salary, good benefits and relative stability and wondering if I should have optimized for those characteristics. The creative freedom of the gig and start-up economy extracts its price in uncertainty and not everyone hits it big.