Masters in Business · Wednesday, September 9, 2026
Tyler Gardner argues that the greatest risk for a professional is not in trying something new and potentially failing, but in remaining in a safe, W-2 job for decades with capped upside. He encourages individuals to pursue their entrepreneurial aspirations, emphasizing that returning to a stable job is often feasible if the new venture doesn't succeed.
“So you just set up the polar concept that if I go to a job like this, it's more risky than if I don't. Whereas I always try to push people just a little bit to say, look, the biggest risk is you sit in the current job you have for 20 years as a safe W-2 employee. And that's fine. I get it. You got the bills to pay. But your upside is so capped, you have no idea.”
“And the risk to me is that you get your one life taken away for 20 to 30 years and you're not focusing on a daily basis on the things you want to focus on.”
“The concept of risk is way more applicable in my mind to losing out on what you could have done than if you go try something. And if it doesn't work out after a year, after two years, after a real effort, what I don't think enough people understand, you can go back.”