Foundin’ Ain’t Easy: How to Beat Founder Anxiety as a Millennial or Gen Z

Mar 25, 2020

Author: Brian Dougherty, Jumpstart Foundry Chief Operations Officer
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Foundin’ Ain’t Easy: How to Beat Founder Anxiety as a Millennial or Gen Z

Founding a health startup is one of the most exciting and impactful things an individual can do. Few experiences provide a better opportunity to affect the lives of others and quickly learn new skills while also carrying the potential for considerable financial upside. From time-to-time; however, founders may experience a loss of confidence and enter “the dark place.” These episodes are often the most unpleasant and least discussed parts of being a founder.

The good news is that while it’s only natural for confidence to ebb and flow based on achievements as a health startup founder, these bouts of anxiety may be exacerbated in certain age groups. After observing many startup founders, I’ve found these experiences of apprehension to be considerably more common with founders under the age of 40 (Millennial or Gen-Z generations) when compared to Baby Boomer (Boomer) generations.

  • The problem: Higher expectations with less margin for error
  • Two main triggers of anxiety: the impact of failure and the likelihood of its occurrence

This blog seeks to illuminate several potential underlying causes of this disparity with the hope of reducing the likelihood of unwarranted anxiety in younger health startup founders.

The Impact of Expectations on Millennials/Gen Z vs. Boomers

Scenario 1: We have an individual named Alex that needs to cross a rope bridge. The 30 ft rope bridge is suspended 1 foot above a pool of water that’s 1 foot deep. Alex is informed that he has one hour to cross. This situation does not make Alex anxious. Sure, falling in could be temporarily unpleasant, but there would be little to stop him from drying off and giving it another shot. Plus, given the generous deadline for crossing it, there’s plenty of opportunity to take your time and try again.

Scenario 2: Now let’s take the same bridge, suspend it 100 feet above the same pool and add in a few hungry alligators for good measure. We also reduce the timeline for Alex to cross to 30 seconds. Alex is now, understandably, extremely anxious.

These two scenarios respectively highlight the difference between the expectations Boomers experienced versus the expectations Millennials or Gen Z experience. Unfortunately for Millenials and Gen Z, both expectations and impact of failure are considerably higher than that of Boomer generations.

The Impact of Failure on Millennials/Gen Z vs. Boomers

Gen Z/Millennial generations attained 3.5x more college degrees than Boomers, highlighting the expectation for Millennials and Gen Z individuals to attain a college education. The price of education at a public university, when adjusted for inflation, has also increased by 3.5x compared to when Boomers attended school. The minimum wage, however, has actually decreased, when inflation is taken into account (1970 minimum wage is $1.60 = $10.91 in today’s money).

An individual in 1970 could work a full time job for 2 months of the 3 month summer and completely pay for a year of college. To do the same in today’s economy would require the individual to work for almost 9 months full-time, which is practically impossible as a full time student.

The point I’m making is that for Boomers, college was not only less of an expectation, but the impact of failure was considerably lower. An individual could attend school without subsidies and pay for it with a part time job. For Millennials and Gen Z on the other hand, the importance of completing college on the first attempt and as quickly as possible is set from an early age and repeatedly emphasized throughout adolescence. The stakes are even higher as the cost of admittance almost forces students to operate at an extremely high-level for years where any mistake or minor setback (i.e, one bad test score, one ‘B’ grade, one suspension) could result in loss of admission or financial aid.

The Millennial and Gen-Z populations were forced to operate at this level without any opportunity for reprieve during their formative years. No wonder they have a tendency to lean in to the fight or flight response and have trouble relaxing.

The Solution: Embrace Failure

One of the keys to succeeding as an entrepreneur is to embrace failure. Failing fast and often is key to pivoting your position and ultimately finding product market fit. The years of being hardwired to operate in “failure is not an option” mode makes this difficult for Millennials and Gen Z’ers. Shaking themselves of this tendency, I believe, is one of the key reasons that founders who have spent just 3 years (that’s 3, not 30) working in the industry have an 85% higher chance of a successful exit. This allows them to learn that the business world actually does carry some margin for error that is significantly greater than what conditioning taught them.

Taking a Note From the Boomers

While circumstances differed greatly between Boomers and Millennials/Gen Z, there are still plenty of lessons that can be learned from Boomers.

I’ve had the privilege of working in corporate America with individuals of the later generation. While excellent mentorship abounded, the most jarring aspect of working closely with later generation colleagues was their ability to be fine with partially-formed plans. After spending the last 20 years walking the tightrope, threading the needle and avoiding even minor failures through detailed planning and borderline prophetic issue spotting, I’m now expected to “go with” these guys that just confidently believed everything would work out. And you know what? They were right. While there were still instances where things didn’t work out, they were few compared to the number of initiatives that were successfully completed.

The key difference here was—they weren’t afraid to fail.

What I learned from asking my boss and mentor, was that he had seen many projects blow up through the course of his career. By being subjected to those failures, he gained an understanding of how to look out for indicators that a project was going to go off the rails. More importantly—unlike grades and sports where the outcome of the contest is often all or nothing—he learned that just because a project heads toward the ditch, doesn’t mean it can’t be steered back in the right direction.

Finally, even in the event that an initiative did fail, he was still standing. Granted, some could consider this survivorship bias, but he was still an extremely successful CIO of a multi-billion dollar organization. A failure, while not ideal or desirable, was not a death blow to his career or his confidence.

In Conclusion

For Millennials and Gen Z members that are just starting out and haven’t had the privilege of working with more experienced individuals, the prospect of learning through failure and not getting worked up until it’s time to take action is difficult—but necessary. It’s the mindset that allows people to remain calm and focused, even when it seems that the walls are crumbling around you (because they probably aren’t). Even if your brain has been hardwired to avoid failure and things around you seem to be crumbling, that’s when you need to focus harder than ever to steer your health startup back on track.


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