Managing in the Age of Uncertainty
Is entrepreneurship the best career path for millennials and gen-z?
“Don’t do something you love, do something you’re obsessed with.”
Serial entrepreneur — and millennial — Alyssa Nolte likes to buck convention.
“I disagree you should find a career where you focus on your passions,” she tells me. “The best entrepreneurial opportunities are about solving problems — and obsessing about every detail of the problem until you solve it.”
It’s an incredible distinction — and great advice for anyone thinking about starting their own company. I reached out to Alyssa because I’m asking myself how young people build career paths in the age of AI where the corporate ladder is evaporating before our very eyes.
Entry-level job postings are down 30 percent since chatGPT was introduced. If millennials and gen-z can’t count on the traditional job market their parents enjoyed, should they count on themselves?
Everyone is different — so I don’t want to make some blanket generalizations about entrepreneurship and young people. What I will say with certainty is the corporate ladder is dying or dead. It’s being replaced by how people tell their personal career stories, a chapter at a time, role by role.
All my experience has taught me that starting something from scratch and getting to market will enhance anyone’s career story — succeed or fail — in three ways:
The entrepreneur’s journey is a story of grit, perseverance and creativity — all characteristics employers look for in employees.
An entrepreneur will undoubtedly hear feedback about themselves and learn strengths and weaknesses, all vital to telling a story about yourself.
At the very least, an entrepreneur will end up with a larger professional network.
Software is the most accessible entrepreneurial opportunity today
Here is the most optimistic reason to consider entrepreneurship: the cost of entry has never been lower.
In 2000, it took $5 million to build a software product.
In 2010, it took $500K to build a software product thanks to the cloud.
In 2020, it took $5K to build something in software if you could code it yourself.
In 2025, you can launch a software company with less than $500 thanks to AI doing the coding for you.
What I love about meeting young people like Alyssa is I learn things that blow my mind as a boomer. She tells me to visit a Reddit group called, “Micro-SaaS” — where you can literally browse thousands of ideas about problems that need to be solved with software.
And then there’s this thing called “vibe coding” where, as Alyssa told me, “You turn your obsession into a product.” Fancy name aside, coding this way involves an AI software agent writing code based on human prompts.
The more I talk to Alyssa, the more it dawns on me that she is describing a profound shift in thinking for this moment in time: The emphasis is on obsession, not the coding. Many of the great thinkers I’ve featured in this newsletter have emphasized the importance of human-ness to set a career path. Obsession is among the most human of emotions.
Love is not the answer — “Building in Public” is
I’ve been convinced by Alyssa that we’re at an inflection point: it’s time to stop telling millennials to “do what you love.” “Everything that I’ve loved that I’ve tried to monetize I end up resenting it,” she says.
Here’s a sobering fact: Millennial entrepreneurship rates are actually LOWER than Gen X at comparable ages - starting fewer businesses in their 20s and early 30s than the previous generation. It turns out that acting on passions is much harder than it sounds (especially if you have student debt).
To me, obsessing over a problem and “vibe coding” a solution sounds a lot like the concept of “building in public.”
If I had to give advice to any young person today it would be to “build something in public.” Tell your world and network what you’re doing. Share it across your social channels. In the Career Story Builder tool I launched (my “building in public” effort), one of the six questions to answer to tell a best-selling story centers around building something in public — proving you are career ready to use AI with an actual artifact, not just your knowledge.
Homework: Try Vibe Coding
If you are obsessing about something, it is likely frustrating the hell out of you. Open up Claude, Lovable or Bolt and just start asking it questions about how to solve the problem. For even a boomer like me I started in Claude and ended up with Career Story Builder.
As Alyssa told me: “Young people have strategic nativity; I didn’t know that it would be so hard, and I didn’t know that I would fail over and over and over again, and then once I was in the thick of it, well, there was nowhere to go but through.”
Amen to entrepreneurship. It’s never been easy, but it’s never been more accessible. And it a great chapter to a career story, if not an actual career.
Try Career Story Builder
Recently I launched an AI-powered tool called “Career Story Builder” to provide a mentor, coach and buddy to help people write best-sellers about themselves — and why they’re ready for the next role.
Give the Career Story Builder a try. It’s free and unlimited. I’d also love to hear your feedback about how to make it better. It’s new and I’m sure it can be improved. Send me a DM with any thoughts.
In Summary: Principles of Managing in the Age of Uncertainty
I left Cisco to answer this question with research and evidence: What does the manager of the future look like? What are millennials and gen-z seeking in a manager? Which behaviors, tactics, skills or processes matter? What’s it going to take to attract and keep the best people over the next decade? In short, how to be a great manager.
Based on this research, the core philosophy of this newsletter is rooted in one idea: successful managers in this moment in time, for this generation of talent, need to be “career dot-connectors.” The next-gen doesn’t expect to spend their entire career on your team — that’s an idea boomers grew up with. A job on your team is like a chapter in a career story to the current generation. If you want the best people on your team, you have to connect the dots between roles on the team and the career opportunities of the people working on the team.
What is the“Age of Uncertainty”? If the industrial age was about taking predictable steps up the ladder, the age of uncertainty is about finding or discovering the path of a career without any predictable steps, without an obvious ladder — it’s why being a career dot-connector will differentiate you as a manager.
How to be a Great Manager in the Age of Uncertainty: Be a Career Dot Connector is available on Amazon.
What kind of manager are you? Take my free self-assessment and learn about yourself.
So true. Great interview and advice.