Is the Great Millennial Career Crisis Solvable?

👀 Hello! Well, it’s been a doozy of a week. Another creator found massive virality by regurgitating my thoughts and ideas on the Millennial Career Crisis without credit. You can read about what happened– and my response– here. What sets me apart from this creator (and the many who have hopped onto the trend since), is that since I’ve been trying to crack the Millennial Career Crisis for 11 years and writing about it for 5 years, I already had a working thesis on how we move forward. So that’s what I’m sharing with you today!

The question: Can the Millennial Career Crisis be solved?
My answer: Yes, but it’s not just on you + me.

We solve the Millennial Career Crisis by replacing the old promise of "arrival" with a new guarantee of mobility.

Millennials were trained to hunt for the perfect job that will finally make things click, but we’ve seen that that’s a trap in a labor market built on constant churn.

The new goal should be: individual clarity + optionality.

1) You + Me: Shift from “find your one calling” to “build your career operating system”

What individuals can do (without pretending it fixes everything):

• Stop using job titles as the unit of identity. Use problems you solve, conditions you need, and strengths you compound. (The Energy Resume approach is basically the antidote here: it’s a map of what actually fuels you.)

• Design around constraints, not fantasies. Not “What would I do if I were fearless?” but “What would I do if I wanted to still like my life in 18 months?”

• Treat the job search like a flywheel. The “try harder” narrative burns people out; the “experiment smarter” approach creates momentum.

• Build a two-track plan:

  • Track A: the next role that stabilizes income + builds market leverage

  • Track B: the assets that reduce long-term dependence on any one employer (skills, relationships, portfolio proof, audience, products, advisory, fractional work– whatever fits). This is called a Portfolio Career.

This is the psychological shift: from “arriving” to iterating. Millennials were promised that we would eventually arrive, but instead the success metric is agency.

2) Organizational: Stop managing humans like disposable line items

Companies can’t keep preaching loyalty while operating like commitment-phobes. If we want to reduce the crisis at scale, organizations have to rebuild the employment transaction deal in ways that match modern reality.

What employers should implement (and what we can advocate for):

• Transparent progression that doesn’t require management. More “expert tracks,” skill ladders, and pay bands people can actually see.

• Internal talent marketplaces that work. Real mobility pathways: short-term projects, rotations, internal gigs, reskilling budgets that aren’t performative.

• Layoff hygiene. If layoffs happen, treat them like a failure of forecasting (not an inevitability) and standardize severance, benefits continuation, and redeployment support.

• Workload truth-telling. Stop praising “high performers” for absorbing dysfunction. Reward sustainable systems, not martyrdom.

• Respect the transaction openly. The future of work is transactional; pretending it’s a family just creates betrayal. A healthy transaction is still a relationship—it’s just honest.

3) Policy and economics: Make stability possible again

You and I cannot “self-help” ourselves out of housing costs, medical risk, childcare expense, and debt burdens that shape every career choice. If we’re serious about solving the crisis, the floor has to rise.

High-impact levers that we must continue to demand:

• Portable benefits (healthcare, retirement, paid leave that travel with you across jobs, contract work, and unemployment gaps)

• Childcare support that actually reduces career penalties for parents (especially women)

• Housing supply + affordability policy (because “career choices” don’t mean much if geography traps you)

• Stronger wage growth mechanisms (bargaining power, pay transparency enforcement, fair scheduling, misclassification crackdowns)

• Public investment in reskilling that’s linked to real jobs (and not just tuition funnels)
  

  This is the macro shift: just like a climate crisis is less about “personal responsibility” to use paper straws, this Career Crisis is systemic.

4) Culture: Rewrite the meaning of success for the post-linear era

Millennials are grieving a story we were sold: that ambition is a straight line and “making it” looks the same for everyone. We need a cultural update that treats non-linearity as normal, not shameful.

Let’s build these new cultural norm:

• Decouple worth from productivity. Not as a cute slogan, but as an actual practice: rest, boundaries, identity beyond output.

• Normalize career “seasons.” Not everyone is in a climb season. Some are in a rebuild, care, health, exploration, or consolidation season.

• Treat your ambition like a volume dial that you get to adjust based on where you are in your life, not a personality trait that you either have or you don’t.

• Name the system out loud. When people understand the economic and organizational forces at play, shame loses its grip.

This is the cultural shift: from “prove yourself” to build a life.

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Love the newsletter but want more? Did you know I put together an entire course called Pivot with Purpose? Think of it like a supercharged version of all the best content from this newsletter, tailored to help you nail your career goals.