The future of careers.
5-year paths inside 30-year systems.
Rich Future is a newsletter about the future of work and money, written by a CPA. By day, I advise startups on finance strategy. By weekend, I write for builders and investors who want foresight on opportunities before they’re priced in. If you were forwarded this post, you can subscribe here.
I’ve been thinking about careers.
For most of modern history, a career lasted about 30 years. You trained once, entered a field, then gradually advanced inside it. Your career had a shape that was legible to you and everyone around you. Your parents could explain said career to their friends at dinner. For me, that was my finance career.
That structure is crumbling.
I’m seeing a growing number of LinkedIn bios that read like resume speed dating.
Founder.
Advisor.
Writer.
Former operator.
Angel investor.
Recovering 9 to 5er.
Occasional DJ.
Career professionals are cycling through different careers every 3-5 years… sometimes by choice, and more commonly, because industries are evolving faster than any single skillset can keep pace with. Most of the conversations I see around this shift focus on the career part. How to pivot. How to reskill. How to stay relevant. That’s fine.
What I find more interesting is that every major system of adult life was designed for the 30-year career. We're living 5-year life paths inside 30-year systems. What happens when the assumptions our systems were built on stop being true?
Financial planning assumes a predictable income curve: accumulate steadily from age 22, peak around 50, draw down in retirement. Pensions, 401k strategies, disability insurance, 30-year mortgages pegged to 30-year income trajectories… these financial vehicles are built on the assumption of stable employment, but they stop working if the average career now resets every few years. There’s a growing skill gap (and infrastructure gap) tied to this shift from maximizing earnings on a single trajectory to managing transitions between them and maximizing your earnings across multiple careers, often simultaneously. Most financial products haven’t caught up to this yet which means most financial advisors haven’t either.
Geography was a one-time decision for most of the 20th century. You moved for the job and stayed for the job. But if work is happening in 3-5 year chapters, then geography becomes a recurring question. It gets harder to justify a permanent move to the city where your industry is. Renting makes more sense for more people for longer chapters. Real estate markets that depend on employer-driven migration (ie: Seattle, Detroit) lose their growth engine. And there’s cities like Austin, where there are about equal inbound and outbound population flows. It’s interesting to consider how many other cities will become revolving doors. I think we’re about to see a wave of businesses serving people who don’t stay anywhere for 30 years with things like portable financial products, flexible housing, and platforms that enable people to plug into community across multiple cities.
Identity is another system that feels under-explored. I’m seeing more content and online coaching aimed at helping people transition from one career identity to another which is partly growing in popularity because of AI’s disruption to the job market but if careers are 3-5 year chapters, we’re looking at 8-12 identity transitions across a working life. An identity crisis isn’t a one-time, mid-career event anymore. Grieving an old version of self begins to follow a recurring rhythm. There will be people who can’t metabolize that and experience every transition as a personal crisis. Most of the identity-transition support emerging today assumes you’re moving toward the next stable identity. That assumption may not hold. I see psychological flexibility as one of the most important skills of the next decade.
Education is one of the clearest systems built for the 30-year career. The traditional model assumes you front-load training, enter a field, and compound that knowledge for decades. A four-year degree for a 30-year career had clear ROI. But a four-year degree for one 3-5 year chapter?… Not so much. Learning must evolve to become continuous, modular, and less tied to any single domain. Meta-learning (learning how to learn) and cross-domain thinking become core competencies, leveraged across chapters.
Relationships were historically organized around stable work identities. If both people in a partnership are cycling through career chapters on different timelines, the relationship has to be more flexible than either career. And if your work friends churn every few years, you’re rebuilding social connections from scratch each chapter unless you’ve invested in relationships that exist outside of work context.
Every major system of adult life was designed for stability: financial, geographic, psychological, educational, relational.
Income followed a curve you could predict at 22.
Income no longer follows a curve you can predict at 22.
I’m on my third chapter now, building Rich Future. Next week, we’ll be celebrating its one-year anniversary! Will save my in-depth reflections for then but for today I’ll say that I’ve learned more about careers, identity, and relationships in the past 12 months of building a media business than I did in 12 years of corporate finance.
We’re living 5-year lives inside 30-year systems.
The people who see that early will build richer futures.
A few other things on my radar this week...
Anthropic invests $100M into the Claude Partner Network to help enterprises adopt Claude.
Peter Sarlin is helping companies prepare for the age of quantum computing via new startup, QuTwo. Previously, he sold his company to AMD for $665M…
AMI Labs, co-founded by Turing Award winner Yann LeCun, raises $1.03B to build world models. World models are the next AI wave.
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