From one job to a portfolio career: My exact pivot timeline
Turns out, I do everything
What happens when you find yourself doing several things well—all at once— and people start paying you for them?
That’s how my “portfolio career” started.
Not with a master plan, but with a series of overlapping interests, opportunities, and increasingly blurred boundaries among work, play, and creative pursuits.
I’m not sure where the term portfolio career was coined, but Anna Mackenzie writes a very popular newsletter about it.
Content entrepreneur | Agency Founder & CEO | Bestselling author Featured in Forbes, The Wall Street Journal, Business Insider, Bankrate, Cheddar TV, and HuffPost | Join more than 6,480 people on the internet who follow me for discerning lifestyle, travel, and money content:
This kind of career path suits generalists—we’re cross-functional, and essential for companies who need people with adaptability and problem solving skills. Many stacks of skills, in fact.
What is a portfolio career
A portfolio career is what happens when your work life stops being defined by a single job title, or even industry, and instead becomes a collection of overlapping roles, skills, and income streams.
My own portfolio career didn’t start with a grand plan. It started with one job. Then a corporate job and a startup job. A desire for a career change. Some freelance clients. Then a project that turned into a product. And many retreats to creativity.
I recently saw this post from Justin Welsh, the AI content work-fluencer who is a beacon for my pals like Amanda Goetz, when it comes to building a newsletter and content business.
I don't follow too many work- or career-fluencers, because I find many of them talk at people or speak in overly simplified platitudes.
It's mind-numbingly boring.
But the ones I do pay attention to are those who have actually built something impressive and are humble about it, and perhaps most importantly, are generous with knowledge and transparent about their journey.
This post prompted me to break down my own career phases, which look a little like this:
Phase I
2002: Hired in financial services at a loan brokerage, learned the ropes, left
2003: Hired in financial services at a Fortune 250 homebuilder, promoted, left
2006: Hired as a VP at one of the nation’s largest banks
2008: Left for business school, pivoted to financial broadcast journalism
Phase II
2009: Hired for a major financial TV news network in New York
2010: Hired for a major financial TV news network in London
2011: Contract for news network not renewed. No work visa → back to New York
Phase III
2011: Hired for retail jobs. Hired for freelance work at a Business Intelligence firm and marketing agency
2012: Hired as a global marketing manager for an international rug design company, fired
2013: Hired as a content manager for a financial services marketing company, worked remotely
2014: Published my first book
2015: Laid off
2015: Hired as a content manager for a major fintech startup, placed on PIP (performance improvement plan), left
Phase IV
2016: Started a business, a financial content agency
2017: Self-published the sequel to my first book
2020: Accepted an earn-out/acquisition offer to sell my company to a bigger one
2023: Fully exited, completely and utterly burned out
Phase V
2023: Started writing weekly Substack for mental fortitude, continued with seasonal consulting work for content clients
2024: Started food writing
2025: Creating and building new things
Phase I was all about learning a skill pretty much straight out of college, and a super rewarding time professionally and financially.
Phase II was an exciting beginning for a shiny new trade, but with low financial reward.
Phase III was me slogging to find a new career fit. I eventually did, and learned a ton about leadership, different work cultures, and what it would take to build a profitable, remote business.
Phase IV was me building something from the ground up and selling it. But I sacrificed a lot and exhausted myself.
Today is all about building, inventing, and creating—and applying all of my learnings in the work I do for myself and others.
My career definitely wasn’t linear; it didn’t always resemble a ladder. Perhaps more like the branches of a tree.
Maybe one day you’ll find yourself writing, consulting, building, advising, teaching or creating digital products; doing many things well, all at once, and being paid for them.
What matters most is that you eventually find a rhythm that suits you, your values, and gives you what you need to be happy.
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Until next time,
Shindy
On Instagram + TikTok
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