I Got Laid Off Twice. Now I Work For Myself.

How Losing Two Jobs Made Me a Better Strategist, and Taught Me to Build a Portfolio Career

Kintsugi, the Japanese art of mending pottery with gold.

First I got laid off. Then laid off again.

Four years ago, if you’d asked me what I did for a living, I would have reflexively rattled off a single job title, with one line and one company. Read as: I was a very loyal employee…

These days? I’d need a second slide because I’m a Foucauldian “entrepreneur of the self”.

I’m a consultant. And a writer. And a strategist. And a mentor.

Sometimes, I’m also a fractional executive, a crisis counselor, a ghostwriter, and on particularly chaotic Fridays, a reluctant bookkeeper. Although AI has really helped with that last one…

Welcome to the portfolio career.

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What Is a Portfolio Career?

It’s not just having “a bunch of jobs”. It’s building a professional ecosystem. One where your income, identity, and impact aren’t tied to a single employer’s whims or a LinkedIn headline. A portfolio career is part strategy, part self-preservation, and part creative defiance of the old 9-to-5 social contract.

Some of it pays in cash, some of it pays in kind, and some pays in community.

Some of it doesn’t pay at all…. but it might, someday.

I started mine by accident. I was laid off. Then laid off again. At some point, I realized I could keep chasing the elusive “next big role”, or I could start curating a life that fit me better than any single title or corporation ever had.

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The Big Myths (and Bigger Truths)

Myth 1: You need to have it all figured out.

• Truth: You need one thing that someone will pay you for. The rest grows from there.

Myth 2: It’s risky.

• Truth: Putting your entire livelihood in one company’s hands? That’s risky. Diversifying your income? That’s called hedging. It’s smart risk management.

Myth 3: You’ll look flaky.

• Truth: You’ll look dynamic. If your narrative makes sense, people won’t question the patchwork, they’ll admire your quilt. Besides, previous generations honestly have no idea what it’s been like growing up as a Millennial and/or Gen Z in the post-2008 global financial crisis world of work. (I don’t necessarily agree with this take, but see here for a more aggressive view on the elite gerontocracy).

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How I Structured My Portfolio:

1. Consulting: Through my LLC, I advise on business development, M&A integration, and HR transformation. Sometimes for startups. Sometimes for private equity. But always on my terms. This has been really empowering.

2. Writing: Between Substack, Kindle Direct Publishing, and royalties that barely cover my espresso habit, I’ve built a small but mighty readership. Like anything, it compounds over time.

3. Mentorship and Pro Bono Work: This is where my heart lives. Mentoring LGBTQ+ founders and early career professionals through organizations like Out4Undergrad. Supporting students who don’t know what they don’t know is also very empowering. Showing up for others just like mentors once showed up for me ensures I pay it forward.

4. Contract Gigs: These are the wild cards. A 2-month project here and a 3-month engagement there. I take them when they align with my values and when they add something new to the mix. And, when I get to work with exceptional people and emerging talent.

5. Passive Income: This one’s still a stretch, for right now. As I alluded to last week, it doesn’t yet pay the rent… but hey, in the last 24 hours, I made 10 cents from someone in Australia! And symbolic income still counts… and compounds over time.

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What I’ve Learned (Thus Far)

• Your resume can be the menu: Not everything has to be bundled into one job. Give people options. And if you’re early career, get as many diverse experiences as possible. You’re building up your skills-based repertoire.

• You can design your work around your energy, not the other way around: I learned this way too late in life. If something isn’t working for you, flip the script and rewrite the rules: maybe you’re a morning person, maybe you’re a night owl.

• People respect intentionality: If you own your professional narrative, they won’t ask why you’re doing so many things. They’ll ask with amazement how you pulled it all off.

• The traditional career path is increasingly fictional: Or at least, less of a default path than it used to be. As a Millennial, I learned this the hard way: laid off 2x. I now wear this with a badge of honor. Because, honestly, who hasn’t been laid off in a post-pandemic world?¹

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A Portfolio Career Isn’t for Everyone. But It Might Be for You If:

1. You’ve been laid off and don’t want to feel that powerless again.

2. You have career trauma from a less than sane workplace. (And who doesn’t?)

3. You’ve outgrown the constraints of a single title, role, or org. chart.

4. You’re multi-passionate and have always struggled to fit in one lane.

5. You’re craving a life that’s more bespoke-custom than cookie-cutter.

6. You don’t play office politics, or you play to lose…

And If three or more of these apply, you’re probably already curating a portfolio career… whether you call it that or not.

Whether you’re a mid-career exec or fresh out of college, this applies to you if you’ve ever wanted more autonomy in your work.

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Final Thought: From Patchwork to Power

I used to think of my career as something I needed to fix, like a broken porcelain platter that I had to piece back together, and more importantly, get back on “track”.

It was as if I was falling behind others whom I went to school with, or worked alongside, on the linear path of professional advancement.

Now I see it more like kintsugi, the Japanese art of mending pottery with gold.

The cracks aren’t flaws in me or my career. They’re features, and they’re the visible evidence that I’ve lived, pivoted, endured, and kept building despite the challenges. If there’s one thing I know, it’s that I’m incredibly resilient…

Any company would be lucky to hire someone like me as an employee. But someone like me now works for himself.

This isn’t a Plan B. It’s the portfolio career.

- Alex Randall Kittredge

Current Fractional Business Development Lead. Fractional People/Operations Consultant. Former Senior Program Manager. Fractional Chief of Staff. Strategic Advisor. Substack Essayist. LGBTQ Career Architect. Dog Dad. Husband, and last but not least “Guncle”.

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If you’re building a career that’s less like a ladder and more like a mosaic, you’re not alone. Subscribe and let’s design it together. Or hit reply. I’d love to hear how you’re stitching or glueing it together.

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Coming soon: How to start a portfolio career while still employed.

1. In April 2020, the number of unemployed people who were on temporary layoff soared by 16.0 million to 18.0 million, reflecting the effects of the pandemic and efforts to contain it. In total, nearly 21 million people in the United States were unemployed at the peak of the coronavirus pandemic.

In late 2021 and early 2022, when employers realized they’d over hired, and the Federal Reserve began to raise interest rates, companies once again laid off workers. (Sometimes the very same employees they’d just hired at a premium). Call it LIFO, FIFO, or poor strategic workforce planning, it’s just plain unfair to employees caught in the lurch of the business cycle.

Source: Bureau of Labor Statistics

Legal Disclaimer: Any references to individuals, companies, or events, past or present, are made in good faith and are not intended to defame, malign, or harm the reputation of any person, organization, or entity. The views expressed are solely those of the author and do not represent the views of any current or former employer, client, or affiliated organization.