podcast

We're in a new world of work and business and the truth is that a portfolio career isn't a fallback. It's a deliberate choice to build income across multiple streams, and more women are making that choice right now. I sat down with Anna Mackenzie, founder of the Anna Mac Stack Substack community, to talk about what it actually looks like to build one from scratch. And honestly? This conversation had me nodding the entire time.

What a Portfolio Career Actually Is

I feel like a lot of people hear “portfolio career” and think it sounds complicated or like something only certain people can pull off. It's not. At its core, it means you're not relying on one income stream, one client, or one business model. You build a collection of revenue sources. Fractional work, digital products, mentoring, advisory roles, creative projects. Anna calls hers the C-suite: coaching, consulting, fractional, creative.

The term's been around since the 1980s, but it's hitting mainstream conversation right now for good reason. And if you've got a retainer client, a side project, and a course you've been meaning to launch? You're already closer than you think.

Get Clear on Your Skill Stack First

Before you diversify anything, you need to do what Anna calls a personal inventory. Get clear on what you actually do and what you can prove. I feel like this is the step most people skip because they assume they know. But Anna's found the opposite with her mentoring clients, especially people coming out of full-time roles. They struggle to articulate their skills in a way that translates into something people will pay for.

So start there. What's your skill stack? What proof points do you have? The answers direct everything else.

And so once you know your value, you know where to start building. Anna's first year was what she called a “year of yes.” Every virtual coffee. Every event. Every LinkedIn connection. Every conversation. Her thinking was simple: every opportunity comes through a person, and the more people you know, the more doors you can open.

Validate Before You Build Anything

This is probably the biggest thing I took from this conversation. Anna built the Portfolio Career Operating System, a Notion-based business management tool for people managing multiple income streams, but she didn't build a single thing until she'd tested the demand first.

She posted a note on Substack and LinkedIn. Simple. Just asked if people would be interested. Three hundred people signed up within twelve hours. That was her green light.

And so she built it, gave early versions to ten mentoring clients for feedback, iterated, and launched. That first launch generated over $50,000 with a 5,000-person email list. Not because she had a massive audience. Because she validated first and launched to people who'd already told her they wanted it. [INTERNAL LINK: how to launch a digital product to a small audience]

She also used a reverse sale, a six-week launch window at an early-bird price that increased at the end. That final push drove a significant spike in sales. Worth noting.

Shoot Your Shot Wednesday

This is the part of our conversation that went viral for Anna, and I'm not surprised. Every Wednesday, she sends a cold email to someone she considers completely out of her league. A journalist she wants coverage from. A founder she wants to learn from. A dream client. She puts on a playlist, writes a well-researched, thoughtful email, hits send, and moves on.

The result? Clients won. Podcast guests secured. Connections made. One woman who adopted the same ritual ended up working with Esther Perel for two and a half years.

I was like, yes, because I did a version of this back in 2015. I cold-emailed Lisa Messenger with no introduction, no existing relationship, just a genuine ask. She ended up speaking at two of my events. We don't need to overcomplicate this. Sometimes it really is that simple. You just have to ask. [Read: personal branding strategies for women in business]

I feel like the reason Shoot Your Shot Wednesday resonated so widely is that most people are scared of cold outreach. They assume the answer is no before they've even sent anything. The weekly ritual gamifies the brave move. You're only committing to being bold once a week. That's it.

The Most Important Thing You Can Have Right Now

Anna put it simply: being high agency is the most important characteristic you can have right now. Actively seeking opportunities. Going after things instead of waiting for things to come to you.

A portfolio career requires that energy. But it also gives you something a single income stream never can: resilience. When one thing slows down, another picks up. When one door closes, you've got others open.

The bottom line is this. You don't have to burn your business down to diversify. But you do have to start. Get clear on your skills. Build your network. Validate before you launch. And shoot your shot every single week.

If you want support building a brand that creates real demand for your offers, Amplify Accelerator is where we do that work together.

Connect with Anna:

• Anna Mac's Substack: Anna Mac Stack
• Portfolio Career Operating System (Anna's Notion-based digital product)
• Instagram + TikTok: @annacmac