Fractional work looks simple – and exciting – from the outside. 

You leave corporate, land a client, and price your time. 

You breathe easier because you do the work you’re passionate about. 

In many ways, it’s wonderful. 

But here’s what doesn’t get talked about enough: 

The real challenge of fractional life shows up in about six months. 

In a bonus episode of The 2x2 Podcast, Anna Wondany – founder of Hey CMO – walked me through the network she built to support every fractional leader.

What struck me isn’t just the features; it’s the gaps she’s trying to close. 

Because most fractionals are missing the same five things at the start: 

Let’s dive into each one. 

For the full walkthough of Hey CMO, watch our bonus episode:

Most independents are excellent at their craft – like building a GTM strategy from scratch, redesigning a pricing model, or architecting a sales pipeline. 

They’re less excellent at what makes a practice succeed: 

Personally, I think I gave tons of money to the IRS in my first year – because I didn’t know any better about taxes. 

Now, I have the whole tax strategy down to a T. 

No one hands you a business owner playbook when you leave corporate, and I learned it the hard way – same as most independent consultants or fractional executives. 

What you don’t need isn’t more inspirational stories. 

You need a practical guide about business formation, pricing, positioning, and everything important during the first five years of your new career.

You need a system from someone who’s already been there. 

Ask any fractional about their tech stack and watch the spiral begin. 

Some of them don’t even know what a tech stack is – but those who do, usually have too many or not enough in their process. 

Think of domains, project management platforms, email tools, AI note takers, CRM. 

There are about 50 versions of each of these.  

But I only have four essentials in my tech stack: M365, Asana, Ramp, and ChatGPT Plus. (Add in DocuSign, if you have the budget for it.)

How I came up with these four is a long process of trial and error paired with hours of research – because I love tinkering with technology. 

But Anna’s team made it easier for everyone. 

They vetted many tools. Not just a simple list of “here’s what exists,” but a curated database of: 

If you’ve ever embedded a tool only to find out it doesn’t integrate with something else, you know the pain. 

Check out their database here. 

While fractional work promises the opportunity for higher margins than a typical corporate job, you can only serve so many clients at once. 

We did the math for this before. 

If you want to make $400K a year, you’ll need three clients paying $12K/month. 

You can increase your rates depending on your niche and experience level, but it can only work to a certain point. 

Once you aim for $600K a year, you’ll have to rethink how your business works. 

First, raising your rates is imperative. Then, it’s time to bring in some help – whether it’s another senior operator, a team of juniors, or a few team members to handle your admin and ops. 

I think this is where Anna and I went through the same path. 

We both brought in peers to support some projects, hired some juniors for team-based delivery, and outsourced some internal tasks to others who can do it better. 

But what’s surprising is that most independents don’t think this far ahead. 

They build the source of income, but not the infrastructure to scale. 

Fractional work is liberating, but it’s also isolating. 

And loneliness isn’t just social – it's strategic. 

When you leave corporate, you lose the meetings, along with: 

You become the entire leadership team and more. 

While the problem itself if universal among fractionals everywhere, they feel more personal when you’re solving them alone: 

These aren’t questions you can easily Google. You need someone to answer them knowing your context and their own personal experiences. 

That’s why Anna Wondany worked so hard to create the Hey CMO network. 

It’s an application-based community that fractionals can join – not 500 people shouting at the void of a Slack channel, but a tight-knit community where everyone can feel comfortable enough to speak. 

Fractional work isn’t new anymore, but it has had different names over the years. 

Even if fractional executives can explain what they do crystal clear, some clients still have a hard time setting expectations and understanding what the work actually entails. 

Companies still don’t fully understand the fractional model. 

They don’t know how to hire it, structure it, or value it. 

But part of Anna’s mission is building a marketplace – where businesses can find fractional leaders and understand the model at the same time. 

That’s ecosystem thinking. 

Anna Wondany showed us how Hey CMO worked — not just for CMOs, but for every kind of fractional executive.

She built a brand and community not for herself, but to help others navigate the same path. 

And whether or not you ever join a network like hers, the lesson still stands:  

If you’re going to build a fractional career, you need to start with the foundational support.  

Otherwise, it’s just freelancing with a fancier title. 

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It’s a relatively new function in Excel introduced early last year. It automatically removes empty rows and columns from the edges of a dataset.  

No more manually resizing ranges. 

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Small upgrade. Real efficiency. 

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