Fractional Work: A Gateway Drug to Greater Success

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There’s just something about the oil and water mixture of the Great Resignation and anti-work movement clashing with talent shortages, hustle culture, and tightfisted capitalism that has spiked a powerful yearning for being your own boss. 

Or are these ubiquitous trends just several folks living out their fantasy of giving their boss the finger?

Some folks may be waking up. 

Realizing that a company can ax 15,000+ employees, have open jobs for the same roles, then report record profits to shareholders. But that’s none of my business.

What is my business? Well, it is being guilty of perpetuating the entrepreneur trend. It’s a dangerous game.

I wrote the obnoxiously titled: You’re Not Crazy: Trading Your Six-Figure Job for Entrepreneurial Freedom Is the Right Move for Entrepreneur back in early 2017. Before, it was cool. And before the emotional toll of tanking two multi-seven-figure companies.

Since I’m generally hypocritical by trade, I need to maintain my brand and pick apart the trend, even though I’d consider my entrepreneurial journey a success.

If being your own boss is your hard narcotic of choice, you should know what you’re getting yourself into with the gateway drug of fractional executive work, hustle culture, and freelancing. 

I suspect the same applies if you aspire to become a CEO—except your gateway drug is a full-on masochistic ass-kicking up the corporate ladder. Though it’s true that not everyone experiences the same side-effects during ‘the climbing years’ to C-suite success – reading about it is more fun with a sprinkling of added drama.    

While this article is about fractional work, let’s dissect the allure of being an entrepreneur first. Then we’ll discuss how to borrow some entrepreneurial pros—while lessening the pain of the cons. Spoiler, fractional executive work may be a good middle-ground. Maybe not.

You Are Your Own Boss 

Hell, yes, my dude and dudettes! You have done it! 

The admiration you get for figuring out life and sticking it to the man is exhilarating—some may even call the experience addictive. So get over to social media and share your solopreneur journey to inspire others. 

As with most things, we’re drilled with highlight reels and the tip of the iceberg. It feels great to control your destiny; however, being an entrepreneur is not for everyone. 

And we should talk more about that before you dabble with dangerous substances.

The audacity of it all creates considerable friction with family members and friends. You could buck up and pretend you don’t have fear, but those around you aren’t usually as accommodating. As a result, the journey can be emotionally isolating and shallow.

YouTube influencers would have you sluff your friends, alienate your family members “that just don’t get the grind,” and burn your bridges and ties to society. All in the name of a neon God and the hustle for a big offshore bank account and Insta-models lounging on your rented Lambo. 

That’s bullshit. Or at least it should be bullshit if you’re not trapped in the ethos of a 16-year-old incel boy.

I’ll share an account of my experiences down this path—as it can be like pulling teeth to get other entrepreneurs to open up about the speedbumps and shortcomings they faced. 

If I’m being honest, I was a 16-year-old boy for about a decade, but mostly didn’t want the seductive big-ego crap.  

It’s important to note that I didn’t become an entrepreneur out of greed or the allure of freedom—no matter how sexy those promises sound at the surface level.

Instead, I followed a path to survive. 

I lived with a scarcity mindset and started freelancing to supplement my full-time jobs. Not unlike how executives today are moonlighting with fractional consulting gigs while winding down a job they’ve lost interest in or starting a new job search. 

When I freelanced, every conversation became an opportunity—and every opportunity was a chance to survive. It was feast or famine—and I’d eat what I killed, which is a gross metaphor for sales, by the way. 

Instead of being a kid—I took freelance writing projects for a few hundred bucks. Unfortunately, scrapping for cash led to addiction—the incessant need to get more money, simply knowing I could if I worked harder. 

As a result, the meaning of my life eroded. I became a ghost of a man—shallow and meek. 

I’ve always had a bad relationship with money but having the capacity to break the monotony of bi-weekly paychecks with new income broke me mentally. I still struggle with this. 

Why would anyone focus so much of their life on this empty and fear-based lifestyle? How do you turn it off?

Well. Whether my fault or not (often it was), I have been burned repeatedly by what I call the “meat-grinder” of toxic Silicon Valley startup culture and tech. 

Working with early-stage startups is risky business. 

You’d often be out on your ass before you even knew the scope of your job. I also have a grip of clients that can share harrowing testimony of their version of startup hell. Just ask. 

Startup work is not typically the sunshine and rainbows we see floating around the aptly named unicorn companies.

With rent in San Francisco averaging $2800 for studios, it was adapt or die. Unfortunately, unemployment is a fast track to homelessness—or multi-generational living if you’re blessed with family or friends to pick up your pieces. 

So, when presented with the opportunity to buy a few more days of shelter and food, side hustling becomes more understanding, albeit an often destructive financial fix. 

I’m not another Millennial bitching, I swear. But it is very difficult to afford to “launch your career” these days. 

Either way, blame the dot com bubble, the Lehman Brothers, Covid, or fiscally irresponsible money printing. Times have been hard, times are hard now, and times are getting harder—at least financially speaking. 

You feel it too. 

The hard lessons I learned during the come-up were to be scrappy, never rely on one source for your financial well-being, always be open to new opportunities, and negotiate your ass off. Oh—and that job security is a myth. Loyalty is an employer talking point—not yours.

What’s more relevant for you is how these lessons can catapult your career, support you through tough negotiations, and help you create multi-revenue streams. 

If you can successfully launch additional revenue sources via fractional work or other means, it can lead to endless career opportunities that become relatively effortless over time. But it’s not as easy as copy and paste.

Let’s break it down. 

You’re Either In, Or You’re Out. Right?

Much of our world has relatively black-and-white rules. 

A common perception is that if you’re not actively employed, then you must be unemployed. And if you’re unemployed, you must be looking for employment. 

Where is the gray area? What is the in-between? Why must we expect to put all the eggs in a single basket and stay on the treadmill of corporate mediocrity?  

Enter the appeal of fractional executive consulting. 

Sometimes, especially with small companies, executive expertise is needed but out of reach. Or seasoned guidance is mission-critical, but it needs to be more affordable. 

Hey—there’s a real pain there. And my fellow founders know this pain intimately well. You want a Ferrari but have the budget for a Tercel. 

For executives, that means there is opportunity. 

You can fill these expertise gaps, roll up your sleeves, and share your knowledge—but you have to challenge your thinking on how you negotiate status-quo employment. And you may need to be okay with opportunities that only equate to 5 – 10 hours of work per week.

Companies such as Cerius Executive Management and Chief Outsiders — and accomplished executive recruiters such as Jack Meeks — have considered a more innovative approach to executive recruiting. I have no affiliation with the firms mentioned, but I have known Jack for years.

They’ve recognized the need many companies face to attract — let’s say, more affordable but expertly skilled — human capital. As a result, they have business models that support fractional leadership opportunities.

Other firms, such as GLG, Tegus, and Guidepoint, have been doing similar work of connecting executive leaders with short-term expertise needs for years. 

Albeit, these resources have been relatively inconsistent and scattered sources of revenue in my experience. They’re not opportunities I’d bank my mortgage on. But other more experienced and specialized industry experts often swear by the extra cash from working with these firms. 

The point I’m making is—part-time work is becoming less and less taboo. 

You don’t have to be a corporate junkie or an entrepreneurial junkie. You can simply be a junkie that thinks outside the box! Score. Pun intended.

Are You Ready To Make Some Real Money?

Finding fractional work is often a masterclass in networking, sales, and crisp negotiation, primarily if a firm does not represent you. Of course, it helps if you’ve established your career as a respected go-to expert and can specialize your position in the market. 

But specialized experience is not always necessary, especially if you have a relatively affordable rate vs. commensurate with how competitive your knowledge is in the market. Fancy speak for saying you’ll take less money than you’re worth. 

I recommend that first-time fractional work seekers ask a no-brainer rate to win the deal—or ask the other party what they believe your value to be. 

I recognize that this is contrarian advice to the negotiation tips I provide; however if it’s your first time doing fractional work—it’s your first time. You’ll need to find your rhythm before you demand a rate that damages your reputation or makes others scoff. 

A good rule of thumb is that your clients should feel like you delivered 5x to 10x the value they paid. Otherwise, they won’t feel like they got a good deal—or they won’t become the raving fans you need them to be to fill the rest of your time with more clients. 

Suppose you’re moonlighting and cheating on your current employer (and haven’t pre-negotiated these intentions in your contract). In that case, I recommend you set low expectations with any new fractional work to earn. 

Ultimately the needs of the company you’ve committed to with a W2 should come first. Not necessarily because they deserve it, but because you hold yourself to high integrity and respect others. Fancy talk for tell the truth and don’t sink into shady deceitful moonlighting.  

Now let’s say you’re a free agent. 

You’re interviewing with companies, and you have an offer. The company values what you can bring to the table and want to get started right away. But, if you’re being honest, you’re not too happy with your offer, and even negotiation Gods couldn’t turn this fluster cluck around. 

Perhaps it doesn’t meet your compensation needs, or you can’t get a good read on whether the team is full of philandering scumbags. Big middle finger to you, Dan Price.

Fine. It happens, and you shouldn’t take it personally. 

But before you blindly accept the role from a position of frailty or confidently and politely decline… Is there another option?

Is there a world where you can start working with the team on a short-term contract? Half-time? Both parties can peek under the covers and see if you’d like to work together.

Ultimately, hiring an employee is a risk. Accepting your next executive job is a risk too. What if you screw up? Is there a PAID option where you can get more information about the working relationship without continuing to interview and negotiate all your time away for free? 

I don’t know. 

You may not know either. But start considering that there are more than ACCEPT or DECLINE when presented with new opportunities. 

Furthermore, I’d like to posit the pros and cons of fractional work (aside from you getting addicted to whoring yourself out to a half dozen companies at a time to get a buck).


  • Opportunity for multiple revenue sources. The negative repercussions of losing a job are lessened because your income is spread across sources.
  • Creates a networking effect. Working with several organizations gives more executives exposure to your work. 
  • Accelerates top-level learning. You get to learn from a diverse group of experiences and business challenges.
  • Creates leverage. Creative problem solvers who don’t need to rely on YES or NO employment possibilities have less to lose, more confidence, and stronger negotiation skills.
  • Try before you buy. Getting paid to learn about what the company will be like before you fully commit can provide the necessary breathing room to make a better decision.


  • More replaceable. Canceling your contract is as easy as saying no. W2 protects your employment notably more. You’ll have to always be on your game to earn the next deal. (You should be anyway).
  • Not committed. Companies want to see team players. You may not be perceived as a team player if you position yourself in this manner. Tread lightly.
  • Outsider. You’re expected to impact our team, but you’re not one of them. Being an outsider is a similar stigma that many remote workers feel while ostracized from the HQ. You may also experience reduced access to company resources and information.
  • Limited decision-making authority. Building C-suite alignment and trusted relationships are easier when you are committed to a company. Popping in for a few meetings can limit your ability to influence the necessary change you’re (hopefully) paid handsomely to provide.
  • The agency paradigm. If you’ve ever worked at an agency, you’ll have an innate understanding of how difficult it is to manage multiple clients simultaneously—particularly when your clients experience hard problems. As an executive, it’s your job to handle hard problems. You may find yourself wishing that you increased the scope real quick.
  • Ongoing perception. Working as an advisor or fractional executive can damage your brand if you’re not mindful and keen on narrative mastery. I’ve seen too many executives grinding through how to talk about contracts, consulting opportunities, and short-term gigs. It’s still relatively taboo for many—and perhaps they are right to raise red flags. Are you committing to becoming a fractional executive? Or are you committing to be a W2 executive? Riding the line is very challenging, and you should have a strong opinion.

In summary, there are a lot of nuances to ponder if you want to leap into fractional employment or your own consulting company. It’s not a decision to make lightly or to flip-flop on.  

When you get a taste of that sweet, sweet drop of self-employed/created success, you need to know that it’s a slippery slope that’s likely not as sexy as others describe. It will change your world in both positive and negative ways. 

The same can be said for those that want to be a CEO. 

Lots of people have an insatiable lust for power. However, very few can wield its corrupting influence and maintain integrity. 

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