Encourage Freelancing. Thank Me Later
Concerned about your employees taking on extra work? It's warranted to an extent, but blocking it may cause more harm than good.
This week's #SEOForLunch is sponsored by North Star InboundIn typical Nick fashion, I want to talk about a topic that is largely ignored (but regularly discussed over beers)… freelancing, side projects, contracting, or whatever else the cool kids are calling it today.
I posted a controversial take on LinkedIn, arguing that side work should be a core component of obtaining coveted roles.
Let’s unpack what I meant, why people lost their minds, and what you should actually do as a leader.
Thank you to this week’s sponsor: North Star Inbound.
Turn Your Blog Into Your Biggest Sales Engine
Brought to you by North Star Inbound–the sales enablement SEO agency.
How? Focus on high-impact SEO strategies that target the most profitable opportunities.North Star Inbound has a proven track record of creating top-converting blog pages that deliver
thousands of leads,
hundreds of thousands in directly-attributed revenue,
and rapid payback periods on SEO spend.
They focus on the 10% of pages with the highest ROI for your brand. Basically, your content becomes your most effective sales tool.
There’s no better way to loosen tight budgets than to grow revenue quickly.
Intrigued?
Let’s Define A Few Things
One thing the heated conversation made obvious: nobody agreed on definitions. So let’s fix that.
Personal projects
For this conversation, personal projects are any paid work outside a primary 9–5 job. That might mean consulting for non-competing businesses, building or advising on a SaaS tool, or getting paid to contribute an article to an industry site.
Coveted roles
Roles where people want to “climb the ladder” into bigger titles, more responsibility, and higher compensation.
Boundaries
Some people treat any extra work past 40 hours as hustle culture and lump it in with 70-hour workweeks. The reality of business today is not ideal, and it is not fair. That is exactly why side work becomes an unfair advantage.
Side Work: The Unfair Advantage
In a perfect world, every role has time carved out for learning, experimentation, and skill growth. If you already fund that properly, you can pat yourself on the back.
Most companies do not. People are told to “do more with less,” work extra hours, and get a 3 percent raise for being “solid, not great.”
Side projects fill the gaps: skills, control over compensation, and access to new opportunities.
When you say “no” to side work, here is what you lose.
Curiosity and commitment signals
In similar roles and structures, it is hard to see who is a true driver and who is just collecting a paycheck. Side projects act as a filter. People who choose to build on the side are telling you they care about their craft. If you block that, you make it harder to see who to promote, mentor, or pay more aggressively.
Technology and tactic range
If all your work lives in one CMS with a dedicated content and PR team, your marketers are growing in a tiny sandbox. They may never choose a tech stack, write copy that has to stand on its own, or pitch and win coverage without your brand behind them. Side projects force them to learn the parts your org shields them from.
You pay for potential you never unlock
You already pay for talent. That does not mean you get the full return. The people tinkering on their own sites, apps, or freelance clients are stacking reps you benefit from on Monday morning. The ones who only ever run the same playbook look experienced on paper but lack the pattern recognition senior roles actually require.
You quietly push your best people out
High performers will chase growth somewhere. If they cannot get it with you, they will build it elsewhere. “No side work” often translates to “please take your ambition to a competitor.” They do not always leave for a higher salary. They leave for more ownership and permission to build.
If you are worried about conflicts of interest, fine. Set guardrails. Define what is off limits. Be clear about non-competes. But if your default posture is “absolutely not,” do not be surprised when the people you most want to keep are the first to walk.
The Backlash: Time, Burnout, And Fairness
Before you run with my argument, you need to understand why so many people hate it.
A lot of your team is already at the edge. They work 45 to 50-hour workweeks, commute, juggle kids, care for parents, and still try to be present partners and friends. To them, any hint that side work should be part of the deal reads as “you are lazy unless you sacrifice your family for your job.”
Then there is life outside marketing. Some of your best people want evenings for bikes, guitars, soccer, cooking, gaming, or just sitting on the couch without thinking about SEO or paid search. They do not lack ambition. They simply refuse to make their entire identity their job. That rest and those interests actually make them more creative and sustainable.
The fairness problem is real. If you implicitly favor candidates who can pour extra hours into side projects, you skew toward people without caregiving responsibilities, chronic health issues, or heavier life loads. If “must have side hustle” becomes an unofficial hiring filter, your diversity takes the hit.
There is also a very reasonable camp that says, “Just be great in your 9 to 5.” Their point: innovation and experimentation should be included in paid hours. If you want people testing and learning, you should carve out space and budget for it instead of pushing everything into nights and weekends.
They are not wrong. If your culture is a wall of tickets and no time for real thinking, the problem is leadership, not a lack of side hustles.
Where I Agree & Where I’m Stubborn
If people have to grind nights and weekends to keep their jobs, that is not hustle. That is a resourcing and prioritization problem. You control headcount, scope, and targets. If hero hours are the only way to stay afloat, the culture is broken, not the employees.
You also control whether learning lives inside the workday or gets pushed into whatever scraps of time are left at night.
If you want curiosity, testing, and innovation, you should be paying for it. This looks like:
Time on the calendar for experimentation and R&D, not “after you get through the sprint”.
Budget for tools, courses, conferences, and overall testing.
A review process that does not punish people for utilizing the benefits above.
That is the minimum if you want a team that keeps pace with how fast marketing is changing.
You also should not punish people for side work. If someone runs a small site, takes on a limited number of freelance clients, or builds a non-competing app, that is usually a positive signal. Handle conflicts with clear rules.
Blanket “no side projects” policies tell your most ambitious people to build their future somewhere else.
Here is where I am not moving.
For highly competitive, high compensation roles, side projects are a real edge. Not a moral requirement. Not a purity test. An advantage.
People who have built something on their own usually show up with:
Ownership: They fix problems instead of forwarding tickets.
Extra reps: More at-bats, in more situations, than someone who only operates inside one process.
Pattern recognition: They have broken things, shipped things, and watched real users react before pitching the idea for your brand.
The market keeps rewarding that. Not the person who suffered the most. The one who accumulated the most useful experience.
Compromise, Balance, Not Big Bad Boss
If you want to balance hustle culture with a full buffet of skill building on your dime, the formula is simple.
Inside work hours, you give people real time and budget to learn, test, and innovate. Growth is part of the job, not a hobby they are expected to squeeze in after their kids go to bed. If you want experimentation, you fund it.
Outside work hours, you do not demand side projects, but you acknowledge reality. People who choose to build something on their own often develop faster. When you see it, you recognize and reward it, not treat it as a threat.
No one should have to burn their life down to keep a job. That is on you to fix.
But you also cannot pretend that someone who keeps stacking real world reps on the side is the same as someone who only ever moves tickets from “in progress” to “done.” When the next coveted role opens, you and your competitors will fight over the first group.
So what do you actually do with this?
Set your stance in writing. Be explicit that you support reasonable side projects, outline what is off limits, and define conflicts of interest. Remove the fear and whisper culture around it.
Build the learning buffet on your dime. Carve out recurring time for testing and R and D. Give a modest budget for tools, conferences, and experiments. Hold leaders accountable for protecting that time.
Use side work as a signal, not a requirement. In hiring and promotions, treat side projects as a strong positive, not a checkbox. An excellent 9–5 track record with real ownership and results should still carry serious weight.
Reward outcomes, not volume. Promote and pay the people who create leverage for the business, whether their extra reps came from internal experiments or personal projects.
If this entire conversation annoys you, look at your attrition and how often you are scrambling to backfill senior roles. This is your signal to reconsider your stance.
If you are an employee reading this, share it upward and be honest with yourself, too. If you want to be paid like an A player, you need to show up like one, not ask for top rewards while avoiding risk and refusing to do more than the bare minimum.