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Side hustles are no longer a fringe activity. They sit right in the middle of a broader shift in how work is structured, how roles evolve, and how employees see their place in an organization.
But how should an employer deal with this new workplace reality where employees may be juggling more than just their 9 to 5? Does it necessarily signify a lack of commitment? Can it actual be of value in terms of engagement and retention?
For Mark Abbott, CEO of Ninety.io, the conversation starts with the changing nature of work itself.
“Because of the way businesses are changing, there are certain positions we have had that happened last year where we transitioned a part of the way we build software from having a QA group to what’s called an SRE," Abbott explains. "We had a bunch of great engineers who were QA engineers, but the transition made it such that most of their seats were no longer necessary. The reality was less than 10% of those seats really made sense anymore, so we laid off those people, and it sucked. I don’t think I’ve said publicly, we could have done it much better than we did. But there are those dynamics where the nature of things inside an organization no longer makes sense.”
That sense of shifting ground underpins everything. Side hustles are not just about personal ambition or extra income. They exist within the context where roles are disappearing, evolving, or being reshaped by technology. They are a necessity for some workers.
“I think you’re seeing that right now across a number of different areas, certainly within customer success. You can see AI becoming better and better at addressing the vast majority of customer issues. Our AI-enabled interface between us and our customers has gone from deflecting 25% of the issues to over 85%. That’s huge. The reality is that you just need less people in customer success. Then you look around and say, are there opportunities for people to go elsewhere within the organization, especially if they’re good. But sometimes the seats are no longer there, so job security is an issue.”
Different employees, different expectations
Against that backdrop, the idea that every employee wants the same career path starts to fall apart. Abbott points to a more nuanced view of the workforce.
“One of the things I like to talk about is, what’s an entrepreneur and what’s appropriate internally from an employee perspective. There’s a book called The Archetypes Effect by James Root. Bain surveyed 48,000 people around the world, and what they found is there are six employee archetypes. The reality is not all employees want the same thing. You have some employees who are operators and just want to do 9 to 5 and do their job well, and they have other interests. As long as they show up and do the 9 to 5 well, having outside interests that do not conflict with that work, I don’t see why any company would have an issue with that.”
“There are other archetypes, like artisans. They just want to do a great job for you on a 9 to 5 basis, and as long as the outcomes are great, you both feel good about that relationship. They may or may not want to pursue outside activities.”
It sounds straightforward, but only up to a point. The tolerance for side hustles depends heavily on the type of organization and the demands placed on employees.
“The reality is there are situations in a company, especially in a high-growth, fast-paced organization dealing with a lot of ambiguity, where leaders are looking for their teams to give them everything they’ve got, within reason.”
“In those situations, there’s not a lot of room for people to have side jobs. If you go to an extreme, like China’s 996, 9am to 9pm six days a week, and you throw something else on top of that, then you’re just not going to be a great teammate. It’s complicated. I think employees and employers need to be honest with one another about the nature of the company, the nature of the seat, and what the employee is looking for.”
Drawing the line on side hustles
That honesty, Abbott suggests, has to be practical, not theoretical. At Ninety.io, the approach is straightforward and somewhat granular.
“We’ve been very direct about it. We go person by person and seat by seat, and we have a conversation. Generally speaking, if you’re in a leadership position and your side hustle is teaching yoga on Saturday, that’s alright, no issues. But if your side hustle is really starting a company and we become aware of it, we have a conversation. We’ve had people show up on LinkedIn touting their side hustle. It’s like, wait a second, let’s have a conversation around that.”
Underneath those conversations sits a broader framework built around trust.
“I’m a student of the concept of trust, and I believe that trust has three dimensions to it - character, competency and connection. Competency is straightforward, can I trust you to do your job from a skills and experience perspective. Connection is cultural, but it’s also about the mission. The work we’re doing is extraordinarily ambitious, and we want people who deeply care about the mission, the company and their team.”
“We try really hard to make sure our employees trust us and that we trust them. We’ve gone out of our way to say we will do everything we can to take care of you as long as there’s a great seat for you here, as long as you’re performing well, and as long as you’re a good cultural fit.”
Performance, culture, and commitment
That last point is where side hustles collide with reality. Performance and cultural alignment are non-negotiable.
“The red lines are if someone fundamentally can’t execute the roles and responsibilities associated with the job. The red lines are if we don’t believe they’re a good cultural fit. As you move up in the company, the level of work, the complexity of the work, and what you need to be good at all increase. The bar gets higher.
“We’re a very team-oriented company. The metaphor I like to use is we’re playing ball in the Premier League. We’ve got 11 players on the field, and we’ve got to have what it takes to play in extra time if that’s necessary. When you’re playing at that level, you’ve got to give it everything you’ve got.”
“In our company, I want everybody to be on the A team. But it’s about levels.”
That sense of levels brings the conversation back to where it started around different roles, different expectations, different allowances.
“This gets back to the archetypes. We do have places in the company for operators and artisans. To the extent that an operator or an artisan wants to do something on the side that brings them some money, that can work.”
“We have a couple of amazing designers right now. They do great work and they truly give us the extra time when we need it. One of them produces beautiful art on the side, and that’s awesome. So it really depends on the nature of the seat in terms of what’s healthy for us.”
Open conversations, not blanket policies
What is clear is that one-size-fits-all rules do not work when roles and expectations vary so widely.
“Our job is to help develop our employees and give them the challenges. I’m reticent to go down the path of relying on side hustles to develop skills because there’s more than enough work to be done. We’re a team-oriented company and we expect a high level of commitment.”
“I think the key is open discussions and honesty. Having a really good relationship with people you’re responsible for and understanding who they are and which archetype they are is critical. The research shows that close to 60% of employees never want to be a manager, yet many organizations assume everyone wants to keep rising up the ladder.”
“Have a conversation early on, even in the hiring process. This is the nature of the seat, this is the pace, this is the pressure, this is who we are as a company. Then every quarter we have conversations with our employees about where they are and what their long-term aspirations are. It’s about having a healthy, high-trust relationship.”
And ultimately, that relationship is measured in how well organizations balance competing demands.
“We want to be very balanced about high care and high performance. Not medium care and medium performance or low care and low performance. We’re very focused on leaders who are good at balancing care versus performance at a high level, and because we have these conversations, we’re capable of coaching people and helping them get to that next place.”
How to handle the ‘hustle’
Five ways to make it work for everyone..
1. Judge it role by role, not with blanket policy Side hustles are not inherently a problem. The key is whether they fit the the role. High-intensity, ambiguous roles leave little room for outside commitments, while more defined roles may allow flexibility.
2. Prioritise performance and cultural fit Side hustles become an issue only when they impact delivery or alignment. If an employee cannot execute their role or no longer fits the culture, that’s the real red line - not the side hustle itself.
3. Encourage transparency early and often Open, honest conversations are essential. Set expectations at the hiring stage and revisit them regularly through structured check-ins so there are no surprises around outside commitments.
4. Distinguish between ‘light’ and ‘serious’ side hustles There’s a clear difference between low-impact activities (e.g. hobbies, teaching, creative work) and building a business. The latter demands deeper scrutiny and discussion due to time, focus, and potential conflicts.
5. Build decisions around trust, not control Effective management relies on trust across three dimensions: character, competency, and connection. When trust is strong, side hustles can be navigated constructively rather than policed reactively.
