Today I speak with Nola Simon, a remote work futurist and leadership expert about Portfolio Careers & Remote Work 2026 and Why Flexibility and Optionality Isn’t Just a “Nice to Have” anymore – It’s Now Survival.
We talk about The Trust Crisis at Work and Why Return-to-Office Mandates Are Failing Women and working mothers first.
From Corporate Employee to Remote Work Advocate
Mel: I’m so excited to have you here today with me.
We’re going to talk about the future of work for women, for mothers and what we’re moving to because you are a remote work futurist, but also you are a LinkedIn top voice, 2024, 2025.
I’m really happy you can share some of the learnings and the trends and where you see work going.
Nola: Thank you so much. It’s a pleasure.
Mel: It’s interesting for people to see what kind of background you’ve come from and how you moved into this very interesting space of guiding companies and people towards meaningful work and how we can connect better.
How did you find your place here?
Nola: So I’m in Canada. I’m 45 minutes north of Toronto.
And I’ve actually always lived in a small town north of Toronto since I was a baby.
And I come from financial services. So I work for a global insurance company who also happens to own a bank.
Toronto traffic is around the worst in the world. My commute actually grew to be two hours one way. My kids were born in 2005, 2007, and by the time they were school age, it became challenging for me if something happened during the day to get home to them. So it was a challenge, and we had limited family support.
So that’s where I started with hybrid remote.
There happened to be somebody else that shared the same babysitter, and she worked in the same company as me. She had been there so long that what they had granted her was permanent remote. And so I went to my boss and I’m like, well, if she can do it, why can’t we work out something? And that’s how he started getting involved in pilots. This is all the way back in 2011. I started advocating for this. So by the time I actually left the company, I had actually transformed over to a fully remote employee.
KEY LEARNING: Flexibility often requires advocating for yourself and finding precedents within your organization.
Don’t assume the answer is no—look for proof that alternative arrangements already exist.
I think that’s very much a topic for women.
Being able to work remotely, it just gives us women, mothers, particularly, a chance to have some agency again in the kind of work that we pick.
Mums sacrifice pay and the type of work they do in order to be able to care for their families and to be a good parent.
So I think helping companies and also workers achieve some level of normalcy and something that we feel is very much an integrated part of our lives is really important.
Who Nola Works With (And Why Caregivers Need Better Support)
Mel: So is this the kind of work that you’re doing right now? Who do you work with and how do you support?
Nola: So the ideal is always organizations who are interested in supporting their employees better.
So that could be government, that could be nonprofits, but it could also be organizations who just have a vested interest in wanting to support their female employee, actually, any caregiver really better.
So it doesn’t have to be women, doesn’t have to be parents. There are people who have to struggle with elder care as well, too.
I used to have a friend who, she had older parents who had never really learned English, her parents were Italian, and to get any kind of support workers to come in and be able to support them, she had to facilitate it because she was the only person who understood their medical history and she was the only person who understood the language to be able to convey it because it’s a rare skill to have that support in the language you need it.
And Canada is very multicultural. So that’s not a unique thing.
So it could be any company that’s interested in providing support to caregivers.
KEY LEARNING: Caregiving isn’t just about children—it includes elder care, family medical coordination, and language barriers. Organizations that understand this retain better talent.
AI, Humans, and the Work That Actually Matters
All of a sudden, there’s this narrative that we’re going to need fewer employees, that AI doesn’t need to work or sleep or how does this integrate into work?
Well, AI doesn’t need to be in an office either because it’s not real.
So if we accept that that’s going to actually impact how we work as well, too, which it might, then it’s our vested interest in how we make life and work more human, because the work that humans are going to do is going to be not the stuff that’s transactional that AI can quickly pick up.
So the work that humans do is relational. It’s the compassion, the generosity, the wisdom that only humans can bring.
But in order to bring the best of us so that we’re performing that type of work better, we have to be happy. It’s in company’s best interest to create conditions that employees are going to thrive in. And one of the ways that employees thrive is if they have the autonomy and the agency that you were talking about, we can make the experience of work for humans.
Even if we’re using AI to augment the work, that’s how we can make it better.
KEY LEARNING: If AI will handle transactional work, human value will come from relational work—connection, compassion, wisdom. This requires companies to prioritize employee wellbeing and autonomy, not just output.
So it’s not just what’s happening in 2026, but where do we see this going? And what has to happen because organizations have to rejig how jobs are done, what tasks are done, and what that work really looks like.
The Real Reason Behind Return-to-Office Mandates
Mel: There was so much media coverage and so much movement pulling people back into the office. And you shared an article around this as well, where that’s coming from and why that’s happening. Why is that happening?
So I want to pause here for a very quick moment because if you are listening as a woman navigating work and building meaningful work for the future, this part matters.
What Nola is describing isn’t just a workplace trend. It’s a structural mismatch between how work is designed and how women actually live.
The return to office conversation and the erosion of trust that she mentioned, the fear around AI, none of this is happening in isolation and especially for many women, mothers, caregivers, and multi-passionate women like we are, the costs of pretending it’s just business as usual is simply too high.
What I wanted to listen for in the rest of this conversation is this. Where do you still have agency and what can you build in a way that works for you and how?
Because even if organizations are slow to change, you are definitely not powerless. And that’s where we move to next, from waiting for permission to designing work that actually supports your life and your family. So let’s continue.
Nola: What’s happening with the return to office mandates that are so often in that news and the whole circular debate that’s happening with that?
It’s really just companies are invested in commercial real estate. So the infrastructure is there. It’s a paradigm they think that work has to be in order to go forward.
And we don’t want to sacrifice our identities and that perception of power and control. Just because you need extra time and flexibility, we need to see you here in person because that’s how we trust that work works.
Honestly, it comes down to that investment in real estate as well, is if you accept that flexibility is the way of the future and that people are going to be working less in an office, what does that mean in terms of the value in the future, whether we’re looking three, five, 10 years from now, what does that look like?
And how do we adjust to that? People aren’t really having that conversation.
KEY LEARNING: Return-to-office mandates aren’t about productivity—they’re about protecting commercial real estate investments and maintaining traditional power structures.
This is why leadership messaging often contradicts employee experience.
But what I’m finding is people, individual employees, and that includes leaders themselves, too, are making decisions that get them closer to the flexibility that they need to support their lives and making those choices that’s going to actually prepare them to do the work that’s going to get them more in line with what they have to be.
How Policy Lags Behind Reality (And How to Work Around It)
I did it.
If you actually look back just even at my story, when I first started asking about remote work, we didn’t have laptops.
There was only a specific team in our office that had laptops. We all had desktops.
So you literally had to be in the office to be able to access the computer. That’s not the case now.
The majority of staff obviously have laptops. They have phones. They have different devices that they can use to connect.
But it’s the policies and procedures and the way that the organization is structured to be able to provide that work.
I had to switch teams because only one particular team was allowed to do any kind of remote connection into the office at the time.
So I made the choice to switch teams, even though I enjoyed my team members, I needed the flexibility.
You have to be very clear of your terms. People are going to start making those decisions to get more of the flexibility to provide the support that they need for their teams.
KEY LEARNING: Sometimes flexibility isn’t about changing your company—it’s about making strategic moves within it. Audit what teams, roles, or departments already have the setup you need, then position yourself there.
The Trust Crisis That Nobody’s Talking About
It’s for all this talk of collaboration, for all this talk of the experience in the office is better.
There are people who know that that’s not true because their work isn’t actually designed to be collaborative, and you don’t listen to them.
There are so many studies that come out that say that trust is really eroding in leadership, and that’s a critical thing.
So employee experience is well down, trust is eroding, and then you add AI into the mix, and the narrative around AI right now is we can use this to eliminate headcount, so therefore we don’t need staff at all.
That doesn’t actually improve the trust.
So now you’ve got this fear that’s being introduced as well too.
This is how it’s working currently, but I’m not sure what this is going to look like in a few years because I don’t see that trust improving.
So I think that unless organizations and leadership start to look at this and how behavior and psychology really play into it, they’re going to find that it’s very challenging to attract the best of the best if they continue with this return to office narrative.
KEY LEARNING: The combination of return-to-office mandates + AI replacement narratives + lack of transparency = trust erosion.
Pay attention to this pattern—it signals a company in identity crisis.
You’ve always had a central head office, but you’ve got branches around the country.
Those people are working remotely together. And so the branch is in person, but the head office staff is working remotely to those branches.
It’s always been that way.
It’s really just what we’ve called it and the narratives that we’ve built around that.
So if you don’t feel as a leader that you can build those types of connections and collaborations, that’s a skill issue.
So you need to up skill because it’s the way of the world.
And if you’re actually online stating that you cannot build connection that way, how do you think it’s going to work with AI when it’s becoming more and more asynchronous and there’s it’s just the opportunity to actually connect it needs to be studied it needs to be connected and if you can’t connect remotely in a world where connection is the norm then that’s a you problem.
Voluntary Attrition and the Hidden Agenda
And then you start seeing layoffs because that’s the other thing is that’s where the trust gets undermined is, are people actually hoping for voluntary attrition when they make these announcements because their head count is too large?
And if people leave voluntarily, no severance is required.
So that’s where it’s like employees who have discernment are looking at these patterns and seeing that the actions and the words don’t necessarily line up with what the intent is and what the strategy is.
So leaders are saying one thing and doing another.
And that’s all undermining trust.
And that’s not going to get better with this narrative around AI with the potential of impacting jobs and headcount too.
KEY LEARNING: When return-to-office mandates are announced suddenly or rigidly, ask yourself: is this about performance, or is it about reducing headcount without paying severance? Pattern recognition here is protective.
So what is your intention about workforce in general?
How do you see work, the future of work?
And how does that involve humans?
It becomes a really essential conversation to have because if your vision is to have maybe to reduce your organization from 500 people down to maybe you’re hoping for 20 to maximize your profits is that an organization where you see yourself being set up for success?
Who are the people that you want to keep and people are assessing this which people always do because it’s their livelihood.
They pay attention to what leaders say.
They pay attention to the feedback that they ask for and then how they take that feedback and enable it and action it.
And what they often see is that they give all this feedback and then nothing happens. Nothing changes. And that’s undermining trust. And so when you’re constantly seeing this and it’s a repeating pattern, are you going to make the decision to stay or are you going to make the decision to get a different job, make different choices that’s going to make you feel more secure? And people will do that, especially women.
Why Women See Through It First
Women are really good at detecting patterns and communication in general.
So women historically have been the community builders.
If you look at the employee resource groups that are formed, a lot of times the people who are leading those types of employee experience situations, the HR arm is very heavily female dominated.
So are ERGs. So it’s the women who are noticing how people are really connecting.
And a lot of that work is always being done for free. And I actually think it should be paid for one.
But also, it’s the most valuable work that we’re doing out there because that’s how people are really connected.
KEY LEARNING: Women’s pattern recognition isn’t paranoia—it’s a skill.
If you sense misalignment between leadership’s words and actions, trust that instinct. It’s data.
So again, are you as a leader paying attention to the way that your organization actually works because there’s the values, the mission, the statement, everything that you’ve crafted and you’ve put on paper and you put posters around your office about how you want the organization to work?
But what’s the behavior on the ground?
+What’s the real culture in your organization?
Because culture is an offshoot of behavior and are you actually living the values that you say run the organization or are you actually living other values that play out in behavior?
The Rise of Fractional and Portfolio Work for Women in 2026
So I think it’s interesting too about the way organizations work is a lot of times they’re now bringing in fractional and contract people.
They’re having these people work interrelated.
So now you’ve got full-time employees.
You might have some part-time employees, but you could have contractors, and then you could have people who are fractional.
They’re working on different types of contracts. How does that get managed? How does that all interplay?
It becomes a really different thing because the contractor isn’t going to want to attend your all-hands anything session because, well, you’re talking about benefits that they’re not eligible for.
And they work in a different way than the full-time employees.
So that’s where it’s like that whole collaboration piece is interesting because organizations aren’t necessarily going to be just comprised by the full-time employees the way they have historically.
There’s more flexibility in how we’re actually working with people and attracting people with the best, most competitive skills.
KEY LEARNING: The workforce is already fractured into full-time, part-time, contract, and fractional roles.
This creates opportunity for women to design hybrid career portfolios that fit their lives.
Portfolio Careers Aren’t Side Hustles—They’re Safety Nets
That’s the other aspect that I see for women in particular as well, too.
How do you build in that flexibility that you might need when pay isn’t really changing and companies aren’t really promoting and everything is frozen, and you still need more money because everything is increasing in cost because of tariffs and just the way of the world right now, that portfolio career where you can actually work online.
You can get paid through a blog.
You can work part-time as a community manager.
You could do part-time job as a census taker. That sort of thing.
It’s all like you’re building out a community, a portfolio career where you have a central job, but you might be doing the other things on top of that too.
You’re then CEO of your own business and full-time employment is just actually a part of it because there’s no limit to who have assets and ability to walk away from you if the environment that you create isn’t the environment that they need.
They have options.
Mel: Is that what you, where you see the future of work now going for women, particularly portfolio careers and build different income streams for ourselves?
Nola: Honestly, that’s a trend that’s been going on for a very long time.
Selling Mary Kay, that sort of thing that people have done on the side.
And historically, it did tend to be women who would do those types of things because it was the parties and that social aspect and that community thing is how can you benefit in those types of networks and those types of relationships.
This is an extension of that possibility has grown beyond just who you can actually host in a party in your living room on Saturday.
So it becomes the normalcy in the future.
Because right now, especially as a corporate woman, I think it’s still very much normal to have your 100%.
That’s what I’m doing.
And your identity is kind of locked into that role and job profile.
Well, I think that that is true, but it’s also fear-based because, and it’s a way the policies are designed because a lot of times organizations, especially large global organizations have a lot of rules about how you can have a second job, what disclosures you have to do if there’s any kind of conflict.
How to Build a Safety Net and Optionality While Still Employed
In the organization I worked with, they didn’t necessarily, they had rules in place where they didn’t actually want anything that was knowledge related.
So you couldn’t go out and sell insurance for another company, that sort of thing.
But I worked with somebody. She was a photographer. She was in the communications team.
Always ran her photography business on the side because it had nothing to do with the main business of the organization.
So she would take pictures of families and weddings, all that stuff, had nothing to do. And the organization had no problem with that.
Because it was clearly something that she was doing on her own time.
Operating completely separate had nothing to do with the reputation of the organization.
So do I think is possible for employees to create that kind of stuff and do that on the side?
I think it’s honestly a really good thing if you have the ability to do that because she also got laid off.
And with her, she started right away because that business had already had a 10-year runway. And she didn’t have any blip in income because she just went full-time with the photography business and was able to actually be really successful.
KEY LEARNING: A side business with a long runway becomes an insurance policy. When layoffs happen, you don’t start from zero—you scale what’s already working.
Mel: So building that alongside your normal role and as a strategy for the first few years, as a safety net, as a strategy into the future?
Nola: Exactly.
Everyday Futurism: Running Scenarios Before You’re Forced To
So when you’re thinking about identity and your work and your relationship with your organization, I encourage people to run scenarios of what happens if.
So if you look at your organization, the organization I used to work with, they would do layoffs every November, it was clockwork. Is it likely at one point that I won’t survive that?
What does this look like?
And run those scenarios. What does it feel like if you lose that?
And how does it impact your identity?
How does it impact your work?
How quickly do you think you’re going to be able to find another job?
What does your network look like?
Do you have an updated resume?
Who would you turn to?
Who would support you?
Who would help you?
And if you’re, this is futurism.
This is what I call everyday futurism.
It’s not that you’re running predictions.
It’s imagining what would happen if something became true.
And if you’re noticing trends, especially if you combine the trends, so, for example, if you’re seeing the idea of portfolio careers and you’re also seeing the idea of AI and then you’re also seeing the idea of organizations laying off staff, if you’re looking at the convergence of all those three, create a scenario where you wake up one day and all of that has actually come true.
What does it feel like? What does it look like? When you wake up in the morning.
Who are you living with?
Who are you responsible to start to imagine it and start to feel it in your bones?
And then you can start to see what options are maybe going to feel better for you as an individual. And then you can start to live that.
KEY LEARNING: Everyday futurism = imagining multiple “what if” scenarios and emotionally rehearsing them. This builds resilience before crisis hits.
The Power of Pre-Living the Future
There was actually a large scale scenario that the futurism company that I studied with did.
And they did it 10 years before the pandemic happened.
And it was a scenario based on what would happen if there was a global pandemic and they knew from that that there would be difficulty with masking there would be difficulty with rituals so weddings and funerals and people wouldn’t want to stay home and miss that type of thing that gathering instinct would become challenging.
They knew from their scenario that they’d run that this would be a problem and so but they imagine that 10 years beforehand.
So after the pandemic, they actually followed up with people who’d be part of the scenario initially to see how they had handled the pandemic and whether it was stressful for them.
And the people who had been part of the scenario, what they found was because they had imagined what it would feel like and how they would cope and what their reactions would be and how they would influence and how would impact their work, they coped so much better than people who had no idea that that was ever coming.
They reported really positive impacts because they had run those scenarios.
KEY LEARNING: Mental rehearsal of future disruptions builds psychological immunity. People who imagined pandemic scenarios coped significantly better when it actually happened.
So you can prepare yourself for the possibilities of what you think the future might bring. And whatever that is, you can create that. You can imagine that yourself. There’s no one right answer. It’s just what do you personally hope and believe and see happening. If you prepare yourself and it never happens, oh well. But if it does, your heads and tails above where you need to be.
Seven Takeaways to Carry Forward about the Future of Work for Women 2026
- Stop waiting for work to go back to normal. Design your own normal. If your job disappeared tomorrow, what would you want your work life to look like? Start moving toward that now.
- Treat flexibility like a strategy, not a request. Audit your role: which parts truly require you to be in a specific place? Use that clarity to negotiate.
- Build optionality before you need it. One income stream = one point of failure. Choose one low-pressure way to expand your income and skills this year.
- Practice everyday futurism. Run scenarios: What if my role changed? What if my company downsized? What skills or income streams would help me feel confident?
- Trust your pattern recognition—it’s a leadership skill. When you notice repeating patterns (disengagement, fear, unclear leadership), use that insight to inform your next move.
- Separate your identity from your job title. You are more than one role, one company, or one chapter. Your transferable skills travel with you.
- Build self-trust through small repetitions. Make one decision this month that prioritizes your future self, even if it feels uncomfortable.
Thank you so much for listening today. We will catch up next week. Have a beautiful week.
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(Images: Headshot by Kendra Forester)
