Five Pillars of Work: The Power of Intentional Community Building
How to rebuild your sense of belonging in a portfolio career.
Last week, I shared my five pillars of work framework for transitioning from a traditional job to a portfolio career and I was honestly blown away by the response. So many of you resonated with it, reached out to me, shared your own stories, and showed me just how timely this conversation is.
As promised, I want to go deeper into each pillar unpacking the real challenges I faced and share the things that worked for me. I’d like to start with the Community Pillar. The thing no one tells you when you go independent is that you’re not just redesigning how you work but also rebuilding how you belong.
And belonging is not a nice-to-have. It’s one of the most fundamental human needs sitting right above safety on Maslow’s hierarchy. Psychologists define it as “a subjective feeling of being an integral part of one’s surrounding systems - family, friends, work, or community” (Allen et al., 2021). It is a powerful, often underestimated driver of motivation and emotional well-being. It affects not only how we work, but how we show up: with energy, confidence, and creativity.
So before we dive into how to rebuild community and belonging in a portfolio career, let’s recap what actually breaks when you leave a traditional job and the unique challenges that tend to show up along the way.
Dismantling the Community Pillar
Being employed, community and a sense of belonging come ready-made. You belong to an office, a mission, a team and even if you don’t love it, it provides an anchor. You share lunch breaks, inside jokes, and a company identity. Community forms around proximity and shared goals. And also in your private circles, your job gives you credibility and belonging.
When you leave a job, you’re not just changing what you do but you’re dismantling a social architecture that once told you who you were. In this transition many people wobble.
Not going to an office or having colleagues around can feel surprisingly isolating. You might miss being part of a shared mission, a team moving toward the same goal.
Meanwhile, you’ve changed but your environment hasn’t. Friends or family still see you through the old lens. You might feel judged for doing ‘less serious’ work, or for exploring things that don’t fit the traditional script. You might actually experience social devaluation and judgment regarding unconventional career choices (“I enjoy working a day at a café for fun but constantly receive stupid remarks for such endeavors”).
After a while, you long for peers who get it, who also stepped off the conveyor belt and are building life differently. Stepping outside your bubble and expanding your community is the hidden catalyst here.
The Power of Perspective
Stepping outside your bubble during the transition phase is so powerful because it expand your perspective. As my Substack friend Jill Reilly says:
“You can’t see beyond the familiar from behind the same desk, in the same meetings, talking to the same people.”
When I quit my job, I had no idea what to do next. In my existing circle, the reasonable thing was to find another full-time role. On LinkedIn, I’d get suggestions for ‘Head of Customer Success’ roles - I could do the same job I had before just at a different company. Talking to people on traditional paths would get me advice like “Maybe it’s easier to just get another job.”
Our perspectives are always shaped by our environment. It wasn’t until I started stepping outside the familiar that new possibilities appeared. It can be moving to a new city, joining a different community, reaching out to someone that inspires you or reading a great book - each expands the mental map of what’s possible. I met people who thought differently. I discovered I was a generalist. I found Substack and the idea of portfolio careers and with that, a new map of work opened up. My Substack friend Brian Wiesner is obsessed with serendipity: when you step beyond your existing network, one surprising encounter can lead to another in ways you never anticipated. Totally agree.
On a new path, doubts and insecurities will show up, that’s natural. But it’s key who you share them with and the perspectives they bring. Surrounding yourself with others who are also figuring things out as they go can be invaluable. They provide inspiration and encouragement when fear sets in. Exposure to people on similar journeys helps normalize those anxieties and often offers ways to reframe them.
By designing intentional communities, you break free from the familiar, surround yourself with people and environments that challenge your assumptions and invite curiosity and growth.
Unlearning Corporate Belonging
Yes, the traditional job hands you belonging on a silver platter and your community comes built-in through colleagues, office culture, and team rituals.
I’d question though whether colleagues, bosses, or team members ever truly made up your ideal community in the first place. Most of the time, you don’t choose them but instead, you inherit a group with whom you may feel pressured to maintain a professional image instead of being yourself.
While it’s certainly possible to find great community at the office - I sure did - many people I know say they ‘don’t want any deeper relationship with their colleagues’, ‘would never hang out with them in their private life’, or frequently ‘struggle with toxic work cultures’ or ‘narcissistic bosses’. Demanding, inflexible, in-person jobs often leave little room to nurture the relationships that matter most to us: with partners, family, and friends. Personally, I valued saving my social energy for my own circle, rather than coming home exhausted from the office and having nothing left but the urge to retreat to the couch alone.
Ultimately, we are complex and multifaceted, with diverse interests and needs. It’s unlikely that a single workplace model can serve everyone’s sense of community.
Intentional Community Design
In an increasingly global, interconnected and multicultural world where our work, identities, and interests stretch across countries and channels, belonging becomes a creative act: something you design with intention.
Modern belonging is fragmented, yet deeply intentional. It reflects who we are - multifaceted humans with many interests - and asks us to design ecosystems of connection that can hold all those parts. By nurturing these interconnected elements, we craft a sense of belonging tailored to our unique, evolving lives.
In case you haven’t noticed: This all screams portfolio career. The same way we’re now mixing projects, passions, and income streams, belonging can no longer come prepackaged in a single workplace. We weave together micro-communities to create our own circles of belonging. It’s no longer a single office or city, but an ecosystem made of places, people, and spaces that make you feel seen, safe, and inspired. It moves fluidly between physical and digital spaces: Co-workings, cafés, Whatsapp, online communities, a running club or local projects.
In my six years of remote work and a year on the portfolio career journey, I had to figure it out on my own. So here’s what helped me design it intentionally.
1.) Choose your place to live intentionally
Where you live will influence everything else: your community, your work, your sense of self, your health. When I quit my job, I packed my life into boxes and moved to Lisbon. The city is full of freelancers, creatives and people doing life differently and being surrounded by them rewired my sense of what’s possible. That’s the underrated power of place: it shapes your idea of what a ‘normal’ life can look like. You can read more in my article ‘where you start over matters’ if you’re interested.
2.) Find your third places
Co-working spaces became my substitute for a traditional office. I had a dedicated place to work, enjoy lunch breaks, grab coffee between tasks, play a game of ping-pong, or join afterwork drinks - except this time with people I actually liked. Sometimes, it was a relief not to have bosses or team members constantly around. I pushed myself to work hard, even without supervision. While some hesitate to spend money on memberships, I think sitting alone at home in sweatpants for months straight will cost you more in sanity. Even if you only go one or two days a week and opt for a more affordable option like Croissant, which offers subscription-based access to multiple co-working spaces around the world, it makes a valuable difference. If a traditional co-working space isn’t an option, consider alternatives like cafés, creative hubs, sports clubs, yoga studios, beach clubs, or boutique hotels. Increasingly, new concepts tailored to remote work are emerging, offering creative substitutes for the office environment.
3.) Design your own co-workers
As mentioned, one of the biggest challenges of self-employment is missing the sense of a shared mission that naturally comes from being part of a team. However, in your portfolio career you can recreate that collective energy by intentionally choosing projects, collaborators, or fractional roles that align with your values. For example, fractional work lets you take on a role for one to three days a week, often paid on a monthly retainer. This arrangement makes you an embedded part of a team, providing stability and connection while still leaving ample time to pursue your passions and build diverse income streams aside. Take the best of both worlds to design your perfect mix. While not working on the same mission, I do also quite enjoy co-working with my partner or with friends. You get to decide who to spend your precious time with.
4.) Meet new people in person
When I quit my job, I made it my mission to meet people again. On a professional level, I started showing up at every climate-related event I could find: informal drinks, book clubs, conferences, talks, you name it. Half the time, I considered faking a migraine on the way there, but I went anyways and it paid off. I met fascinating people in a field I wanted to enter and even made real friends. Beyond work, I built an entirely new social circle from scratch through hobbies, yoga, random café conversations, and communities built around shared interests. The options today are endless: the café across my street hosts a weekly running club, a spa nearby runs sober board game nights, another space organizes surf-and-art retreats, and projects like Timeleft and One Thousand Club make it easy to meet new people. Every week, there’s a new creative idea bringing strangers together for in-person experiences.
5.) Curate your digital world
Of course, not everyone has the option to relocate. Some may prefer living closer to nature rather than in a bustling city with more social infrastructure. Others might simply favor a more digital lifestyle. And even if you reside in an ideal city, the digital layer remains a crucial element to enrich and expand your community.
Curate your socials intentionally
After leaving my job, I radically re-curated my LinkedIn feed. I unfollowed companies that no longer interested me and hid updates from people I no longer felt aligned with. You don’t have to remove connections, just visit their profile and use the notification bell to choose ‘all,’ ‘most relevant,’ or ‘off’ for their updates. I began following inspiring companies and individuals, and before long, the algorithm transformed LinkedIn into a genuinely motivating space. It stopped being a stress-inducing scroll and started feeling like a group chat full of people doing cool things. You can apply the same approach across all your social platforms.
Schedule virtual coffees with inspiring people
Try a simple exercise: think of three people, either in your network or outside it, who inspire you, and reach out to schedule a virtual coffee. At first, I was terrified. “What if they think I’m weird? What if I waste their time?” But most people are surprisingly open to genuine curiosity. After a few such chats, it became second nature to connect with interesting people around the world and one even led me to discover Substack and portfolio careers, which became the foundation for everything I do now (hello serendipity). So, don’t overthink it. Curiosity is a good enough reason to reach out. And a good conversation with an inspiring person can go a long way.
Join online communities (but maybe not twenty at once)
Over the past year, I joined more online communities than I can count across my diverse interests (Pathless Path, Work on Climate, The Portfolio Collective, Read for Planet Book Club, Moral Ambitions, Bankless, and more). I certainly went a bit overboard, but after some trial and error, I narrowed down to the ones that fit me best. These communities helped me find like-minded people on the same journey, e.g.
, who I had multiple amazing calls with already.
6.) Share your reflections publicly to attract your people
This is something I completely underestimated at the start. I never saw myself as the person who posts online. It felt intimidating and I worried about saying the wrong thing, getting negative comments, not being taken seriously, or friends judging me. But I realized that there’s another side to this coin. The positives I had totally underestimated. Sharing my thoughts publicly became a magnet for the right people. I started meeting others who think like me. Opportunities began landing in my inbox. Coffee chats with strangers turned into friendships. A small community started forming around the ideas I care about most. So whether it’s Substack, LinkedIn, YouTube, or anywhere else, I can’t recommend it enough to put yourself out there. You never know who’s listening.
7.) Read and listen your way into a new perspective
When I couldn’t discuss certain topics with my immediate network, I turned to books, podcasts and Substack articles for alternate perspectives and motivation. Surrounding myself with ‘other thinkers’, even if it was one-way, proved essential, especially when doubts about my new path crept in. Sometimes, the right podcast at the right time is better than a pep talk from anyone you know.
8.) Get a guide
Navigating the transition into a portfolio career can be disorienting, and guidance helps whether it’s a mentor, a peer, a mastermind group, or even an AI coach. Find someone further along the road, a thought partner to bounce ideas around and help navigate this messy middle. The right guide helps you stay accountable and grounded while you build a portfolio career on your own terms. For me, it was invaluable.
Belonging, In Retrospect
As you see, there are different ways how to intentionally design your community in a portfolio career. Not all of them will work for everyone. But that’s the whole point. You can pick the ones that suit you to craft a sense of belonging tailored to your unique life.
If you think I had it all figured out before quitting or came in with a clear strategy, rest assured I didn’t. This has been an ongoing journey of experimentation and trial. Writing this piece is part of my effort to look back, connect the dots, and offer you some ideas that hopefully make the process feel less daunting.
Redesigning community intentionally might sound hard, but for me lead to greater alignment, sustained inspiration and a community mix that suits my real self.
📚 Read the full Five Pillars of Work series:
The Five Pillars of Work: How To Transition From A Job To A Portfolio Career
The Five Pillars of Work: Rebuilding Vision from the Inside Out
The Five Pillars of Work: The Power of Intentional Community Building (this one!)
Upcoming: Three articles on the missing pillars Structure, Identity & Money
👥 Portfolio Career Mentoring:
Rooted in my Five Pillars of Work framework, I offer two mentoring pathways designed to help you transition into a portfolio career.
Great article. I used to hate going to the office in my first corporate role that was hybrid and I thought that all I wanted was to work solo. But now as I build my portfolio career, I enjoy meeting other people navigating their own journeys and co-working with them, whether virtual or in person. I realized that previously in my hybrid role, I didn't want to go to the office and meet with people because it felt forced but now I enjoy working with other people because I get to build my own community of people on similar "pathless" paths. I also really like the idea of sharing reflections publicly and this is something that I probably need to do more of.
I'm enjoying reading your breakdown of the five pillars of work! I think it can be easy to underestimate the power of community in opening up possibilities – not just in terms of opportunities, but in terms of what is actually possible for you and different ways of being in the world. Great article!