The Secrets to a Fulfilling and Sustainable Transition to Freelancing

By Claire Harbour and Antoine Tirard

In the last few years, according to our friend and colleague Gianpiero Petriglieri, approximately 150 million workers in North America and Western Europe have left the relatively stable confines of organizational life — sometimes by choice, sometimes not — to work as independent contractors. Most companies are only beginning to realize the full benefits offered by the growing ranks of full-time independent talent—which have increased by  91% since 2020, according to one multi-year study’s 2023 issue*. These striking and ever-growing statistics should align nicely, you might think, to create a free and productive market of freelancers, smoothly moving from one status to another, and happy HR leaders, plus profitable, smooth-running companies. But it is not that easy, and the journey from employment to being a freelancer is not a simple one. 

We are both freelancers. We each chose this route a long time ago, deliberately and with a powerful set of values driving our choices. Our reasons are not the focus of this article, though they do give us great perspective and there is a significant overlap with what led us to follow this path and the stories and trends we have explored.

We wanted to dig into some stories of those who have made that transition from employee to freelancer, to find out what it takes to survive and thrive, whatever the reason for the shift. We wanted to understand how freelancers create connections to place, routines, purpose, and people — that help them endure the emotional ups and downs of their work, gain energy and inspiration from their freedom, and continue their professional development journey. 

Emmanuel: a Tech expert’s uncharted journey from startups to freelance freedom

Emmanuel grew up in an internationally mobile family. His father was a technocrat in a traditional career, while his mother parlayed her passion for English literature into an entrepreneurial venture that she pursues to this day. He had a “pretty nice childhood” with plenty of free time to indulge his wide-ranging curiosity, constantly tinkering to find out “how stuff worked”.

From the outset of his study years in the U.S., Emmanuel used his guts, supplementing his not-quite-full scholarship with part-time on-campus jobs. At graduation, feeling a distinct lack of clarity as to how he would eventually enter the world of work, Emmanuel was serendipitously invited to interview at a large technology firm on the other side of the country, in Seattle. While he could not imagine a future with the giant, he did love the city, so pragmatically stuck around, and joined a small, specialist software consultancy.

Years of rewarding work followed. The consultancy had links to a maverick Silicon Valley company, an underdog at the time, a giant now. They did “really cool stuff with incredible clients”, with access to the very top projects coming early for Emmanuel. He loved the work and the team as much as he enjoyed kayaking, hiking and skiing in the environs of Seattle. Luck played a big part, Emmanuel underlines, as he progressed fast, due not only to his talents, but also to the context of a star company doing exciting work. However, after a couple of rounds of acquisition, he and some colleagues concluded that the culture had shifted in a way that no longer suited them. They quit, taking the largest customer along, and launched into what would be Emmanuel’s first startup experience.

Luck played a role again – it was the second half of the 90’s and the tech industry was in a meteoric rise — and their business thrived. In 2000, Emmanuel chose to “step off the treadmill” with a move to Europe, and took an MBA as a “soft landing” to make the shift. His timing was less fortuitous, as the Dotcom bust hit, and he “did not even bother with on-campus recruitment”. Once again, the more independent spirit won out, and Emmanuel co-founded another startup which had a good run for some years. But ultimately, it proved the entrepreneur’s adage, “being too early is indistinguishable from being wrong”.

It was shortly after that Emmanuel began an accidental freelance career, with luck once again playing a role – he started getting calls to build “apps” for a recently launched product whose success was at the time far from certain – the iPhone. The work flowed in by word of mouth, including strategic projects developed in strict secrecy. Several intense years on, a former-investor-turned-friend convinced him to co-found a fintech venture, predicated on new regulations aimed at leveling the playing field in a musty corner of the vast financial world. The law of unintended consequences struck, and the venture struggled to achieve adequate traction as the regulations ended up having the opposite effect to what they set out to do. This was when Emmanuel slowed down, burnt out, and started actually reflecting on how he wanted to work. He began thinking about freedom, and multiple other neglected interests.

“Startups are about imbalance; you have to give them your all. And all around me were freelancers who had saner, more balanced lives!” While he was strongly aware of the contrast, Emmanuel did not do a structured exploration of what should be next. It was more that he created space and time to feel his way into things. He cooked, he hiked, and while he took this time, his friends would begin to ask him to help him with their “thorny problems”. And this is what he has been doing since.

The biggest gear shift has been in terms of focus – from one single ambition to multiple diverse projects, at different stages of progress. But his experience of entrepreneurship has saved him there. A freelance career “is like a one-person startup, you have to deal with everything yourself”. 

For freelancers, networking takes center stage – however, Emmanuel sees himself as having the obstacle of “lack of exposure, and not being a consummate networker”. When challenged on this perception, it is clear that he has nevertheless created a strong and close network over the years. His clients know how to find him despite the low profile he keeps. His reputation leads to excellent word of mouth growth, which has given him the luxury of selecting the projects most aligned with his interests and values.

His new identity as an expert hands-on advisor to CxOs, as someone who deeply understands technology and can bridge to business needs and the inevitable uncertainty they come with, is a natural one for him, and creates “fun, because I get to dig deep into a lot of different aspects”.

Emmanuel is aware of the need to nurture his network, but isn’t yet satisfied with his current professional persona. “What I do is not easily defined. I think of it as wrangling hairy monsters, and there are no groups or conferences dedicated to monster-wrangling!”  Yet informal connection and mentoring are common. His partner, a successful freelancer in a very different field, is someone whose approach he closely observes. He is aware of his own limiting beliefs, and deliberately seeks out other perspectives.

One precious result of his freelance life is the time and energy he has for other activities and ventures, whether managing the family investments, or devoting more time to mindful living, saving water or getting to know the community around him in Barcelona, to where he is in the process of moving. “The time I am in is right here, right now. And I am muddling along; experience has taught me that I am OK with muddling along”. His desire is to bring additional impact with work on climate, and so, true to form, he is back to studying “chemistry and corporate governance”. The muddling tinker is not done yet.

Striking a balance: Alicia’s quest for purpose and fulfillment while earning a living 

Alicia was born in Ecuador, to a local mother and American father, who was a development consultant. His career meant a childhood in several continents, countries, cultures and languages, leading to a deep appreciation for diverse and varied experiences. Encouraged early on to believe that she could “do anything you want”, Alicia excelled across a broad range of activities, from dance, music and art to volleyball, coaching and community service. Her education was broad through the International Baccalaureate and then a Bachelor’s degree in International Affairs, with room for many electives. An internship in London led to both a first job there as a market research analyst and a Master’s in Innovation and Entrepreneurship Management.

She had never felt pushed in a particular direction, career-wise, but had inherited her father’s ambition and partiality for global development. The main expectation was to excel at whatever she undertook. This had always been a challenge, as naturally being superficially good at a many particular disciplines was one thing; getting really good at something, as well as remaining passionate and committed was another.

All of her early jobs in marketing and operations were obtained by a mix of privilege and deliberate connections. “I index about a third of my achievements to the cards I have been dealt in life. It doesn’t diminish my hard work or erase tough times, but it acknowledges that I had a different starting point.” She continues to open up opportunities for herself through networking and cultivating relationships. Much of her work is the fruit of these events, online communities and warm introductions.

In 2020, the pandemic struck, and Alicia’s venture capital job was furloughed. This was a blessing, as the financial cushion allowed her to explore new ways of working and pursue different opportunities. She had recently  connected with an executive search firm through the fund. The firm was undertaking a large marketing initiative and knowing Alicia’s expertise already made it easy for them to ask her to collaborate. Those projects went well, and led to further work and referrals. All growth was organic, making Alicia’s shift to independent consulting feel achievable. “That’s how a lot of this starts: a conversation, that then leads to a project. People don’t need to be sold to; they want to be understood.”

Having experienced burn-out in her full time role just before Covid, Alicia once again pushed her limits as a consultant. There is a common curse of successful generalists: “If you are adept at figuring out solutions for your clients, then you get exposed to more areas of the business. Because I can do it, then I get asked to do it. But just because I can, doesn’t mean I should. And that’s on me to communicate. It takes time to learn and practice how you can direct people and resources in a focused direction.” Alicia continued to explore how she could be  more deliberate in her services.

She mapped out her skills and assessed how they met her objectives: what she was good at, what she enjoyed doing, who she would need to partner with, and the time-to-financial payoff. Having hit on the idea of productized website design, Alicia was convinced that this would allow her to define and scope projects precisely, with a clear beginning, middle and end, plus a specific deliverable. The work brought together many of her varied skills and interests, and would allow her to “dose” the amount of projects she took on, thus staying in control of her own time.

Alicia has created a reputation as a smart and effective website designer, who speaks the various languages of strategy, design, communications, and marketing. She is also purposefully active daily in online communities. She aims to add value in online conversations, and backs up this activity with attendance in at least one physical event per week, wherever she might be. Recent topics have ranged from a personal branding workshop, freelancer meetups, Latinas in Tech and so on. Her philosophy is that if it sounds fun, she’ll go, and since her target clients are also her peers — service-based independent professionals and small business owners — she knows that sharing experiences and referring partners is productive and enjoyable.

Alicia is clear and deliberate about the nature of her work, and the kind of clients she wishes to attract. She knows how to recognize the type of people she does and does not wish to work with, and can by now spot both green lights and red flags. Her desire is to be a partner to any client, and looks for a reciprocated attitude of collaboration. 

Alicia has reflected on her shift of identity:  “I’ve only just turned thirty. I’m sure my priorities will continue to shift. They certainly did multiple 180s in my 20s”. She wants to work in alignment with her values, taking pride in what she does, and making work fit into her life, not vice versa. “While of course, I want to find purpose and enjoyment in my work, it is a means to an end. I am trying to carve out a life where I can travel, relax and explore hobbies, and integrate it all with work. Work to live, not live to work”.

Due to a chronic health condition, Alicia is very mindful of her work-life balance.  She has to balance her financial aspirations, level of involvement in a project, and future-proofing with her lifestyle goals. She does not want to build a company, nor hire any staff. She wants a sustainable lifestyle.

Beyond the exchanges with her various tribes, Alicia takes her learning seriously, while trying to keep it fun. “No one is going to test me on this. Learning should be enjoyable.” She reads daily, “possibly too much information!”, and is enjoying the mix of learning from videos, courses, fiction and real life conversations.

As for what next and beyond? “I get projects and roles across my desk weekly and I am not closing doors along the way, as long as they are interesting and balanced”. Alicia strongly believes in fair compensation for expertise. Aside from some pro-bono mentoring or mutually beneficial conversations, she charges for her time and doesn’t welcome aimless “can I pick your brain for an hour” requests. The art of establishing those healthy boundaries is so critical to an independent professional and Alicia, while still young, is smashing that one. Her thoughtful, purposeful development is not over yet.

Crafting a career: Kah Ying’s freelance odyssey through language and life

Kah Ying grew up in relative comfort, socially speaking, in Singapore. She was the third child of four, and, as far back as she can remember, she was candidly told that she was “unwanted”. Although this was a heavy burden to bear, she found a way to parlay her situation into one of freedom. While older siblings were under pressure to conform and perform, she was left to her own devices, with no sense that she needed to succeed, or become a doctor, lawyer or accountant. So Kah Ying created and immersed herself in her own solitary and imaginary world, in which she bicycled around and around her family’s  little garden, stopping to perform her own little plays and dramas. Inspired by her frequent trips to the island’s excellent public libraries, Kah Ying constantly invented scenarios, with a plethora of characters, voices and perspectives. It mattered little to the young girl whether the protagonists were soft toys or herself. And even less whether she used Mandarin or English; she just adored losing herself in the story, the language and the ideas. Her horizons expanded even further when she was 11, as the family moved to Pakistan, as part of her father’s work for the United Nations, and so her fascination with language was given yet another dimension.

Many teachers, relatives and friends recommended that she become a teacher, to use her facility with language, but Kah Ying questioned her ability to be a good role model for her pupils. She resisted the trending suggestions, choosing to study English Literature at university in Australia, where her father had a position as a researcher and her mother created a thriving dressmaking business.

Initially choosing to study politics “to be useful”, Kah Ying realized she was not inspired, and turned to her true love of literature. She was “good at being a student and getting good grades”, which made her consider whether her destiny lay in academia. At the same time, her failure to be admitted to a master’s program in writing led her to suspend the typical dream of aspiring writers of writing the next great English-language novel, while working freelance as a copywriter and editor.. She came to see there was endless opportunity for learning and growth in this area, even as she continued to engage in personal writings inspired by her life.

In particular, these personal writings took on a real-life impetus when she gave birth to a son, Sebastien, who is autistic and non-verbal.  Firstly, she “was brought right back down to earth, now stopping her endless floating” in her subject-matter. Secondly, she realized that “seeing life through words was just not enough”. Persisting as a freelancer, but building her own client base seemed like a logical and easy way for Kah Ying to proceed. She now required more flexibility with her work, to tend to Sebastian’s needs. 

By working with individual clients, especially those with academic writing to be done, she could not only juggle as logistically necessary, but also indulge her taste for deep immersion into new topics. She would swing from anthrax and bio-terrorism to literary texts with agility and the deep pleasure of research. This was further helped by the fact that the internet and its wonders were just emerging as tools accessible to the ordinary person. 

So, Kah Ying, for the past couple of decades, has built herself a freelance career in which she has as much work as she needs, if not more, and finds the deep intellectual stimulation with every single project. She “loves to be able to make weird, obscure stuff comprehensible to the layman”, and feel that she is doing service by opening up the minds of many.

Her work comes by word of mouth, and the power of testimonials and recommendations is crucial to her ongoing success. She does express envy of her friends and connections who are more able to be sociable through and around their work. On the other hand, she actually delights in spending all day inside, at her desk, with the curtains drawn to keep the rest of the world out. 

There was one brief period of experimentation with employment as a teacher, but Kah Ying soon found herself in conflict with authority and removed herself. Her struggle with conformity leads her to look for learning “on the job” as opposed to formal training, but she definitely values the opportunity to be constantly learning, in an interdisciplinary way, from her work and the idiosyncratic life she has built for herself and her small family. 

Maybe it would not suit everybody, but Kah Ying has found the route to her own personal happiness, along with a large and satisfied clientele, and a future as deeply learning driven as she wishes.

Freelancers’ dilemma: juggling isolation, purpose, and networks for long-term success

Whether by choice, plan, or slow emergence, the choice of working as a freelancer is not for everybody. The isolation is real, and the question of how to keep up the flow of work never disappears. The array of choices as to how to maintain and develop one’s skills is clearly as endless and potentially confusing as if one were employed, and the issue of network and community is a reality, but one to which the attitudes vary just as much in this world of increased freedom of choice.

What is to ponder, then, is how an individual creates, more or less consciously, a situation in which s/he thrives. If we look at Gianpiero Petriglieri’s hypothesis of place, routine, purpose and people (see box), we can observe that all of our subjects have figured out their place, with deeply differing approaches. Manu, with his almost serendipitous arrival in Seattle, and now finding his way in Barcelona, is molding his lifestyle to that particular place with deep awareness. Alicia is enjoying keeping things flexible with regard to her location – for now, between London and Madrid, but, with the range she has previously experienced, it could be anywhere next. And Kah Ying is firmly attached to Singapore, and even more so to her little office with the drawn curtains, keeping distractions away. The routines of work seem to have evolved naturally for all of them, finding and setting the rhythms of their work, as well as the nature of their clients. Clearly, more years of practice allow greater comfort with this, so Alicia is still to some extent the novice in this respect. But even for her, the choice of working to live rather than vice versa pushes her to and allows her the freedom to select what she does and how.

As for purpose, all three of them appear to be incredible examples: Kah Ying has the deeply personal purpose of constant immersive learning and adaptability, while Manu is preserving his time and energy for projects that count deeply for him. And finally, Alicia is using her independent status to mark out her territory, to allow herself space for “all the rest”, beyond just doing great work for clients. 

And the people? Interestingly, the two older subjects would argue that they “don’t really network at all”, though we feel this is not only over-modest, but also simply not truly recognizing all the reputation and connection work they have done over the years, which make their lives appear to be simple now. Alicia, on the other hand, has a devoted and deliberate approach to how she connects with both peers and potential clients, and may well be saying the same sort of thing in twenty years.

As part of its regular research into the growing phenomenon of freelancers and their place in the workforce, consulting firm BCG states: “The war for talent is over… Talent has won. This year’s study confirms that more and more diverse profiles are embracing the freelancer status with an aspiration for more flexibility and independence.” Freelancers are a unique talent pool with high potential. Organizations of all sizes can choose to benefit from this, by deciding when and how to get access to specific, often scarce, skills, both soft and hard. This is not a temporary blip of any kind at all.

If you are contemplating a life of freelancing, or indeed if that status might only be a temporary, possibly obligatory rite of passage, there is much to learn from these three stories, and also an excellent reminder that the approach does not need to be actually perfect: just good enough for now. There is currency to be gained from building comfort of place and routine, as well as from connections and reputation, but it is quite possible to begin to do more than survive, with just a few of those elements, as long as there is the consciousness that more is required to be in full thrive mode.

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Ten things to think about, if faced with the possibility of a freelancing career

In their 2018 Harvard Business Review article, “Thriving in the Gig Economy”, Gianpiero Petriglieri, Susan (Sue) Ashford, and Amy Wrzesniewski summarize their study findings and explain that many of the gig workers have created a “holding environment” for themselves by establishing four connections: (1) place, (2) routines, (3) purpose and (4) people. Based on our interviews with other gig workers and the stories of Manu, Alicia and Kah Ying, we have added a fifth connection centered around learning. 

Place

• Consider how you might set up physically, from a cozy office, or a flexible location across workspaces, cafés and hotels, and find the solution that suits you
• Decide how you wish to fit into the geography that you have chosen, and use it to create community, inspiration or purpose

Routines

• Think deeply about both what you need and what you want, with regard to the total time you work, and the particular times of day/week/month; this may well need regular review, as your life evolves
• Create the space you need for the stuff that is not obviously “work”, whether that is networking, doing your favorite activity, or getting involved in passion projects

Purpose

• Whether it is a simple wish to work less and prioritize other things, or indeed a big hairy mission, being conscious of how your work fits in to this purpose and vice versa is going to give you success
• Tying your purpose to your work can be satisfying – can you achieve that?

People

• Those who know us well will recognize our enjoinder to be constantly creating connections – whether instigating new ones or maintaining and deepening existing relationships
• And, being open to what relationships might bring, whether directly or indirectly, is crucial.. creating goodwill, whether with clients or friends and acquaintances, will undoubtedly at some point bring new and additional support, whether business, financial or peripheral

Learning

• Some prefer extra and ongoing diplomas, others just get their kicks from constant on-the-job immersion. Figure out where you lie in this respect, and enjoy the journey
• Recognize that the isolation of freelance work could threaten your ability to develop with the world, so being more conscious of what and how you continue to learn will be crucial

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