The Four Stages Of Early Freelancing

According to MBO Partners, 60% more professionals joined the freelance revolution as fulltime freelancers or side-giggers moonlighting on off hours. Estimates suggest over 65 million freelancers in the US alone, and many more working as freelancers full- or part-time internationally.

With so many professionals now joining freelancing without significant experience, and depending significantly or entirely on freelancing, an understanding the arc of freelancing is important. So, what’s the experience of early career freelancers? How does the freelance journey change as experience grows? And, how can freelance platforms and marketplaces support a more successful transition?

Some context is important, and a useful starting point is how freelancers describe their strengths and interests. While freelancers describe themselves overall in positive terms, there are some areas that suggest early difficulty in solopreneurial work. The data below are from the Global Survey of Freelancing, a global survey of 1900 freelancers co-sponsored by the University of Toronto, representing 77 freelance platforms, and 30 countries.

While freelancers see clear strengths, they rate themselves less well in other areas critical to managing a profitable, growing, business. They are tough graders in areas like networking, making business connections, risk taking and persuasion, all competencies that are crucial to success. And they are less than enamored with their planning and time management skills, their attention to planning ahead about working relationships, and a low sensitivity to how others see them.

With this profile, it wouldn’t be surprising if new freelancers were frustrated by their early experience as a freelancer. And, in fact, that’s just what new freelancers report. The findings appear to show that newbie freelancers seem to go through four distinct phases or stages as they decide whether, when, and how they’ll pursue their freelance interests.

The Four Stages of Early Freelance Experience

Stage one: Can I? Looking at the data for freelancers in their first year, it’s evident that freelancing is at least somewhat frustrating. Preparation is needed in so many areas: forming a company, completing legal requirements, deciding whether and which platforms to join, creating a profile and website, contacting potential clients, and sending out initial invoices. And, whether working in tech, creative channels, management consulting, or any number of specific specializations, most freelancers find their first year to be demanding, often quite a bit more demanding than they expected. This aligns with the “exploration” stage of career development: “Is this my passion, does it motivate me, and am I suited to a freelancing life?”

Stage two: I can! The 1900 freelancers who completed the survey make it clear that there is life – and light at the end of the tunnel – after the first year. Freelancers who have initial experience, more than one year, are almost twice as satisfied with their freelancing career as they were at the start. In short, they have transitioned from “Can I?” to “I can!”. In specific terms, they see themselves building expertise in interesting areas, more nearly achieving their financial goals, working with attractive colleagues and clients, and enjoying a higher quality of life. By no means are all freelancers in this category upbeat: the percentage describing themselves as highly positive while above 50% in most cases, is less than we would hope. This fits with the “establishment” stage of career: “I have the competence, confidence, and experience needed to succeed.”

Stage three: But is this the direction I want my career to take? Its evident that while many more freelancers in stage two are bullish about freelancing, slightly less than 50% are highly positive about whether freelancing offers an attractive career opportunity. As the data point out, the period from 3-5 years is one of reflection and, often, retrenchment and redefinition of one’s career goals and interests. There is a drop in satisfaction and positivity as the long-term nature of a freelancing career becomes clear, and freelancers begin to decide whether it is right for them. We would expect ambivalent professionals to drop out of freelancing in favor of fulltime employment, reduce their interest from fulltime to part-time, pivot in the way they choose to freelance, or decide to increase their ambition and leave solopreneurship for an entrepreneurial path. This is also the stage where individuals size up their options, for example: “Is freelancing the right long term career path for me?”

Stage four: This is my path (for now). The data suggest that around the five-year mark, professionals grow into their swim lane. The late HBS professor Clay Christensen might say they understand “the job to be done.” There is an upsurge in optimism and satisfaction among freelancers. It likely reflects the greater professional success that more experienced freelancers are experiencing, and probably other factors as well. One might expect a stronger and more loyal client base by this time, a network of colleagues with whom they collaborate, and a better knowledge of how to freelance professionally and commercially. As well, this is a narrowed population since those who’ve decided against a freelance career have left the field or downshifted from fulltime to part-time.

Here is a summary of the four stages of early freelancing:

Interestingly, the team at Wethos.co, a platform for freelancers and independent business owners, found a similar dynamic in their informal conversations with members. Here is their description of the journey based on the experiences of their community members.

Implications For Platforms

Our findings recommend a plan for more thoughtful support to helping freelancers with career services and coaching than is typically the case. The Freelancer First Philosophy has begun to grow in popularity, and it describes how platform leaders can help freelancers to experience greater success by building into their platforms three different forms of “intelligence” – freelancer intelligence, client intelligence, and engineering intelligence. A group of 15 freelance platform CEOs from 10 different countries have been meeting for the past several months to share their best practices in creating more of a Freelancer First strategy and culture.

This research points out that early freelance education – delivered through onboarding by platform teams or community organizers – isn’t enough to support the longer-term success of their freelancers. As freelancers turn the corner and experience greater success, they need more and different tools to support their growing business. And, as they begin to enter phase three and question whether freelancing should be their longer-term future, coaching or educational help in thinking offers great value.

More freelance platform leaders are beginning to pay attention to the continuing career needs of their freelancers, beyond a helpful push getting started. In part it’s a philosophical shift in support of the Freelancer First Philosophy. But its also good business to offer support in areas that increase the loyalty and commercial success of freelancers on their platform. When Contra or Topcoder provides tools to increase the productivity of their creatives, or Toptal offers early coaching to its freelancers, it also helps itself. So do Catalant or Wethos when they provide their freelancers with access to unique industry knowledge or pricing data, or Folq when it curates the right match of skill and experience. Similarly, Uncompany and NerdApp help their bottom line by engineering ways to automate or eliminate time-wasting activities for clients and freelancers.

It wouldn’t be surprising for company proprietary platforms, or talent clouds, to also begin to pay greater attention to the career interests and needs of the freelancers on their platforms, as the team behind Bubty recently pointed out in a Freelancer First workshop session.

And remember, it's just early innings in the freelance revolution.

Viva la Revolution!