This is the second part of our series on freelancing and the gig economy, exploring the 3 major challenges to consider if you’re going to be successful working independently. 


It was about an hour into my conversation with Joshua. He’d been recounting the many diverse chapters of his career working in PR, internet start-ups, international journalism, and ad firms. And now he was sharing the realities of his new day-to-day as a freelance professional pursuing a mix of creative assignments in New York’s bustling advertising and entertainment industries.

Underneath the rapid-fire delivery and the animated gestures that accompanied his tales of the ups and downs and hopes and fears that he was now experiencing, there was also a palpable sense of calm and self-assurance. It was like he’d finally arrived at a destined place in his life and career.

The freedom and independence associated with freelancing played a significant role in Joshua’s decision to go independent. And the same is true for countless other freelancers.

Perhaps the most exciting thing about freelancing is that autonomy — the personal freedom you experience. But being your own boss also has its burdens. A frequent challenge is the high amount of ambiguity you face in many of your critical decisions. One such area of uncertainty is setting a course for your own career and navigating the key decision points of where to head next. This can be especially unnerving for those who’ve spent time in more traditional organizational settings.

It’s similar to the difference between sailing in an enclosed harbor versus the open ocean. In one setting, land is constantly in sight, detailed maps help you avoid obstacles, and beacons and buoys guide the way. In the other, you have nothing but waves and sky in view. As one freelancer explained: “There’s no HR for you to go to for guidance and support. You have to define yourself and your ambitions and be your own advocate.”

It’s impossible to completely dispel the fuzziness and fog of a freelance career. But successful freelancers have found ways to effectively manage the uncertainties. For many, it starts with looking within.

Many successful freelancers demonstrate high self-awareness. They maintain a clear sense of who they are, what they want to accomplish, and why. This keeps them grounded and realistic, and provides an inner compass for their career outlook. Given the dynamic nature of freelance work and their own changing life circumstances, they understand that their self-insights may occasionally need a fresh look.

A freelancer adviser on leadership and talent explained that, “Terms like values, career, success, and purpose all take on new meaning and need to be examined carefully when you are freelancing.” For some, it comes down to re-framing what they once thought and believed. One freelancer reflected that, “I still think of what I’m doing now as a career, but not in the traditional sense.”

Quick tip: Develop a core purpose statement. If you’re not familiar, just search online and you’ll find a number of step-by-step resources. Better yet, check out some of our leadership brand tools.

Introspection will only get you so far. And taken to extremes, it might get you even more lost in the fog. Outside-in approaches are also needed. Savvy freelancers take pride in their independence and self-reliance, but they recognize and accept that they can’t do it all on their own. They put energy into seeking out others and building a strong network. This includes engaging in ongoing dialogue with other freelancers about the career decisions they face and how they’ve approached them. They also place a high premium on having one or more professional mentors who can be counted on as a source of clear feedback and unbiased advice.

A diverse network of professional relationships provides more than support and guidance — it can also be a critical source of inspiration. A freelancer in brand marketing enthused that, “I’ve gotten more creative as a result of interacting with my [professional] community.”

Quick tip: Identify at least 3 people who can be an informal advisory panel to provide you with support and guidance over the course of your freelance career.

Remember, there’s no HR department when you work for yourself, and there’s more ambiguity about what career advancement looks like. You’ll need to define those for yourself, but that doesn’t mean you need to go it alone. Following these tips — including developing a purpose statement and an informal advisory panel — will make it easier to answer some of those daunting, long-term questions.



Ask yourself these 3 questions before making the jump to freelance.


For those of you who aren’t currently freelancing but are giving it some serious consideration, hopefully this gives you perspective on the realities of this type of work and the differences from what you might have experienced thus far in your career. If you’d like to dive deeper on that topic, please attend this complimentary webinar on Jan. 18, sponsored by MBO Partners.

2 thoughts on “Freelance Success: How to Strategically Chart Your Career Path

  1. I can only agree to the importance of knowing yourself and what you have to offer. Becoming a trusted advisor and partner is a journey in self awareness and self management.

  2. Ellis Jackson says:

    I am intrigued by this freelancing career, I never actually looked into it that far. I can see how challenging it could be given the fact that you are, in a sense: “navigating by yourself on the open seas”, it is interesting to me and it seems like giving it a shot. Just a quick question if I may, how does one start in this business? What tools are needed for a beginner and where would be the best place to start? How much money are you making a year? Is this a high stress job or not that stressful? These questions came to mind. I think that this blog post has been interestingly helpful to me in educating my young mind on freelance work. Thanks!

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