When And How To Take The Leap Into Freelancing

By: Samantha Anderl

According to Upwork’s 2021 Freelance Forward survey, 36% of the U.S. workforce is doing some kind of freelance work, and the total number will likely only grow—with some sources predicting that over 50% of the U.S. workforce will be freelancing by 2027. People are leaving their full-time jobs or supplementing their day jobs with side gigs in order to help bring home more income and even add a little inspiration to their day-to-day.

However, as someone who co-founded a tool to help freelancers, I know how making the leap into freelancing can be daunting, especially if you’ve had W-2 jobs most of your working life. In this article, I’ll explore the pros and cons of freelancing, how to know when it’s the right time to start and how to kickstart your freelance career if and when you’re ready.


Pros And Cons Of Freelancing

Before going freelance, it’s important to weigh the pros and cons of this career path. First, here are some of the unique advantages of freelancing:

  • Flexibility: As a freelancer, you have the freedom to choose your working hours and the projects you take on, which can be incredibly inspiring.
  • Autonomy: You are your own boss. You get to call the shots, at least when it comes to how you manage your business and who you work with. That means you can turn down gigs that just don’t resonate.
  • Variety:Freelancers often work on a variety of projects for a variety of clients, which can keep things interesting. You’re less liable to get bored with your day-to-day, which I find all too common with full-time work.
  • Earning potential:Freelancers can often charge higher ratesthan traditional employees, so there’s ample potential to earn more money than you would as an employee.
  • Creative freedom: As a sole proprietor, you get to choose your branding, services and positioning. This can be super liberating for creative thinkers who like to experiment and take risks. There’s no bureaucratic process for getting approval—just you and your own judgment.


But it’s not all rainbows and butterflies. Here are a few freelance cons to keep in mind:

  • Ramp-up period:It can take a while to build a full client roster. It’s rare for freelancers to fill their schedule as soon as they’re open for business.
  • Sourcing clients:Working for yourself also means doing work you might not want to do—like prospecting and pitching to potential clients. It’s up to you to generate your own business.
  • Inconsistent income.Freelancers are often paid per project or on an hourly basis, with full payment coming in sometimes weeks or months after the work is complete. That means their income can fluctuate—and they’re responsible for invoicing and bookkeeping.
  • No benefits.Freelancers don’t receive paid-for benefits like health insurance or paid time off, and those can come at steep costs when paying out of pocket.
  • Self-management. The double-edged sword of working for yourself is that you’re totally responsible for managing your own time and self-motivating, which can be difficult for many of us.


How To Know When It’s The Right Time To Start Freelancing

Deciding to become a freelancer is a big decision. It’s important to make sure you’re truly ready before taking the leap. Here are some questions to ask yourself first:

  • Do you have a marketable skill? Freelancers typically have a specialized skill set that they can offer to clients. Bonus points if you have people who can vouch for those skills too.
  • Do you have some savings? Freelancing can be unpredictable—and so can life in general—so it’s important to have some savings to fall back on during chaotic times.
  • Do you have a network?Your connections are gold as a freelancer. Tapping into your network for potential clients or collaborators can reduce your ramp time significantly.
  • Are you tired of the 9-to-5?If you’re feeling burnt out by the traditional work structure and you want more autonomy and flexibility, freelancing might be the right choice for you.

Different Ways To Approach Starting A Freelance Career

No two freelancers have the same exact journey. We all have our own unique reasons for choosing to go freelance and personal circumstances that either help or hinder us. But there are some well-worn strategies for beginning your freelance journey:

  • Start freelancing on the side.If you’re not ready to fully commit to freelancing, you can start by taking on freelance projects on the side of your full-time job. This can help you build your portfolio and network while still maintaining a steady income.
  • Reach out to your network. Let your friends, family and professional contacts know that you’re looking for freelance work. They may be able to connect you with potential clients so you can start having conversations before fully committing.
  • Move to part-time.If you have the bandwidth to reduce your work hours from full-time to part-time (and you’re okay with losing out on full-time benefits), maintaining a part-time job can be a helpful way to transition. You still have some degree of structure and consistent income that way, which allows you to ease into the flexibility of freelancing instead of going from zero to 100.

Freelancing can be a super rewarding career choice, especially if autonomy is your priority. But it’s important to carefully consider the pros and cons before making the leap. Be honest with yourself: What do you value? What kind of life do you want to lead? Does working for yourself support that vision?

If the answer is yes, then it may be your time. And if you do decide to jump in, I’m rooting for you.

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