Freelancing: A Viable Alternative to the Traditional Career You Expected?

freelancingWhile a full-time job may be the target of your job search, it’s worthwhile to examine the opportunities available to you through freelance or consulting work. If applicable to your field, freelancing can offer a great way to get a foot in the door. It can also help build your resume or navigate a career transition.

Between the first furlough and the second round of layoffs at my last employer. That’s when I decided working for someone else was no longer for me. Part of that decision stemmed from an increasing uneasiness around putting my earning potential and job security in the hands of someone else. Perhaps someone who might handle it with the same delicacy a toddler handles a handful of dirt.

The second factor in my decision? The romanticized vision of freelancing I had put into my head. You know the one – getting up at 10am (that happens sometimes) and not having anyone to answer to (except, well, your clients). Setting your own schedule, choosing your own projects, and essentially living life and work on your own terms. Eventually, and with the generous understanding of my fiancé (now husband), it was enough to take the leap and make a go of working for myself.

Self-employment comes in many forms. Whether you’re freelancing for a singular client onsite, freelancing simultaneously for multiple clients from your own office, or running a company with its own portfolio of dedicated products and services. And while it’s equal parts difficult and rewarding, freelancing simply suits some people better than working for someone else.

Thinking about making the leap? Let’s take a look at the some of the high’s, low’s, and gotta-know’s to help you decide:

Freedom to Choose vs. the Feast or Famine

Pro: You get to pick your own projects (and who you work with).
Con: There’s the whole “feast or famine” thing.

I once worked as a recruiter for Digital People in Boston. In the five years I worked there, I saw the market fluctuate about 4 times. It swayed rapidly between an abundance of jobs and not enough freelancers to fill them (because they were in demand by their own clientele), to an abundance of freelancers and not enough jobs to employ them (because the market was down). This full cycle happened at least twice, and it’s normal even on a smaller scale in any business with busy and slow seasons.  For me, it’s common to have my best month ever right next to my worst month of the year. Not due to a lack of effort, but simply because of the fluctuations in the marketplace.

So while it’s great to have flexibility to choose who you work with, and what types of work you engage in, set yourself up for success by actively learning the different trends, seasons, or other factors that might influence your industry or market. For me, most people are fulfilling their end of summer vacation plans in August, so it tends to be slow in terms of resume and job search needs. But everyone is in high-gear from September through Thanksgiving, before the holidays hit.

All the Money You Deserve, If You’re Willing to Ask for It

Pro: You get to set your own rate and path for growth.
Con: You have to become great at asking for money.

Money is almost always a factor in the decision to go freelance, whether it’s a concern over not being able to generate enough to make a sustainable living, or making the move because you feel underpaid in your full time time role and know you can make more billing your own hours.

Freelancing gives you the power to look at what the market commands and set your own rates accordingly.  But the flip side of that is that you have to be comfortable asking people for money.  Asking for money, or being steadfast in your operating guidelines when a client wants an extension on their invoice can be uncomfortable, but in business it’s essential if you want to stay afloat. If you want to learn more about this, I encourage you to read Jessica Hische’s article on the Dark Art of Pricing.

Be Ready to Take the Good With the Bad

Pro: As the face of the company, when you receive praise, it’s all about you.
Con: As the face of the company, when you receive criticism, it’s all about you.

One of the the most difficult things about freelancing is that when a client is unhappy with something (and it WILL happen), it’s all directed towards you – there’s no more bigger company face to hide behind, in most cases.  You have to be willing to problem solve, negotiate, occasionally settle for less than you’d like in the name of your reputation, and take the bad with the good.  The upside of this is that when praise comes down the pipe for a job well-done, that’s all you!  It’s important to ask for feedback, references, and testimonials too, particularly with service-based businesses, as people rely heavily on referrals when making a purchasing decision.

When It’s Time to Make the Leap to Freelancing

Thinking it’s time to pursue a career shift into freelancing?  Let’s do it!  And here a few guidelines to get you started off on the right foot.

  • Set up systems to track everything. This is so important, and will serve as your basis for determining what is, and what is not working in your operation, and where you need to make changes accordingly.
  • Hire a reliable accountant. This is not a ‘table it for later’ item. This is a ‘go no further until you’ve checked this off the list’ necessity.  You do not want to be sorting through invoices, expenses, and payments come tax time.
  • Get laser-focused on who your target customer is. Even though this can shift throughout the lifecycle of your freelance business, you have to know going into it who it is you want to serve, and what you can offer them.
  • Start building (or tidy up) your digital presence. Even if you haven’t yet made the leap, start putting the word out there around what you (will) do, and build a reputation for yourself, particularly if you’re pursuing a freelance venture outside of your current career (like I did).  Then when you’re ready to take on clients, you have an established online presence and some credibility.

In the End

Freelancing can be incredibly rewarding and profitable. But like job searching or career changing of any kind, it involves careful strategy and planning. It also includes an understanding where you do your best work and what your core skills are. Finally, it means knowing how you can use those to bring value to a particular audience.

Is freelancing the right move for your career?


For this post, YouTern thanks our friends at Brooklyn Resume Studio.




DanaAbout the Author: Dana Leavy-Detrick founded Aspyre Solutions, focusing on small business development and career consulting. Her mission is to support creative and socially-conscious small businesses. She also offers career transition coaching and business consulting.

Dana has helped hundreds of professionals execute effective career plans to find and DO the work they are passionate about. She has also presented seminars on navigating careers, transition and work-life balance to several colleges and universities. Her advice is featured on MSN Careers, Fox Business News, NewsDay,, GlassDoor and Follow Dana on Twitter!



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