Are You a Daredevil Freelancer?

Business is a game of risks.

If you’re a freelancer, then you’ve probably already engaged in some level of risk. (Especially if you’ve quit your “day job” and are now relying on your freelancing business to support yourself.)

Even though most freelancers engage in some degree of business risk, there are certain freelancers who have a higher tolerance for risk than others. In fact, a few freelancers even seem to be attracted to risk. You might call them “daredevil” freelancers.

You know the type — whenever there’s a new program, tool, or business opportunity this freelancer is sure to be found in the thick of it. Whenever there is a new idea, they jump quickly, often without looking carefully first.

So, how does business risk-taking affect the typical freelance business? Is risk-taking a key to business success, or a surefire means to crash and burn?

Advantages to Taking Risks

Taking risks definitely has its advantages. Some benefits to business risk-taking include:

  1. Those who adopt a successful new technology trend or program early (early adopters) tend to benefit the most from it (practically and financially). Think about those individuals who wrote the first blogs. Of course, not all of them stuck with it, but many of those who did are top bloggers today.
  2. Early adoption allows a business to develop an expertise in something before the market becomes glutted with experts. Expertise is often based on length of experience — the longer one has used something, the more expert he or she is perceived to be. By default, early adopters are more likely to become experts.
  3. Early adopters often have access to “perks” such as charter memberships or even product freebies that are unavailable to those who come on board with a product or service later in the marketing cycle.
  4. Choosing a technology or trend before everyone else can give a company the reputation of “being on top of things.

There’s also a downside to taking business risks.

Disadvantages to Taking Risks

Some disadvantages to business risk-taking include:

  1. Early adopters are more likely to be caught in fads, or even become victims of scams. Since the amount of information available about new technologies, products or services may be limited; an early adopter may be caught in a scam without realizing it at first.
  2. Taking the wrong business risk can cost a freelancing business a significant amount of time and money that they may not really be able to afford. It takes time and usually money to implement something new. If that something turns out to be a fad or useless, then all that money and time is wasted.
  3. The technology or program may not be fully developed. Many early adopters may find themselves in the role of unwitting product testers (which may require them to spend additional time getting an item to work properly).
  4. A company that adopts a new technology or business opportunity that is later shown to be a fad or worse, a scam, may look foolish to its clients and customers.

While there’s no guaranteed way to always pick a winning trend, there are some guidelines that can help.

Some Things To Consider Before Taking a Risk

Should you jump on board with a new technology or business opportunity?

The trick, of course, is to avoid taking business risks with fads and instead invest in long-term trends. That’s easier said than done, though.

While there’s no way to know for sure if a particular technology or business opportunity will become widely used, there are five questions freelancers should ask before they take a risk:

  1. Can I afford this technology/product/opportunity?
  2. Do I have the time to learn it and/or upgrade my systems?
  3. Is the company/people sponsoring this reputable?
  4. Is there a real need for this technology/program/product?
  5. How difficult is the technology/program/product to use?

Getting solid answers to these questions may require a lot of thought and research on your part, but doing so will help to ensure you are making a smart move in taking a risk.

Share Your Experiences With Risk-Taking

Do you consider yourself a daredevil freelancer? Why, or why not?

Have your experiences with business risk-taking been mostly positive or mostly negative?

Share your stories.

Top photo originally by jurvetson, customized by FreelanceFolder


  1. says

    Wow! I have to say that I absolutely love this graphic (especially the words “The Freelancer” on the side of the truck).

    This is exactly the picture image that I had in my mind when I wrote this post.

    Good job Mason for finding that one!

  2. says

    @Laura — Glad you like the photo! I actually edited in the text on my own, I thought it was fitting :-)

    As for my risk tolerance, I’m definitely on the riskier side by most definitions. I think the important thing is to know and understand the possible outcomes of every risk you take (good, bad, and ugly) and be prepared to deal with them no matter what the case.

  3. says

    Hi Mason!

    Wow! Your editing of the photo turned out well.

    (I was wondering how you managed to get a photo of a truck with the words “The Freelancer” on the side. LOL)

    I agree with you that it’s important to evaluate possible outcomes of the various risks that you take, but I’m not sure we can always know the results. (At least not for sure. . .) Sometimes an educated guess will have to do.

    However, I do think that this is something that one tends to become better at with practice.

  4. says

    I took a big risk when I quite my full-time job to go freelance… and within a few days of leaving, I took another big risk by getting studio space.

    I couldn’t afford it at the time, (i was very much in debt!) but I had a really good feeling about the space, and the other people working there, and I knew I wouldn’t be able to work (productively) out of my house.

    I knew that if I took a chance and made it happen, I would be opening myself up to opportunities. Sure enough, work came flooding in, which more than paid for the monthly studio rent, and it gave me a place to run workshops on the weekends.

    My riskiest decision ended up being the most rewarding, financially and otherwise.
    I think you just have to go with your gut. My gut never lies :)

  5. says

    I was learning how to design and code websites back in 1996 when the Web was extremely new to the everyday user. And now, designers that I know have a learning curve to overcome not only when it comes to web graphics but also the technical skills in order to get their designs and desired interactions to look and work as originally intended.

  6. says

    Great article Laura, I’d have to say risk taking IS key to any successful business venture. You’re always taking a risk when it comes to the unknown but I like to think of it this way, even if your risk doesn’t work out you’ve still leanred something. Take what you’ve learned and try again.

    I remember reading somewhere that before many businesses became successful they had at least 1 failure first. Their success came from never giving in to failure and learning from it.

  7. says

    I am definitely a risk taker. You have to be, if you are to treat freelancing as a business, as Elizabeth says.

    I believe all (willing) freelancers have that daredevil streak – otherwise, we’d be looking for jobs!

    Risk taking has definitely been positive for me. Everything from finding my niche to the clients I work – or don’t work with – now has been the result of risks I took as a freelancer.

    The only risk taking that hasn’t paid off has been in the technical area. So now I hire a VA to help manage my blogs, lest I blow up another one, LOL!

  8. says

    Well I am definitely in the class of risk-taker and I fear that I both won and lost big. When it gets down to it I learned far and away more from “losing big” than I ever did from all those times I bet and won. My advice is get on Mission and take the risks that you need to take to move forward, you may get hammered a few times but the rewards are well worth taking some intelligent risks.

    Nice thoughtful post Laura!!

  9. says

    Often, success comes only with risk.

    To a certain degree, even not risking is risky, so
    it all depends how you look at it.

    The point of the whole thing, though, as I see it is to
    TAKE ACTION without procrastination.


  10. says

    I like Igor’s point above, trying to take no risk is often riskier than taking one.

    Seth Godin gave a great TED talk on this very topic a while back. I know you can find the link on the web site or (hesitant self promotion…lol) with a review that I did on my site a couple of months ago.

    Seth really hits it hard. He says that in today’s world, safe is the riskiest thing you can possibly do. With the speed of change now there is no qestion in my mind that he is right.

  11. says

    I resisted freelancing, because I figured I didn’t have the risktaking temperament for it, but actually I’ve been very happy and successful with it — and not everyone with a salaried job can say the same. In fact, I think the past year or two has shown us that having a salaried job can be just as uncertain and risky as freelance work. At least we have more control over it.

  12. says

    Great point Rebecca!

    Risk can be a good quality, but sometimes non-risk takers are successful too.

    Also, as you point out, even the “safe” alternative might not be so safe.

  13. says

    LoL… I have a raft of windows open with different articles in them to edit and loving editing as I do…well… lol… somehow I keep winding up here.

  14. says

    I figure I took a big risk 17 years ago when I quit my job to do freelance PR consulting. But in reality it wasn’t too much of a risk, as I’d been doing it as a sideline and by then had worked with a guy and had a pretty good stable of clients. So mine was very much a calculated risk with few negatives. Plus, I had a husband’s salary behind me! I’d say I’m not too into risk. I need to break out of my comfort zone, in fact. I was forced to do that eventually, just by virtue of the fact that my work (in the home-building industry) went kaput nearly two years ago. So I had to find new ones, and branching out has been very good for me.

    Yet I still need to challenge myself. I need to find ways to be more creative in work, and to investigate new ways and new media. So I’m embracing a great book on taking risks in work, “YOU UNSTUCK” by a professional coach (and entertainment industry veteran). Great stuff — it gives you the tools, and the hope, to get you past your sticking points, and to figure out the best ways to take risks and have them succeed, leading you to take bolder risks. It’s not just for work — it helps get you unstuck in life, finances, relationships, whatever.

  15. says

    I must say that I am a risk taker, but it comes with the territory.

    In order to succeed as a freelance writer, you have to expand your horizons which means stepping out into unchartered territory to explore new and unfamiliar projects. This move can be daunting, but highly rewarding in terms of financial security and raising one’s visibility.

    Playing it safe would harm my bottom line, cause me to lose confidence in my abilities, and probably make me miserable.

  16. says

    Really great article. As a newbie to freelancing this resource is so valuable. I have a question for you all though. Some of you have said that the risk payed off and work came flooding in and I would like very much to get a space to work in as I think it would help me get in the mindset of work. But until I get in a steady stream of work this feels like to greater risk. So my question is, how did you get the work to come flooding in! It seems very hard to get people to have faith in you when starting up, agents for example. Do any of you have any advice on how you got your first steady stream of work coming in? Maybe this could be another article if it hasn’t been already.

    Thanks, great site!


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