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The Freelance Mindset: Do You Have What it Takes to Succeed?

  • By Jeanne Yocum
  • November 25, 2020

What does it take to succeed as a freelancer?

Obviously you need the skills and knowledge to deliver the services you promise to provide to your clients. But after nearly 30 years of freelance experience, along with watching the careers of numerous freelancing friends and colleagues, I have concluded that you also must have a certain mindset if you hope to succeed over the long haul as your own boss.

Here are three elements of the mindset that will keep your freelance career on track, along with ideas on how you can build strength in these areas if they aren’t already part of the way you approach your business.


Every freelancer faces rejection from time to time. A version of “No, thanks” will come your way with some regularity. But you can’t let this get you down; you must be tenacious in working toward your goal of running an independent business. If a new business opportunity falls through, you must get right back in there and seek the next opportunity. You can’t let any of the challenging aspects of building a viable business deter you from moving toward your goals.
Tenacity is also important at other times, such as when a client is slow to pay your bill. You have to be tenacious about reminding them (nicely, of course) that they owe you money and you expect to be paid promptly. Dunning clients is never pleasant, but it has to be done. (Although certainly I would advise that if you repeatedly have to dun a client, this is a client who should be fired.)

If you are someone who will shy away from asking for what you’ve earned, you might need to look into getting some training in assertiveness, negotiating, or communications. Gaining skills in these areas will help you become more comfortable when tough messages need to be sent to clients, subcontractors, or vendors.

Read: 5 More Traits You Need to Succeed as a Freelancer

Every freelancer faces rejection from time to time. A version of “No, thanks” will come your way with some regularity. But you can’t let this get you down. Click To Tweet


If you’re just embarking on your freelance career, take time to consider that this is probably the first time where you have the ultimate decision-making power about your work priorities and about how you’ll spend your time and resources. It can be daunting to realize that you are now responsible for every single choice that gets made about your business. And doing that effectively requires a high degree of decisiveness.

Every day is filled with decisions that need to be made about the direction you’re taking your business, what you need to do next to move forward, and about the work you’re doing for your clients. You need to be able to make these decisions in a timely manner and then stick with them. People who keep changing their minds about what to do next, usually because of a lack of self-confidence, can have a hard time bringing the required level of decisiveness to their work.

Understanding your own decision-making style can help here. Are you someone who has to research everything to death? If so, you probably need to lighten up a little bit on that or else decisions will never get made. Also, it helps to have a friendly sounding board for when you’re making really big decision. A fellow freelancer who has been there/done that can often provide objective feedback on the options available to you. Keep in mind that as time goes by and you gain more decision-making experience, it should become easier to trust your instincts.

Related: 5 Signs You Might Be Cut Out for Freelance Work

Risk tolerance

Freelancing is hardly risk-free; in fact, the list of potential hazards is long and daunting. Every freelancer has cash flow worries and has had to chase clients for overdue money. We all worry about juggling all those competing client demands. We all have clients who fall behind on their own deadline commitments and cause us to have to work overtime to get a project back on schedule. We all lose clients for reasons having nothing to do with the quality of the work we deliver. All of this and so much more requires having a high degree of risk tolerance as part of your freelancing mindset.

Freelancing almost by its very nature will involve some stress and perhaps sleepless nights. This can be quite problematic if you have a low level of risk tolerance. However, the good news is that with experience, you will learn how to obviate at least some of the risks you face. For example, you’ll learn to ask for deposits before starting work for new clients so your cash flow won’t be quite so compromised if they turn out to be slow payers. And, as I mentioned earlier, you’ll learn to fire clients who are repeat offenders when it comes to paying late.

As you succeed at facing and conquering the perils that come your way, you will gain confidence in your ability to stay the course and succeed. So risk tolerance is something you can build over time.

It is also helpful to have self-confidence, self-motivation and optimism as part of your mindset when you are freelancing. But if you focus on developing and strengthening the three elements I’ve discussed here – tenacity, decisiveness and being risk tolerant – you will find that being your own boss is a smoother, less stressful, and more rewarding experience. Good luck!

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