10 reasons freelancers fail & how to avoid them

Freelancing sure comes with it’s struggles, but a lot of it comes back to us and the decisions we make. This rapid fire blog shares 10 of the most common freelancer struggles and how they can lead to failure with a quick tip on how to avoid them in your budding business. By Haley Berryman.

  1. Failure to keep things simple

    You don’t need to launch a course, a product, an affiliate program, seven tiers of services right away. Believe me, it overcomplicates everything and you run the risk of burning out. Just do a couple of things really really well and go from there. You won’t know what you love delivering if you don’t just start with that. And I know the noise from the outside world can inspire you to want to do more, but I urge you to stay in your lane, and just do you to begin.

    Hot tip: Start with one thing, and deliver it well before expanding. Simplicity is your friend and will set you up for a long happy freelancing career.

  2. Failure to invest

    Two things to consider, even early in your journey is outsourcing, and systems. Outsource the jobs you hate or that are draining your precious energy. Or free yourself up for more important tasks by automating repetitive tasks. Sure these two things will require some investment on your part, but if done well, you’ll make it back.


    Hot tip: List out all of the thing that drain your energy and that you do on repeat, and figure out a way to spend less of your time on them through outsourcing or systems.

  3. Failure to manage time

    You’ll soon learn that time is your most precious currency. Look at ways to optimise it. You are responsible for your day to day structure and how you use your time, so become aware of when you work best, and where you get disorganised or waste time. Time tracking tools and timers like Pomodoro can help you gain awareness so you can make the most of your time at the desk.

    Hot tip: Try time tracking for a week or more user Toggl and work in focused sprints using a tool like Pomodoro.

  4. Failure to listen

    First, if you fail to listen to your clients and the feedback they are offering, you could be driving your biz down to doomstown. Remember your customers have valuable intel that could guide your direction and offer up valuable opportunities you may not have seen yourself.

    Hot tip: Survey your clients and ask for feedback to improve your offering and seek new opportunities.

  5. Failure to grow and evolve

    Business is about discovery, and IMHO, it should be fun. Rememeber you’re the boss. Don’t be afraid to cut things loose that aren’t working and try something else. Just do it quickly.

    Hot tip: Fail fast. If somethings not working, it’s ok to ditch it and try something else. If you’re not sure how to evolve, hire a coach to help you.

  6. Failure to rest

    All work and no play makes for an unhappy and burnout freelancer. I’m sure you chose this path for freedom, flexibility and creativity. Am I right? All of those things require space to make happy.

    Hot tip: Block time in the calendar to do whatever you please. Daydream, draw, nap, jump in the ocean…whatever it is, just be sure you stick to it and enjoy these tiny pleasures that come with freelancing.

  7. Failure to treat freelancing like a business

    Unproductive habits, a lack of discipline, no real purpose or direction can mean we float about not really doing anything meaningful. Make sure you dedicate time to be the CEO. Write down what success looks like to you. Be proactive in developing action plans to get you there vs just reacting to whatever comes your way.

    Hot tip: Allocate time to be the CEO of your business at least once a month and use this to reflect, vision and intentionally set goals to create a biz you’re proud of.

  8. Failure to do the work

    This is a weird one, but so often people are looking for the magic bullet or quick fix. You know that habit…”If I do this course then I’ll be able to start selling this service” or “when I’ve made this much money, then I can start sharing on Instagram”. You download dozens of free guides and participate in every challenge that lands in your inbox, hoping it’s going to have the answer to your success. But nothing beats doing the work. That means putting one step in front of the other and just starting! It will take you places.

    Hot tip: Don’t wait for the perfect time for anything. You’ll never be fully ready. Get out of your comfort zone, get in the ring, and start creating, doing, failing, learning and growing.

  9. Failure to charge enough

    Failing to charge a decent fee is only going to create an unsustainable business and breed resentment. If you’re not getting fairly compensated for your hard work, you’ll soon get despondent and enjoy what you do less and less.


    Hot tip: Set your rates well from the start, or if you’re just starting out and want to do some free work, give yourself a time limit on this and raise rates every few months to reflect your growth.

  10. Failure to set boundaries

    This is so common, but boundaries are everything in business. Set the with yourself first, for example don’t say to work when it doesn’t light you up out of fear. Set them with your clients, for example, don’t say yes to that extra round of changes if it’s making you feel icky and stressed inside. When you have strong boundaries you’ll show up with confidence and learn to trust yourself, which is exactly what you have to do as a solo operator.


    Hot tip: Be clear on what you will and won’t do, and don’t be afraid to say no.


Written by Haley Berryman

Almond latte drinking, nature lovin’, mama of two. Endlessly coming up with ideas for others. Hippy at heart. Says ‘babe’ way too much. Shares personal musings on topics including freelancing, marketing, wellbeing and happiness. Connect @haleyberryman__ or haleyberryman.com.