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3 Massive Freelancing Obstacles (& how to overcome them)

overcoming obstacles as a freelancer
Table of ContentsUpdated Sep 30, 2024

Building a freelance business that fulfills you and provides you with the lifestyle that you want and deserve takes equal parts talent, gumption and stick-with-it-ness. Forget about waiting for the muse to visit. We have to make it happen. Every. Single. Day.

So, what does making it happen actually mean?  It means committing to our dreams and doing our best to overcome the obstacles that threaten to delay the results that we want.  The thing about obstacles is they’re much easier to overcome when you know what they are, so here are a few oldies, but goodies, along with strategies to get past them.

Obstacle #1 – You don’t know how to do something

We all have dreams.  Perhaps yours is having a phenomenally successful gallery show, becoming a best-selling author, or launching an on-line store. But when we see others successfully doing what we dream of, we assume they must have been born with the knowledge and skills needed to make it happen.  That’s just not the case; they figured it out as they went along. And you can too.

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Strategies:

Ask for advice
No matter what you’re doing there’s someone who’s done it before you. There are no medals for re-inventing the wheel, so ask people you admire how they did it.  Most people are more than happy to share their experiences.

Ask for help
Here’s where you network comes in.  Now you know what you need to do, figure out who you know that can help.  Feel shy about asking? Make it a habit to help others, and you’ll soon recognize what goes around, comes around.

Hire someone
At some point, you’re going to come across something that it’s simply not worth your time and effort to figure out yourself. This is a good time to hire another freelancer to work with you.

Don’t stop learning
There are tons of free or cheap resources courses available to you. Check out The Muse which has a fantastic roundup.

Fake it till you make it
In a world of authentic marketing (of which I am a huge proponent), I understand that ‘faking’ anything can feel disingenuous. Here’s the distinction that will ease those feeling. Faking it is not about tricking others into believing you can do something. It’s about tricking ourselves into believing we can do something, so we can push through the fear.

Obstacle #2 – You can’t see how you’ll reach your goals

Our need to see the whole picture before we believe it can happen is a classic self-sabotaging strategy.  We talk ourselves out of something before we even try.  The sooner you release that, the sooner you can get down the work of making your idea happen.

Strategy
Break your goal down into steps.  If your dream is to work with higher-paying clients, those steps might include:

  • Articulate what you do more effectively so that it resonates with your dream clients
  • Review your fee structure. If you’re charging too little, you’ll continue to get small clients
  • Figure out where the dream clients are congregating (e.g. conferences, fairs, associations) and network there.

Obstacle #3 – You fear failure

This is a totally understandable fear and one that everyone struggles with.  But here’s the thing. Since we don’t know how to do everything right out of the gate, some level of failure is inevitable.

Solution
It’s not whether we fail that counts, but how we respond to failure. Allow it to crush you and you’re in for a bumpy ride.  See it as a learning experience (after you’ve licked your wounds of course, you are human after all) and you’re in with a fighting chance.

Entrepreneurship is a full-contact sport. Obstacles are there to challenge us because challenge is exactly what we need to stretch and grow. What strategies will you take action on first?

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Written by Justine Clay

Staff at Millo.co

Justine Clay is a speaker and business coach for creative entrepreneurs and freelancers. Through a series of clear, actionable steps, Justine will teach you how to identify what makes you stand out from the crowd, create a marketing message that resonates with your ideal clients, and build a successful and fulfilling creative business or career. Sign up for Justine’s free guide: How to Find High-Quality Clients and Get Paid What You’re Worth and start making monumental changes in your creative business or career today.

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