When Is It Time To Quit Your Job & Go Freelance? w/ Josh LeClair

January 28, 2019

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Too often the safety and security of a “real job” keeps us from following our own professional dreams. But for those of us who realize that we have a deeply ingrained desire to do something else, to follow our own creative journey, the time comes where we have to take that scary leap and give it a go.

Today’s guest just did something amazing and terrifying, he quit his job of four years and went full-time freelance. Josh LeClair, a Studio Sherpas Community member, now has his own freelance business based in northern Michigan and has been working with some really great brands.

In today’s interview, Josh shares his journey of deciding on a career as a photographer and then pursuing it on his own terms. The decision was full of uncertainty but not regrets. We consider just what goes into a move like this and how to know when you’re ready.

We also talk about how you can best help clients. It can only come from forming a relationship with them in which they trust you to do the best work for them. We discuss how to identify a client’s area of need and how you can communicate that to them in a confident and helpful way.

Are you ready to go freelance or have recently made the switch? What were your struggles and how did you overcome them? Tell me about it in the comments below!

*If you’re looking to grow your video community with exceptional programming with unforgettable networking, unlike any other event, be sure to check out our sponsor for this episode WPPI. Attend 5 days of awe-inspiring seminars, hands-on sessions and exciting photo walks from the industry’s most rousing photographers and content creators. Get all the info here!*

In this episode:

  • The internal and external struggles to overcome when deciding to pursue a creative freelance career
  • Knowing when you’re ready to take the leap and go freelance
  • The less than glamorous but crucially important parts of starting a business and how to prioritize them
  • How to find and keep clients when you first go freelance by directly reaching out to them to form a connection


“The pure joy that comes with learning and growing and building this business has been absolutely amazing, even over the last four years. So that’s what led me to step out on my own.” [12:39]

“The way that I’m getting a lot more work is just educating; sitting down with clients and talking about them and what they think their needs are and going over what we can provide for them. And that’s really what’s gotten me a lot of work.” [22:25]

“If there’s anybody out there who’s actually thinking about doing this or it’s been on their mind for a while, I want you to realize that there’s a ton of people who don’t do this immediately. They’ve gone through being an assistant, multiple jobs. It doesn’t matter what it is. Every one of those experiences you can take away something and you can learn so much.” [32:44]

“I can’t tell you how exhilarating it is for me to finally send that email that I’m resigning, I’m done, my business is on its way, and I’m going to do this thing and I’m going to see wherever it takes me.” [34:38]


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