Hello Better Biz Academy fans! In this week’s post, I’m going to address whether or not it makes sense to trust a freelance mentor who is no longer freelancing.

Have you subscribed to my channel on YouTube? Check out the video I made on this topic or read on for the transcript.

What’s Different About a Mentor Who is an Active Freelancer

This is actually one of my pet peeves in the freelance economy with freelance coaches and course creators. There’s nothing wrong with transitioning out of a freelance career and working with products, courses and coaching packages for freelancers. However, there can be a real danger to those freelancers if they are not aware of the fact that this person is no longer active in the freelance marketplace.

Every so often, I see guides and courses for people to launch a freelance career as a virtual assistant, a writer, or some other type of freelancer by a person who is no longer actively freelancing or who maybe freelances an hour or a couple of hours per month. Now you can still learn great things from these freelancers but somebody who gets paid $400 to write one blog post per month doesn’t have the necessary background to help you launch a sustainable freelance writing career.

That means you’re actually at a disadvantage as the freelancer taking courses from this person because they are not teaching you what you really need to know about growing your freelance writing career and landing more than one client or landing sustainable work so you have repeatable income every single month.

There’s a real danger in assuming that a person who’s been really successful selling online courses about freelancing has the necessary know-how to teach you how to build a sustainable freelance business. If 90% of their income is coming from selling you courses about how to freelance instead of freelancing itself, that’s something you want to take into consideration with your mentor. They may have information that’s applicable about freelancing as a very small percentage of their time and income or they may be knowledgeable about methods that worked months or years ago, but they’re not truly active in the marketplace experiencing the same challenges and issues that you may experience as a freelancer. This is something to keep in mind when you’re purchasing a course or one-on-one mentoring from a freelancer.

What to Look for in a Freelancing Mentor

When I invested in freelance mentoring last year, I chose to work specifically with two people who were actively freelancing. They made money from selling courses and coaching freelancers but they were still very much in the trenches, so to speak — pitching clients, negotiating contracts, dealing with problem clients, etc. I wanted their insight in that way because I knew that they would know the things I was talking about. They weren’t just referencing methods that may have worked five or ten years ago when they were freelancing. They understood the day-to-day issues of handling a thriving freelance business. It wasn’t about one client doing one project per month. It was really about repeatable success and the day-to-day life of a busy freelancer.

Find a Mentor Who Has Done What You Want to Do

When you’re thinking about finding a mentor who can help you go to the next level or purchasing their course, you want to find someone who’s done exactly what you want to do. When I launched my freelance career in 2012, my first freelance writing mentor ever was someone who had built a business that looked exactly like what I wanted. I saw that she had sustainable freelance writing clients on retainer and was very successful at keeping those clients for a long period of time. I chose to purchase her materials and communicate and work with her because that was the exact same model that I wanted to create my freelance business off of.

If you’re taking freelance mentoring from someone who freelanced a little bit or freelanced years ago but now mostly makes their money converting people like you into paying coach customers, then that’s something to consider. Do you ultimately want to get to a coaching business yourself where you’re coaching other freelancers or is your primary goal to grow your freelance service business? They’re two different things and the insight that you get from people is going to vary based on their individual experience.

You want to find someone who has built what you want to build and learn from them. You don’t want to be given advice that doesn’t really apply to you over the long run because this person is just successful at doing a portion of the day-to-day business of a freelancer or does it so rarely that they don’t have a ton of experience dealing with client problems, drafting up contracts, reinforcing boundaries, or writing a scope of work. You want someone who knows exactly what you’re talking about and you may want a person who is actively doing that right now, instead of making their entire income off of you paying for their coaching services.

I see a lot of freelancers who are really enticed by these flashy courses from someone who maybe was a virtual assistant, project manager, graphic designer or freelance writer at some point in time but is no longer doing that, is no longer involved in the marketplace or brags about how much money they made once by writing a blog post. That’s nice but that doesn’t transition into landing freelance writing contracts on the regular and building up a stable of reliable quality clients that you love working with. Those are two different things.

You can still learn from people who have transitioned out of freelancing or did it years ago. There are a lot of valuable lessons you pick up as a freelancer that you don’t necessarily forget or that remain applicable. However, if you’re looking for hands-on insight and strategy, you want to get the support of someone who has been there and can help you strategize and build your own business as effectively. Make sure that you read the fine print on people’s sales pages about exactly what kind of support you are going to be getting and factor that into your decision when you are looking for a mentor.

Check out my other posts about freelancing for more tips!



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