Working with a business coach

Toward the end of 2024, I felt like I needed some new perspectives in my business. I’ve been a freelancer for a long time, which has its pluses and minuses:

• Experience is an asset in many aspects of freelancing. With experience comes confidence, and experience also tends to bring access to clients who want to throw money at a problem and get it solved quickly and well. 
• But, experienced freelancers (including, but not limited to me!) also tend toward complacency (the feeling that well-paying work will always be there, which isn’t always true), “this is the way I do it because this is the way I’ve always done it,” and a resistance to trying new things. 
• Even experienced and successful freelancers get in ruts and feel frustrated. As I wrote in my 2024 wrap-up post, I’m not dissatisfied with how much I earned last year ($125K), but I’m frustrated that I set a goal of 140-150K (the freelance equivalent of a six-figure salaried job) in 2021 and I’m still not there. 

My first initiative was to join a few groups for freelance writers. I figured that “word people” have a lot in common, regardless of the specifics, and that these would be good places to get some fresh input. This proved to be correct, with the bonuses that:

• Many freelance writers market a lot, so they have a lot of input on marketing techniques, and they normalize the idea that it takes a lot of marketing to find good clients.
• Many freelance writers work for clients with large budgets (as in the example I gave last week, of a writer who earns $15,000 a month from three clients total), so it doesn’t seem weird to want those types of results for yourself.  
• At least some freelance writers earn what I would consider a lot of money; one of the writer groups I’m in has a substantial sub-group for people earning more than 200K a year. I’m not at that level, but I feel like I can get some good input on how to get there. 

I was already feeling energized by the ideas I got from these groups. Tip #1: If you need some fresh ideas in your business, get outside the echo chamber of the people you usually talk to. Join some groups for people in an adjacent line of work, or related to one of your specializations. Hang out with more people who are the kind of freelancer you’d like to become.

Enter the idea of a business coach 

I joined Jennifer Goforth Gregory‘s Facebook group for content marketing writers (it’s great!), and decided to attend a few events put on by the group members. This led me to a free question and answer session by Treasa Edmond, (not an affiliate deal), who is a writer, business coach, and the host of the Boss Responses podcast. I really liked Treasa’s style as a person and a businessperson, and a couple of people in the Jennifer Gregory group mentioned that they were doing individual coaching with Treasa. This sparked an idea: maybe I should do that too! More on the specifics in a moment, but first…

Why work with a business coach?

Now that I’m on the tail end of coaching (I chose Treasa’s three-month VIP Business Accelerator and started at the end of November), I think there are three main reasons you might want to work with a business coach:

• To get help in turning a brain dump into a plan (that was me)
• To feel accountable to someone else for working toward your business goals (I don’t need help with the follow-through aspect, but it was definitely helpful to know I had to report back to Treasa)
• To get insider tips on breaking into a new market (this was not my goal, but for example if I wanted to get into ghostwriting, something I’ve though about in the past, I think I would work one-on-one with a coach in that market) 

In my experience, most freelancers who seek business coaching make a few mistakes:

• Expecting significant results from a small investment of time and money. I now see why most business coaches require a three-month commitment; because it really takes that long to see some changes. 
• Mis-identifying what they do and don’t need help with. To be fair, you don’t know what you don’t know about yourself. But, because I know that I’m an Upholder, I know that I basically always follow through on something I’ve committed to doing, but I’m resistant to trying new things and I’m very risk- averse. Maybe you’re the opposite: you need someone to rein you in! Either way, it helps to know this before you select a coach. 
• Focusing on micro goals instead of macro goals. This was me: I approached Treasa with a specific idea of how to increase my income, and I was convinced that it was the way. Treasa immediately got me to zoom out, and focus on ways to make more money that also align with my larger lifestyle goals of personal fulfillment and location-independence. 
• Not being open to pushback from the coach. It’s never fun to be disagreed with, but the coach isn’t there as your yes-person. Treasa strongly disagreed with me on a few things I do in my business, and that was honestly very helpful. 

How things worked out for me 

Treasa’s three-month one-on-one program was perfect for me (again, not an affiliate deal). We did a 90-minute goal-setting session, then met every other week for an hour (six times total), plus did “deep dive” sessions where she taught me how to use Scrivener (something I had been resisting for a while) and how to make PDF workbooks for my courses (this isn’t a new idea, but I’ve never done it before). This cost me $1,500 ($500 per month for three months, and the prices may or may not be the same if you do her program in the future). Coaching was something I wanted to do for myself regardless of the return on investment, but it’s worth noting that I made back that $1,500 twice over, in the first month of coaching, by negotiating higher rates with a couple of new clients. 

If you’re interested in a group coaching program, people in Jennifer Gregory’s group also rave about Jenni Gritters’ Sustain program. 

I achieved a number of things that had been bugging me for a while:

• Scratching a bunch of things off the “ugh” list: a new website for my direct language work thanks to Amanda Calvin’s pre-made website templates, a new e-mail signature thanks to a challenge group in techforword, and The Nudge Kit (password: nudge), a resource I had been meaning to design for about 300 years. 
• Trying some new things for Training for Translators: a free webinar (again, not rocket science but I just never do this), a free preview of March Marketing Madness, using some different graphics in my e-mails, reconfiguring a few classes. 
• Making a timeline for writing books. I tend to write a book when the spirit moves me to write a book (sounds crazy, but it’s true, I have no book-writing strategy whatsoever). I now have one book ready to go (Getting Started as a Freelance Interpreter, to be published this spring), and two more outlined in Scrivener. 
• Raising my rates for a few specific services. I had been feeling for a while that I was under-charging for things like keynote speaking engagements. Treasa helped me work through this (both the logistics and the underlying mindset) and it’s been very successful so far. 

Point being, I think that whatever your goals, coaching can give you some new insights and the perspective of someone who doesn’t share the limiting beliefs that you probably have about yourself. If you’ve worked with a business coach, reply to this e-mail and let me know how it went! Or if you try it, let me know how it works out for you. 

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