Boss Responses

#71: From Employee to Freelancer with Jessica Farmer

Treasa Edmond Episode 71

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In this episode, Treasa and guest co-host Jessica Farmer tackle Paul's question: How do you transition from traditional employment to freelancing, and how do you find your first client? 

Treasa shares her intentional transition story, while Jessica reveals how getting laid off after nine years became her best career move. You'll learn why you shouldn't take too long making the decision, the finance setup Treasa wishes she'd done from day one, and why joining a freelancer community before you transition is helpful. 

ALSO TALKED ABOUT

  • Why everyone's transition looks different
  • The employee mindset trap
  • Jessica's story: Getting laid off and finding a large project within days from her network
  • The finance book Treasa wishes she'd read from day one: Profit First
  • How to find your first clients
  • Why you should join freelancer communities BEFORE you transition
  • Minimum viable product mentality

About Jessica Farmer

Jessica Farmer is a UK-based freelance content writer, editor, and manager, with nearly 15 years' experience. She Ioves untangling tricky topics to help readers understand complicated concepts. She particularly enjoys working with clients in the B2B/B2C SaaS space and marketing products that help users learn something, achieve something, or do something with a little more ease or efficiency. 

A former Managing Editor, Jessica is all about quality, consistency, and super-clear communication. She specializes in crafting medium to long-form content marketing assets such as thought leadership articles, SEO-driven blog posts, and case studies.

Connect with Jessica:

About Treasa Edmond

Treasa Edmond is a content strategist, business coach, and podcast host who helps freelancers and consultants transition to confident business leaders. She's been referral-based for five years, rarely needing to prospect for new clients, and teaches practical frameworks for pricing strategy, client boundaries, and business systems through her coaching programs and the Boss Responses podcast. Her goal is to help you build the business you need so you can live the life you want.

Connect with Treasa:

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Treasa Edmond (00:00)
Hey there, welcome back to Boss Responses. With all of the layoffs we've seen in the last two years, there are a lot of new people flirting with the idea of starting a freelance business. That's both a good thing and an unfortunate thing. It's good because there are some immensely talented professionals who will be joining us and offering services on their terms. It's unfortunate because many of them only have corporate experience and they're still stuck in an employee mindset.

Today's question is all about how you transition from a job to a freelance business. I made that transition intentionally. Jess, Jessica Farmer, our guest co-host this week, was laid off and started freelancing while looking for a job. Then she decided freelancing was her future. Even if you're already an established freelancer, I think this episode is going to give you some food for thought.

Let's get into it. you're a freelancer, business owner, or anyone who deals with clients, you're in the right place. I'm your host, Teresa Edmond. I've been dealing with clients and running my business for nearly two decades. And in that time, I've dealt with my share of doubt, imposter syndrome, and not knowing what to say when a client asks a question I wasn't ready for. I created this podcast to empower you with the boss responses you need to grow your business.

Each week, my guest co-host and I will bring you five episodes packed with practical insights. Monday through Thursday, we answer your questions. And Fridays, we dive deep to explore how our co-host embraced their role as the boss of their business. Welcome to Boss Responses.

We are back for day two with Jessica Farmer. Jess, what is the question for today?

Jessica Farmer (01:49)
Hi Treasa so today's question is from Paul. He asks, I'd love to hear tips on transitioning from traditional employment to freelancing. Also, can you talk a bit about how to find your first client?

Treasa Edmond (02:03)
This is such a good question because everyone transitions in a different way. I actually planned mine a little bit and I started out with clients. So I had freelanced kind of as a side thing for three or four years before I went full time. And mine was editing dissertations. I wasn't sure if I could make a full time living editing dissertations. And then one of my dissertation clients came to me and said, do you do writing as well? I really like what you do with my writing and I'd like to.

potentially form a collaboration. And they became an anchor client right out the door. So I got incredibly lucky. I did planning though. So I looked at who I wanted to work with, the types of work that I wanted to do, how I could really draw on my areas of expertise. And I grew up in the business world. My parents have always had businesses since as long as I can remember. So I...

knew you have to make decisions, you have to look at cash flow, you have to set up some of that stuff. I still wasn't prepared. So I still got out there and I started freelancing and my taxes the first year and people in the US are going to understand this. I don't know how it is for you Jess, but my taxes the first year were a very rude awakening. Then we kind of got that under control. I highly recommend

taking a good look at exactly what you want to do. And if you're going into something like content writing, look at Jennifer Goforth Gregory's book. It helps with a lot of that setup and things you need to consider. There are a couple of other really good books out there for freelancers. And I'll link some of those in the show notes if you want to go find those. But the biggest thing is figuring out what's going to work for you and realizing that you don't have to have all of the things.

So I know a lot of people, it took me two years from the time I decided I was going to go full time until I actually went. And I finally went because I could not stand my job for another year. And I loved my work and I loved the people that I worked with. I just didn't want someone else to be my boss anymore. So I know a lot of freelancers are in that situation. They were so uncomfortable. Something became so uncomfortable that they jumped ship.

and started freelancing. And then there are people who were laid off or had a life change that necessitated that they stay home and work. There's all different reasons and all of those transitions look different. Here's one thing that I wish I'd had when I started out, the finance stuff. And we're going to talk a little bit more, I think it's tomorrow, on structuring your business so that you can take vacations and such. I didn't do that for the first five or seven years of my business.

And it was horrible. And then I found a book called Profit First, and I'll link that in the show notes as well. It's the best book ever for setting up your business finances. And if you do it from the beginning, it makes life so much easier. Even if you are seven years into your business and you're still having issues, go find Profit First and read it. As to how I got my first clients, I started in, this is funny, I was just talking about this with Jess. I was editing dissertations and

Doctor of Ministry projects. My dissertation clients started coming back to me and asking about other services as they got out into the world and started doing their businesses and their academic careers and stuff. That's how I found my first clients. It was all referrals and it's still how I run my business to this day. So I was so lucky that I didn't have to go out and beat the path and find the people and say, hey, do you need a freelancer?

I do that a bit more now with a content strategy, but my ghost writing is still sent referral. I do have some clients that come to me, but usually it's because I've seen something I've posted on social. There are a lot of good resources out there about finding clients. If you're doing LOIs, once again, I recommend Jennifer's book or her blog. Her blog is amazing, but she has a five sentence LOI that is brilliant. And I really highly recommend that you don't reinvent the wheel. There's no need.

adapt it so that it works for you. That's the thing you're going to want to do with your business from day one. How did you make that transition? I know yours was a little not necessarily your choice.

Jessica Farmer (06:30)
Yeah. So I was laid off and I wasn't quite sure what I was going to do about it, but I'm not somebody who likes to have nothing to do. And obviously there's a more practical need as well to keep working. So I knew that freelancing could be something that might kind of keep me going.

Initially, while I looked for a next job, I spent nine years in my like employed career working for an accounting software in the UK called Sea Agent. They actually make accounting software for freelancers. So I actually spent nine years writing about being self-employed and, and all the things to do with being a freelancer, including the tax and finance stuff. So I was lucky to have that as a grounding, but I also.

I guess wasn't too afraid of exploring it as an option because I knew that it was something that could be done. Where I guess the first thing I did was let my network know kind of what had happened in my career. And it took me a couple of days to kind of find the right words to share that news. But as part of that, like a lot of people do, I said that I was immediately available, interested.

happy to consider freelance contract work while I thought about my next step. I was very fortunate that one of my recent employees reached out to me over that weekend offering me ⁓ a large project that would basically take me up to the end of the year. This was started in November, so that was just ⁓ a total gift. I was so grateful and continue to be. That brought me the time to

and hang of some of political bit more carefully about what I wanted to do next. I felt like I didn't have to fire out a million applications and have a big project to work on. So I was busy and actually I started just exploring what other freelancing work could look like. And I discovered there's this whole other world out there, which is a, an important person. Even someone that writes about freelancing for their job, you don't really know.

kind of waltz up there until you start looking. And I was fortunate that I had a few other responses from people that were interested in working with me and based on my LinkedIn post and the people who were good enough to recommend me who I'd worked with in the past. I guess I was at a point in my career where I'd built up a pretty solid network. know, the more sort of explore those opportunities, the more I thought, this is kind of... This is fun. you know, there's...

some potential here and the more I felt like that, the less I felt excited about the sort of employed roles that were cropping up. I also realized that to really do this properly, you probably have to kind of go all in and treat it and maybe not do a side quest for a permanent role. Now a lot of people do both and I totally understand that.

fortunate that I could make that choice at that point. So yeah, of great to December, I was feeling pretty good about it and then made the decision to spend 2024 really committing to the Philanthroans life, the business and to seeing what I could make of it. So it all happened quite organically for me.

Treasa Edmond (10:14)
It's wonderful. I wonder sometimes if that's not the better way. You know, it just happens. You're forced into it. And it could be you forcing yourself into it or someone else forcing you into it. But I think there's a motivation there that doesn't exist when you just make the decision. I'm just going to do this. And then you work towards it. One of my pieces of advice on this is don't take too long. If you decide you're going to transition from traditional employment to freelancing,

set a deadline and then stick with it. That's your first big boss decision. So you need to make a commitment to yourself and then follow through with that commitment. If you don't, then you're going to equivocate about every decision you have to make the entire time you're running your business. Also, if you are not quite sure, if you want to make that transition, if you're just...

thinking about it. Or you talk to someone who does freelancing and you're like, that sounds nice. I could do that. Or maybe you're getting ready to have a child and you're like, I don't want to go back. I want to be able to work from home and at least be with my baby, even if childcare is there. Then one of the things I recommend is go into a community of freelancers. So there are some really good Facebook groups. Jennifer Goforth Gregory has one. If you're a writer, freelancing females, if you're a woman.

Look at some of the questions people are asking and some of the problems people are having and take an honest look and see if that's something you're willing to deal with because it's going to come up at some point. ⁓ But also look at the successes people are talking about. And on LinkedIn, look at some of the successes people are talking about. And now, of course, it's online and you don't know these people, so you have to take everything with kind of a grain of salt. Is that a saying in English?

Jessica Farmer (12:08)
I should say I live in Scotland because if I don't correct you, somebody listening will be mad at me. I know a place by living in Scotland and firstly we say a pitch of salt. ⁓

Treasa Edmond (12:22)
That's awesome.

So when you're talking to or when you're looking at posts in groups, especially on Facebook, take it with a pinch of salt because sometimes people will ask a question and it's actually like audience research or they're looking for clients. I mean, there's all these sneaky ways to do things. I'm a big value adder. I prefer to add value rather than trick someone into working with me. And I made that decision early on, but look at what they're doing and talk.

to them, network with them, join a group of freelancers and have a conversation with them for a couple of months if that's part of your process. I would highly recommend you make that part of your process. Tell people, hey, I'm going to be transitioning from traditional employee-match freelancing six months from now. And in the meantime, I would love to have regular meetups with a group of freelancers so that I can ask more questions and get more clarity on things. And then pick freelancers who are experienced in their business, who have been doing it a while.

who have gone through all of the trials and tribulations, and then for that six months, ask every question you can. Most of the rest of it, you can hold on and build it as you need it. If you wait until you've built everything, you're never gonna get it done. I'm still building my website and I've had it for 20.

Jessica Farmer (13:41)
Totally, totally. have a background in working for startups and I think that kind of minimum viable products mentality, you you build the smallest good version of the thing and then iterate on that. think this is a, it's a good mindset to have when we're thinking about these sorts of building blocks of business that are good to have, but they don't have to be perfect.

Treasa Edmond (14:09)
I hope that was helpful. And I hope that anyone out there who is looking to transition and wants to be a freelancer, come join us. It's fun. It's not for everyone, so be honest with yourself on that. But we're here for you if you need us. All right, I gotta come back tomorrow. Tomorrow we're actually going to talk about making sure that you have space in your budget to take breaks and have an emergency fund and all of that fun stuff. See you tomorrow.

Jessica Farmer (14:36)
Bye!


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