Boss Responses

#67: Freelance vs Job: Which Is Actually More Stable? with Ed Deason

Treasa Edmond Episode 67

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If you've ever looked at your bank account during a slow month and thought "maybe I should just get a job," this episode is for you. The pull of stability and benefits feels strong, especially when running a freelancing business feels uncertain. But employment doesn't actually equal stability, and you can build everything you're craving into your freelance business.

In this episode, Host Treasa Edmond and business coach Ed Deason break down why this isn't about weighing pros and cons, it's about going all-in on whichever path you choose. You'll learn why splitting focus between freelancing and job searching hurts both options, how to reverse engineer your business around the life you actually want, and why one employer is far less stable than multiple clients.

WE ALSO TALKED ABOUT

  • How to build benefits and stability directly into your freelance business structure
  • Ed's story: what happens when a billion-dollar company goes bust overnight
  • The real question: What do you want from your business?
  • Why most freelancers should work 20-30 hours per week, not 40
  • The psychological safety trap: feeling safe vs actually being safe
  • The employee mindset trap that keeps freelancers from building the business they want


About Ed Deason

Ed Deason is a business coach specializing in working with founders and entrepreneurs ready to scale, pivot, and build their ideal businesses. With over 15 years' experience and an MBA, Ed's coaching has helped clients gain clarity, confidence, and achieve real results.​

Connect with Ed:


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:

Related Episodes:
Listen to Treasa and Ed's in: How to Ask for Referrals Without Feeling Awkward, How to Handle Freelancing When the Economy Slows Down

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If you'd like to support the podcast, click that link above. Those lattes help keep us going and are much appreciated!

Treasa Edmond (00:00)
Hey there. Welcome back to Boss Responses. Today, Ed Deason and I are tackling a question that may hit a little differently depending on where you are in your freelance business journey. Should you go back to a traditional job for the stability and benefits or can you build those things into your business? If you've ever looked at your bank account during a slow month and thought maybe I should get a job, this episode is for you.

Ed and I break down why employment doesn't actually equal stability, how to build the security you're craving into your freelance business, and why trying to do both at once might be the worst option of all. Let's get into it. If 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 three with Ed. Ed, are you enjoying the week so far? All right. What is the question for today?

Ed Deason (01:33)
absolutely.

Okay, so day 3 question is, I've been freelancing full time for a while now, but I'm starting to wonder if I should go back to a salary job, especially for the stability and benefits. On the one hand, I love the freedom I have now and don't want to give that up unless I really have to. How do I weigh the pros and cons of freelancers versus going back to a traditional job? It's an apples and oranges comparison and I'm not sure where to start.

Treasa Edmond (01:59)
You know, it kind of is apples and oranges. It's two completely different worlds. I have two, maybe three responses to this. you can build that stability and benefits into your business. You can absolutely build the stability and benefits into your business. So if that's your concern, figure out how to do that if freelancing is what you love. How do you weigh the pros and cons? Just make a list. mean, why are you weighing the pros and cons? And the biggest thing is control, right?

If you choose to control your business, you have that control. You never have that control in a job. Someone else is always in control. It doesn't matter if they think you're the bee's knees, they will let you go at a moment's notice if it's not the right business decision. So it's not about people and business. Very few businesses operate with the people in mind. You can do that as your own boss. So you can build the business around your life, which I think is obviously the best way to do it.

I think the question here isn't should you weigh the pros and cons. It's are you all in on your freelancing business or are you not? If you are, then you need to focus on building that business to where it can offer you the stability and the benefits. If you are not, and like I said before, there's nothing wrong with that, then you need to go all in on finding a job. it's an, I've had this conversation so many times lately. This is an

all or nothing situation. If you split focus, you're hurting your business or you're hurting your job search. Splitting focus in this situation is never a good thing. I pivoted my business a couple of years ago so that I could start this podcast and so that I could start teaching content strategy with strategy bosses. And then I've added in the coaching now, which is amazingly fulfilling. I took a brick and mortar job. It was remote, but you know, it's the same thing.

For the first time in 17 years, I swore when I left and started freelancing almost 20 years ago that I was never going to work for someone else again. I talked myself into trying the J-O-B because I wanted stability and benefits while I pivoted my business so that I wouldn't have to do as much client work.

I love the people I worked with. The people were nice. I did not enjoy it. I'm an expert at what I do, but when you're in a position like that, you are not the expert. Someone can always override your great idea. And it was just so, so frustrating. And now I actually treated the job like a client, which they didn't quite know what to do with that. It was a...

unique situation. like, you know, I can make this better if you give me the freedom, but you got to give me the freedom. Still yet, you know, it was one of those situations, ⁓ SaaS business, layoffs.

not something I want to do again. So I've gone all in on my business. And it's been rough. That means a lot of late nights, a lot of getting stuff done because I'm so multifaceted at this point.

But I think the decision to go all in was right. And now, you know, I've been in the position where I'm doing all of these things. I'm kind of trying to figure out where I want to go next. So I've brought back in some client work and I started up my referral network again. And I started doing that hard work and reaching out and finding the people. But I knew exactly what to do because I already had the system set up from before. So, and it's a temporary thing, but it's in my business.

And if I had said, okay, I'm going to go find a part-time job to make ends meet while I'm making this new pivot, I think it would have been a horrible mistake because that's time and effort I couldn't have spent in my business. Not to mention 40 hours in a full-time job. You don't spend 40 hours working. There's just most of it's meetings and people wanting your attention and Slack conversations and emails. And it's mind numbing.

And now I'm back to 20 hours a week with client work and coaching and building stuff. And then the rest of the time I can spend working on my business and it's a whole different ball game. So it's not just an apples and oranges comparison. I think it's like an apples to wooden blocks. There's just, it's not a comparison. If you want the thing, if there are certain things you are wanting that you think only a salary job can give you.

Figure out how to create those in your business. I've been there, done that recently. So I feel pretty strongly about this. But what do you recommend in a situation like this?

Ed Deason (06:50)
don't

think I'm going to disagree with you on any of that. I think the point you made about if this is important to you, build it into your freelance business is the most relevant point someone can take away from this. If you want less of a problem in the UK, right? But if you want health insurance, then you build that as a cost into your business. If you want freedom, then you build that as something into your business. You know, if you want stability, then you work out how to build that into your business. Just because you have a freelance job, doesn't mean that it cannot be stable. It cannot have benefits.

Those they're not mutually exclusive. And I think, you know, I think one of the really interesting points is right. There's this kind of belief that employment equals stability. Yeah. And who is more stable? An employee with one employer or a freelancer who has 10 clients. And what happens when the employer shuts up shop?

Yeah. What happens when one of the clients shuts up shop? Yeah. I was employed in a six-figure role up until about 18 months ago. A business that had, was making over, the parent company was making over a billion dollars. What do you think happened to my role? What do you think happened to the business,

Treasa Edmond (08:08)
betting they wanted to cut costs and you were a cost.

Ed Deason (08:13)
They actually went bust. A billion dollar business went bust overnight. If I had been freelancing at the time and that business had been a client of mine and had gone bust. So what? I've got nine more clients.

Treasa Edmond (08:27)
and you can replace them.

Ed Deason (08:29)
replace them. But I was in a situation where I had an eight month old son. I was in this place where I'd never been unemployed before, overnight. I think this is what people need to bear in mind. You think employment equals stability, but actually having a diverse, large base of clients, that equals stability.

Treasa Edmond (08:49)
Yep. For our Friday episode, we're going to talk about a lot of things I think are really relevant to this situation. So I don't want to go into those too deeply. Every single coaching client who comes in to talk to me, and I asked this in our consultation call, and then we go into it pretty deeply in our first 90 minute session. It's not how much money do you want to make. It's

What do you want out of your business? What kind of freedom do you want? Do you want to be able to pack up at a moment's notice and go work from anywhere? Do you want to be able to take every Wednesday morning off for a Pilates lesson? Do you want to be able to only work four hours a day while your kids are at school so that you can be with them fully other times? So I want to find out what they want. And then we reverse engineer and talk about, now let's structure your business so that you can get that.

How much do you actually need to make an hour? You know, how many hours a week do you actually need to work, which it's usually way lower than people think it is. The thing with the freedom situation is, and I actually know someone who she fully believes she should be working 40 hours a week on her business. And I'm like, that's a job. That's not a business, that's a job. Sometimes you'll work the hours a week on your business because it's one of those weeks. Most of the time you should probably

be working 20, 30 max. And a good portion of that should be working on your business, not just client work. It's the difference, I think, between busy work. So a lot of that's pricing, the type of clients you have and stuff like that. And really building the business that works for you. And I think this entire situation here comes down to if your business is not working for you,

try changing your business before you seek out other solutions, unless the other solution is the right one for you. If pros and cons are what does it for you, talk to someone. Let's make a list. Go to a business coach and say, hey, this is the issue. If you don't want a business coach, the business coach also can totally take emotion out of it and look at it very logically for you and say, well, why are you thinking this is a con? I mean, they're going to call you on it if you're kind of going in the wrong direction.

So sometimes you just need outside honesty in your life. I think that's the thing. So how do I weigh the pros and cons? If you must weigh the pros and cons, find someone who can be totally disconnected from the situation and help you do that because you can't. And then if I don't think that you do though, I honestly don't believe that weighing the pros and cons is the best solution. I think figuring out what you want is the best solution and then figuring out which option gives you that.

Ed Deason (11:37)
Yep. The only other thing I think I'd add is something around kind of psychological safety. It feels safer, doesn't it? Being in a job, it feels safer. It feels like, well I'm unemployed. Yeah. And I think just, just reflect on that. Is that, is that what you want? Is it actually the kind of the idea of safety that appeals to you? And just be honest with yourself because it's okay to go, actually, I don't want to worry about.

getting clients, I don't want to worry about these things. Okay, cool. Then getting a job is probably your thing.

Treasa Edmond (12:10)
Yep. I actually, and I don't think she'd mind me sharing this. I know she wouldn't because she put part of it in a testimonial. I worked with a client a while back who was very insecure about what happens if my business tanks. It was just overwhelming her. And I'm like, you need a buffer zone. You need a safety net. You need nine months in savings to, if something happens, you have nine months to figure it out. And she's like, well, that's impossible. And I was like, okay, so let's talk about what you're charging clients.

four extra clients where she just put that money in savings, four clients, that's one extra project for the next four months would give her that buffer zone. And all of a sudden she wasn't worried anymore. She's like, have room for like three extra clients a month. thought, do them all in one month, get it out of the way. But yeah, you just have to figure out what the problem is and how your business can solve that for you. A coach helped me with that. A coach helped me figure out

how to build the business that gave me the life that I wanted. Because I did want to go to Pilates twice a week. And I'm like, I can't, that's during work hours. And he's like, who sets your work hours? It had never, I was so firmly in employee mindset back then that I did not even think about the thought that I did not have to work eight to five every day. And to me, that was so revolutionary. I can't even tell you how fast my business changed after that. All right, so come back tomorrow when we are going to talk about

how to make space for the business side of freelancing. And this is one of those topics that I think is a must, not a nice to have. So I'm really looking forward to that conversation. But Ed, thank you again for more great advice and I'll see everyone tomorrow.


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