When is it Time to Go from Side-Hustle to Full-Time?

Stay updated


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.

Table of Contents

After you’ve had a bit of success as a side-hustler the question that always comes next is, “When is it time to go from side-hustle to full-time?”

After all, things are starting to pick up. You’re starting to be a bit more confident in your skills and in your ability to make money with this new part of your life.

But, how can you be sure it’s time to make the leap?

This Week’s Guest

This week, I’m talking to a web designer that did just that. Her name is Jessica Hagmeir.

Jessica was working at a corporate job, and she was doing fine. But, all of the sudden, the company she was working for shut down. And, rather than jumping right back to the old way of doing things, she decided to take what she had been doing on the side and make it her full-time gig.

Fast-forward a year later and she was already hiring her first employee.

It wasn’t an easy path BUT ultimately it was one she knew she had to take.

For Jessica, it wasn’t about the money, it was about being “the master of her fate.” And, that’s what it comes down to for a lot of people deciding whether they should go from side-hustle to full-time gig.

If you can no longer handle having your future decided by a boss and the pain of having to deal with that is worse than the pain of losing the security that comes from drawing a stable salary, it might be time to go from side-hustle to full-time business.

Of course, it’s probably not wise to jump feet first without taking a good look at what is required to be successful. And, Jessica learned a lot of that along the way.

Being Your Own Boss

When you’re your own boss, you have to own up to your own faults. There is no such thing as PTO at first. If you’ve got a project due and you get sick, guess who has to keep working?

So, it’s important that you realize all of that before you decide to go from side-hustle to full-time.

But, ultimately, you can never completely remove all of the risk involved and you’ll eventually just have to go for it.

And, that’s exactly what Jessica did. And, she’s her to tell us what she learned.

You’ll Learn

  • What to look for to know you’re ready to go full-time for yourself
  • The keys to being successful when you finally go full-time
  • How to bring your own uniqueness to the table even when there’s a lot of competition
  • How to overcome your own doubts when you’re starting a business
  • When it’s time to hire your first employee
  • How to grow a community when you’re a solopreneur
  • How to know when you should go back to only working on your business part-time


Chris: [00:00:00] After you've had a little bit of success as a side hustler, you made some money, you're starting to get pretty confident in your skills. The next obvious question is when do I take this thing from side hustle to full time gig? And that is exactly the question that we are answering today on this episode.
Are you ready? Let's go.

What's up everybody. Welcome to another episode of this self-made web designer podcast. I hope you can hear the smile in my voice as I'm talking to you, or if you're watching on YouTube, hopefully you can see it behind the microphone and the mustache that I'm still going strong width. I'm glad that you're here for another week of this self-made web designer podcasts.

We've got another fantastic guest. Her name is miss Jessica Hagemeyer and Jessica took the leap about two years ago from being a. Full-time employee at a corporate job to becoming a full time web designer. She started her own agency and only a year later was hired hearing her first employ yeas. So you learned a lot along the way, and she is sharing that experience with us so that you can be successful when it is time for you to make the leap.

From side hustle to full time gig. But before we dive in, I've got to ask, have you subscribed to the self-made web designer podcast? Have you left? Oh, writing. I want to encourage you to do that because it helps other. People find this channel, this podcast and learn from it as well. I love what DL writer said.
He said, this guy knows what he's talking about and when he doesn't. He straight up says so, and that's true when I don't. I tell you, when I bring on a guest who does know what they're talking about, I decided to start making a side business of building websites before I found self-made web designer, but Chris's knowledge and encouragement solidified my confidence.

Hey, I am so thankful to hear that and honored that you would listen. This is a lot of fun, and hopefully we're building a community of people who. Are encouraging each other to go for it and to keep going, no matter what they face as freelance web designers. Okay. Are you ready to dive in with miss Jessica on how to know when to go from a side hustle to a full time gig?

Okay, let's go well, Jessica Hagemeyer. How are you? Thank you so much for being on the self-made web designer podcast.

Jessica: [00:02:47] Thank you for having me, Chris, I really appreciate it.

Chris: [00:02:50] Yes. So tell us a little bit about your background, who you are, where you've come from, what you do now and how you got from the beginning to what we.

Jessica: [00:02:59] I mean, I'm a little unconventional in how I've lived my life.

So I actually, I have been freelancing, well, I taught myself how to do graphic design and website design about 10 to 12 years ago. And I've kind of had just been doing it on the side for pretty much that entire time. At the end of 2008, I was incorporated 2018. Sorry. I'm getting older. So at the end of 2018, I was actually in corporate America and I was working for a cybersecurity startup.

And about two to three days before Thanksgiving, they just decided that they no longer wanted to be in business. So I took that as an opportunity to kind of figure out what I wanted to be when I grow up. And even though I'm still trying to figure that part of it out, I have, I knew that I could at least use graphic design and website design to try and make some money, you know, while I was kind of figuring it out.

I knew I didn't want to go. Jumped right back into corporate America. So decided to kind of do the freelancing route for a little bit. That ended up going a lot better than I anticipated. And so I officially made myself a business in August of 2019 and then hired my first employees. Part-time employees and contractors in January, no, February of 2020.

And then we all know COVID hits. So that's kinda been my ride thus far.

Chris: [00:04:23] Yeah. That's awesome. So what was that decision like when you had lost your job in the cybersecurity company and decided to go ahead and go for it? What were you thinking? What were your fears? What were your hopes and dreams and how have things looked from those first few days?
You know, what you were thinking it was going to be like to what it actually is today.

Jessica: [00:04:46] I had already gotten a taste for kind of being an entrepreneur. Because in 2007, I decided to start my own magazine. And that was what really prompted me to kind of start living graphic design and website design. I just got bored at work.

One day I wanted to start a magazine and I had no. No idea what I was doing and I had no money to be able to pay anybody. So I did that for quite a few years and it was ended up being semi-successful. But for various reasons, I decided to go back into corporate America that time from about 2012, being fully immersed back into corporate America to 2018, I had, I worked for some really good companies, but I also hit a lot of ceilings and I dealt with kind of.

Knowing that I want to do, achieve more. I wanted to succeed more. I wanted to make more, but there were frameworks in place that were allowing me not to be able to do so. So when the cybersecurity company dissolved, I took it as an opportunity to. Even if I didn't know what I was going to do or how I was going to do it, I took it as the sign, so to speak that I needed to step away from corporate America and I needed to figure out how to kind of make it on my own because.

If I was going to make more, if I was going to have more control over my life, then I had to be the one to do those things.

Chris: [00:06:11] Yeah. That's awesome. It's real similar to a lot of people that I've talked to, who've been on the show who have felt and done the same thing that, that you have is that desire to be master of your own fate, so to speak.

And so I think that's, that's probably a key factor for people who are listening, who would maybe question it, am I cut out? To go on my own or should I stay in this career? Like what, what, what are my, what are my options here? So you've probably talked to a few people who are asking themselves that same question, because inevitably, you know, like when you do something, if you blaze a trail for yourself, people go, Hey, how did you do that? I want to hear about your story.

So, so what do you tell people who come to you and say, should I do this? Should I, should I. You know, take something, that's been a side hustle and go to being this my full-time gig. Like what are, what are some things that you look for? How do you encourage them as far as that goes?

Jessica: [00:07:07] And it's funny that you say like master of my own fate. Cause I actually had that tattooed on my body. Like I am the master of my fate. I'm the captain of my soul from Invictus. That's tattooed right here on my arm. Actually. I think that that kind of, that's the essence of what it really takes to be able to be an entrepreneur.

You have to be willing to own everything. You have to be willing to own all of your failures and your successes. And I think. If you're going to go out on your own, or like, if I would give advice to somebody to go out on their own one, you have to have the desire to do something more than what you can do by punching a clock.

And it has to be more than a monetary value because initially you're not going to be making the same amount of money that you were in corporate America. You're just not even if you're working at McDonald's, like you're still gonna have co startup costs. You're still gonna have fees and expenses. And it's going to take longer to get contracts signed is going to take longer to get work done than you ever anticipated.

So I think you have to have a bigger desire than something monetary. And at the end of the day, like you have to own your own BS. And if you're not willing to 100% own your faults, as well as your strengths, if you're not willing to take accountability for everything that might fail and everything that will fail, then you're not going to be able to be successful as an entrepreneur because at the end of the day, no matter what it is, it's always on you.

You could have 10, 20 employees. If the job isn't done, if you don't deliver to the client, if the contract doesn't design, whatever it is, it's on you. And so if a person is kind of inherently not owning their own crap or, you know, owning their own BS, or if, you know, they kind of are looking for other people to either take care of them or to delegate to, or you know, that sort of thing, then.

This is probably not the right path for you or for them.

Chris: [00:09:04] You're getting real deep, real quick. I love it. You're you're cutting to the core. So, so I'll, I'll, I'll flip that question on you. What's some, some of your own BS that you had to kind of come to grips with when you first started and how did you get past?

Jessica: [00:09:17] I am very much my own worst enemy in terms of, I am my own worst critic. And I probably feel like I'm capable of less than most people in my life. So understanding that I'm ordinary at the end of the day, I'm ordinary. There's nothing special about me. I'm not the smartest, I'm not the prettiest. I'm not the most successful.

I don't have any inherent talent that I was, you know, born with. So for me, it was kind of owning all of the things that just made me. Who I am, or, you know, just being like, I'm good at everything, but I don't Excel at any one thing. So it was kind of owning all of that in order to use it as a strength, rather than looking at it as a weakness.

And until I went out on my own and became entrepreneur entrepreneur, I looked at those kinds of things as weaknesses versus understanding that there was value in them and that I could actually use them to my advantage.

Chris: [00:10:16] Sounds like there was some comparison going on of looking at other people who had probably done this before and going, I might not be like them, but I have something unique to offer.

Jessica: [00:10:26] Exactly. And I think that that's why, you know, so many people, especially nowadays, like they want to charge for their expertise. So they want to charge, you know, for classes or for courses. Like we're seeing a lot of that right now. But I think that there really is a lot of value in people who have made it for themselves and who do have a lot of knowledge.

And just sharing that knowledge. Because even if you give somebody all the tricks of the trade, or even if you let somebody know, you know, everything that, you know, you still have your own special way of doing things and you still have your own special way of interacting with their clients and how you work works for certain people.

So. Helping others and kind of giving that information out. A lot of people look at that like as a negative, but at the end of the day, like you're not cannibalizing your own clients. You're not cannibalizing your own source of income. So. You know, why not kind of give that information out? Why not help somebody get, you know, the younger version of you get to where you are quickly.

Chris: [00:11:26] Yeah. So being generous with your expertise, being generous with what you're offering to clients, even if it doesn't ever turn into getting a paycheck from them.

Jessica: [00:11:34] Yeah, absolutely. Like my old boss used to always call it, like giving them the pickle. Like if you order a sandwich, you want a pickle, you know, you don't want to say pay for the pickle.

You don't charge for the pickle, but you give that extra value. To show that you're invested, that you care, that you see value in the person buying the sandwich.

Chris: [00:11:53] I love that. I'm going to I'm going to use that. If you're listening, you should, you should tweet it right now. What did you say?

Jessica: [00:11:59] Give them the pickle.

Chris: [00:12:01] That's great. Yeah. So, so where's the line there? Where, where do you go from adding that extra value to being taken advantage of?

Jessica: [00:12:09] It comes down to setting boundaries and communicating. So as you're first getting to know a client as your first time kind of working with a client, you do, you definitely deliver what you promise to deliver.

You probably try to deliver it faster. Or better than what you planned on and you kind of create that groundwork that you know, create what the expectations are going to be on both sides. And as that relationship develops, you'll kind of get the feel for, you know, knowing the clients that you want to give them the whole pickle versus, you know, the quarter pickle.

If you're at Jimmy John's, you know, they have that, they have the big pickles and they kind of in quarters. So I think it's, you have your certain standards. You have your certain processes that you start with, but as you get to know clients more, and as you know, which of those clients are not only going to be valuable to you personally, you know, for the next quarter, the next year or however long it is.

But also those clients that are referring you and that are, you know, giving you Google reviews and giving you Upwork reviews and sending their friends and their family and, you know, peers and other companies to you, those type of relationships will definitely make themselves known. And those are the relationships that you really, really want to nurture and do whatever you can on both sides to deliver.

Chris: [00:13:30] Want to take a second and tell you about a free course that I have available at self-made web designer.com over 1000 people have been through this course, and I am talking about the web designer starter kit course. I map out in four videos that you get through email, all the steps that I took to get.

To where I am as a web designer. And I went from knowing absolutely nothing. I was clueless to in two years, doubling my income with a freelance web design side hustle. I made this because I know you can be successful. Doing the same thing. And the web designer starter kit course is the first step for you on your journey to being a successful thriving, freelance web designer or having a full-time career.

So I can't wait for you to check it out, go to self-made web designer.com and sign up today.

So let's talk a little bit, go back a little bit in chat about going out on your own. You know, w one of the things I think that a lot of people face when they leave the corporate world and step into full-time freelancing or full-time business, is it can be kind of lonely, you know?

And like you said, owning your own stuff. Like if you can't do something and you don't have a team around you to kind of help, it is way more difficult than if you're one piece of the puzzle. So how did you navigate hrough that? And are you doing different things now to kind of build a community and build, you know, a group of peers or even like you said, hiring your own people? What did that look like for you?

Jessica: [00:15:21] Sure. I think initially one thing that. Kind of set me up, set me apart from a terms of, I had no option, but to succeed, whatever that might look like is, you know, that I do have a kid and I'm a single mother and I've been raising my son on my own since I was 18 or so. Yeah, since I was 18, cause he's almost 18 now.

So So I had, if I was going to go out on my own, I had to succeed. I had to bring in a paycheck. I had to make things happen. And, and if I didn't, then not only would that negatively impact myself fun. If I then turned around and said, well, it was this client's fault, or it was this or all of these external factors, then I'm creating a very negative.

Example for my son. And that was something I was very aware of and something that I didn't want to do that kind of was the thing that initially kept me moving and kept me going as I got busier. And as I was getting more and more referrals, and as I was, you know, I constantly had stuff on my plate. I knew that, okay, I can officially, I can make this a business.

So that's when I made it, you know, incorporated. I got my business bank account. I got my EIN, all of that kind of thing. Once I did that and business, you know, Everything didn't implode because I took that big step. You know, business kept coming in and that sort of thing, I kept getting busier and I felt myself not delivering the way that I would normally deliver, because I had, you know, I took on a lot of work cause I was not going to say no to work.

Because I'm a single mom. Why would you say no to money? And, you know, I was taking on clients for the same reason. So I knew at that point, if I'm going to actually grow this as a business, this is not a time to bring in more people because I can't do everything myself and what it might cost me to hire somebody.

If I keep it on the path that I'm keeping on, I'm not going to be able to deliver in the way that I say we're going to, I'm not going to meet deadlines. I'm going to lose clients and it's going to cost me more in the long run. By not bringing on somebody and not paying somebody than it would to just go ahead and make that move now, even if I can't technically afford it, I knew at that point I couldn't afford not to do it.

Chris: [00:17:28] Yeah. That's good. That's good insight. So talk a little bit, maybe about the peer-to-peer relationship. Is there anything that you do to. You know, reach out and build connections with people who are doing the same thing that you're doing and, and try to find advice or trying to find encouragement. Like how have you navigated that?

Because, you know, again, like, like I mentioned, it can be a pretty lonely world when, when you're a solo preneur kind of doing things on your own.

Jessica: [00:17:53] I like that term. I haven't heard that one before. I'm going to steal that one. You can have the pickle, I'll have to look in there.

Chris: [00:18:00] Well, the trend is that you just take whatever at the beginning and you add a preneur to it. And it's like this new, it's this new thing that people say.

Jessica: [00:18:08] LIke mom prenuer and I can't say the woman version of it. Yeah. Okay. Sorry. I digress. I do struggle in that area. I kind of struggled networking for the same reasons, but like, I know I need to do those things. So one of the things that I do. To kind of help myself is if I am going to a networking event, I know it's a little different now that we're in COVID, but I also live in Texas where apparently COVID doesn't exist here for most people.

So when I do go to networking events, I take a buddy. And I know that might sound childish at 36, but my best friends are also, they all have kind of their hands in their own business or, you know, side hustles and that kind of thing. So even though it's directly related to what I do, you know, If I'm not the most outgoing person in the bunch, my, my friends definitely are.

They're kind of the icebreakers for me. And since I'm comfortable with them in a situation, then I immediately become more comfortable in this situation. I mean, there's been times that they've gone with me to events and they've had absolutely no reason to be there. And they literally just went because they knew that I needed a friend that day.

So I do that. And then I also probably one to two times a week, at least I work out of my house. So even though I have like, you know, my whole office set up. I work from a sports bar or from a restaurant. There's two here that I go to and I just kind of switch off between which ones I want to go to.

And so then I kind of, I'm in front of other people, I'm dealing with other people I'm talking to other people, there's human interaction. So even if nothing specifically comes of it from a business standpoint, you know, those kinds of situations, forced conversation and they forced interaction. And it's really easy for us.

Who likes to go into hermit mode when we do then go out and we try to talk to people it's hard for us to, you know, I sometimes I can't even talk or articulate what I'm trying to say, because I'm so out of like, out of practice, just having a regular conversation, long story short, it kind of goes back to what I was saying before.

And like, I know where my weaknesses are. And so instead of trying to just. Say, okay. This is my weakness and I'm going to deal with it. I try to put myself in positions that forced me to address them, even talking on podcasts, like this kind of thing. I always get nervous about. But I put myself in the position because ultimately I know it's going to better myself.

Chris: [00:20:31] You're doing fantastic. No reason to be nervous about it. One of the things that comes up quite frequently when people are thinking about launching out and starting their own thing is the benefits that you now have to provide for yourself. So. And this is probably going to get maybe a little bit more practical than what we've been chatting about.

So things like health insurance, things like 401k and, and, and the PTO and stuff like that, you know like when you're sick and you've got a deadline and it's your own business, you can't take a pay day off. What does that look like for you? How did you, how did you sign up for health insurance? How did you figure out what you needed to save for retirement without having to have an employee who does that for you?

Jessica: [00:21:12] So I might not be the best example for that. Because even when I was in corporate America, I never had health insurance. Like there was a span of maybe eight months even after, you know, the affordable care act and all of that launched. I never had health insurance losing those types of benefits for me.

That part of it, wasn't a risk and I wasn't missing out on anything. Flash forward though. I'd like to where I am now. My business has definitely grown. We've brought on more people. We're now in the position where I feel like the business could very easily stagnate because this is my sole source of income.

So all of my bills and all of my finances and everything having to be paid strictly by the business and then puts pressure on the business to actually be able to grow. So something I'm even like looking into and considering is potentially crazy as it sounds, finding a company or working with the company for, you know, a year or two years or however long to take away some of the pressure off of my business, because I do now kind of have processes and systems in place for people to kind of take on some of the work that I would normally do myself.

And so that way I can take the pressure off the business. So continue to grow the business, but then also, you know, my personal finances or my personal health or all of that, doesn't negatively impact the growth of the company as a whole. I love that.

Chris: [00:22:38] And I think, I think this is so key because I think a lot of people, when they, when they feel like they're. They they're about to, or, or thinking about jumping in full-time to a business. They, they think, okay, if I, if I go part-time again, that they've failed or that it wasn't successful and, and you're looking at it, and you're just saying maybe it's time to pivot so I can continue to grow this thing. So I, I think that's huge. I think that's a huge part of success and growth.

Jessica: [00:23:04] I, I agree completely. And honestly, two years ago I would have looked at it as a failure. 100%. I would have looked at it like, Oh, I didn't do what I need to do. Or, you know, X, Y, and Z, whatever reason, but looking at it now. And maybe it's because I do have, you know, part-time people and contractors and that sort of thing who rely on me.

Like, I feel a responsibility to them and I feel responsibility to, for me now, like the business isn't necessarily just like. I'm doing the business. So I have a sense of freedom. It's now it's like it's creating jobs and it's creating opportunities for other people and going into it. I didn't necessarily think that that was the route that I was going. But now that I'm here. I don't take that for granted

Chris: [00:23:47] And another part of it too, is now when you go to a job and say, here are my requirements, you there's a lot more confidence in what you're saying, because you realize if you come in underneath what I'm asking for, I'm just going to go do it myself.

Jessica: [00:24:04] Exactly. And like, you know, now it's like, you know, your value. Even at that point, because you know, like I can pull in this much money by myself and I can pay people and I can bring quality of life to other people and still take care of my kid and take care of my dogs. So I'm sure you've heard in the background.

I'm really starting to figure out my value. Not just as a business owner, but you know, like as a whole entire human beings and there's power in that.

Chris: [00:24:31] I can't wait to hear more about your journey in the future a few years down the road to see how you're doing. So I'd love to have you come on and give us an update sometime in the near future. But until then, tell us where somebody might go to connect with you online.

Jessica: [00:24:44] Outside of my website, which is websites. My company is websites by design, but it's spelled websites, X design. So you like a four by four. If you're building the foundation of something, you know, we say something is 10 feet by 12 feet.

So it's websites by design, but website's X design.com and then Instagram is my playground. So that's where I like hanging out. So I'm, I think I'm a little too old for Tik TOK or else I'd probably be there, but Instagram is the same it's websites, X design. Or my personal Instagram is gorgeous web design. So G O R J E S S web design

Chris: [00:25:24] Man, such awesome insight from Jessica. And I love the idea that she's not married to her first idea of. Being in a full-time business, she's pivoting, she's looking at things, she's asking herself the right questions. And ultimately that's what it takes to be a successful freelance web designer or freelancer in general.

It takes looking at what's happening and maybe changing your mind about certain things, but not giving up and not admitting defeat. Maybe admitting a pivot, maybe admitting having to take a few steps back. But you're still going for it and you're still gonna figure it out. And I know that Jessica will, and she'll be back on the podcast to tell us about her journey.

Well, next week, we've got another fantastic episode. It's going to be awesome. And I hope that you're with us next week to hear a little bit of good insight, hopefully some good encouragement for you to keep going or to get started wherever it is on your journey. I know it's going to be a ton. But until then, don't forget if you don't quit, you win.

A green door and knob to symbolize the decision of going from side-hustle to full-time


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.



Leave a Reply

Your email address will not be published. Required fields are marked *

Join 1,000s of other web designers, web developers, UX designers, product designers and freelancers and get a weekly email that will help you grow.

Invest 5 minutes a week & Improve your freelancer/web designer skills

Come learn the same steps I use to land projects for $6k+ on Upwork. You'll walk away knowing:

• How to stand out from other freelancers
• A cover letter template that wins
• Profile MUST HAVES that most freelancers miss

3 Simple Steps to Land High Paying Projects on Upwork

This free, 4 video course will give you all the tools you need to start freelancing as a web designer and earning extra money.

• How to get started from scratch
• How to find your first clients
• How to charge higher rates

Become a web designer and land high-paying clients