The MapleMoney Show » How to Make Money » Career

From Side Hustle to Full-Time Gig in 12 Months, with Clint Proctor

Presented by Wealthsimple

Welcome to The MapleMoney Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. I’m your host, Tom Drake, the founder of MapleMoney, where I’ve been writing about all things related to personal finance since 2009.

Have you ever wondered if your side hustle could become your full-time job? Or whether or not you could see yourself doing what you’re doing now, for the rest of your career? You’re not alone. My guest this week asked himself the same questions, and he joins us this week to share his story.

Clint Proctor is a full-time freelance writer from Daytona Beach, Florida. Just over a year ago, however, he was a pastor on staff at a large church. As Clint explains, he loved his job, but when he looked down the road ten or fifteen years, he didn’t feel as though it was the right path for him. As Clint puts it, just because you love something doesn’t mean you have to do it for the rest of your life.

Clint explains how his passion for personal finance quickly led him into a freelance writing side hustle in 2018. Soon after, He realized that the potential was there for his writing to replace his job as a pastor. Within 7 or 8 months, he managed to make the leap, and he now writes full-time.

Clint offers some advice for others who want to get started freelancing, and explains the important role that community plays in building a successful business. If you have ever dreamed of a career change, you don’t want to miss this week’s episode.

Our sponsor this week is Wealthsimple. The biggest myth about robo advisors is that they are all tech, and lack the personal touch. If you’re curious about moving over and have questions, you can now book a 15 minute call with an experienced Wealthsimple portfolio manager. Head over to Wealthsimple Chat, and book your appointment today.

Episode Summary

  • How Clint started his freelance writing side hustle
  • Balancing a side hustle with a full-time job
  • From side hustle to full-time freelancing in 7 months
  • The idea of trading time for money
  • Clint’s advice for anyone who wants to get into freelancing
Read transcript

Have you ever wondered if your side-hustle could become a full time job? Or whether or not you see yourself doing what you’re doing now for the rest of your career? If so, you’re not alone. My guest this week asked himself the same questions and joins us to share his story. Glenn Proctor is a full-time personal finance writer from Daytona Beach, Florida. But one year ago, he was a full time pastor. Find out how he made the leap and why.

Welcome to the Maple Money Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. The biggest myth about robo-advisors is that they’re all tech and lack the personal touch. If you’re curious about moving over and have questions, our sponsor, Wealthsimple, now lets you book a 15 minute call with an experienced portfolio manager. Head over to to book your appointment today. Now, let’s chat with Clint…

Tom: Hi, Clint. Welcome to the Maple Money Show.

Clint: Hey, Tom. Thanks for having me on today. It’s an honor.

Tom: I’ve been talking to you a bit and one of the things that kind of struck me as a little interesting is you’ve kind of gone from having a day job to striking it out on your own as a freelancer. We’ve heard that story before. But what’s been interesting, too, is that you’re looking at the next thing too which is looking for a new side-gig. I like this cycle of “what’s next.” Let’s start from the beginning. When you had a regular job, what did that look like? What were you doing?

Clint: I live here in Daytona Beach, Florida. My dad is a pastor of a fairly large church here in the area. I came on his staff right out of college. I was a pastor on his staff at the age of 22. I enjoyed the next six or seven years of my life with nothing but positives to say about that. But I was getting closer to 30, a time when you start thinking about the next phase of your life. I realized I was in a unique situation where I knew my dad (being the senior pastor of the church) was not going to be forever. I didn’t want to be that person to “come after him” to take over the reins. Maybe he would have wanted that, but I didn’t want to be his heir-apparent. I always said there’s enough pressure in life just trying to succeed (and not fail) much less having to worry about blowing up your dad’s legacy. So I said, “You know, dad, I don’t want to be the guy to come after you. And I’m probably not going to be able to stay here after you’re gone either.” He may have another 10 or 15 years left but do I want to be looking at a new career in my mid 40s, or would I rather be thinking about that now? It was a hard discussion because I’m close to my family. But they understood. I had to go through this time of searching, trying to figure out what my next thing would be. When I was around 18 years old I really got passionate about personal finance. It was just something I cared a lot about. I would teach people and help people with personal finance on the side. It was my only real passion other than what I was doing at the church so it was a natural avenue for me to look into. But I had no idea in what capacity I wanted to help people. I just knew I wanted to help people get out of debt. I wanted to help people avoid debt, pay off student loans and have the financial freedom to live the life they wanted. I went from being a financial advisor to teaching economics and personal finance in the school system. Then along came blogging. And the reason that came to mind was because I had learned so much about personal finance from bloggers. I knew nothing about blogging. I didn’t even know what WordPress was, but I knew that I had a little bit of an aptitude for writing. I thought, “I can do this too. I can be on page one and make a full-time living being a blogger in a year.” That was a little bit naive. But, I started my blog and gave myself something like a year thinking, “If I can do this within a year then I’m going to launch out as a full-time blogger. Then I will quit my day job and go that direction.” I went to FINCON in October of last year. And one of the guys I met there said, “Hey, have you ever considered freelance writing? If you really love personal finance and helping people with money a blog can be passive income. But you can make money now with freelance writing.” I didn’t even know what it was, honestly. So I went to this freelance writer’s place where there were all these different editors and got the opportunity to pitch myself to a few of them. That’s kind of what started my freelance writing, side-hustle. But again, the whole reason I went to FINCON in the first place was I wanted to build my own blog. I haven’t let that dream go, but I kind of put it on the backburner and became fully invested in the writing career. I told my dad, “By the age 30 I’m going to be doing something that’s helping people with money.” That due date was coming. I just wanted to get into a job that would pay the bills as quickly as possible. Talking about money and things I was passionate about, freelance writing became my side-hustle in October of 2018 while continuing on my pastoral duties as well.

Tom: You mentioned a couple of interesting things there. One is this idea of seeing where your job was headed. A lot of times you hear people quitting their job because they didn’t like it or they were making more money doing other things. But in your case, you saw a lack of future—at least not the future you wanted. Do you find that’s common with people or just something unique in your case?

Clint: Yeah, I think it’s unique. Firstly, people I worked with at the church thought it was a very strange concept. Are you unhappy? Are there issues? But there honestly wasn’t. I just saw the end of the tunnel. I don’t think a lot of people do that. They find themselves 10 or 15 years down the road wishing they would have looked ahead and thought about it earlier. And so, yeah, I think that was important for me. I also think it’s important to realize, just because you can enjoy something doesn’t necessarily mean it’s what you’re supposed to do forever.

Tom: The other thing that kind of interested me there was, you mentioned getting into personal finance because you became “the guy.” I never really thought of it that way, but I think I was in that spot at one point, too. When you’re at work (in my case it was a corporate office) standing around the water cooler, everybody is coming to you for advice on what to do with things like RRSPs and things like that. It sounds like you found yourself in a similar situation where you were the smartest person in the room. And it doesn’t take a lot sometimes. You just have to have a slight more interest than the regular person.

Clint: Yeah. I have a little bit of an obsessive-compulsive nature with anything, whether it is Star Wars, Marvel or tech. Once I get into something I’ll research it. Once I got the bug on how I could maximize my income—I knew I was never going to be making a huge income as a pastor so I wondered how I could hack this to get the most out of my income and squeeze every penny out of it. Also, how can I reduce my expenses? What are ways that I can get real estate more affordably? I can go on and on and on. I was feeling more comfortable. My wife and I felt we had more financial freedom than people making two or three times our income. And they couldn’t understand it. They’d ask, “What have you done?” I would meet with couples or individuals for cups of coffee. It was just something I really, really enjoyed. So this next phase of my life has been a natural outgrowth from that.

Tom: I think that’s something people can look at if they’re looking at what they can do as some form of a freelancer side-gig. See where your interests are, and where you are that might be just one step ahead of people. You don’t have to be an expert. Many people think they can’t do it, but you just really have to be one step ahead of the people you’re trying to help. That’s all it really takes.

Clint: I completely agree.

Tom: With your job, what do the hours look like? Are they just regular 40 hours, full-time? Or are you doing more?

Clint: Pastors have interesting schedules because you have to work on Sunday, obviously. So that limits the ability to be doing a lot of work on the weekends. I was at the office Monday through Thursday. My day off was Friday, but Saturday I typically worked. I would go see people. I did a lot with the children’s programs so I’d go see some of the kids that rode the bus. We also had funerals and weddings. I mean, weekends, Saturdays just seemed to always have something going on. For my side-hustle, I really had to do it from 5:00 am to 8:00 am and then I’d do my 8:00 am to 5:00 am. Sometimes I’d have to work at night as well. That’s kind of how I built it, on the side.

Tom: So you’re waking up to work at 5:00 in the morning?

Clint: I woke up every morning at 5:00. I’d usually be at Starbucks by like 5:35 am. Then I’d work until I went to my job at 8:00 am. That’s how I did it for about seven months.

Tom: That’s similar to me other than I was more of a night owl. I can’t imagine waking up at 5:00 am to do that, but it’s definitely the same grind. If you want to balance these two things you have got to figure out where it’s going to fit into your life.

Clint: I guess it’s good if you don’t need a lot of sleep. I’m one of those people who doesn’t require a ton of it. My wife is the night owl. Maybe I shouldn’t have, but I felt kind of bad leaving her alone some nights in order to get writing done. But I thought if I could live off of five and a half hours of sleep, then I could still stay up with her until 11:30 at night, then wake up again at 5:00 am. It works for me.

Tom: You were doing three hours of writing and then eight hours of your regular job, right?

Clint: Correct. My writing was typically 15 hours or more depending on if I had to do some work on Saturdays or at night. But that was kind of where I was at.

Tom: You mentioned you’re really busy in the weekend but were you doing full days during the week? Or were you regaining some time back then?

Clint: No, I never really had any time during the day. The office is open from 8:00 am to 4:00 pm and we’re expected to be there during those times. I did have some flexibility. I was salaried. But I couldn’t be sitting in my office working on a paper. That wouldn’t have flown. So between the work we had to do with follow-up, curriculum or training, or other events, I never really did any writing from 8:00 am to 4:00 pm on any day.

Tom: My dad’s retired now. He was an Anglican priest here in Canada. I used to bug him that he only worked Sundays, which, obviously, is not the case. But it was sort of the only real, public-facing day you had to be there. To me, as a kid, it seemed like he was just driving around. I didn’t get it about all the hospital visits and everything like that. So it is a full-time job?

Clint: Yeah, yeah, absolutely. It was a full-time job. And sometimes, depending of what’s going on, you get called out in the middle of the night. You know that because your dad was a priest. You get called out for hospital visits or different things like that. The church has a lot going on, on the calendar as well. It kept me busy. But thankfully, I was able to get onto somewhat of a schedule. I’m not a good person at scheduling. Trying to figure out where I might have 30 minutes to work on stuff? I’m not really good at that kind of scheduled thinking. I have to get “in the zone.” I’m still very much like that today. I set my calendar and pretty much stick to it. When it’s time to go home, I go home and just turn off my work brain. My writing brain was in the morning. I would turn it off once I got to work where I’d turn on my pastor brain.

Tom: As you’re doing this what made you come to this point where you felt this was working out well and you were ready to make that leap and transition out of the job?

Clint: There was a big learning curve. Thankfully, my first client was not a high-paying client. I say that because I had to learn a lot from them about what it takes to be a writer. They were willing to help me along because they weren’t paying me much. I wasn’t expecting to be fully polished. I was learning a lot about research, sourcing and how to format stuff. I took a course on freelance writing too. That really helped me learn a lot. By about December or January, I said, “Okay, I think I know what it takes to be successful at this so I’m going to go hard for it.” Within the next three months, I landed five or six clients and I thought, “Wow, I can do this. This can happen!” It’s one of those things where you land one major client to add to your portfolio—it really gets a lot easier from there. By May I had almost fully replaced my day job income. I was probably at 80 or 90 percent. Then I launched out in June. I had basically nixed my day job by the middle of summer. It was intense. It was crazy.

Tom: You mentioned taking a course. What course was that?

Clint: It was Holly Johnston’s course. It’s called, Earn More Writing. Lance, the guy I mentioned earlier that I met at FINCON told me I should take her course because it had helped him. He was a full-time freelance writer so I used his affiliate link and took the course. It was really the best investment of my money I could have made at the time. As I said, I’m a full-time writer now and pretty much almost a six-figure freelance writer. At that time I hadn’t made a penny. It’s been about a year since I took that course. So yeah, it was worth the money.

Tom: We’ll include that in the show notes because I think freelance writing is a great opportunity to make money. A few times on this podcast (and on other people’s shows) I’ve kind of hated-on blogging just because it’s such a slow build to make a blog successful. Freelance writing, like you said, even if you’re not getting paid big at first, you’re getting paid compared to blogging where you might be doing it for free for six months or more.

Clint: Absolutely. For me, it was because I really loved personal finance and wanted to start writing about it. With freelance writing, I could write an article for my blog and have 100 people visited this month, or I could write for this other site and maybe have 10,000 people read it. While income was part of the consideration for me, it was also that I was actually going to be making a little bit of a difference, too. If I put a lot of work into this article for Business Insider, Credit Karma, I might help somebody. To me, that was exciting. Even if my blog grows, some of these places I write for, I still kind of like the platform because it truly is my passion. I don’t completely understand how people say, “I’m a freelance writer and I write about whatever; pets, personal finance, tech, fitness…” Personally, I couldn’t do that. I do not hate on anybody who does. But for me, it’s just kind of in my wheelhouse. It’s what I truly care about, and I enjoy helping people.

Tom: Yeah, you said you started this because you wanted to help people. And really, when you’re on a bigger platform, that’s how you help people. Instead of helping 100 people you can help thousands of people. And you can get paid at the same time.

Clint: Exactly.

Tom: So now you’re established as a freelance writer. I want to kind of cover this idea of how you’re refocusing onto your blog. And now you have a podcast as well. You sort of consider this your side-hustle, right?

Clint: Correct. I never stopped posting on the blog even while I was building my freelance side-hustle. I would always post at least once or twice a week. Sometimes I didn’t get that once a week post out if it was a crazy week but that was my goal. I always knew if I can work a full-time day job and build up 50 to 75 percent of my day job income only working 5:00 to 8:00, why should I not be able to put more attention to my blog once all those 8:00 to 4:00 days are open to do freelance writing? I should be able to find more time for my blog. I realized that the carrot dangled in front of me with more money with freelance writing was going to be serious, then I would need to be disciplined enough to say, “Okay, I’m going to still set aside some time to dedicate to my own blog.” Because I do realize at some point down the road I may not want to always be trading time for money. That’s where I’m at right now. I’m fully okay with that because I’m making good money and trading time for money. But at the same time, if I want to go away for a month with my family, I’m just not going to have income for a month. I can save for that, but I won’t have income for a month. I want to build up passive income streams. Not just with my blog, but that primarily is where I’m focusing right now. I’ve tried to figure this whole thing out and I haven’t got a really good formula yet. I told myself I was going to do freelance writing Monday through Thursday and take Friday off for my own blog. I haven’t been very successful at doing that. Right now, it’s more like when I get an afternoon that I know is empty, then it goes to my blog. Yesterday I worked on an article for my blog and posted it this morning. I am writing—it’s just not necessarily with the schedule I would like to. But I have only been a full-time writer for about four months so I’m still kind of figuring this whole thing out.

Tom: Yeah, I like the idea of separating days like that. That does make sense once you get to that point. I’ve seen a lot of freelance writers who (since it’s working out so well for them) just go all-in on that. Some of them sell their sites. They may be offering different services now. It’s not always writing. They could be doing other forms of freelancing. They sell their sites and just go all-in on this one thing. I respect that idea but I kind of prefer yours where you want to keep some diversity there. It’s not all-in on one thing. Start building something else. I’ve said this before with people—if you want to drive with Uber, great. You might be able to make $1,000 a month on the side but that’s still on the side. You should either keep your other job or look at other options of freelancing or side-hustling. I prefer to kind of juggle multiple things instead of just going all-in on something. It sounds like that’s kind of where you’re headed as well.

Clint: Throughout the majority of my life I’ve been able to live on a fairly low income and I’m happy with that. I don’t require a lot to enjoy life. I’m at the point where if I was working 50 hours making a certain amount of money when, instead, I could work 25 hours and make half that much, I probably would be okay because spending time with my family and on the things I enjoy, matters to me. Not that I’m lazy or don’t value work, because I do. I don’t think I’m ever going to be somebody who doesn’t want to work because I actually get a kick out of working. At the same time, I don’t want to have to work every single moment of my life because that makes me unhappy and it makes my wife unhappy, too. So I’m trying to keep that balance. To be honest, I didn’t make a lot of money as a pastor so I thought I’d be okay with a certain amount of income from freelance writing. But now that I’m in this world, you can definitely get very competitive, very quickly when you see all these people making more than you. And as a competitive person, it kind of ticks me off. I have to be them, to be successful now, even though where I’m at now I would have considered crazy just a year ago. So you’ve got to be careful looking at other people’s successes and getting the “green eyes of envy” in any world you’re in.

Tom: A couple things you touched on there sound like you’ve just got to realize where your work life balances. You don’t have to work 40 plus hours. But you also shouldn’t be too jealous of that person doing better than you. You just have to be content with where you’re at.

Clint: Yeah. I think the people who are making a lot more than me, have got more experience than I do. And they are probably working harder than me so they deserve to be making two times as much as I am. I’m pretty happy where I’m at. I have time to build my blog which is my long-term goal.

Tom: Do you have any advice for people that want to head down this path? Maybe it’s not freelance writing, but any kind of freelancing, where should they be looking to start?

Clint: That’s a broad question because it does depend on what they want to do. I would say get involved in a community of people who are already doing what you want to do. Then go deeper. For me, FINCON was that first step. FINCON is a huge community of podcasters, writers, and financial planners. But in that subset of the FINCON community of freelance writers, it was big. Honestly, I can’t remember ever asking for a referral or anything from anybody. I just tried to be around and comment on people’s posts and offer help and encouragement when I could for the first few months because I think a lot of times you see somebody just swoop into a community and all of a sudden they’re trying to be the star within three weeks. And then they’re a “shooting star” because all of a sudden they’re gone. I just wanted to prove that I was going to be someone who wanted to implant myself into this world for the long-term. I never looked at anybody and said, “Oh, that person could really offer me an opportunity.” I think people can sniff out when you’re trying to use them just to climb the ladder. I just try to be around and meet good people, honest people, who are hardworking and successful. Slowly but surely, they send opportunities my way. It doesn’t matter what you want to do. Take somebody out to coffee that has been successful. Don’t expect anything out of it but just do it to learn from them. Join Facebook communities of people who are in the area you want to start in. Then take courses if there are courses available that are proven to be really helpful. Those are some ideas, I would say.

Tom: Yeah, I love the community point because even if it’s just a Facebook group, there is a Facebook group for any possible thing you could decide you wanted to do. I’ve seen everything from freelance writing to things like how to make succulent decorations. There are groups for anything you can think of. And if there’s not, then you should probably be the one starting that. Otherwise, there really is help out there. There’s blogs that can tell you how to do things. There’s the ride-share guy for Uber (to go back to that example). There’s definitely loads of information and community help on anything.

Clint: And when you meet people it makes a huge difference. My highest paying client is Credit Karma. They were my first clients. I didn’t actually (work for) publish with them until after the other client I mentioned earlier who is my lowest paying client. I started getting paid by them but didn’t have anything online actually published when I first signed my contract with Credit Karma. The only reason that happened was because I met the Editor so meeting people and putting yourself out there is very important. Don’t sell yourself short. Sometimes I think we psych ourselves out of opportunities by not just going up and shaking somebody’s hand and having a conversation. By avoiding it, you’ll never know if an opportunity would have presented itself in the first place.

Tom: I think this has been very inspiring for anyone looking to escape their day job but also look for that next thing and keep it going. Can you let people know where they can find you online?

Clint: Sure. Absolutely. My site is called, Wallet Wise Guy. So is my website, my blog. You can also see the new podcast I just launched, which is also called, Wallet Wise Guy podcast. You can find it on any podcast apps. You can also follow me on Twitter, @walletwiseguy, or on I’d definitely love to connect with any of your listeners and readers, and I appreciate the opportunity to come on the show today.

Thank you, Clint, for sharing your story and for showing us that making a career change is never out of the question. You’ll find the show notes for this episode at If you’re on Facebook, I would love for you to join the Maple Money Show Community where you can ask questions, share your best money tips, or just hang out with people like yourself who are interested in all kinds of money related topics. You can search for the Maple Money Community on Facebook or head to And as always, thank you for listening. Your views, comments, emails and social media shares keep me motivated to continue bringing you interesting topics and expert guests. Thanks again, and I’ll see you next week.

Personal finance was kind of a natural avenue for me, but I had no idea in what capacity. I just knew that I wanted to help people get out of debt, avoid or payoff student loans, have financial freedom, live the life they wanted. - Clint Proctor Click to Tweet