The MapleMoney Show » How to Make Money » Income

From Hobby To Side Hustle To Self-Employed, with Robb Engen

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.

There is no shortage of online entrepreneurs who will tell you that if you buy their course or listen to their webinar, you’ll be on your way to instant riches, quitting your job, and following your dreams. Does it sound too good to be true?

My guest this week escaped the 9-5, but it didn’t happen overnight. Robb Engen is the personal finance blogger behind Boomer & Echo. Last year, he left his corporate career to focus on his blog, freelance writing, and fee-only financial planning service. He joins the show to let us know how he made it happen.

Robb kissed his 9-5 job goodbye in 2019 after the income he earned from his side hustles began to exceed what he was making at work. But success on the side didn’t make for an easy decision. Before leaping to self-employment, Robb and his wife did some careful planning to make sure they had a large emergency fund set aside in case of a setback.

Robb’s entrepreneurship journey began over 10 years ago when he started blogging as a hobby. We discuss whether blogging is still a viable way to make money and if the potential is there to make a full-time living. Robb believes it’s possible for some but not the reality for most. However, if you view a blog as a business platform, you can build other income streams that you may have never thought of. This is perhaps why blogging remains so valuable as a tool of entrepreneurship.

Do you prefer to invest in socially responsible companies? If so, our sponsor Wealthsimple will help you build a portfolio that focuses on low carbon, cleantech, human rights, and the environment. To get started with Socially Responsible Investing, head over to Wealthsimple today!

Episode Summary

  • When corporate revenue doesn’t keep up with inflation
  • What made Robb leave his full-time job
  • The value of having multiple streams of income
  • Why a blog can be a tremendous business platform
  • Any side hustle can help you reach financial freedom faster.
  • Are there negatives to the laptop lifestyle?
  • Finding ways to unplug as an entrepreneur
Read transcript

There is no shortage of online entrepreneurs who will tell you that if you buy their course or listen to their webinar, you’ll be on your way to instant riches…quitting your job and following your dreams. Does that sound too good to be true? My guest this week did quit his job for the laptop lifestyle, but it didn’t happen overnight. Robb Engen is a personal finance blogger behind Boomer & Echo. He left his corporate career last year to focus on his blog, freelance writing and his fee-only, financial planning service. He joins the show to let us know how he made it happen.

Welcome to the Maple Money Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. Do you prefer to invest in socially responsible companies? If so, our sponsor Wealthsimple will help you build a portfolio that focuses on low carbon, clean tech, human rights and the environment. To get started with socially responsible investing, head over to today. Now, let’s chat with Robb…


Tom: Hi, Robb, welcome to the Maple Money Show.

Robb: Thanks for having me back, Tom.

Tom: So it’s been over 100 episodes since you were last on the show. For people that want to check that episode out, it’s episode 27. They can just go to Back then, you and I were both complaining about the usual corporate and public sector raises that don’t keep up with inflation. You get your one or to two percent. You can try to look at it positively in that it might pay a bill. But ultimately, when you consider inflation, we were both getting behind every year. What was interesting about that episode was you walked through this concept of coming up with other streams of income to supplement your day job. I’m a big fan of this, too. I think everybody should have something on the side just to diversify a little bit. You’ve had your blog for a long time but you had started a fee-only advice practice. Can you pick up from two years ago and just tell us what things have looked like for you since? What has changed?

Robb: The lack of raises didn’t change. I got a small promotion that amounted to about a four percent increase. But really, over time, I was barely treading water in terms of keeping up with inflation. I’ve been side hustling for a long time, over 10 years now. I got to a point where between the blog revenue, this new fee-only planning and my freelance writing, it came down to the point of math, really. I’m working 40 hours a week making, let’s say, $50 an hour and I’m side hustling for about 15 hours a week making almost $200 an hour. So I’m thinking like, “This is crazy. If I could drop this…” which is hard. It’s tough to leave a guaranteed paycheck with benefits and a pension. I’ve got kids and still have a mortgage rate. It’s tough, but when you just break down the math and understand that if I could take away those 40 hours and even put a fraction of that back into my side hustle, I might come out ahead. That’s really what I spent the next year thinking about that ultimately led to a decision to leave my day job.

Tom: We were in similar situations where your side hustle becomes bigger than the day job but it’s still nice to have two incomes. I get that you did the math and realized you could probably make more. But how confident did you feel about that at the time? It’s not a guarantee that you can trade that time for new money.

Robb: No. And the fact is, could you scale the $200 an hour (so to speak) and actually put 40 hours into that sidekick. No, I didn’t know. I’ve never really put that much into it. But I came up with about a two to three year plan. If my income from the side gigs are really ramping up, I’m going to save that money. If not, I’m going to just take out our normal dividends that we took out of our business account to top up our income and I’m going to save the rest. And I’m going to save, let’s say, 18 months’ worth of income. At that point, I’ll feel secure enough to leave the day job and know that even if things took a while to ramp up, I’d be okay just because I could pull from this large scale emergency fund. What ended up happening was that 18 month timeline got condensed. We took a big trip last summer. We went to Scotland and Ireland. It was a 32-day trip and it was really a chance to kind of explore. We’ve never really done a big trip like that. We went with our kids who were 10 and seven at the time. I didn’t do a ton of work at all. I wrote the odd article or update and it was great. That’s when I realized I could do this type of work from anywhere. And I loved this idea of just dropping everything and traveling. So, I came back to work and the public sector in Alberta is obviously under tremendous pressure with the fiscal situation in the province and some real deep cuts coming to our area. I worked in post-secondary. They were even talking rollbacks of wages, let alone freezing. There were going to be cuts. In fact, there were positions eliminated, which inevitably means more work gets piled on to who’s left. And so I’m thinking, “Okay, my 40-hours is going to turn into 50 hours.” The pressure is going to mount to come up with new strategies for increasing revenue and cutting costs with less time to focus on what I really was passionate about, which was the financial planning and writing. Ultimately, it just kind of came to a head where I realized this was not going the way I wanted it to. Forget the 18 months or the two years, I’m going to pull the trigger now. And that’s ultimately what I ended up doing.

Tom: I love that you had the 18 month emergency fund. At least it was some kind of cushion. It’s a very responsible way to make this plunge. I often hear people say to just do it and don’t worry about the finances. Everything will work out. Their backup plan sounds reasonable but what I’m not a huge fan of is, if it doesn’t work, you can just go get another job. That’s not always the case then. And maybe that job isn’t something you would like if you’re comfortable in your current job. The idea of starting somewhere else because maybe you went several months to a year attempting this entrepreneurial journey and it didn’t work out, I’d prefer you save up enough money to cover yourself for a bit longer so you can kind of keep testing it out.

Robb: Yes, it ended up being about nine months. That’s what I ended up saving. It’s not what I wanted but it was enough to really still get me going. The other part of it was I still had these multiple streams of income. Even in the side hustle, there was blog revenue, freelance writing, and financial planning. All three of those streams were growing. I had some pretty much guaranteed writing gigs and the fee-only financial planning service was growing. I was getting referrals from all over the place in Canada. I was even putting people on waiting lists. So right there I know I’ve got these streams of income coming, and I know that at least for the next three to six months, I’m pretty solid in terms of transitioning. And then let’s see what those extra 25 hours a week bring to the table. What ended up happening this year—and I’ll step back and say I don’t recommend everyone quitting their job three months before a global pandemic. I’m working from home so it hasn’t really affected us all that much. What does impact a lot of people across Canada is, obviously, their finances. The number of financial planning inquiries has gone up. The eyeballs on my blog and other freelance writing has grown as well because people are wanting to know. There has been a financial shakeup whether they’re saving more money or not. And so ultimately, it’s led to more revenue. I’m not putting the extra 25 hours a week in so I’m able to have this balance which I really wanted.

Tom: You mentioned three streams of income you have as a business, the blog, the freelance writing and the fee-only advice. But ultimately, those all grew from the blog. Normally, I tend to tell people that starting a blog is not a great way to make money, because often when people come to me asking about making money, they’re really looking to make money now. So often I’ll tell them they’re better off starting as an Uber driver. If you want to get paid for that day’s work, blogging is not where to start. With you, this has been over a decade process to get to where you are now. Obviously, when you started your blog, I assume you did not have this big plan for all these different streams of income coming from that. How much does passion play a part of this when you’re starting something like a blog? Even if you just have a hint that maybe it will go somewhere else? I assume you agree that people aren’t just going to get paid on day one.

Robb: Oh, for sure. I saw an entrepreneur kind of tweet to follow your passion, quit your job and start living your dream from day one. But just like you said earlier, it’s not realistic for a lot of people. Maybe 10 years is too long. That’s how long I took to quit the job and do my entrepreneurial gig. But they have to be realistic. You have to be passionate about whatever it is you’re doing. If it’s something you can’t see yourself doing for the next 10 years, it’s probably not something you’re going to quit your job and do full-time. There’s nothing wrong with being Uber drivers or having a snow shoveling business in the winter. If you can find a way to add an extra stream of income, great. If that ramps up your savings goals and gets you to financial freedom faster, all the power to you. But this idea that it’s going to be some path to riches or some get-rich-quick scheme, it couldn’t be further from the truth. We saw some of the bloggers in the States who started really early either ended up selling their blog or just making enough from their blog to do it full-time. It was pretty inspiring though. We already knew we liked writing about this. We liked building an audience and engaging with them. Knowing you can make an income from that is pretty inspiring. What inspires me is that is the number of ways you can earn income online. You build your blogs in a different way than I have attacked or approached my business and others do the same. Whether it’s someone who’s really strong in freelancing to someone who’s really strong as a brand ambassador or influencer then branching out to freelance writing or financial advice, social media managers, managing editors of other sites… There’s just so many ways that you can take your passion into whatever different area you end up doing.

Tom: I actually had Ashley Barnett on the show back in episode 098 and she really opened my eyes about that. I was kind of coming off a little “anti-blog” when she pointed that out. She became a full-time editor from having a blog. And you’re right, there’s people that go down the social media route or with Facebook ads. When you start a blog, you are learning all the tasks. You have to you have to be a website designer and know social media—know how to write. All of this needs to come together. Different people are going to find different strengths within that. But if you lean into that, maybe that first blog you start isn’t the primary thing in the future.

Robb: You’re learning a new skill. You’re going to learn what you hate and what you are really good at and what you love doing. So use that as an enhancement to your resume to find what that passion is. A lot of times we just come out of school, get a job and that’s where you park yourself hoping you advance up the career ladder. We never really branch out to say, “Hey, what if I was doing something I really enjoyed?” It doesn’t have to be the thing. You don’t have to end up quitting your job and doing it full-time. But you’re fulfilling yourself and expanding your horizons a bit. And maybe, just maybe, it turns into something where you do pivot into a new career.

Tom: And that’s a great point. It could truly be a new career. If you’re doing a job that you don’t like much but you’re learning new skills, those skills can apply somewhere else where you could eventually apply for a different job in a whole different career. Those skills can still pour over. It doesn’t have to be you going out on your own. You can find something that you enjoy. That’s what I was thinking about with the passion idea. That’s just good career advice in general. If you don’t like what you’re doing, you’ve got to find something else.

Robb: Yeah, and don’t feel like you’re stuck. There are a lot of jobs out there. What we are doing today, Tom, in thinking about that… When we were coming out of high school, these jobs didn’t exist. There was no social media manager. There were none of these “online” type of jobs that existed back then. What I’ve found was my streams of income kind of evolved over 10 years. A lot of times at the beginning it was just AdSense and things like that. We were just taking advantage of the eyeballs that were coming your way for clicks. And then you realize, “If I do that, I’m just sending readers away and what I want to do is develop a community here—an audience I can engage with.” Then there was talk online about developing a product to sell. Or, in my case, a service. Where do most of my financial planning clients come from? They’ve been reading my blog for a number of months or sometimes a number of years. My approach to that evolved over the years as well into something that I was passionate about, but also kind of keeping my skills up with the trends on what was happening in the online space.

Tom: That’s a great example of flowing with it a little bit. You don’t need to decide you’re going to start whatever side hustle you chose. It doesn’t have to always look like that. Things are going to change, especially when you talk online, whether it’s blogging or something else. Maybe someone wants to be a YouTube superstar (like my kids want to be). The idea is that over the span of 10 years things can look completely different. That’s a long time in Internet years.

Robb: Yes, you have to be constantly evolving in this business. You have to ask, “Do I expect my business to look exactly like it is right now, in five years or ten years?” No, you don’t. But it will keep evolving so you have to find the niche that suits you, that you’re really passionate about and want to serve. I’m finding that already because I really enjoy the financial planning and helping someone one-on-one. But what’s fallen off is the writing. I’m not writing as often on my blog. And I’m probably not writing as often freelancing either. I’ve got this real passion and obviously inquiries are coming in which helps so I see it evolving. Once this pandemic is behind us what I really want to do is go on the two big trips we had planned for 2020. We had a trip to Italy and a trip to England and Scotland in the summertime and we had to cancel. I just saw myself trying to take advantage of when the kids are off school. I’d work sometimes remotely as needed, but I just really enjoy that kind of location, independent-type of lifestyle which I never really got to experience this year yet. But I am looking forward to that, eventually.

Tom: We often see this idea of someone sitting on the beach working on their business. I know you mentioned a couple of these things… One, you’ve got to leave some of the work behind. And two, sometimes you’re going to be doing some of that work on vacation. What do you see as the negatives there? I think there’s a bit of a risk to maybe hurting your income while you’re away. Or you’re giving your time and not enjoying the trip as much.

Robb: One of the risks would be that right now, because of the circumstances we’re in where we are in, we’re essentially locked down. I’m at home with my family but there is only so much Netflix you can watch. That is why I started my blog in the first place. I pour that time and energy into creating something—working on things I’m passionate about. But at the same time, I recognized this on our trip from last summer, it’s valuable to unplug. When I made the decision to give my notice and hand in my resignation, my wife and I went away to Vancouver for our anniversary. It was just a little five day getaway last October. Being able to talk about our plans for the next year and the travel we had planned to do, for 10 years I’ve been doing the full time job plus ramping up a side hustle. We had savings and I knew I was going to make money so it wasn’t really about just more, more, more. I’m going to work like crazy when I can, and I’m going to unplug when I can. I’m going to find that balance. It didn’t really work out that way this year. We’re locked down and so I’ve put more energy into working and growing that business just to make sure this was the right move and we’re going to be okay. But I really look forward to the time when I can say “no” to certain business that I don’t want or just say, “Look, I’m not taking any new clients for the next three weeks because we’re going away.” I have to be able to do that but that hasn’t been proven yet. And I totally get where you still (as an entrepreneur) want to pour every hour into your work. But my kids are eight and 11 years old now. They’re not going to be this age again so I want to take advantage of these years before they’re off into post-secondary. I want to spend as much time as possible, see the world as much as we can. I think I’m doing something that enables me to do that. So, that’s the plan anyways.

Tom: I love that you’re making an active decision to potentially give up some income to spend time with your family.

Robb: Yeah, it’s true. You just need to full stop. My wife works with me. She manages my schedule. She asked me the other day, “What are you taking off for Christmas? The kids are going to be off on the 18th and they’re not going back until the 11th of January. Let’s block out your Christmas schedule so you’re not taking clients over this time.” It’s just not something I was used to in those 10 years of side hustling. Now I’m home and I’m going to put in that work. I also have someone to helpfully nudge me into making those active decisions.

Tom: I think a lot of business owners will have that issue. It’s easy to never take off time. You no longer get those vacation days and sick days. You’re always on so I’m glad you’re taking that step to give yourself some space.

Robb: Yeah, and it’s so important. It’s so easy to fall into the trap of answering an email at night or finishing off a client’s inquiry, writing another article or just thinking about your business rather than saying, “Look, I’m just going to unplug.” There’s nothing wrong with binge-watching some Netflix from time-to-time.

Tom: So you’re making these decisions to take some time off and that will hurt your income. It doesn’t sound like you have too much risk right now of not having income for other reasons like the business falling flat for a month. But it could happen. Either way, whether it’s your choice or not, do you budget a little differently knowing that you will have a regular income by choice or not?

Robb: You know, it was a really weird year because when I left my position, I took the commuted value of my pension rather than leaving it in the plan. And with that, a portion of the money went into a locked-in retirement account. But another portion got paid to me in cash. Because I didn’t have any salaried income, I took that cash. There wasn’t as big a tax hit and I was able to leave. Remember I talked about the business and trying to save up 18 months’ worth of income and I only got to nine? Because of the way this all played out, I got this payout from the pension and was able to kind of live off of that and continue to save inside the business. So in effect, I will end up saving about two years’ worth of income. But it definitely makes you think about budgeting a little bit differently. Something we still haven’t really figured out is how are we going to pay ourselves? Is it a salary or dividends? For 10 years it was dividends. My wife and I could split some income that way. But if I take dividends, I’m not paying into Canada pension plan. I’m not creating RRSP room. On the other side, I don’t have a health spending plan anymore. So, if we continue to take dividends, there’s some issues around what kind of plan I could get (even under the business) so I still have some decisions to make. I kind of just used this year as a way to get used to what this “flow” is like, make sure the business is viable, and how I want to structure my day. But come next year, I really need to make some tough decisions on budgeting such as, what that monthly cash flow looks like now and what are we going to do for health insurance or health spending? How are we going to pay ourselves in a tax-efficient way that makes sense for now and into the future? There are still lots of decisions. I’m still learning.

Tom: It is a constant process. Just you’ve been doing it one step at a time over a decade. If someone wants to start something now and they’re okay with this idea that it might take five or 10 years to get to the point from starting something on passion alone to potentially replacing their job, what’s your advice to them? Is it to start a blog? Is it find something else? What would you do if you were just telling someone to start something that could grow into something in the future?

Robb: First of all, you’ve got to look at your own skill set, what you are good at and what you could potentially turn into income. If it is a blog you may have in mind, again, there are so many blogs out there that it’s said the chances of striking it rich are pretty slim. I don’t necessarily agree with that. I think if you really are a subject matter expert and have the passion and consistency to put in the work, you could grow it to something that you could eventually do full-time in some capacity. Or it could lead to some other opportunities. But you’ve got to look at your own skill set. Are you good with woodworking? Are you good at making things in general? Are you an artist? Are you comfortable just clearing people’s snow in the winter? I’ve just heard of so many side hustles. You can even turn snow shoveling into kind of a full-on, property management type of business for a condominium or something like that. It’s just finding something that you know you are good at but you’ve got to put in the work. There’s just so many people that, at the end of the day are just tired. You’ve got kids and you haven’t seen your wife or your husband… The last thing you want to do is put another couple hours into another project that may or may not pay off. So you’ve got like it. Again, it goes back to that passion. It doesn’t have to be a blog but it’s got to be something you can do with your skill set and see yourself doing for a long time. There’s nothing wrong with pursuing your passion into something that’s not going to make you any money. If you just love to play the piano, you took lessons when you were a kid and you just want to take that up again, great. Creativity is probably great for your mental health in expanding your mind and good for stress relief. It doesn’t have to turn into moneymaking but it would be great if it could. I think you told me once, if I could make $200 a month, that’s my heating bill. If you turn that into $1,000 or $1,200 a month, that’s my mortgage. You just kind of keep snowballing it.

Tom: Yeah, I did start off with very small goals. Back when we started, it wasn’t so well known that there were people out there making these big dollars with blogging. We both started with this idea it was more of a hobby. It wasn’t a real thing. But nowadays I often see income potential in everybody’s interests. I’ll be talking to one friend who is really into golf and I tell him if he started a golf blog or some kind of YouTube channel just as a bare minimum goal, he might get some free golf equipment or something like that. It doesn’t mean you can replace your day job. There are different steps to this. And like you said, if you can make $200 it’ll do this… And you just keep working it up. That kind of idea with a side hustle is great. Not everybody has to leave their job. It’s just a nice accidental outcome at the end. Just the idea of getting yourself ahead somehow. Going back to what we said before on a previous episode about raises that don’t keep up with inflation, you’ve got to do something that puts yourself ahead each year and makes you feel a little more confident. One of the things I found in my job is, I actually became a better employee once I had a certain percentage that I was making in the business because I just felt a little more freedom to speak my mind. A lot of people ended up appreciating that. I didn’t feel like I had to protect this job because this was the only thing the family relies on. It’s nice just to have that little cushion even if it doesn’t replace your job.

Robb: I totally agree with that. I’ve seen that, especially in my last couple of years of work. I felt like I could break away at any time and I’d be okay. And you’re exactly right, you’re freer to speak your mind when you might have stayed quiet before. And ultimately, that’s kind of what led to the little mini promotion or whatever you want to call it. It’s expanding your skill set. The reason why I’m drawn to the blogging or online type activity is because, one, it didn’t exist many years ago. I see moneymaking potential everywhere too. I see it in social media. I see it in blogging and what those blogging opportunities lead to whether it’s just some free product you’re talking about, something you’re a subject matter expert on—people will want to read it. You think that nobody does or that there’s a million other golf blogs out there but someone will be drawn to your story or the way you tell it. You’ll have something unique. I don’t have a podcast or a YouTube channel. That’s not my area of expertise, but I’m amazed. I’ve got a nephew that has a YouTube channel and my own kids want to start one. They would rather watch someone unbox a toy than play with that toy themselves. I’m just amazed at the income earning potential “online” and I think it’s only going to grow. That’s one area that I’m drawn to. One more reason is because you can do it from anywhere, including your own living room. So, while your spouse is watching Netflix, you could write a blog post, respond to comments, build your community. I think it’s just a cool way to earn a living.

Tom: Well, thanks for catching us up. I think this is inspiring people to look at things a little differently. It just takes a little creativity some small goals. It doesn’t have to be a way to “get out of your job,” but a way to give yourself a little leeway. I hope people appreciate that concept. It’s these little bricks to build the wall—that kind of thing. Can you let people know where they can find you online and what you’re up to?

Robb: Sure. I’m at That’s where my financial blog is. You’ll also find my fee-only advice service there. I’m active on Twitter. My handle @robbengen or @boomerandecho as well. That’s probably the easiest way to find me.

Tom: Thanks for being on the show.

Robb: My pleasure. Thanks for having me again.

Thank you, Rob, for coming back and sharing your story. It’s inspiring to know that there are so many ways to build hobbies that make money, whether the goal is financial freedom or escaping the 9-to-5. You’ll find the show notes for this episode at Are you a member of the Maple Money Show Facebook community? If not, I’d love to connect with you there. It’s a great place to ask a question or share a recent money win to encourage others. To join, head over to to share with the group. I look forward to seeing you back here next week when Gloria from Miss Findependent joins us to discuss how she’s staying frugal and mindful during this interesting year.

There’s nothing wrong with (driving for Uber), or the snow-shovel business in the winter...if you can find a way to add an extra stream of income, great. If that ramps up your savings goals and gets you to financial freedom faster, all the power to you ” - Robb Engen Click to Tweet