Being a Digital Nomad — Sitting Poolside with Bob Haegele from The Frugal Fellow

The Sitting Poolside interview series

When people think of retirement, scenes of beachfront homes, rounds of golf, or reading by the pool come to mind. Sitting Poolside is a series of interviews that challenges that notion and other financial misperceptions. The series name pokes fun at the stereotypes, but it’s also an opportunity to discuss people’s real stories and unique insights. So grab a piña colada and pull up your lounge chair!

Bob Haegele from The Frugal Fellow

Bob Haegele is a freelance personal finance blogger at The Frugal Fellow who kicked his 9-5 to the curb. Through his writing, he’s helping writers create a life that doesn’t keep them chained to a desk all day long. He also loves to travel and is building a lifestyle that will let him see the world while still making a living.

Bob Haegele

Leaving his desk job

Mr. SR (MSR): What inspired you to start The Frugal Fellow? What’s your vision for the site?

Bob Haegele (BH): I want to help people build a better life. The FIRE movement is great, but much of it focuses on “retiring” in 15 or 20 years. I use quotes because it’s usually taken as a given that even if you leave your 9-5, you may still be working, but maybe in a different career. In other words, FI without RE. And that’s what I wanted to do, but 15-20 years seemed way too long to me. I was a part of the rat race lifestyle for almost 10 years, and I was at a breaking point. I suspect I’m not the only one. The goal is to help like-minded individuals create the life they want — even if they aren’t ready to “retire” yet.

MSR: The premise of Semi-Retire Plan is similar — if you know you want to do some work (that you enjoy), you can leave your 9:00 to 5:00 even earlier than full FIRE

What does your work life look like now?

BH: I am still working, but not in the traditional sense. I’m doing a variety of things – other than the blog, I am also freelance writing and dog sitting/walking as well. That’s my new favorite thing. It’s more like part-time hours though since I am still building client bases for both.

That said, I’d be willing to work full-time hours once I (hopefully) have enough clients. Getting to FI is still very much a goal and I want to get there ASAP. Still, I actually enjoy this type of work (unlike the 9-5), so it’s really not bad.

Life changes

MSR: How has your life outside of work changed since leaving your previous desk job?

BH: I would say it’s changed in subtle, yet powerful ways. My work “schedule” is much more fluid and flexible. Sometimes I’ll be out and about at 2 p.m.; other times, I’ll be working on something at 11 p.m. The funny thing is that a lot of people have more fluid work schedules nowadays — the difference is that they are typically on salary, whereas I’m doing paid work.

Also, when people ask me “what do you do?” I used to say tell them and follow it with “it’s a job.” Meaning it paid the bills, but I didn’t enjoy it. I don’t do that anymore. I just tell people who I do without feeling the need to qualify it.

MSR: What are your long-term plans?

BH: The biggest thing that I’m working on right now is becoming a full-time digital nomad. It’s not easy, but if I can make it happen, I can potentially get to FI much faster.

I’m looking to do house sitting so that I don’t have rent or a mortgage. It’s competitive and can be tough to break in, but I’m working on it. That might mean I won’t be able to do the dog walking thing anymore, but that’s why I have my blog and freelance writing. These are flexible gigs that can be done from anywhere. If I can do that and make my expenses almost nothing, I’ll be FI in no time!

MSR: On your site, you talk about being a millennial and lacking a real financial education growing up. I can appreciate that — those are both true for me, too.

Was there a certain moment that “flipped the switch” and put you on the path to taking control of your money? What resources did you use to equip yourself?

BH: For me, it was when I started listening to the ChooseFI podcast. Brad & Jonathan weren’t the first ones to talk about this, but they happened to be starting out just after I had finished repaying my student loans (2017 or so). Since I was debt-free at that point, I knew I wanted to take my finances to the next level, but I wasn’t sure exactly how — until I heard about FI. That was a light bulb moment for me.

MSR: You share on your site that you left your job in February and that the 9:00 to 5:00 life was not a good fit for you. I think most or all Semi-Retire Plan readers understand that feeling. What  aspect of working 9:00 to 5:00 made it a poor fit for you?

BH: To be honest, it was pretty much every aspect of it — but most of those come back to not having any semblance of freedom. No freedom to go where I wanted or do what I wanted — both in terms of making money and even just having fun. After all, Americans get very little paid time off.


MSR: What’s the most helpful book you’ve read recently?

BH: I’m currently reading Deacon Hayes’s You Can Retire Early and I’m finding it quite helpful. I will probably write a review post for it soon. I am admittedly pretty bad at planning things ahead of time (which is ironic since I usually think ahead). But he lays out a framework for the steps you need to take to retire early. I think this is great stuff since many people in America (and elsewhere, probably) aren’t even aware of this stuff.

MSR: What advice would you give someone who is on the path to semi-retirement or early retirement?

BH: If you’ve ever heard “invest early and often,” there’s a reason for it. Investing can get complicated, but the short version is total-market index funds. Invest as much in them as early as you can. The unfortunate thing is most of us make less early on. Regardless, invest as much as possible. This will allow your investments to grow and compound.

Also, don’t be afraid to be different. In other words, don’t “keep up with the Joneses.”

And, lastly, you might have to take a leap somewhere along the line. This is especially true if you are retiring without being FI. Yes, it might be a bit risky and it might be scary. That’s why I would never do it without at least some savings. That way, you have a buffer. Plus, you can always go back to the 9-5 if absolutely necessary. However, if you want it badly enough, I honestly believe you’ll find a way to make it work.

MSR: Bob, thank you for sharing your story with us. I really appreciate your “create a life you want now” approach!

Mr. SR writes about personal finance, decision-making, and early semi-retirement here at Semi-Retire Plan. He has been featured on MSN, Yahoo Finance, and G2.

Mr. SR is a fan of college football, Taylor guitars, and extra-large coffee mugs.

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