I have a confession to make: I have three jobs. Well, maybe four.

At least that’s how my wife words it. The thing is, I feel like this is the least work I’ve ever done in my life.

A few times a month, I catch a ride up to KATL and from there blast off to new and interesting places all over North America. I’ve gone for a run on an island on the Saint James River in Richmond, eaten amazing Turkish food in Atlanta, swum and spectated on a gorgeous beach in Nassau, and people-watched with another pilot for hours in an outdoor cafe in the middle of a walking mall in Charlottesville. I always get to stay in hotels nice enough that I’d bring my wife back to stay. This job also involves me getting to fly fast jets. In exchange for doing this, my company compensates me well for my trouble.

My second job is serving a reservist for the US Air Force Academy. A few times a month I get an email with a (usually stupid) question from some high-schooler (or the poor kid’s tiger parent.) A couple times a month I do a Skype call with one of these high schoolers and chat for an hour, before spending another hour or so writing some notes about our call for the admissions board. Every once in a while I’ll get a call from someone in Congress, like American hero John Lewis asking me to spend a couple hours at a sort of Military Service Academy college fair. I hang all my air medals back on my chest and stand around telling war stories (and answering more stupid questions) for a while. It’s not the most exciting thing I’ve ever done in the Air Force, but it is fulfilling. It’s a nice excuse to put the uniform back on every once in a while.

I take exception to my wife calling this a job because I only spend a few hours a month on it, and I don’t get paid. If I keep doing it for another 5-6 years, I’ll eventually get to “retire.” Then, when I turn 57 or so, I’ll get to start collecting a pension. Don’t get all excited though. If I live until I’m 97 (here’s to hoping) the lifetime total compensation I’ll collect in pension money will be $72 for each hour of work that I’m putting in now. Yes, I’ll get some discounts on health care in there to sweeten the pot, but it’s not actually much money. I’m pretty sure some honest math would tell me I’m a fool and that this USAF Reserve deal is nothing more than a vanity project. I can afford to do this though because 1) it doesn’t take that much time, 2) my other job is enough to support my family, and 3) I enjoy it.

My wife considers writing for TPN to be my fourth job. (We’ll get to #3 shortly.) I don’t get paid for any of this writing (yet…we focus all our resources toward making TPNx awesome.) This also means my schedule and my subject matter are almost entirely under my control. I like that flexibility. I frequently write on the 2.5 days per week that my wife is at work while my kids are also at school, but most of my writing happens while I’m on the road for job #1.

Although this job doesn’t pay, I enjoy it. I started almost by accident, seeing that the same questions tended to get asked and answered over and over again on the TPN Facebook group. I had a persistent platform to hang long-form answers for future reference, and some practice writing on that platform. As a military pilot with lots of civilian flight experience (and now experience as a major airline pilot,) I felt like I had more informed and complete answers than some of the WOM that tends to float around Facebook comments threads.

Since I started writing, I’ve frequently been told that my work is helping people. I’ve also helped review applications and resumes for old Air Force buddies, and I’m proud to say that I am directly contributing to the USAF’s 10%+ pilot shortage! I view our industry as a limitless resource for at least the next 10-15 years. I lose nothing by helping all of you find the perfect airline job, so I’m happy to do it, whether it pays or not.

Then there’s my 3rd job. I consider myself to be a freelance flight instructor, but lately, I’ve focused most of my CFI attention on Icon Aircraft. I’ve been drooling over their amphibious light sport aircraft, the Icon A5 since it was first announced about a decade ago. When my wife and I decided to separate from the military and started trying to decide where to settle down, I may or may not have slightly favored Tampa knowing that the Icon Flight Center for all of the East coast is located here.

Then, I was perusing TPN one day and noticed that an Icon recruiter was looking for part-time flight instructors.


I had been wishing for over a decade that they’d post that exact request. I’d freshened up my resume and submitted it before I even realized what I was doing. Less than a week later I was at Peter O. Knight airport interviewing. I’ve been teaching in the A5 ever since, and let me tell you: I love it! How could you not when this is your office?

If you like this picture, I bet you’ll also enjoy Icon’s latest promo video:Play Video

They use music and cinematography to add drama to this video, but flying this airplane is honestly even more fun than it looks here. Icon’s founder and CEO is Kirk Hawkins, a former F-16 pilot. He knows what a good aircraft should be able to do. He designed the A5 to be capable, fun, and versatile…and he got it soooooo right. On my average training flight we takeoff, climb to 300’, and we’re doing splash-n-go’s in Tampa Bay less than 2 minutes after liftoff. Important training events include laughing at the benign stall characteristics of an airplane designed with a spin-resistant airframe, performing minimum radius turns (~500’ radius without trying hard,) and parking on the beach next to amazed boaters and jet-skiers at Beer Can Island. You cannot beat the fun of threading a channel between two islands at 10’ AGL to hit a smooth spot landing.

I’m not telling you all of this as a sales pitch. Honestly, most of us probably can’t afford one right now. (Well, they did just announce a fractional ownership program. If you went in with a few friends…but I digress.) I’m telling you about this “job” to show you how much fun a side-hustle can be. I love flying the Icon. If I had my own, I’d want to go fly it every day that I wasn’t working at jobs 1, 2, and 4. As an Icon instructor, not only do I get exactly that, but they pay me for going to the trouble! The rates don’t even approach what I could make by just picking up Green Slips at Delta in my spare time, but they aren’t anything to sneeze at either. I get paid far better than any other flight instructing job I’ve ever seen. At this level of pay + fun, I’m making out like a bandit!

This job doesn’t detract from my Delta flying…I only fly for Icon on days that I’d be home anyway. It mostly doesn’t detract from my family time either. Since I’m a part-timer and my family’s survival doesn’t depend on the (princely) daily rate Icon gives me, I get to tell them when I’m available to work. For me, that is usually while my kids are at school and my wife is at work.

I emphatically advocate that military pilots leave active duty ASAP, join the airlines, and continue flying (or not flying) with the Guard or Reserves if they aren’t ready to give up military service. Or, better yet, leave the Reserves alone altogether. While pay has a large role to play in this argument, I can’t emphasize enough that it’s really about Quality of Life.

As a military pilot, I could never have dreamed of taking this job. I try to give Icon a minimum of 5 days a month, and they don’t operate on weekends. A military pilot (or any other every day, non-flying working stiff) just doesn’t have enough leave to cover that. Even then, I was always so busy with meaningless, queepy administrivia on active duty (when I wasn’t flying or deployed) that I couldn’t have spared the time from work anyway. Being an airline pilot turned that time equation upside down though. I now spend as many days not working at my primary job as most military pilots spend at work. Most of my non-working days are during the week, meaning I have lots of free time to pursue other things that I enjoy without impacting family weekend time.

As well as Icon pays, I still probably wouldn’t have pursued this as a full-time job. I’d know I was giving up hundreds of thousands of dollars per year (as an eventual airline Captain) and any flight instruction job can become a grind if you have to do it 5 days a week, 50 weeks a year. Being an airline pilot gives me the best of all worlds. Since I make far more than enough money flying big jets, I can afford to do a job I love for (relatively) lower pay. Since it’s only part-time, I find that I always leave Peter O. Knight airport wishing I could have flown a little more. What’s the last job that made you say, “Gee, I wish I could spend more time at work!”

But enough about me…

Do you love your job so much that you can’t get enough of it? If so, congrats! If not, what would you rather be doing instead?

There is much ado on the internet about side-hustles and the so-called “Gig Economy.” For some people, these are a great way to increase household income and help make ends meet…or even save for later. For others, it sounds like a lot of extra work for not nearly enough money.

I see what they’re saying. At Delta, I can make more than $2K for one day of flying on premium pay (on 3rd year pay, on the smallest aircraft in the company.) Unless I go full Walter White, I’ll probably never find a side-hustle that pays as well as just working more at Job #1. However, we need to return, yet again, to the critical pilot realization that it’s not all about the money!

Let’s try an exercise where we stop using the term “side-hustles” and try “hobbies” instead. What do you love doing with your free time? I know some people who live and breathe golf. If they have a couple spare hours, they’re out playing 9 holes. Their birthday cakes are decorated to look like golf balls. Their house is carpeted in astroturf. (Okay, I made that last one up. I don’t know anyone that afflicted.) If golf is what you truly love in life, you’ll find a way to do it. Maybe you play during your lunch break, right after work, or on weekends. Maybe you can even convince your spouse or children to go with you so that you’re not taking time away from them. However, if you work a full-time job, you’ll never get as much golf as you’d like…and trying to fix that will cost time that you could be spending on other important endeavors.

As an airline pilot, you actually can golf as much as you could ever want. I know captains who play every single day when they’re not working. They bid layovers that allow them to play the best courses in the world. They can afford the greens fees because captain’s pay starts at $227/hr. Being an airline pilot gives golf-loving pilots the time and means to enjoy their hobby nearly every day of their lives, in a way that most jobs never could.

Let’s try another scenario: maybe you live on Florida’s Emerald Coast. You love fishing, wakeboarding, and even just boating for the sake of boating. Unless you live on the water (and as a military officer that’d optimistically be a financial stretch) you just don’t have time to take the boat out during the week. You probably go most weekends, but it’s still not enough. Wouldn’t it be great to have a job that gives you 200+ days a year free from work to spend on the water?

You could do this just for the pure enjoyment of it. However, there’s nothing to say that you couldn’t take other people with you on occasion. If you happened to know a Network of 21,000+ pilots you might even be able to find airline people who’d pay a couple hundred dollars to go fishing with you for the day on layovers. Suddenly, you’re getting paid to enjoy the day fishing…like you would have done anyway except now you have some company.

If you wakeboard (or rock climb, or box, or do many other sports) you are probably familiar with the fact that you can significantly enhance your performance by blasting music while you carve (climb, punch, etc.) A friend of mine discovered this years ago and started shopping for speaker boxes for his wakeboarding boat. He found that his only options came with high prices and unimpressive quality. He had a need, a garage full of tools, and some skills, so he built a set for himself. They turned out really well, and someone suggested he try making a set to sell on eBay. Before he knew it, he had a growing business. He was able to provide a product far superior to anything on the market, at a price that generated seemingly unlimited demand. To me, this story sounds a lot like Burton, Compaq, and other companies that started organically and went big.

Unfortunately, Half Pint was a full-time military pilot who was spending half of his life deployed. As much as he enjoyed working in his shop, this just wasn’t giving him enough return to justify the time it took. I don’t fault him…I think I would have made the same decision. However, imagine what this could look like for an airline pilot:

You have 18-25 days every month free of obligation from your real job. That job pays more than enough to cover all your needs and still consider retiring decades early. Even if you reserve all 8 weekend days as 100% family time, you still have more than a week every month that you could spend on…something.

So, you do a minimal amount of planning, build some templates, and set up a serious shop. You invest in some decent tools (you’ve been wanting to anyway because…MORE POWER! ARGH ARGH ARGH!) You do a bulk purchase of materials. You build a run of 10 boxes, systematically grouping similar cuts or other steps in the process to minimize time wasted repeating measurements and saw adjustments. You assemble your boxes in parallel and put just a little extra effort into finishing them. You enjoy it because you’re out working in the garage on your day off…like you’d probably rather be doing anyway.

I suspect that with just a little forethought and practice, you could cut the time to produce a really nice product in half, if not less. Then, you can offer these for sale at a price that helps set demand at a manageable level. Suddenly, you’re making real money for something that you enjoy doing for fun anyway. If you weren’t going to spend those days flying for your airline anyway, you just discovered a manageable, enjoyable side-hustle.

Maybe you enjoy spending 2-3 days per month on this “business” and that’s enough for you. Or, maybe the entrepreneur bug bites and you realize that you could really make something of this. You could rent space in an abandoned commercial building, get some more equipment, and hire some high school kids. You improve your design and the finish of your product, you come up with some additional designs, and you train your new employees to build boxes faster and cheaper than even you can, without sacrificing quality. You start an actual website and put some effort into marketing. Can you see where this is going?

If you’ll allow me to conflate two separate examples, I have a friend who has effectively done this and his business is a raging success. TPN member (and fellow U-28 pilot) Brian Steorts is the founder and CEO of Flags of Valor. It’s a company run and staffed by veterans (whom he pays far better than a bunch of random high school kids) that make gorgeous wooden flags. When I say that his company is doing well, I mean it. How many small business owners can say they’ve presented a hand-crafted American flag to the President in the Oval Office?

Brian isn’t doing this as a side-hustle anymore. He works full-time at Flags of Valor. I don’t know how much money he makes. I suspect that it isn’t quite competitive with airline captain pay, but what an awesome opportunity! Building a business from the ground up, creating something that helps veterans find great jobs, supporting your family through your brains and hard work, building a platform that you can use to speak for and honor others who serve our country. Brian’s job fulfillment must be through the roof.

You may not want to go full-time entrepreneur, but you don’t have to. As an airline pilot, you absolutely have enough time, means, and spare brain capacity to get something like this going. Statistics show that the vast majority of small businesses fail. One of the best parts about doing something like this as a side-hustle is that you don’t have to care whether you succeed or not. If things don’t work out, your primary job will still put food on the table. This also means that you have full control over how much time this additional work occupies in your life.

There’s a proverb about a rich businessman who takes a vacation to a small fishing village. He meets a local fisherman who lives a simple, but fulfilling life. The businessman tells the fisherman that he should think bigger…he should turn fishing into a giant, multi-million-dollar business empire. The fisherman considers the idea, then asks, “And after I make all my money, what will I do?” The businessman excitedly describes a life of retirement in a small fishing village…the exact life that the fisherman is already living.

Why pursue a side-hustle if you already have a great life? My friend chose to give up his speaker box business because he already had everything he needed. I don’t believe in side-hustles for the sake of just making more money. If you don’t know how to live a good life with the money you can get flying at a major airline, earning more won’t do you any good.

However, what if you have time and means at your disposal and you find something that you’d be doing anyway? I don’t think that “something” has to make any money. It could be golfing or wakeboarding. It could be hiking, playing in a band, volunteering, or coaching little league. However, if you enjoy doing those things anyway there is nothing morally wrong with also making money from those activities. If the primary job that gives you all this time also provides enough to money meet your needs, then you will never find yourself beholden to demands from this side-hustle. Need to pick up a sick kid at school? Want to take a few days to attend a friend’s wedding? Did your spouse “ask” you to paint the house? No problem, your side hustle can wait. Even if that means the economic side of it completely collapses, it won’t do your family any lasting harm.

So, what’s your point Emet?

My point is: side-hustles (or just hobbies) are a great part of life. If you work a regular full-time job, you probably don’t have much time, if any, to pursue these activities. However, as an airline pilot, you have both the time and the means. It’s awesome.

If you’re debating about whether to leave a full-time job to become an airline pilot, I suggest that you should not leave side-hustles (and hobbies) out of the equation! Would your life be more enjoyable if you got to spend less time writing quarterly awards packages and performance reports, and more time on your side hustle? If so, that should weigh into your calculus.

I feel like it’s also worth considering the economics of potential side-hustles when you consider the money side of this decision. The major airlines pay far better than the military (or most other jobs) for far less work. It’s possible to run a lucrative side hustle without negatively impacting your family time or burning yourself out. There are many side-hustles that an airline pilot could use to put this into practice. May I humbly suggest a couple, though this list is nowhere near exhaustive. (I’d love to hear your examples in the comments.)

  • Flight Instruction. I know many professional pilots who hear this one and tell me to do rude things to myself. I get it. After military and airline flying not everyone wants to sweat it out teaching kids turns-around-a-point in a 40-year-old C-150. However, there are so many other kinds of flight instruction out there. Go find a place where you can teach tailwheel, aerobatics, or seaplane flying. Go find a company that needs instructors to teach in a unique aircraft. Get involved with an organization that flies warbirds. My students at Icon have included a senior test pilot at one of the world’s two biggest aircraft companies, and a CEO who flew himself (and his wife and dog) to training in his personal Cessna Citation Mustang. These aren’t brainless teenagers who are constantly trying to kill you. They’re serious people, spending serious money on an amazing airplane. They’re great students and the flying is a blast. There are many jobs like this available, and as an experienced professional pilot you’re far more qualified for the job than some poor, young aviator who’s trying to step from instructing in C-172s to something a little more interesting. These jobs are ripe for the picking.
  • Real Estate. I actually know a few pilots who are also licensed real estate agents. The commission on a single-family home is usually 6%, split between the buyer’s and seller’s agents. Think about agents you’ve worked with in the past and the amount of time they actually had to spend working for/with you. As an airline pilot with 18-25 days off per month, do you think you could manage to sell at least one home per month? If each house costs $200,000, you’re looking at an extra $6,000 per month, or $50,000 per year. How much more work would it be to double that? I know many people who would hate this job, but I also know plenty who enjoy working with people. For the right kind of person, this could be a great way to spend a week each month and a ridiculously easy way to make a lot of money.
  • Programming. The demand for computer programmers far outpaces supply in our world. If you know Java, Javascript, or Python, you can absolutely find lucrative opportunities. Don’t know any programming? There are all kinds of free courses and library books that you can use to teach yourself how to program. Worst case, you could pay for an online course or audit one at your local college. It’s a lot of work, but you have upwards of 20 days a month to put toward it, not counting free time at layover locations. If you spent even half that in an honest effort you could be capable of working as a professional programmer in 6-12 months. Programming is like solving a puzzle. It’s logical and systematic and lots of fun for someone with the right mindset.
  • Teaching. No, I’m not saying teach reading, writing, and ‘rithmetic at your local public school. There are all kinds of demand in our country and world for teaching though. You can be a part-time professor at an online university. You can create courses for sites like Udemy. (TPN co-founder Matt Swee can actually set you up with your own platform for hosting an online class and I bet his hosting rates tend to be much better than the competition. Shoot him an email!) If you do anything from working out, to shop work, to fishing, to martial arts, and beyond as a hobby anyway, you’re probably good enough to find someone who will pay you to teach them what you know. Anything you do in person can also be posted on a YouTube channel, from which you earn advertising revenue and attract new clients. One definition of “expert” is being slightly better at something than someone else. If you are passionate about something, and have some skill/experience with it, you can find someone who wants to learn.
  • Building. This is a pretty broad term. Maybe you’re a skilled handyman/handywoman and you’d enjoy taking on select carpentry projects. Maybe you know how to weld, or install solar power systems, or work on cars. I’ve met several pilots who are serial kit aircraft builders. One gentleman builds a different RV each year, flies its initial 40 hours, and then sells it for a lot of money. He enjoys the building process, and he’d be doing it anyway. Why not make money while you enjoy working in your hangar and flying brand-new airplanes all the time?

I’ve also flown with or know airline pilots who have a variety of side-hustles, including:

  • TPN Sponsor and owner of Emerald Coast Interview Consulting, Aaron Hagan (
  • Several people who work for ECIC as one-on-one consultants
  • TPN Sponsor, blogger, and published author of Cockpit2Cockpit, Marc Himelhoch (
  • TPN Sponsors Kim and Chris Uhland who founded the logbook conversion and upkeep service MilKEEP (
  • TPN Sponsor, writer, and career consultant Charlie Venema from Checked and Set (
  • TPN co-founders Adam Uhan and Matt Swee, who have taken us from a tiny Facebook group to a Network of more than 25,000 pilots with a website, blog, podcast, quarterly journal, and now an annual conference. (
  • A deputy sheriff
  • A collegiate lacrosse coach
  • The president of a school board
  • An occasional Falcon 7 FO, but only for cushy international trips, and only when he feels like it
  • The primary US dealers for two different types of light sport aircraft
  • The owner of an aircraft insurance company with several hundred million dollars of assets under protection
  • A certified financial planner who works at a large investment firm
  • Musicians who regularly play gigs (for money and free beer)
  • Consultants for other interview prep companies
  • The owner of a company that sells commercial-grade generators and other heavy equipment
  • A graduated Air National Guard Wing Commander who flew military aircraft including the F-16 for 27 years. (He’s also a senior Delta captain right now)
  • Pilots doing countless other jobs in the Guard and Reserves
  • Pilots who work part-time as flight instructors for major defense contractors (in the US only)

Like I said, this list is far from complete. Elon Musk, Jeff Bezos, Richard Branson, and the late Paul Allen all have rocket ship companies. The possibilities are truly limitless.

If there’s something you’d love to do more of in life, becoming an airline pilot may be the way to go. It gives you the time, money, and capacity to pursue almost anything you want. You should do it, when you feel like it, for fun. However, if you’re not careful, you may find yourself making even more money from it. Rough life, huh?

If you’re wondering whether to become an airline pilot or not, I highly recommend it. You may not even have a side-hustle in mind, but it’s funny how things just appear when you find yourself with time to spare. Don’t discount the value of a side hustle while you’re doing the math associated with your decision. Whether it’s just beer money or another significant stream of income for your family, it never hurts. The Quality of Life value associated with spending more of your life doing what you want is almost incalculable.

If you don’t know where to start…check out Yep you guessed it. TPN is creating a Side Hustle that teaches you how to start a side hustle!

I’ll leave things here for now. I could probably write more, but I’m on my way to open a business checking account. Please don’t tell my boss, but I love teaching in the Icon so much that I’d be tempted to do it for free. In the meantime, I need a place to stash the money she keeps insisting on paying me anyway.

Okay, one more thing: Icon is hiring flight instructors. They’re delivering several aircraft a week and someone has to train all those owners. The A5 is a unique airplane, so insurance companies want special training for their clients. Kirk Hawkins, the CEO, is an Air Force pilot, so you shouldn’t be surprised that I instruct “TX” courses for his students. It’s a very well put together syllabus that’s very fun to teach.

If you’re interested, they need part-time help in Vacaville and Tampa. However, they also want a network of Icon Authorized Factory Instructors (IAFI) throughout the country. Ideally, a customer will be able to come to you for training, instead of flying all the way down to me. If you live near a major city with some water and people who love adventure, you might be perfect for a part-time IAFI job.

I’ve convinced a few people from Icon to come hang out at TPNx. They’ll be ready to tell stories about flying the A5, and you might even be able to get an idea of what your next side-hustle might look like.

BogiDope is a proud sponsor of The Pilot Network, and this post is republished from their site with permission. You can read the original post here. You can also get more great TPN content on the TPN Community Website, on their free TPN-Go app (iPhone or Android), in their quarterly TPNQ magazine, and on their Podcast.

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