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I Quit My Dream Job After Burning Out and I’ve Never Been Better. This is How I Started Over.

Updated: Apr 5, 2022

Above: Belle has shown me how to survive and adapt in her own English culture, including driving on British roads in the countryside. Before the moment I handed in my resignation letter to the Chief Pilot, I was extremely nervous, my stomach tied in knots. I should have been elated, I thought. My new job began in two weeks and my terrible airline pilot lifestyle was already melting away (you can read about that experience in my article, Why I Left an Airline Pilot Career Worth $8.2 Million). The decision before leaving my flight career was agonizing because I was leaving my childhood “dream job.” At first, it felt like I was throwing myself out of the plane without a parachute. My ex-fiancee had already moved out. My house, worth less than I bought it for, was impossible to sell in the housing crisis market even if I tried. My new job required a significant pay cut from my airline captain pay, and I knew I’d struggle to pay my tuition debt, which was already mounting. I was working seven days a week between my internship and the airlines, plus taking night school and coursework on my few evenings at home. Despite all of this, I knew I was making the right long-term decision. When I told other pilots my plans, many said they wished they had their own way out of the airlines, but didn’t know what to do instead of flying. Others had no room to maneuver because they had huge student loans, big houses, expensive cars, and other major obligations. The Chief Pilot asked me how I found a non-flying job and was surprised to hear I was leaving while no airline was hiring. After the resignation letter left my hands, the immediate relief I felt after no longer being trapped was like dragging myself out from under a collapsed building. Once I pulled free, it was a surprisingly relaxed last two weeks at the airlines. Despite the usual chaos caused by the air carrier’s mismanagement, I was taking it all in stride, knowing I had an escape plan. It made me wonder, why can’t I always have this mindset?

Always Leave Yourself an Escape Plan

What kept me calm was the thought that if I ever wanted to go back into flying, I had enough flight time to open the doors to most flying jobs. This was a key to making big changes in my life, because it worked for all directions of my career: forward, backward, and lateral. The mindset happens naturally if you follow Golden Rule #3: Always Leave Yourself an Escape Plan. It’s a plan that I learned from the airlines, ironically. When flying, you’re legally required to have a backup plan for just about everything. It was also a piece of wisdom passed down from pilot to pilot after waves of airline bankruptcies, career-ending medical issues, AIDS (aviation-induced divorce syndrome), home base closures, and other major life disruptions. One goofy mistake as an air crew and your career is potentially over. A flight crew at my former airline once made the news when they landed a charter flight for the Notre Dame basketball team at Elkhart, Indiana. The problem was that they were supposed to land a few miles away at the South Bend airport, the intended destination. It happened before I even worked there, but pilots still talked about it, especially if you were exhausted from a long day, flying to the same airport with a closed control tower long after midnight. One of the first things you’re taught when flying a plane is how to deal with an emergency. When I was a flight instructor, I saw students deal with it first hand – one of my students attempted a practice emergency landing in a field full of cows while a perfectly good unused airport sat within gliding distance. By not leaving yourself an escape plan, you are setting yourself up to crash-land into the field full of cows. My escape plan was not the airline I was fleeing. Like a refugee, the last place I wanted to go was back home. If I tried to move to another regional airline, seniority dictated my pay and forced me to start over, earning a quarter of my old paycheck. Besides, I knew the quality of life was worse off there. I had an overspecialized undergraduate degree in Aeronautical Science which had too few job prospects to be relied on as any kind of escape plan. In fact, the degree itself needed an escape plan. Flying is a trade which did not transfer to office jobs on a resume.

Four years and over $100,000 in undergraduate tuition and I wasn’t able to get an entry-level office job. I made the tragic mistake of buying an expensive degree for a trade job.

An escape plan is planning for the worst-case scenario. It can be a massive stash of savings, valuable knowledge, a backup job, a side business, dual income with a single income lifestyle, or even dual citizenship (a second passport). To understand the position we’re in when it comes to jobs, I think it helps to start our thought exercise with an absolutely clean slate. What is an escape plan for? Survival.

Survival is as Important As Ever in the Modern World

Survival is a fundamental human condition. Although modern lifestyles have diminished its importance in our minds and allowed us to feel comfortable, it’s as important as ever because most of us are dependent on others for our survival in our money-based economy. People with zero savings or debt don’t realize that by spending everything they earn in their electronic bank account, they are one recession away from a real-life survival scenario as their financial house of cards collapses. This is easy to forget because you can’t physically see people in debt. Instead, you see what appears to be wealth – people with fancy houses and driving expensive cars. In reality, if they transferred their financial lives to a true survival situation, they are walking out in the desert with no sunscreen and one bottle of water, thinking they will be perfectly fine because they have footsteps in the sand to follow to the next oasis. That might work out fine, right up until the next sandstorm hits. We learn to survive naturally in our native environment. Survival situations happen almost entirely in foreign environments, which become inhospitable and unforgiving in comparison. As a pilot, people often tell me this recurring fear of being forced to fly and land a plane to survive, which is a comfortable native environment for me after 10 years of adaptation to it. Likewise, if I was parachuted into the Amazon Rainforest, I’d be incredibly stressed because of my lack of familiarity, even though natives live there comfortably. Let’s reverse the scenario to apply this to our modern life. Assume you were raised by wild animals on the outside and had to re-introduce yourself to society. You know how to survive in the wild, but surviving in the modern job market is now inhospitable and unforgiving because instead of hunting for food, you must earn money to pay for it. What are the most important tools you can use to survive?

The Most Important Survival Tools

It’s difficult to cram all of humanity’s struggles into a simple answer here, but I’m going to give it my best effort. Judging from actual survival situations we’ve all seen, I believe the most important tools are Art, Science, and Discipline.

1. Art

To even comprehend the world you are in, you need to learn the language. Like an immigrant to a new country, the only way to learn a language as quickly as possible is complete immersion in a native environment. The reason I’ve ranked Art higher than Science is because you have to learn the language before anything else. Then you can build upon this to explore thoughts, concepts, reason, and more.

2. Science

To work entirely using a scientific method, requires application of an existing practical knowledge to discover or build a process. What do you do if you are stranded in the actual wilderness? First, you protect and provide for yourself. Investing enough money to retire, acquiring marketable knowledge, or building your own business; these are all methods of making sure that you never get caught unprepared.

3. Discipline

Without this, nothing gets done, and you fall back into your wild animal habits. The best way I’ve found to build discipline is to endure a system that imposes it and not give up. Survival itself is the first and the most effective system ever designed to build discipline. Nearly all of us hit survival milestones in our life when learning to swim or drive a car, and the reality of being in control of our fate forces us to adapt to the new environment. To build discipline, we should find the most challenging environment we can still enjoy and adapt to it, even if that means venturing well outside of our comfort zone. For the past few months, I’ve been adapting to living outside of my comfort zone in the USA after moving to England to be with Belle. Not only is it a drastically different driving environment, but it’s a different system of government, tax, banking, legal, work, and food supply, with language differences, and so on. Belle has shown me how to survive and adapt in her own English culture, including driving, as pictured above. Learning to live in another country feels like survival at first, but it’s amazing how complete immersion forces you to adapt to survive and grow while you learn to be capable and resourceful in new ways. In a similar way, new careers and jobs can feel foreign to us at first, but the same principle applies. How does Art, Science, and Discipline apply to our search for our dream job? Each plays a unique role.

Art – Understand and Interpret Your World

It’s one thing to change from one job to another in the same field or industry. As I discovered, it’s entirely another to change an entire industry, as I did from aviation to finance. The only way you will survive such drastic culture shock is through complete language immersion. To change jobs in the same industry is like learning a language with similar roots and alphabet, like an English speaker learning French, while a new industry requires understanding an entirely different system, like an English speaker learning Japanese. If that sounds like a tall order while you’re already working a full-time job in another language with completely different jargon, it is. You’ll have to be so passionate about your dream job that you’re able to immerse yourself in its language during your free time and still be able to enjoy it. I coded a trading bot in my free time and the language immersion turned out to be invaluable later in my new career. In a typical week I’d read books stuffed in my flight kit about financial disasters during downtime in crew rooms between flights in Chicago. Then I’d work on my graduate finance coursework in the pilot crashpad and go to class on my days off. The biggest hurdle to overcome with employers in professional services is that they want to prove to their clients that you speak their language, not just in person, but on paper. Because of this, when I was changing industries, I had no choice but to finish my graduate degree before I ever worked a job in the financial world. This may not be necessary if you want to be an entrepreneur, but if you want a job in professional services, you must check that box. Employers know that the most valuable candidate is one already fluent in their language with a stellar, proven track record. To change jobs or careers, you have to start working on this today, but if it’s truly a passion, this shouldn’t be a chore. If it’s the right path, you’ll already be so obsessed about it that you enjoy learning about it on your free time.

While moving up from First Officer to Captain at the airlines, I was completely immersed in the financial industry’s language (accounting, economics, and statistics).

How to Build a Track Record

If you haven’t found it yet, keep searching and you will. I found that I enjoyed both coding and trading in my teens, but didn’t think to combine the two until my 20’s when I coded the trading bot. It wasn’t until my 30’s that I first used those skills for an employer, but they had already been practiced over prior years of fascination with the markets and technology. For example, even now I’ve coded and run this website in my free time because I enjoy it. I didn’t realize the importance of a track record in the beginning. Instead, I started firing off resumes for corporate jobs in aviation, thinking that the few classes under my belt were enough to spark an employer’s interest. At the time, the national unemployment rate was over 10%, and in that environment you can almost guarantee that the gatekeepers will screen your resume before it even reaches a decision maker. To reach decision makers, at a minimum you have to meet the requirements on paper. The first issue with my track record was that my resume was entirely written to prove my record as airline pilot. I changed my resume to abilities far more valuable in the business world, such as managing a team and learning complex systems. The second issue with my track record was the lack of business experience, but nobody was hiring, least of all part-time internships for a job-changer like me. I asked a friend of the family if he was willing to bring on an intern to help him with his solo commercial real estate brokerage business, and he was, so I added the internship to my resume. The internship immersed me in the language with practical business experience and provided me with an highly accomplished mentor who already spoke the language. I can’t emphasize enough how instrumental he was in the mindset reorientation I was undergoing. Once I added it to my newly business-oriented resume, I finally hit the trifecta of relevant education, skills, and experience. Within a week, I had interviews with three separate companies: a government contractor, a commercial real estate firm, and a retail investment firm. Now I had the opportunity to speak the language of finance by discussing how I’d analyze potential commercial real estate acquisitions with my interviewers. The last thing I wanted to do now that I had interviews was bomb them. It was six years since my last job interview, which meant I needed some long overdue practice. Since I was already paying for classes, I thought, why not use what was already included in my expensive educational bills? The career counselor at my graduate school not only gave me sample questions for the background and behavioral questions, she gave me a straight-faced practice interview with feedback, which gave me a major advantage over many job candidates who were out of practice. Then, when given the “Tell me about a time you disagreed with your boss?” question, I was more at ease with my answer. If you don’t have access to a career resource, or if it’s been a while since you’ve interviewed, get a friend who can keep a straight face to give you a fake interview. A practice run takes away a huge amount of anxiety.

Science – Practical Knowledge for Survival

Once the behavioral (Art) interview is completed, you’re left with what the business world calls the technical (Science) portion of the interview, but it’s no different from the Science we already have been discussing. It’s a body of knowledge that can’t be avoided if you want to succeed. Using the job posting I had applied for, I found demo versions and documentation for the software my potential employers used, so I could relate my experience to their systems. Then I did some reading to brush up on the specific subject area. After three interviews, I had my choice of employers. The choices were: 1. Start completely over in finance with an entry-level job. 2. Take a government contractor job in aviation which was more of a lateral transition from being an airline pilot. 3. Wait for a hiring freeze to thaw for a mid-level commercial real estate job. I chose the lateral move with a government contractor because my flight track record was most valuable in that career and the employer was responsive and straightforward. When I say my track record was more valuable, I mean that in my decision was one super-important detail – once you’ve chosen a career start-over pay, you can’t go back and change it. Every employer will look at your current pay to evaluate your value in the market. Although I initially took a pay cut from my Airline Captain job, I took every opportunity and quickly moved up to managing a team of six within a year before completing my graduate degree in finance. Leaving my government contracting job after two years was a harder decision than leaving the airlines, because I enjoyed the culture there and learned from some talented people who were willing to mentor. Although I’m still very grateful for the experience and my role was huge for my personal development, it barely scratched the surface of finance and I was restless to use my new degree.

One year after leaving the cockpit, I find myself standing in front of the government and military at conferences, presenting the industry equivalent of “Google Maps” for pilots.

Avoid the Army of Competition

My next move had to be strategic. I now had technology experience with a finance degree, and I knew fintech was the best job to market my new skills, so I started with the big categories (venture capital, hedge funds, etc.) until I settled on asset management. You can learn a lot online about a day in the life of your dream job from insiders to narrow it down. My primary concern after my awful airline experience was quality of life. As I’ve found, quality of life is driven primarily from the industry, then company culture. You may have the best coal mining job in the world, but it’s still coal mining. To find employers that valued my fintech skills, I searched for employers that were searching for candidates with financial knowledge and coding abilities. Then, I narrowed it to private, employee-owned firms (see why in "Go to Rags to Riches in One Grand Move"). Notice the strategy here? If I applied for purely finance, or purely coding positions at the entry-level, I’d be facing an army of competition from college graduates who are plentiful and low cost. By choosing a more experienced position that combined my track record in technology and two skills in my own subject matter expertise, my competition was much weaker or nonexistent. Another method I used to avoid the army of competition was to focus on smaller or private businesses. I often hear people complain about the lack of jobs out there. If they only knew how difficult it was for small businesses or private businesses to get resumes from candidates at all, especially qualified candidates. The temptation for most people is to take the easy route and apply for the brand name jobs. However, if a brand name job is easy for you to find, it’s also easy for everyone else. You can’t see the crowds online, but they are there, massing around the most popular brand names in huge numbers. To find the job with less competition, you will have to search where no one else is searching. Often, with some research, these are more stable or well-paying than the brand name jobs. You can almost always find them entirely through investigative work online, in other people’s work histories, local business publications, and anonymous reviews. Have you ever had a dream job? Looking back at my careers, it very apparent my dream job has evolved as I have evolved until I reached a specialization I was happy with. Personally, I like diversity, and I’m currently at my most diverse by applying finance, coding, technology, writing, and law on a daily basis. You’ll evolve, too. I had no idea my dream job as a kid, flying airplanes, would evolve into the investing world. I didn’t even know anything about the markets until my father gave me a small gift of stock and a brokerage account in my first year of college. At first it was survival and learning to drive a car all over again until I set myself on a path to learn how to “drive” investing, which had its share of early mistakes. To give yourself room for this evolution, ask employers in your interview if they permit you to move within the organization – mobility is key to finding the job that makes you happiest once you’ve settled on a company. Then, once you begin work with the employer, take time to learn from others and you’ll gather valuable insider knowledge that guides you the rest of the way.

Interview Prep

After being selected for an interview, I found as much information I could about my potential employer. I read their white papers, interviews with the founders, software listed in the posting I wasn’t already familiar with, researched anything I didn’t understand, scoured the internet for any inside information, and brushed up on my financial knowledge. By the time I made the interview, I was much more relaxed than before, knowing my current employer valued my work and I wasn’t trapped in the airlines. The interview was technical, challenging, and my interviewers were bright and motivated. Because I didn’t have a financial job background, I brought a business valuation I had done pro bono, which showed my capabilities in addition to the IT track record I had built working for the government contractor. I related the stories of my trading bot and had good discussions about scaling our airport mapping production system. I had already worked extremely hard to reach this point, so now I had plenty of stories and relatable discussions. As long as you’re well prepared, job interviews are nothing to worry about.


Now that you’ve been offered the job, you will be very closely watched in your first 30 days, 90 days, 6 months, and one year. My secret to surviving the ramp-up period of proving yourself is to be disciplined about learning the Art and Science. For getting the most out of the language immersion training on the Art side, keep an ear on everything around you and if you don’t understand something, add it to a list of questions to ask later. When your boss asks you if you have any questions, you’ll show that you’re interested in how the firm does business. This is your survival scenario of being parachuted into the Amazon Rainforest. Find reliable sources of knowledge and write things down. Start mapping out the business to find out where to go and who to talk to. Prove yourself by acing your work until they start handing you more difficult problems. Use the difficult problems as an opportunity to learn. You’ll make mistakes, but own up to them. In your research you want to find a work culture that values openness and transparency, and they will value your integrity. To get a handle on the Science, it will take some dedication in writing things down. Even the most abbreviated of notes is enough to recall an entire conversation. The problems are that most of us can’t remember everything the first time we hear it, and not all of the information you receive is good information or good advice, so it takes some fact-checking along the way to stay on track. As the proverb goes – trust, but verify.


In the early stages you can’t prove much other than you can remember what you’ve been trained and are resourceful enough to find your own answers when possible. Eventually, you’ll start digging into why things are the way they are. Resourcefulness will earn you useful knowledge that benefits everyone and builds bridges to other departments. For example, most people hate reading software documentation. Because of this, I’ve always found it a huge advantage to be one of the few people who even bother to speed read it. When word gets around that you know the answers, because people hate documentation or dealing with technical issues on their own, they will come to you for answers just to avoid reading it, and your research into their question will make you even more of an expert. Over time, this creates a “knowledge snowball” effect that eventually makes you even more valuable to your firm when the more difficult questions arise. Once you begin sharing the useful knowledge within your team, you’ve often given the opportunity to train someone informally, which is practice for a management position. Sometimes I’ve seen people resist being put in the position of training someone else, but it’s often not understood that although training in the short-term seems like stepping away from your own work without receiving any recognition, in the long-term it can actually earn your way up to an actual management position. After spending enough time in a role, you start gaining the ability to see how the the firm functions operationally as though it’s a machine, and you know how more of the pieces fit together. This is the level that senior leaders and executives operate, as each role requires mastery of the underlying elements to make increasingly weighty and difficult decisions as Art, Science and Discipline become more tightly integrated together. With the experience I've gained, I'm now a Financial Manager and work remotely from our home in England, which is the highest quality of life I've ever experienced in a job.

My quality of life has gone from skipping lunch while barely getting flights out on time, to having my lunch breaks with my favorite person in the world.

In short form, this is what I’ve learned after changing careers successfully multiple times:

  1. Golden Rule #3: Always Leave Yourself an Escape Plan

  2. An escape plan is crucial for survival.

  3. The most important survival tools are: Art, Science, and Discipline.

  4. Art allows you to understand and interpret your world.

  5. Science is practical knowledge for survival.

  6. Discipline is built by enduring a system that imposes it through survival.

  7. A person fluent in a useful language with a proven track record will survive the job market because they are valuable.

  8. Avoid the army of competition for your dream job by searching where no one else is searching.

  9. Prepare so much for the interview that you stop worrying about it.

  10. Be as disciplined about your first year on the job as any survival situation.

  11. Use resourcefulness to map your new environment, gain useful knowledge, and take your career to the next level.

Once you've settled in to a job you enjoy, it's critically important to start building ownership as fast as possible. Even if your employer doesn't offer stock options or equity, you can save and invest on your own. See how to do this in my "The 7 Golden Milestones to Financial Freedom" article.

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-Golden Goose Guy


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