Why You Should Quit Your Dream Job

I frequently hear on Financial Independence and Retire Early (FIRE) podcasts and read in FIRE blogs that the RE (Retire Early) part of the FIRE acronym should be dropped. They can’t imagine not working, they say, and besides, they enjoy working.

I know what they mean. I had my dream job, and I worked it even after I achieved full FIRE.  I had quit my career of 29 years in retail and hospitality management, and then I found the perfect job that I loved doing—educating military service members on personal finance. Despite my dream job having everything I wanted, I quit it just one year later. 

And, if you’ve reached FIRE, I think you should quit your dream job, too.

What? Quit you say? Then it couldn’t have been your actual dream job, right? Wrong.

This was my dream job! It had it all: an important mission educating military service members on personal finance, a kind and supportive boss, great co-workers, practically unlimited resources, lots of autonomy, great pay and benefits, no supervisor responsibilities, and the ability to telework as much or as little as I wanted.

Logo for the office of my dream job (I linked it to the FINRED website)

It was the perfect job for me! So why did I quit? 

In a nutshell, we have finite lives. As much as I valued this job, it wasn’t the number one thing I wanted to do AND it was physically and mentally keeping me from doing the things that I valued more.

My top five things I wanted to do were: travel, improve my health (walk and hike more in particular), spend more quality time with friends and family, follow my curiosity (to include learning a language), and read more books. It turned out that the sixth thing I wanted to do was help people improve their personal finances—my dream job.

What We Tell Ourselves About How It Is Going To Be

When I applied for the job, I made a bargain with myself that I would only work the required 40 hours a week. I committed to not work any extra hours or sit endlessly at a desk—a way of life that had plagued me throughout my working life.

I promised myself that I would use my free time to do those top five things I wanted to do. Since I had limited time off (4 weeks per year), I planned to jet-set off with my wife on the weekends to visit family and see new places.

To work on my health, I bought a new standing desk, new ergonomic chair, headset, and a variety of other office items to make my home office as comfortable as possible (I had a dedicated room upstairs with two nice windows). After work, I planned to walk every day and do my daily stretching and body-weight exercises. Also I would read more, study my Spanish, and spend more time with family and friends. It was going to be great! 

Since I didn’t need the money (I was fully FIRE), I committed to spending the extra $125K+ a year after taxes on travel and things that would make life easier, such as housekeeping, lawn care, and eating out, so I could maximize my time off.

So how did I do that year in my dream job, achieving the things that I wanted most in life? The reality was a lot different than what I planned.

Even My Dream Job Didn’t Fit Neatly into Working Hours 

I often worked extra hours despite my promise not to. At first, my justification to myself was that I needed to get up to speed on the new job. But after a couple of months, that justification morphed into a desire to accomplish a lot (and I did!). 

I’ve known for some that when I make a commitment to others, I place that higher than commitments I make to myself. This year of work after I reached FIRE reaffirmed that understanding. Work severely limited my ability to engage in my higher priorities. I didn’t need more money – I needed time. 

Traveling to Asia and having the time to visit the minor temple sights in Cambodia wouldn’t happen if I was working full time

Lots of Travel, But Little Decompression

I took many weekend trips that year. We often left on Friday nights and returned Sunday evenings (or Monday evening if it was a holiday). The fun weekend destinations included New Orleans (once with my wife and once for an NFL game with a friend), Phoenix (to see relatives), Miami (Formula One Grand Prix with a friend), Puerto Rico (for my birthday), rural Virginia (for CampFI Mid-Atlantic), Charleston (for our anniversary), and Thomas, West Virginia (for great bluegrass music).

I also took longer trips: 4 days in Minneapolis for a family reunion, 8 days in Newfoundland with my son, 10 days hiking Hadrian’s Wall in England, and about 10 days hosting our two adult kids over Christmas, though I worked several of those days.

While all of this travel may sound great, I found it to be tiring. There was no downtime between work and travel. On those weekends when I wasn’t traveling, I was researching and booking my airline, hotel, transportation, and excursions. Travel planning takes time.

Because I only had a couple days at each location, I found myself scurrying around when I got there, trying to maximize the visit (the way most Americans go on vacation). I was also traveling when everyone else did (weekends and holidays) and fighting crowds as a result.

My time off was limited by my work, and although I had a generous 4 weeks of paid time off each year, it wasn’t nearly enough. My higher priority to travel and follow my curiosity was being hampered by my dream job.

Did My Health Improve?

No. My sleep was hit or miss as it was often interrupted when I had an important upcoming meeting or project due—I couldn’t turn my mind off easily. Having a job that I cared a lot about was difficult to turn off when I closed my laptop.

Even with the new high-end standing desk, I sat for most of the day. I did get out for a walk most evenings before dinner, but I had difficulty fitting in my stretching and body-weight exercises as work started early. I was no longer biking with my friends on the weekends—it just didn’t fit.  

Hiked 10,000 foot peak in Vietnam. Not working enables lots of hiking, walking and biking in my days.

Did I Find More Quality Time With My Family and Friends?

No. While I did make some trips to visit family, they were limited by my time off (which was split between seeing new places and seeing family) and similar to my sightseeing, it was harried and less quality. I was seeing my family and friends about the same as I did before I reached FIRE—not enough. 

What About My Priorities of More Reading and Learning a Language?

Because I was so engrossed in the important work of my job, I was mentally exhausted at the end of most days. My best creativity and concentration were focused on better reaching military service members with quality personal financial information. After work I didn’t have the mental energy to read the books I wanted to, or focus on improving my Spanish—I found I needed to spend much of my free time mentally decompressing from work.

Relaxing and reading on my porch in Luang Prabang, Laos.

Since Quitting My Dream Job

After quitting my dream job, my wife and I fully embraced minimalism. We sold or gave away 98% of our belongings, turned our house into a long-term rental, and became full-time nomadic travelers with a backpack and a carry-on each. That change has been deeply valuable to us, and it took time–time I simply didn’t have when I was working my dream job. 

But here is where I really saw the effects of quitting. This comparison chart shows my time (counted in quality days) spent with friends, family and traveling during my year of working my dream job vs. my first year after quitting my dream job.

FriendsFamilyTravelTotal
Year During Dream Job13452381
Year After Dream Job43130178351
Quality Days Spent on Three of my Top Five Priorities.
Note: some days overlapped with family or friends on vacation, so I chose what the primary purpose was for each day listed to avoid double counting. It doesn’t add up to 365 because there were about 14 quiet days that didn’t neatly fall into any category, so I left them out of this tally.

By letting go of my sixth priority (my dream job) I have been able to fully achieve my top five.

  • I traveled more than in my previous 13 years combined.
  • I read more books than any year, to include college.
  • I spent more time on my health than I had in decades.
  • I spent 3.5 months practicing my Spanish to include in-person classes and daily app learning.
  • I spent 3x more quality time with family and many friends.

I have found contentment in my daily life and I couldn’t be happier. 

Is It Time to Quit Your Dream Job?

Even if you have  your dream job, that isn’t necessarily reason enough to keep working after achieving FIRE. I recommend that after some soul searching you ask yourself: “Is this job truly my top priority in my life and with my time?” If it isn’t, then ask yourself “Does this job hamper my higher priorities in any way?”  

If your answer is yes, and your dream job prevents you from fully doing any of your higher priorities, it is time to quit. 

Real Estate is Passive or I Make $2,800 Per Hour

What? $2,800 per hour? This must be a crazy MLM scheme or some sort of bait and switch scam, right? 

Not at all. On average I work one hour a month managing my two real estate properties. Each month I clear an average of $2,816 (including my principal and net of expenses and taxes). So my hourly rate is $2800! 

But “passive”? That is impossible, you might say. Yes, really. As I show below, the average percentage of my time (.006%) that I spend each year managing my two rental properties rounds to zero! It essentially takes me the same amount of time as investing in stocks.

For 19 years I have owned one or two rental houses at a time (I have two right now). I like to say I am a lazy landlord, but actually I’m an efficient landlord.

I bought and lived in all of my rental houses before I rented them out. I have calculated that buying is often a better investment than renting (comparable houses), but ONLY if you are willing to keep the house for 7-10+ years, much like long-term stock investing. Since keeping these houses instead of selling was the better long-term investment, I now rent them to other people instead of renting them to myself.

So How Much Time Does It Take To Manage a Rental Property?

Let’s put this in perspective: In the 13 years (156 months) of self-managing my current property in Ohio, I had 87 maintenance and repair expenses. In other words, on average I had a 20-minute issue to resolve every 1.8 months.

Of course, I can’t ignore the upfront and more time-consuming effort to get a lease, advertise, screen tenants, and then handover the property (~10 hours) and the infrequent work of replacing my tenants (6 hours) or renewing the lease (2 hours)–a great house rents quickly. There is also the rental-property related work on my taxes that takes about an hour each year, and maintenance inspections of the properties that take about two hours per property each year. (My trusted handyman actually inspects for me in OH, so now I only visit that property once every 2-3 years). 

On average over the last 13 years, I have spent about 35 minutes a month managing my OH property (not even a full hour!) and I clear over $1000 per month. That’s $12,000 a year for 7 hours of work – a pretty good wage. I make even more on my VA property ($1800 per month) and I average even less time per month managing it (25 minutes). I think you get the point–it doesn’t take that much time to manage a property if you have good systems in place.

Most months, nothing happens except the rent arrives by direct deposit. 

Setting Up Good Systems Saves Me A Lot of Time

  • Number one is finding good renters. I don’t skimp on tenant screening. I always call work and housing references, and I complete credit checks unless they are active duty military, and even then I still collect all the info needed for a credit check.

Great renters are looking for a quality home for their family. They tend to care about their belongings, their credit score, the appearance of the yard, and they will care more about my house. Many of my renters do simple maintenance and repairs themselves, or they are willing to pay for improvements they want. One renter (with the help of her handy dad) offered to install new composite decking if I paid for the materials. The house now has a huge, great-looking deck for 10% of the cost I would have had to pay a company to install it. 

  • Getting great renters requires a great house. I buy houses in desirable school districts and neighborhoods, which I know first hand because I first lived in them myself (my system works for a small number of rentals). I have bought in military communities, and I usually rent to senior-grade military families.
  • I make sure my lease agreement is comprehensive. Setting standards and expectations up front is key to avoiding problems later. My first lease was OK, but every renewal since I have strengthened it with lessons I have learned myself or learned from smart friends with more experience.
  • Set expectations with renters up front on maintenance and communication. I walk through with my new tenants how maintenance and repairs will work. For true emergencies (e.g., no heat in the winter or a water break), I empower them to call for repairs directly with the appropriate company if they can’t reach me quickly and it can’t wait. When they do reach me with a problem, I either have my handyman look at it (with a quick email or text), or I have the renter call a company of my choice (or theirs if I don’t have one lined up already).  I have the bill come directly to me. This saves everyone time as the repairman has to schedule with the renters anyway, and the renters are very happy to be in charge of scheduling.
  • A reliable handyman is recommended but not required. I have a great handyman for my OH property but I have yet to find one for my VA property. While addressing maintenance issues takes the same amount of my time, having a reliable handyman saved me money and improved my confidence in getting quality work. 
  • Take advantage of the quality and often free resources online to make renting a property easier. Online sites like Zillow (no endorsement intended) work great for advertising, tenant applications, and background checks. I invested about 3 hours, one time, to modify a premade lease for each state I rent in to make sure I comply with state landlord-tenant laws. I set up my property management tracking spreadsheet, where I keep a simple on-going record of income and expenses, in about 30 minutes. 

If I only focused on the initial one-time effort needed in the first few weeks of renting out my house, then it may feel like a lot. But over a 19-year time frame, each month it is hardly any time at all.

Skip The Property Manager – It Doesn’t Take That Much Time

Since I have two properties and live far from either of them, I must have a property manager, right? Nope! I learned the hard way that a property manager doesn’t really save you any time. 

If the water heater broke, the tenants contacted my property manager who would then call me about it. Then the manager called a repair person and scheduled the repair with the tenants. Then I was sent the paperwork each month that I needed to file away for taxes with the amount subtracted from my rent (or I was billed if the repair was major). 

Now that I’m my own property manager, the renters text me if the water heater breaks. I ask them to call a repair company and schedule the repair at their convenience and have the company bill me. It’s the same amount of effort on my part and more convenient for the renter to schedule their own repair, but without having a middleman or becoming the middleman between the renter and the repair company.

With a 5-minute call from the tenant (or usually a text with a picture), and a 5-minute call to the company to pay (usually an online payment), the work is done and the problem is solved. I then open up my property management spreadsheet and record the expense (another 5 minutes). So after 15 minutes of work, the problem is solved. 

On more complex issues like working with a neighbor to take down a shared tree, I had to write a good 10 texts back and forth to coordinate the work. It took me a whole hour total to get that job done – whew! 

As my good friend and real estate expert Keith Nugent shared with me at a CampFI, you need to be your own property manager until you understand every aspect of it and then only consider hiring one once you own five or more doors. My experience confirms this. Since I’m not planning to expand my properties past two, I’m never planning to hire a property manager. 

Don’t Confuse Stress With Work

It can be a stressfulI conversation to demand overdue rent or pursue eviction action, but these actions do not take up much actual time. The one time in 19 years I needed to pursue eviction it was definitely stressful, but it did not take much time to resolve. I called a lawyer (it took maybe an hour) who sent the eviction proceedings letter to the tenant. The tenant then left. 

The reason I hear that people feel renting properties is too much work often goes something like this:  “I don’t want to deal with calls at 3:00 am for an overflowing toilet.” I feel that is a worn out trope. For one, an overflowing toilet is almost always the renters’ fault for clogging it, so they would pay the bill for any repair or damage and clean up. My excellent renters have never called me for such things. 

My tenants did call once at 11:00 pm about the heat not working in the winter, and I empowered them to call a repairman directly and that I would cover any extra fee for an emergency response (I don’t skimp on safety). Then I went to bed and slept well. Being called after 10:00 pm has happened maybe 4 times in 19 years and it took me 5 minutes to resolve each one.

I try not to confuse stress with time. Over the years, tenant issues are infrequent and rarely take much time. Even getting quotes for a new roof or windows only took a couple hours. I am responsive and get the problem fixed. 

Is Stock Investing Truly Passive, but Real Estate is Not?

I often hear in FIRE podcasts and read in blogs that stock investing is truly passive – the old “set it and forget it.” While I am a “passive” index fund investor, I have found I actually need to spend some time managing my investments. 

I rebalance every quarter so my funds stay within the percentages of my investment strategy. I spent time calculating my traditional IRA to Roth IRA conversions (I have some after-tax basis). It takes many hours to rollover my wife’s and my 403b, 457b, 401k, 401a accounts to our IRAs. I keep an eye on the stock market and buy when it drops 10% or more (push more bonds into stocks) and then I rebalance when the market recovers. I spend about an hour each year on my taxes related to my stock investments.

I spend nearly as much time on my stock investments as I do my real estate management and both pay me a handsome wage per hour! So technically neither is 100% passive, and neither has to be a lot of effort.

Basic real estate investing in a few houses can be fundamentally as passive as stock investing. If I ever did get too many rentals where I noticed and cared about the higher workload, then I’d switch to a good property manager and drop my level of effort back down. 

Real estate investing, as with stock investing, benefits from up-front research. Setting up a good system will minimize your long-term efforts, diversify your portfolio, and save you money over renting if you decide that the renter of your house is you. 

So is Real Estate Passive Income? In My Book – YES!

So, with all of this talk about how much time it takes to manage rental properties, it can’t be considered passive, right? Let’s run some numbers…

There are 2080 hours in a work year (40 hours per week x 52). I work an average of 12 hours per year on my rental properties, which is .006% of traditional work time. Even if I doubled it with 2 additional properties or quadrupled the time spent, it would still round to zero! 

So, either real estate is passive income or I earn over $2800 an hour! Either way, it is worth the effort. 

P.S. For further information on how being a landlord does not have to consume a lot of time, and how to set up good systems to become a “Lazy Landlord,” check out James Lowery’s presentation at the 2023 ECONOME conference.

The Pursuit of Contentment

“I want to be happy” was how I replied when asked as a youth what I wanted to be in life. Likely inspired by our country’s Declaration of Independence, I bought into the enticing desire of achieving full happiness. It doesn’t work that way.

In the pursuit of a life of bliss, I read several books and listened to numerous podcasts on happiness. I was struck by the happiness science finding that 50% of a person’s happiness is based on genes, 10% individual circumstance (environment mostly out of your control), which leaves just 40% under your control. More than half of a person’s happiness (or lack thereof) is out of one’s control. 

This finding is eye-opening on why happiness is so elusive for so many people. If I was born with a 5% genetic predilection to happiness, and I somehow maxed out my environmental circumstances AND all happiness related measures under my personal control, I could achieve a maximum of a 55% state of happiness. 

That is a failing grade, and I doubt I could consistently maintain a 100% achievement of the areas in my personal control, especially when my genetic disposition was fighting against me. 

I’m More of a Piglet Than a Pooh Bear.  

I have found that my normal state is not one of default happiness. Do I think I am an Eeyore with a 5% genetic happiness disposition? No. But I also don’t think I’m a Pooh Bear with a 45%+ genetic good humor and gentle kindness. 

Unlike Pooh, happiness doesn’t come naturally to me. I am more like a Piglet. I naturally worry. I look for security and close friendships.  Sure, I’ll be brave at times with my friends, but my default is not the blissful happiness of Pooh. 

Happiness carries too much weight. 

Happy moment sitting on a dune in the Sahara

I have learned that I don’t need to achieve the joy of happiness in all the day-to-day things I do or own. My wardrobe, meal, or wherever I’m staying the night isn’t responsible for my happiness, it just needs to fulfill its job. A car doesn’t need to spark joy, just get me where I need to go safely.

Happiness has a short lifespan and it is fundamentally based on comparison (with others and with personal expectations). 

I think about the sheer joy my 14 year-old daughter expressed on her first business class flight experience. Through a series of crazy events, she unexpectedly was upgraded to business class flying home from Barcelona. She didn’t know until she was on the plane. She reveled over each item in the bag of sundries provided and in her ability to order all the pineapple juice she wanted. She was so grateful for the experience. 

But conversely, I have seen people who travel business class frequently who complain about some aspect of the service and take the experience for granted. They have lost that first-time joy because business class has become routine.

The latter is an example of hedonic adaptation where humans will reset expectations as new experiences become expected. As we quickly adapt to life’s changes (e.g., new exciting car quickly becomes our regular car), we are continually chasing the next level item (oooh, look at that better and more expensive car!!!).

As a corollary, getting rid of unhappiness does not necessarily bring happiness. Happiness researchers share that negative emotions such as sadness and fear are necessary for survival, and that suffering is part of the human condition. Achieving 100% happiness would require humans to ignore these other important emotions and states of being. It is just not humanly possible to be fully happy all of the time, and yet we humans continue our endless pursuit of this holy grail.

The more I pursued happiness, the more elusive it became — always just around the corner, but never with me for long.

Instead, I pursue contentment.

Pursuing contentment addresses the hedonic adaptation treadmill problem that the pursuit of happiness tends to create. I have determined what is enough in my life–enough money, enough stuff, enough commitments.

Minimalism was a big help in this. In embracing minimalism, I lessened the emotions and value I placed on items I owned. The things I own, such as a car, watch, clothes, boat, home, etc., are no longer symbols of myself, any of my achievements, or my love of other people. I don’t need to dress nice for other people. I don’t need new things to impress others.

I also fluctuate my life’s experiences to help me maintain an appreciation for the lucky life that I live. In the past year, I have slept on an inflatable camping mattress, two bunk beds, a rock-hard bed that made my hips ache, and several gigantic and comfortable king beds, and many beds in between (62 in all).

The variation keeps my perspective in check. If the bed does its job, then I am content with that. I don’t need an incredible bed every night to appreciate my daily life. The same applies to my food, clothes, transportation, and excursions.  

Instead of asking myself “Am I happy?” I ask myself “Do I have what I need?”  The bar for responses to the latter question is much lower, and I achieve contentment at a far higher rate than happiness. Attaining 100% contentment feels achievable in a way attaining 100% happiness never has.

Of course, I still feel many moments of happiness as I sit on a dune in the Sahara desert in Morocco or hike along a Roman road to the Bachkovo Monastery in Bulgaria, but these highs are no longer my measure for daily success.  I instead measure my daily success by my level of contentment – having enough to meet my needs and pausing to notice that. 

Yesterday, I had a nice take-out meal from Seven Eleven in Japan and I enjoyed it in a park with my wife. Nothing fancy. We had lots of ants join us. There were lots of weeds around. My seat on the concrete step was hard. The sky was beautiful. The mountains in the distance were nice. The buildings around us were interesting. 

Was I happy? Maybe. Was I  content? Fully.

Content moment having a picnic in a park