What Kind of a Childhood Leads to a Life as a Financial Blogger?
I grew up in Alaska as the third of six kids of an electrical engineer and a homemaker. I left the state only three times in 18 years before leaving for college. My parents got the big things right financially, mostly living within their income aside from my father's vice of flying small bush planes. And when I say small, I'm talking about 2 seat planes that will convince you that runways need not be paved, level, flat, long, or straight. But there wasn't a lot of extra money. We drove used cars, we never stayed in hotels on vacation, and we drank powdered milk because the price of real milk in Alaska was so outrageous. One of our favorite snacks was uncooked spaghetti. You get the idea. But we never starved, we were never homeless, and we attended the “rich” public high school on the hillside, even if we lived at the base of the hill.

The plane was required to pay for itself via side hustles like fish spotting and flying hunters around.
My parents weren't really much into saving or investing, but my father eventually retired with a pension and some health care from his job with the state. They had no financial advisor while I lived at home. The only time I can ever remember anything about investing was one time when someone talked my dad into buying some options, and he talked me into going along with him using $500 of my Alaska Permanent Fund dividend money.

I got to play ice hockey, but it was mostly outdoors on the “house” teams as we couldn't afford the traveling “comp” teams.
Needless to say, we both lost our entire “investment.” While there was always the expectation (both in my parents and myself) that I would go to college, it was very clear to me from watching my older sisters head off to school that there would not be any money provided by my parents for my schooling, so I didn't even ask. For some reason, that didn't bother me a bit. I figured that was the way it was supposed to be since most of my friends were in the same boat. We all knew college was going to involve some jobs and some loans.
The College Years
I applied to and was accepted to seven colleges. I had not visited any of their campuses. Most were “semi-competitive” (Rice, University of Chicago, Colorado College, Brigham Young) but in the end only one offered me a scholarship, and so I boxed up my mountain bike and off I went to the land of my birth- Utah. (I know I said I was raised in Alaska, but I was born in Utah, on my first vacation, before my mom decided Alaskan physicians could be trusted after all.) Tuition was covered, as long as I maintained a 3.5, and I barely managed to do that as a freshman. Living expenses that year were covered with my first and only student loan. The terms were exceptionally good. It was an 8% loan from the State of Alaska, but it was subsidized and payments were deferred while I was in college, medical school, residency, and military service. I paid it back 17 years later in one lump sum and with inflation, I figure I paid off a $5K loan for about $3,100 in 1993 dollars. My parents were kind enough to fly me home for the summer and I took up a job at a climbing gym.
I subsequently spent two years “without purse or scrip” in Arizona. While rent and utilities were covered, I lived on about $160 a month, traveled mostly by bicycle, purchased almost no material goods, and learned that I wanted to spend my life in the service of others. The “missionary zeal” behind The White Coat Investor is hardly new to me. Upon returning home, I fell in with a landscaping crew. The work was hard, I made a little money, and a month later I was off to college again. My parents actually did help me out quite a bit my sophomore year. Not only did they fly me to school (and home for Christmas and the next summer), but they covered my rent. I had five roommates and paid $188/month. Aside from that, I lived on the $1000+ I earned from a month of mowing lawns for the next 8 months. Missionary work had taught me to study, and mowing lawns had given me the motivation to do so. Keeping that 3.5 was no longer a challenge, and I had a 4.0 the next couple of years while traveling most weekends playing college hockey. The next summer, I spent a month at the University of Oklahoma, mostly checking the research box required to get into medical school. I spent the rest of the summer mowing lawns again. I remember I wore the bottom off of a pair of boots and came to the firm realization that it was a whole lot easier earning money sitting on my butt than walking 10 miles a day.
I was now into my junior year, and well into the undergraduate “must get into medical school” stress well-known to most readers of this blog. As I finished up medical school pre-reqs and moved into the upper level classes for my molecular biology major and chemistry minor, I also began serious preparation for the MCAT and even more serious pursuit of a fair damsel who was playing her cards close to her chest. She didn't seem to care all that much as I took the MCAT, took my finals, and headed home to the Tierra de la Nieve Eterna.

At 18, I was far more interested in climbing than medicine, much less finances.
I was clearly getting smarter, as this year I had lined up a job in tourism instead of going back to mowing lawns. I spent the summer giving a tour and being the host in a dining car on a train that ran from Anchorage to Fairbanks. The days were 15 hours long, and 7 hours of each day was overtime. One day we went to Fairbanks, and the next back to Anchorage. Then we had a day off before doing it again. After that, we had three days off. If you were really hungry, you could use two of those days to do another round-trip, all of which would be overtime. Add in the tips (and I really hustled for tips), and I finished the summer with $13K in the bank, over three times as much as I could have made mowing lawns. I never felt so rich in my life. Halfway through the summer, Katie showed up at our dinner table unannounced. My roommates had arranged with my parents for her to come stay with us for a few weeks as a birthday present for me. She got a temp job in the post office and got to know my family. Needless to say, she was a bit scarred by that experience and certainly not ready to jump into any long-term commitment. Who could blame her? Even though she was already a junior in college, she was still technically a teenager.
I “bought” my parents' Geo Prizm off them for a $3K note. “Pay us back when you start making money,” the note said, and with a friend, I spent 48 hours over 3 1/2 days driving to school that Fall. Senior level classes, ice hockey, and lots of long walks and talks until the medical school interviews started rolling in. U of Maryland, U of Vermont, AZCOM, PCOM, and finally the University of Utah, no small feat considering I was applying for one of the 15 out-of-state slots. When that acceptance showed up, I cancelled the rest of my interviews except The University of Washington, through the WAMI program, where I would be treated as an in-stater. By halfway through that interview, I was secretly mocking the rest of the applicants for their nervousness, since I had already made my decision, and it didn't involve living in Anchorage, Seattle, Anchorage, and then Seattle again while Katie was finishing school in Utah.

I still can't believe she said “Yes.”
We were engaged at center ice between the 2nd and 3rd period during a game in January. I figured that was my best chance to get her to say yes. The date was set for mid-summer. Then I realized there was no way I was going to be able to pay for medical school like I had paid for my undergraduate education. And I was very sick of being poor. Carrying a full academic load, playing college hockey, donating plasma and holding down a part-time job was getting old.
Katie's father was an accountant in the Air Force, and she had one brother at the Air Force Academy and another in ROTC. For the first time in my life, I considered military service. It sounded like an adventure, her family was obviously very supportive, I love my country as much as the next guy, and we could sure use the money. At the time, the military covered tuition, fees, and paid $922 per month as a living stipend. I had no idea how we were going to be able to spend 2-3 times as much as I had been living on up until that point. We felt so rich we (stupidly) bought a house, thanks to her parents co-signing. Two weeks later, Salt Lake City's first tornado tore through the neighborhood. Our little condo was spared, but we hadn't even moved in yet!
Medical School
Katie was commuting to school on a bus to finish her last semester in the undergraduate Athletic Training program, and I was playing foosball. I mean studying medicine. Well, there was a lot less foosball and a lot more studying after that first gross anatomy test. I was clearly no longer one of the top students in the class like I had been my entire life. There was still plenty of foosball and rock climbing, but a lot of studying too. I passed anatomy, Katie graduated, and she scored an incredibly low paying job as a ski instructor. It did come with benefits though- a free ski pass for her and a $10 season pass for me. Newlywed without kids, rock climbing a couple of afternoons a week in the Fall and Spring and skiing a couple of afternoons in the Winter, plenty of foosball, some great road trips done on the cheap, and finally learning something I was going to use the rest of my life — we willl forever look back on the four years of medical school as some of the best years of our lives.
It's true that I brought all the debt into the marriage and Katie brought all the assets. Not only did she have a $20K “college fund” provided to her by her grandparents (most of which she didn't need for school thanks to scholarships, choosing an inexpensive school, and her constant part-time jobs) but her parents chipped in $300 a month into our budget for most of that first year as she finished up school. That money was the origin of my idea of a “20s fund” for our kids. There is no time in your adult life when a little extra money is so useful like in your 20s, and we're incredibly grateful for the money received and are doing our best to pay it forward.
Katie was a bit restless. That summer she took a job as a physical therapy aide, incredibly low-paying for a four year degree, and realized she didn't want to do that the rest of her life. She applied to PA school a couple of times, but without the luxury I had to apply all over the country (since we weren't willing to split up) and little clinical experience, the odds were stacked against her. Through some friends, she decided to pursue a degree in Adaptive Physical Education instead. She had a grant that covered tuition and even a side job eventually. (It turned out that $922 really didn't cover our expenses especially given our $640 mortgage payment.) We ended up graduating at the same time, her with a master's and me with a doctorate. But not before we started getting screwed by financial professionals.
In retrospect, our first big financial mistake together was buying a house. I mean, who buys a house with a mortgage equal to 2/3 their income in a place they know they're leaving in 4 years? Financial idiots, that's who. While we technically sold it for more than we paid for it, we lost thousands on that deal. What the realtor should have told us was that we had no business buying a house. We refinanced it twice in those four years, both times at a minimally lower rate. But the closing costs were rolled into the loan and one of the times I caught the lender slipping in a pre-payment penalty. What the lender should have told us was that we shouldn't refinance a loan when we're selling in a year or two. A friend came by and sold us an inappropriate whole life policy. I won't tell you which company he was interning for that summer, but it rhymes with Birthtestern Too Cruel. We didn't have much money (especially with a mortgage eating up 2/3 of my income) so he only managed to sell us a $20,000 whole life policy and an overpriced $280,000 term life policy. 7 years later, when I finally dumped that whole life policy, our cumulative return on the premiums paid was -33%.
Financially, we had a positive net worth, which put us way ahead of most of our residency peers. Return tomorrow for part two!
What financial mistakes have you made that others can learn from? What did you do right in your early years? Share your experiences and comment below!
Thank you for your story. It gives a context and a value-based depth to the financial advice [which is good!]. I think of you as a type of “Suze Orman +” [which is a compliment,,,,she is quite good!]…….ok….here is the point,,,,,,I think the values matter a whole lot as does the context within which you learned and exercised those values. I also think that values and emotions are bigger drivers of most financial planning than are the “simple facts of it all” no matter how clear and valid those facts are. Your background is quite similar to mine [working class; smartest person in the class until you were not; lots of odd jobs which are great and teach us a lot; some “good luck” along the way; a very high degree of self-reliance]…….yet, it is in the areas where we diverge that deeper lessons and challenges are revealed [I grew up in a huge family; lots of alcoholism and substance abuse; lots of strange and unhealthy dynamics but also lots of the “good stuff”; I am gay and came out in residency and got divorced and had two adopted children under 5 years of age whom I absolutely needed to support and love and parent; and I had to “bootstrap it” until I was well into my 50’s and the lesson learned it that it is NEVER to late to save, invest, live reasonably, be realistic…..I just turned 70 and my husband and I are very financially secure…..he is a physician also….. and we have a great retirement planned involving working in Africa and continuing on in medicine but in a “community organizing/social change” type of way….but we could not be doing that without having done, the past 20 years, exactly what you so wisely counsel people to do.]……final thought….I think the advice and wisdom that you have to share is very needed at a much younger age…..like 16 years old! Hope that you are able to target that audience in some way.
All the best…..
You seem like a very good person.
Ralph LeBlanc, M.D., M.P.H., Ph.D.
Great to hear a little bit of your story, Jim. Sounds like you were always hard working from the very beginning, which likely liked you up for success early on.
You ask what financial mistakes we’ve made? Here are my biggest two:
1. Applying for personal disability insurance when I was a fourth year med student going into anesthesia… While having an essential tremor. It was also with a northwestern mutual rep just like you. He was also the brother of one of my med school class mates. Iwanted life insurance and he convinced me to apply for DI, too (after saying no twice already). I got denied because of my tremor and my anticipated line of work. I could have gotten the guaranteed policy in residency the next year (only stipulation is that you can’t have been denied). Hopefully this doesn’t bite me, but it has a huge potential to.
2. Having a full ride in college and having the GI Bill put money straight into my pocket that I very promptly spent. Not only could I have saved that money instead, if I knew any better, but I could have saved it for medical school and would have come out debt free since I had a full-tuition scholarship in med school. All I took out was living expenses and the GI Bill likely would have covered that.
Those mistakes alone cost me at least 200k and, if I get disabled, possibly much much more.
Looking forward to hearing the rest of your story!
TPP
This makes a lot of sense. Everyone I’ve ever met from Alaska is a self-sufficient self-starter. Maybe we should move there just for our kids’ benefit so they can learn to be rugged. Of course, their parents would have to learn that first…
Great to hear the roots Jim. I’ve seen lots of climbing pics on your blog but didn’t know you were THAT much of a climbing enthusiast. Nice! Climbing and investing have a lot in common, easy to see how you fell into investing!
Jim, enjoyed part 1 of your story. One question I have for you: your upbringing was obviously a lot different than your own children’s will be. (I am in a very similar situation). How do you feel that will affect their ability to hustle like you did? I always think of the warnings in “Millionaire Next Door” and wouldn’t want my children to be a victim of my own success.
We talk about it all the time. There’s no doubt it will have an influence, but I’m hoping I cancel it out by providing the financial education I never had.
Yes, I talk about this a lot. There is an ancient Chinese quote that goes something like: “The first generation starves to death, the second works to death, the third eats its self to death…” I hope to have none of these experiences for myself or children. Its great to hear your story. If you had come to U of Maryland you would have been a year behind me. Cant wait for next installments (but will have to read them while traveling to Scotland w wife and kids…)
Everyone likes a good origin story. Look forward to the part where you get your personal finance super powers! Hopefully there will be some gamma rays involved 🙂
I really enjoyed learning more about your life. I had always assumed you had parents who were very astute financially and had “shown you the ropes” on how to earn, save and invest. This is pretty interesting to learn that you had to figure most of this financial territory out for yourself. Also interesting to learn that Katie’s family had a big influence on your deciding to pay it forward for your children and that she brought the assets into the marriage!
Interesting. Certainly no silver spoon. You learned from your mistakes in early life and do not dwell on them. This is really good advice. I met Katie at the WCI conference and found her to be impressive.
What a great origin story. I can’t believe you were into foosball. I actually bought a table when I was in high school and got really good at it (my friend and I ended up being the college frat foosball champions at Hopkins one year (yes there is such as a thing as a college foosball championship tournament. lol).
It’s nice to see that everyone makes mistakes but can still recover from them. I already spoke of my mistakes with housing (buying TWO houses while a resident). Fortunately mistakes early in time when relatively not much money involved can be overcome.
Look forward to the rest of the series.
Pool was the issue for us in med school, although to be fair we did pimp each other while playing. Foos didn’t become a problem until residency for me. I often ponder how much smarter I would be if–during those formative years– I spent more time reading and less time at the table….
I feel like you’ve given bits and pieces along the way, but it’s nice to have the whole unabridged version.
Quick question: When I was in college, I had a classmate who was from AK as well. During the summers he worked either at a cannery or on a fishing boat and he made a ton of money (especially on the boat). I don’t remember the exact nature of the work, but I do remember that with one summer of work he could pay for a year of college. Is there a reason you didn’t consider those types of jobs.
# 1 is really unpleasant and # 2 is really dangerous and I get seasick. I couldn’t live at home while doing either one. Plus, my tourism job paid more. (The lawnmowing paid less.)
I figured it had to be one or the other. The numbers I remember made it seem like about 15K/summer for the cannery and about 25K for the boat. I could be remembering wrong and I don’t know exactly how much of the summer he worked. Mid 90s FWIW.
I’ve been following your blog for many months now “peripherally”. But love reading your story- and the fact you had to learn about finances from the scratch (which is inspiring to me since I’m learning too now) and looking forward to reading the rest!
Great to finally get the whole story! I’ve been piecing it together from things you mention in the blog since I found it last year, and we’ve had some interesting parallels: I grew up in Utah, went to BYU (’97), applied to Utah for med school and was shown the foosball table in the lounge, joined the Air force to pay for med school (USUHS ’01), eventually staioned at Langley 2011-13 (I think that’s coming in part 2), I now live in Alaska and even have 4 kids and one is named Maren.
As for a mistake- buying a house coming out of residency in post-Katrina Mississippi (prices up) and selling two years later in ’08 for a loss to the same people we bought from. We thought we’d be there for four years, but we shouldn’t have bought knowing we’d be moving around in the Air Force every few years. We rented after that and loved the freedom when it came time to move again.
Are you my clone?
It was definitely interesting figuring it out. There are a lot of similarities, but not everything. I’m a pathologist and I don’t rock climb or have a blog. I didn’t even learn to snow or water ski growing up; mountains were for camping and hunting, and Lake Powell was for fishing. I’ve also stayed federal and am now in the Public Health Service.
Thanks for your site and podcast, I’ve definitely learned a lot. Love to meet you if you’re ever back up in the Great Land.
Enjoyed hearing your origins jim. Our biggest financial mistakes involved buying a whole life policy (which led me to your message) and co-signing on a loan for the wife’s business. I like to think of these 2 decisions as expensive “tuition” that have led to better financial behavior.
I also applied and was accepted to both the University of Chicago and Rice, but went to a state University for a great scholarship. We must have been looking at the same lists of top schools back in the day. I know I spent a lot of time with the US News & World Report list and the Princeton Review guide to colleges.
Looking forward to Parts II & III, which I’ll be reading momentarily.
Cheers!
-PoF