Olaf – The Mile High Way

Wall St. Nerd


Updated on

February 7, 2023


Guest Post by Olaf from Mile High Finance Guy.

In this article, Olaf gives an account of his own personal finance story. I am delighted that Olaf will be talking about his journey here on Wall St Nerd. Let's go in!

As a child, I was both a saver and a spendthrift; I would gladly save money, but only to purchase things later. As I matured, I became more money savvy but still lacked discipline. 

The Beginning of The Mile High Way

Upon graduating from university, I achieved the feat of having several months of living expenses saved. I had set this goal to afford myself a break between college and the next forty years of working. So, I set off to mountain bike across the western portion of the United States for several months.

After depleting my savings (yet again) and getting an excellent t-shirt tan, I was ready for a prototypical nine-to-five career. Thus, I embarked upon a job search.

Soon, I found myself working for a European winery. I helped the company expand its US presence for many years. Along the way, I discovered the FIRE movement, a radical but straightforward ideology I quickly adhered to and began implementing.

Olafs' FIRE movement

I started saving vigorously and became frugal, but soon found myself at a setback. The winery was at a reflection point, and the owner decided to scale the business down. 

So, I embarked on finding new full-time employment that I could work in tandem while consulting part-time for the winery; the side hustle income was nice! For full-time work, I settled on my newfound passion for personal finance and soon began a career at the country's largest 401(k) provider.

Shortly after starting, I acquired the appropriate licences to provide investment advice and quickly climbed the corporate ranks. It turns out that being a personal finance enthusiast and a financial advisor meshes well.

Being an advisor was rewarding. I loved helping people, and working through the Corona Crash was humbling and meaningful. Further, being an investment advisor allowed me to contribute significantly to people when they were at pivotal moments in their lives. But, I began to burn out from working such an emotionally demanding job, and I longed for more of an educational role after two years. 

Working in a call centre has benefits, but being an advisor in one is challenging due to the lack of decompression time between deep and analytical consultations; usually, I would have fifteen a day. Further, it didn't help that mid-level management implemented changes that I believed were flawed for my division. Luckily, I had a saving grace.


Before and during this tumulus period, I had been saving most of my monthly income. Doing so grew my portfolio substantially, but had come at the cost of becoming cheap. After all, if one isn't careful, the next logical progression from frugality is cheapness.

Now, don't get me wrong, saving and frugality are critical skills. However, becoming cheap is far from transcendence; it is a personality flaw that risks personal ruin.

If you cannot enjoy the fruits of your labour and instead sabotage your happiness and those around you because you refuse to do anything other than save, you are bound to cause damage and be permanently unhappy. 

When someone is cheap, they save money for the sole purpose of accumulating more money due to a scarcity mindset that has run astray. Meanwhile, being frugal is about skimping in some areas, so you can live more meaningfully in others. 

Frugality is all about balance; splurge here, skimp there. Cheapness is the lack of balance and accomplishes nothing positive, only inflicts damage on those under its spell.


So, after much self-reflection, I turned a new page and started to recover from being a frugal addict by begrudgingly loosening the purse strings. Not long after, I realized that my definition of financial freedom was flawed, too. Isn't it strange how times of change can act as a spur for personal growth?

During this period, I realized I didn't desire early retirement. Instead, I wanted the ability to live on my terms, which I already had the savings to achieve. There was no reason to pursue something I disagreed with and no longer enjoyed. 

So, I turned a new page again and quit my job. I tried telling mid-level management their thinking was flawed, but my efforts fell on deaf ears before and after my departure.

While quitting my job with no full-time employment lined up sounds foolish, it was one of the most liberating choices I have ever made. I went on to start the Mile High Finance Guy blog, which I have used as a way to help others, but on my terms. Not long thereafter, I received a job offer to be a financial advisor again.

While at first, I was hesitant, I decided to say yes. After all, life is about the unknown and taking risks. 

Fortunately, I could negotiate my terms since I didn't need the position. My requests were: I didn't want to work more than part-time and desired to function (chiefly) as an educator.

Guess what? My requests were met! 

My new life

Fast-forward to the present, and my blog is growing. Further, my advisory and winery consulting roles are going well. 

I live a life where I am financially free, but cover my living expenses through two part-time jobs that I enjoy. I consider myself very lucky, as much of the work stems from my efforts, but I would be negligent if I left out the factor luck played. 

For those new to the topic, financial solvency doesn't have to be a one-sized-fit-all approach. Instead, focus on what works best for you, and chase that perfect life. (That includes working two part-time jobs while running my blog and enjoying nature for myself.) Life is far too short to spend working on others' terms, so you should aspire to set yourself free. 

My money remains invested primarily in index funds, divided into 40% domestic large-cap, 20% small-cap value, 20% international equities, and 20% REITs. Utilizing these investments helped my contributions grow dramatically during the bull markets up to and after the Covid Crash.

I settled on my allocation after countless hours of back testing various portfolio models. Still, everyone is different, and my portfolio is likely unsuitable for you. I encourage you to research what investment choices would best suit your situation. If you are looking for a beginner's resource, please read my article: You're Investing Wrong: How To Use Portfolio Construction.

Final Thoughts

I hope you have enjoyed my tale. If I can convince you of anything, I hope it is that financial freedom is what you make it and that managing frugality is essential. Frugality can be powerful, but it can also hold negative consequences if you are not careful. So, please don't box yourself into being cheap.

I have learned that my definition of financial freedom differs from others, and I am okay with that. I challenge you to redefine what yours is, as we rarely paint an accurate portrait of what we desire on our first try. 

But, until we meet again, have a great day!

Olaf - The Mile High Finance Guy

Author - Olaf, the Mile High Finance Guy

Olaf is the creative mind behind the Mile High Finance Guy blog. Olaf is a personal finance enthusiast and works in the trade part-time. In his spare time, Olaf is an avid mountain biker and hiker. You can follow him on Twitter @milehighfiguy 

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Hi, I'm Alexander Kelm.

Serial entrepreneur, value investor and angel investor. Founder of Wall St. Nerd. Join me here on wallstnerd.com to learn how to read financial statements, find healthy companies, and invest your money wisely.

Let's chat on Twitter about investing.

  • Hey Alexander! Thanks for the opportunity to share my story. I certainly have learned quite a bit, but I know that further lessons will come. I hope readers find my story insightful and can gleam knowledge to help their journeys progress!

    • Hello Olaf! You’re welcome. My readers and I were very happy to hear your story. I am very excited to see where your journey will take you. Feel free to share your follow-up here on Wall St. Nerd. I look forward to it.

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