“Enjoy the Pilgrimage as Much as the Destination”

[I love hearing how people’s FIRE journeys twist and turn over time. Today’s guest post is from Olaf, a.k.a. the “Mile High Finance Guy” who shares his story and some epiphanies during his pursuit of financial independence. My fav part is Olaf’s overarching conclusion: “Enjoy the pilgrimage as much as the destination.”]


Hi world, I’m Olaf.

I am the Mile High Finance Guy. Today, I would like to share my tale of how FIRE has profoundly impacted my life and the lessons I have learned along the way.

Why should you join me on today’s expedition? Because FIRE took me from the world of wine to financial services to blogging and gave me the courage to take huge risks along the way. So, without further ado, here we go!


Back in 2014, I was a recent college graduate. Having attained a Bachelor of Science in Business Administration, the world was my oyster. But first things first, I needed a break before spending the next 40-plus years of my life climbing the corporate ladder. Or so I thought. 

So, with ample savings on hand for such a scenario, I took a three-month intermission spent mountain biking. Over 90 days, I rode nearly 90 trails between the Mile High City and Moab. Life was good. But as those final days weaned, so did my bank account. So, off to the world of 9-to-5s I went!

Nearly immediately, I fell into an unusual job through who I knew, not what I knew, and I was working for a foreign winery, helping grow their U.S. presence and sales. Fast forward five years, and many cross-country wine tastings, festivals, and dinners later, it became readily apparent that the business needed a new direction. After much research, I determined either a physical tasting room or a virtual approach was required going forward. 

So, I put my job on the line and presented the owner with my thoughts. After deliberation, the owner and I decided the best course of action, given his changing goals, was to scale back spending and move toward a virtual approach that saw my income and time spent cut by 2/3. 

Newsflash: I now needed to find new full-time employment, as my job-turned-side-hustle was no longer enough.

During this time of upheaval, I was diagnosed with a hip defect that my outdoor lifestyle had aggravated (ah, to be a Coloradan) and now needed major surgery in my late twenties. Furthermore, many of my closest friends moved across the country, and another had shown their true colors and required parting ways. Amplifying these events was my inability to find a job locally in my area of expertise.

Soon I experienced anxiety and depression for the first time in my life. When it pours, it rains (or snows)? I do live in Colorado, after all. 

So, with Colorado being a state not known for wine (beer and marijuana are another matter), I pondered my next steps. Thankfully I had a supportive partner who is now my spouse.

During this reflection, I weighed restarting my career rather than heading west toward the wine country. 

But, if not wine, what was next? The answer burned in the embers of my FIRE journey.

FIREing Into a New Job

Shortly into my journey of entering the professional world, I stumbled upon Financial Samurai. The discovery led me to find Budgets Are $exy, Mr. Money Mustache, Physician on FIRE, and many other money blogs. 

Before I could say Financial Independence, Retire Early, I had begun saving a large chunk of my income. I was pruning expenses left and right, using Excel Spreadsheets to craft sexy budgets, and spouting the wonders of compound interest!

Consequently, my immersion into the world of personal finance sparked and provided the ignition for my next professional endeavor: financial services. 

A Rapid Progression and Departure

Within six months of entering the financial services industry, I attained my Series 7 & 66 licenses. Next, I moved from an introductory role into an advisory one, consulting with defined contribution participants regarding their retirement savings. Often, I would advise on what to do with old 401(k) plans. 

(Defined contribution is a fancy way of saying 401(k) and 403(b) plans.)

Then, within five months, during which I had a significant surgery unrelated to my hip, I found myself in the Pandemic Plunge while relearning how to walk

As all hell broke loose in February and March of 2020, the stock market saw breakers triggered daily to halt the sell-off. No longer was the advice that I was giving was theoretical. Instead, it became real. 

The Corona Crash and its Aftermath

During the chaos, I had many heartfelt conversations with individuals who had just retired, were nearing it, or had experienced a layoff. Others had just started investing and were frightened. Regardless, these individuals needed their money to be there for them in days or years ahead, and their accounts were free-falling. 

The most common question I received was how to stop the bleeding. While to seasoned investors, such an idea may seem erroneous, consider that many (but not all) employer-sponsored retirement investors stumble into investing by gaining a job. 

I helped people learn about investing through the many phone calls, reconfigure their portfolios to match their risk tolerance, and raise cash for their immediate living needs (if laid off with no emergency fund). 

At the same time, while many people listened to me about tuning out the turbulence, others didn’t and chose to sell their entire portfolios. However, I respect these choices, as it is their money. It never was my job to force people to do what I thought was best, only to provide them with guidance. If they could not sleep at night, they needed to take action.

After the chaos subsided and the markets stabilized (from unprecedented stimulus measures), life returned to somewhat normal in the financial service industry. Soon after, I received a promotion to a higher tier of the same job, helping clients with higher incomes and net worths. Then, later that year, I had hip surgery after a delay due to the more urgent surgery that had preceded it. 

Upon returning from hip surgery, I soon received another promotion to the top tier within my division. However, that didn’t last long, as four months later, I found myself craving for more and quitting my role due to disagreements with the division’s direction. By this point, I discovered that my job wasn’t aligning with my goals, and the change in upper management and strategy, paired with the constant anonymous grind of working in a phone center, led to me extinguishing this job in hopes of some healing.

Reborn From the Flames

When I quit, my spouse and I were well on the way toward FIRE. But being miserable is an awful thing. 

Fortunately, FIRE gives you the power to say enough is enough and change directions, even if you haven’t reached it yet.

So, with ample savings, a stable and fulfilling job for my supportive spouse, and a side hustle income stream from wine consulting, I said goodbye to my six-figure 9-to-5 job.

However, what began as a sabbatical with no end goal in mind soon turned into a new mission. 

You see, I knew when I quit that I wanted to share knowledge, but I wasn’t sure how. But one day, it struck me: I could share my views and knowledge through a blog, like many of my aspirational figures. Hence, Mile High Finance Guy was born. 

Now, I work two part-time jobs as a winery consultant (for the same winery) and investment advisor while running my blog full-time. I find my life much more fulfilling, but that doesn’t mean that anxiety and depression don’t occasionally make their ugly heads known. After all, to be human is to be imperfect.

My Struggles and Lessons Learned

I have long been obsessive about endeavors I embark upon, as I find balance and moderation theoretical rather than practical. Therefore, throughout my professional journey and up until recently, I struggled with frugality and spending. 

I often pivoted too hard into saving and refused to go out with friends in the past. After all, if the money wasn’t in my budget, it wasn’t there to spend! But such thinking was mistaken. 

Instead, saving and frugality are about enjoying the pleasures of life while cutting down on the things that aren’t. The result is a fulfilled present and brighter future. 

Newsflash: If you cannot enjoy the present without stressing about every dollar, you no longer live a fulfilling life. Instead, you have gone from strategic spending to cheapness (unless you struggle with poverty).

Thus, my biggest lesson learned during my journey towards FIRE so far is to enjoy the pilgrimage as much as the destination, as things won’t magically change once you arrive. 

Furthermore, I put too much of my life on hold to save more. Don’t do that. Find a balance of spending and saving that works for you, as life is too precious to delay or procrastinate away. 

Because money is equal parts math and emotions, finding balance won’t always come easy. But, achieving financial freedom should still be the goal, regardless of how long it takes. 

While you will likely face strain from saving initially, that will probably pass. However, if saving turns into self-imposed deprivation, you have gone too far. 

For me, FIRE has evolved into FI, as I never want to retire early. Instead, I want to do what I want, when I want, and however I want. To me, that means empowering others to learn about personal finance and enjoying the outdoors Colorado has to provide. For my spouse, that means helping others and making an impact, which she already does by working in health care. Thus, while we both may never formally retire (until old age slows us down), you can bet we will be FI until then. 

My 6 Takeaways On Money & Life

  • Enjoying the journey of FIRE is as important as reaching the destination. So, learn to enjoy today because life doesn’t magically change when you arrive.
  • Strike a balance between saving and spending that achieves your goals in the present and future. Ideally, if you aren’t in poverty, find a way to save at least 20% of your income, but preferably more.
  • Money is equally emotional and numerical, so don’t grill yourself too hard about mistakes, and be sure to celebrate your wins!
  • Learn your risk tolerance and invest accordingly, as anyone can enjoy the gains during a bull market, but not everyone tolerates downturns with grace. By investing in a balanced portfolio that matches your risk tolerance, you will be ready to face volatility.
  • Having an emergency fund while you are in your accumulation phase is essential. By doing so, you insure against an unforeseen layoff and provide yourself with a safety net.
  • Ask yourself what you are genuinely trying to achieve with FIRE. If you can implement any of it today, do so! 

Thanks for reading my story. I hope you found it helpful, and I would love to hear your thoughts and questions in the comments below.


[Olaf is a millennial who has a passion for personal finance! When he’s not typing awesome blog posts, he likes mountain biking, hiking, and traveling. Check out more posts over at his blog – Mile High Finance Guy]

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  1. Olaf, the Mile High Finance Guy January 24, 2022 at 10:54 AM

    It is an honor to be featured on one of my favorite blogs! Thanks for the opportunity, Joel.

    1. Joel January 24, 2022 at 11:57 AM

      Heck yeah man! Love your journey, and I see you’re being featured on some other big PF sites lately. Congrats!