Detours on the Road to Financial Independence

by The Darwinian Doctor

Today’s post is about tough choices on the journey to financial independence. What should we do now and what should be saved for the future? My thoughts below.

This post may contain affiliate links.

Life sometimes has an interesting way of forcing us to do some soul searching. Over the past few weeks, three experiences combined to pose to me an important question:  How many detours are allowed on the road to financial independence?  

College reunion getaway

My self reflection and mild existential angst was triggered first by an amazing weekend the Dr-ess and I spent on the East Coast.  With our two boys tucked away under a quilt of trusted parents and nannies, we flew across the country for a college reunion. Without the stress of feeding and watering our young kids, we enjoyed a blissful few days of revelry on the college campus where we met about 20 years ago.  

Although I had been back for the last reunion five years ago, there was something different about this one.  The majority of my friends now have stable jobs and a couple of kids. The ones that don’t have kids probably will never have kids, and the ones without stable jobs are stubbornly pursuing an alternative creative path of their own volition.

The campus was subtly different, with a lot of fancy new clothing stores and restaurants occupying the spaces where I remember old greasy spoon diners and copy stores (remember those?).  The Dr-ess and I spent a couple hours slowly walking around, fondly remembering our years together in college.

Although there was much merriment, none of my friends went overboard.  There were no trips to the ER, no run-ins with local law enforcement, and no egregious property damage.  If this had been just 5 years ago, probably at least one of those things would have happened. Some of our restraint was surely a result of the fact that about half of my friends had their young kids in tow.  Despite the moderation, we all had a memorable weekend suffused with the warmth of each other’s company. We cheered our collective successes and comforted each other over failures.

At the end of the weekend, we had a mushy text exchange between all of us that essentially spoke of the gift of “growing old” with one another.  It was a bittersweet flight home.

The next day, as I was driving to work, I came to the sobering realization that if we keep to this pattern of seeing each other at these reunions every five years, I realistically will only see these dear friends a maximum of 10 more times before we are all dead and buried.  As this morbid thought percolated through my brain, I suddenly had a throat-tightening vision of my life, trickling swiftly like sand through the hourglass of mortality, never to be retrieved.

Ski trip

Another thing that happened recently is that the Dr-ess’ sister invited us on a ski trip next winter to a ski resort in Park City, Utah.  After spending much of my formative years in the north eastern part of the USA, I must admit that I haven’t had any real interest in seeing snow since moving to Southern California 10 years ago.  Sand and sun? Yes! Snow and parkas? No thank you!

But our kids are at an age now where the thought of them spending a few days on the ski slopes with their cousins sounded fairly appealing.  What was less appealing, however, was the projected cost of the flights, lift tickets, lodging, and food in a place like Deer Valley. With some back of the napkin calculations, we realized that for just 4 days of snow, we’d probably end up spending somewhere between $6000 to $10,000.

On the other hand, we really value the time that we spend with my sister-in-law’s family. Although we live on opposite sides of the country, our kids love spending time together during vacations. As parents, we love seeing their excitement during visits.  As someone who grew up without much of an extended family, I cherish the thought of my boys feeling that special blood-connection to people outside of our immediate nuclear family.

But that price-tag is enough to give us pause.  

Life can be short

Finally, I recently read a sad post on CrispyDoc’s blog discussing the unfortunate news that three people in his life have either been diagnosed with cancer or a neurodegenerative disease in just one week!

It pushed him and his wife to reflect on what they would change about their day-to-day life if faced with such a life-altering diagnosis.  Spoiler alert — they wouldn’t change much.

For me, the post echoed off the other recent happenings in my life and caused me to reflect on a slightly different question:  “How many detours are allowed on the road to financial independence?”

Enjoy the journey as well as the destination

Given my high cost of living, I’ve got some lofty goals to reach before I would consider myself anywhere close to financially independent.  But there is a careful balance to strike to enjoy the journey as well as the eventual destination.

Right now, I usually work about 10-15 hours of overtime each week. It’s technically voluntary, but I get the sense that if I asked to go to a regular 40 hour week, this request would be met with stony silence and a blank look from my boss. And when it comes time for partnership in the medical group later this year, I don’t know if I could count on his recommendation if I didn’t have the same “work ethic” as my colleagues.

The upside, of course, is that I get paid more when I work overtime.  Although I’m taxed like crazy, it does at the end of the day speed me on my journey to financial independence.  

But what if I’d rather work less and see my kids more?  What if I’d rather have more time to spend pursuing creative outlets, like this blog?  And what if we wanted to go on that ski vacation for $10,000?

These would all constitute significant detours to hitting my FI number, but it very might be worth it.  After all, the last couple of weeks have taught me that there aren’t endless chances to see loved ones. Whether it’s the inexorable passage of time or an unexpected illness, life may be shorter than we realize.  Unfortunately, if we make the wrong choices today, we can’t just flip over the hourglass of our lives and regain that lost time.


So what did we decide about the ski trip?  We decided to skip it. While we’d love to spend time with the sister-in-law’s family, we’re going to figure out a more cost effective way to do it.  

I’m not sure if I’m consciously choosing every single detour on the road to financial independence. The important thing is that now, my eyes are open.  I’m not content anymore to shuffle down some prescribed path until I retire at 65 or keel over on my own exam table. I can’t prevent random trials that life may throw my way, but I can certainly live with intentionality.

Through careful planning, I’m going to create a life where I have the freedom to retire if I so choose.  I will see my close family and friends more. I will create a financial bedrock to prevent the debilitating stress of financial instability for my family and future generations to come.

I can’t say that I have it all figured out just yet, but I can say that I promise to bring you along for the ride as I evolve towards a state of greater intentionality and control over my destiny.


Thoughts? Please comment below and make sure to join the mailing list!

Subscribe to the Darwinian Doctor newsletter and get a free copy of my eBook: “How to Control Your Financial Destiny”

* indicates required

Want to support the blog?

You may also like

Notify of
Newest Most Voted
Inline Feedbacks
View all comments
Crispy Doc
5 years ago

Loved this one, TDD.

Our time is very limited, and as you realized, those friends flung across the country are going to have limited face-to-face moments in coming years for connection. How do you optimize and prioritize them?

Just having those conversations with your wife makes a huge impact on living intentionally. Will the next family trip be to visit an old college friend? How can you make memories with your sister-in-law without breaking the budget?

Each time you tweak the road to FI to encompass these priorities, it reinforces the end-goal: allocating your time with the most important people.

As for the crazy schedule out of the gate – it’s common to front-load those commitments. Once you reach partner, you will have greater control over what additional commitments you accept.



profile-pic (4)

Hot off the press and on sale for a limited time!

My eBook will give you the tools to get started on the path to financial freedom. Learn about my financial journey and the shockingly simple math behind financial independence. Then find out how to define your Why to fuel your success!

Don't Miss A Post

A Darwinian Disclaimer

Since everyone is different, it may not be appropriate to generalize my doctorly advice to your own situation. Please run all medical, life, and financial advice by your own physician or financial professionals before applying it to your own life! Consider all information for your entertainment only!

Images and Copyright

To the best of my knowledge, the images used in this blog are either taken by my own camera, free stock photos, or considered allowable usage under "Fair Use" law. Please let me know if you believe otherwise.

Affiliate Policy

Affiliate Policy
As you explore the site, you may notice links to goods or services. I may earn a commision if you use a link to purchase any of these. While this blog is really just a labor of love and a creative outlet, if I can "keep the lights on" with affiliate links, all the better. Rest assured any reviews you read here represent my unbiased opinions, and there is no added cost to you to utilize the links. Please go here to read my full Affiliate policy.

Evolution Holdings LLC
All rights reserved.

@2024 – All Right Reserved.

Would love your thoughts, please comment.x